HOLLINGER INTERNATIONAL INC
8-K, 1997-04-16
NEWSPAPERS: PUBLISHING OR PUBLISHING & PRINTING
Previous: DEFINED ASSET FUNDS MUNICIPAL INVT TR FD MULTISTATE SER 8H, 485BPOS, 1997-04-16
Next: ROBERTSON CECO CORP, 8-K/A, 1997-04-16



<PAGE>   1
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                   ----------


                                    FORM 8-K

                                 CURRENT REPORT

                     PURSUANT TO SECTION 13 OR 15(d) of the
                        SECURITIES EXCHANGE ACT OF 1934

                                   ----------


Date of Report (Date of earliest event reported): March 18, 1997

                          Hollinger International Inc.
               (Exact name of registrant as specified in charter)

Delaware                           0-24004                  95-3518892
(State or other                    (Commission              (IRS employer
jurisdiction of incorp.)           file number)             identification no.)

401 North Wabash Avenue,
Chicago, Illinois                                           60611
(Address of principal executive offices)                    (Zip code)


Registrant's telephone number, including
 area code:  (312) 321-2299


<PAGE>   2



Item 5.  Other Events.

         PUBLIC OFFERING. On March 18, 1997, Hollinger International Publishing
Inc. ("Publishing"), a wholly owned subsidiary of Hollinger International Inc.
(the "Company"), completed a public offering (the "Offering") of $260 million
principal amount of 8 5/8% senior notes due March 15, 2005 (the "Senior Notes")
and $290 million principal amount of 9 1/4% senior subordinated notes due March
15, 2007 (the "Senior Subordinated Notes") (the Senior Notes and the Senior
Subordinated Notes are collectively referred to as the "Notes"), priced at
99.5% and 98.358% of aggregate stated principal amount, respectively. Payment
of the principal of, premium, if any, and interest on the Notes is guaranteed
by the Company, on an unsecured senior basis, in the case of the Senior Notes,
and on an unsecured senior subordinated basis, in the case of the Senior
Subordinated Notes. Each Senior Note bears interest at the rate of 8 5/8% per
annum from the date of issuance, payable semiannually on March 15 and September
15 of each year, commencing on September 15, 1997. Each Senior Subordinated
Note bears interest at the rate of 9 1/2% per annum from the date of issuance,
payable semiannually on March 15 and September 15 of each year, commencing on
September 15, 1997. The Senior Notes are not redeemable at the option of
Publishing prior to maturity. The Senior Subordinated Notes are subject to
redemption at any time on or after March 15, 2002 at the option of Publishing,
in whole or in part, at a price of 104.625% of the principal amount thereof,
declining ratably to 100% on or after March 15, 2005, together with accrued and
unpaid interest thereon, if any, to the redemption date. Net proceeds to
Publishing from the Offering were approximately $532.3 million.

         The Company applied a portion of the net proceeds of the Offering to
repay outstanding bank debt of the Company and its subsidiaries in the
aggregate principal amount of approximately $354.9 million. Approximately
$116.4 million of the net proceeds was deposited in escrow to redeem the
outstanding preference shares of DT Holdings Limited ("DTH") and First DT
Holdings Limited ("FDTH"), English subsidiaries of the Company, which are held
by third parties. The remaining net proceeds will be available for general
corporate purposes, including a dividend of $20.0 million from Publishing to
the Company, working capital, repayment or reduction of indebtedness or other
obligations, and capital expenditures. Concurrently with the closing of the
Offering, the Company caused DTH and FDTH to issue the required notice of
redemption to the holders of such preference shares and irrevocably directed
the depositary to redeem such shares at their respective redemption dates in
May and June 1997.

                                      -2-
<PAGE>   3

         A copy of the press release issued by the Company is attached hereto
as Exhibit 99.01 and is incorporated herein by reference in its entirety.

         REORGANIZATION OF THE COMPANY'S SOUTHAM INTERESTS. Effective March 18,
1997, the Company completed an internal reorganization of its interests in
Southam Inc. ("Southam"), a Canadian corporation, which previously had been
held as follows: (i) 18.5% through Hollinger-Telegraph Holdings Inc. ("HTH"), a
Canadian corporation which is jointly owned by two wholly owned subsidiaries of
the Company, and 0.6% through such subsidiaries; (ii) 21.2% acquired from the
Power Corporation of Canada held through Hollinger Canadian Publishing Holdings
Inc., a New Brunswick holding company resulting from the amalgamation of
Hollinger Eastern Publishing Inc. with another indirect subsidiary of the
Company ("Hollinger Canadian Publishing"); and (iii) 10.4% through a wholly
owned subsidiary of FDTH as a result of the Southam share acquisition in
December 1996. The Company's majority interest in Southam is held by Hollinger
Canadian Publishing in which Publishing and Hollinger Inc. own, directly or
indirectly, the following interests: (i) Publishing and its subsidiaries own
100% of the non-voting equity shares and non-voting preference shares and (ii)
each of Publishing and Hollinger Inc. (through its wholly owned subsidiary) own
50% of the voting preference shares which have only nominal equity value. In
addition, the Company retains an indirect non-voting minority interest in
common stock of an intermediate holding company owning Hollinger Canadian
Publishing.  It is anticipated that Hollinger Inc. will pledge its interest in
Hollinger Canadian Publishing as collateral for bank financing arrangements of
the Company and its subsidiaries.

         In connection with this internal reorganization, the Company
substituted a direct pledge of Southam common shares owned by the Company
representing approximately 8% of Southam's outstanding common shares for the
current pledge of 50% of the common shares of HTH (the "HTH Shares") to a
trustee with respect to approximately Cdn.$102.0 million outstanding principal
amount of public debentures issued by Hollinger Inc. (the "Southam-Linked
Debentures"). Prior to the internal reorganization described above, HTH owned
an 18.5% interest in Southam. Upon such substitution, the HTH Shares became
free and clear of the pledge under the Southam-Linked Debentures. As a result,
the Company's interest in Southam which is directly or indirectly subject to
pledge under the Southam-Linked Debentures has been reduced from 18.5% to
approximately 8%.

         As the holder of the Company's Series A Convertible Redeemable
Preferred Stock, par value $.01 per share ("Series A Preferred Stock"),
Hollinger Inc.'s redemption rights related to

                                      -3-
<PAGE>   4

the Series A Preferred Stock were linked to the number of shares of HTH or
Southam that at the time of exercise are free and clear of encumbrances. The
Share Exchange Agreement, dated as of July 19, 1995, between Hollinger Inc. and
the Company (the "Share Exchange Agreement") contained a covenant by Hollinger
Inc. limiting the exercise of its redemption rights as the holder of the Series
A Preferred Stock. The Share Exchange Agreement has been modified to reflect
the substitution of the Southam common shares for the HTH Shares as collateral
for the Southam-Linked Debentures. Hollinger Inc. is now contractually entitled
to exercise its redemption rights under the Series A Preferred Stock
proportionate to the number of such Southam common shares that became free of
the pledge under the Southam-Linked Debentures. The Series A Preferred Stock
has an aggregate redemption price of $79.2 million, of which up to
approximately $45.0 million may be subject to redemption by Hollinger Inc. The
Company expects that shares of the Series A Preferred Stock will be redeemed,
to the fullest extent permissible, during 1997.

         The agreement dated as of July 19, 1995 between Hollinger Inc. and
FDTH (the "HTH/FDTH Share Exchange Agreement"), pursuant to which FDTH acquired
from Hollinger Inc. an indirect interest in Southam consisting of Hollinger
Inc.'s one-half interest in HTH and its direct 0.3% interest in Southam, was
also amended in connection with the internal reorganization of the Company's
interests in Southam. Pursuant to various corporate reorganizations, all of
FDTH's rights and obligations under the HTH/FDTH Share Exchange Agreement had
been transferred to and assumed by Hollinger Canadian Publishing. Hollinger
Inc. and Hollinger Canadian Publishing had ongoing rights and obligations
under the HTH/FDTH Share Exchange Agreement pertaining to the delivery to
Hollinger Canadian Publishing of stock certificates representing some or all of
the common shares of HTH. The HTH/FDTH Share Exchange Agreement has been
modified to reflect the substitution of the Southam common shares for the HTH
Shares as collateral for the Southam-Linked Debentures. The delivery
requirements now pertain to certificates representing shares of Southam common
stock.

                                      -4-
<PAGE>   5

Item 7.  Financial Statements and Exhibits.

         (a)       Financial statements of businesses acquired.  Not
applicable.

         (b)       Pro forma financial information.  Not applicable.

         (c)       Exhibits.

                   1.01     Purchase Agreement relating to the Senior Notes,
                            dated March 12, 1997.

                   1.02     Purchase Agreement relating to the Senior
                            Subordinated Notes, dated March 12, 1997.

                   4.01     Senior Indenture, dated as of March 18, 1997.

                   4.02     Senior Note No. 001, registered in the name of Cede
                            & Co.

                   4.03     Senior Subordinated Indenture, dated as of March
                            18, 1997.

                   4.04     Senior Subordinated Note No. 001, registered in the
                            name of Cede & Co.

                   10.01    Amendment, dated as of March 18, 1997, to the Share
                            Exchange Agreement.

                   10.02    Amendment, dated as of March 18, 1997, to the
                            HTH/FDTH Share Exchange Agreement.

                   99.01    Press Release dated March 18, 1997.

                                      -5-
<PAGE>   6

                                   SIGNATURES

         Pursuant to the requirements of the Securities Exchange Act of 1934,
the registrant has duly caused this report to be signed on its behalf by the
undersigned thereunto duly authorized.

                                             HOLLINGER INTERNATIONAL INC.

                                             By:  /s/Kenneth L. Serota
                                                  --------------------------
                                                  Kenneth L. Serota

                                                  Title:  Vice President --
                                                             Law and Finance

Date:  April 4, 1997

                                      -6-
<PAGE>   7


Exhibit Index

<TABLE>
<CAPTION>
Exhibit                                                                             Sequential
  No.                                  Document                                      Page No.
- -------                                --------                                     ----------
 <S>        <C>                                                                     <C>
  1.01      Purchase Agreement relating to the Senior Notes, dated March 12,
            1997.

  1.02      Purchase Agreement relating to the Senior Subordinated Notes, dated
            March 12, 1997.

  4.01      Senior Indenture, dated as of March 18, 1997.

  4.02      Senior Note No. 001, registered in the name of Cede & Co.

  4.03      Senior Subordinated Indenture, dated as of March 18, 1997.

  4.04      Senior Subordinated Note No. 001, registered in the name of Cede &
            Co.

 10.01      Amendment, dated as of March 18, 1997, to the Share Exchange
            Agreement.

 10.02      Amendment, dated as of March 18, 1997, to the HTH/FDTH Share
            Exchange Agreement.

 99.01      Press Release dated March 18, 1997.
</TABLE>

                                      -7-

<PAGE>   1

                                                                    EXHIBIT 1.01
                    HOLLINGER INTERNATIONAL PUBLISHING INC.
                            (a Delaware corporation)

                          HOLLINGER INTERNATIONAL INC.
                            (a Delaware corporation)


                                  $260,000,000
                          8-5/8% Senior Notes due 2005



                               PURCHASE AGREEMENT



                                                                  March 12, 1997


MERRILL LYNCH & CO.
   Merrill Lynch, Pierce, Fenner & Smith Incorporated
CIBC WOOD GUNDY SECURITIES CORP.
SCOTIA CAPITAL MARKETS (USA) INC.
TD SECURITIES (USA) INC.
c/o Merrill Lynch & Co.
   Merrill Lynch, Pierce, Fenner & Smith Incorporated
Merrill Lynch World Headquarters
North Tower
World Financial Center
New York, New York  10281-1201


Ladies and Gentlemen:

   Hollinger International Publishing Inc., a Delaware corporation
("Publishing"), and Hollinger International Inc., a Delaware corporation (the
"Guarantor"), confirm their agreement with Merrill Lynch, Pierce, Fenner &
Smith Incorporated ("Merrill Lynch"), CIBC Wood Gundy Securities Corp.
("CIBC"), Scotia Capital Markets (USA) Inc. ("Scotia"), and TD Securities (USA)
Inc. ("TD") (collectively, the "Underwriters", which term shall also include
any underwriter substituted as hereinafter provided in Section 10), with
respect to the sale by Publishing and the purchase by the Underwriters, acting
severally and not jointly, of $260,000,000 (all dollar references herein are in
U.S. dollars unless otherwise specifically indicated) aggregate principal
amount of Publishing's 8-5/8% Senior Notes due 2005 (the "Securities").  The
Securities will be guaranteed by the Guarantor on a senior subordinated basis.





<PAGE>   2

                                                                        - 2 -

   The aforesaid $260,000,000 aggregate principal amount of Securities are to
be issued pursuant to an Indenture to be dated as of March 12, 1997, as
amended, (the "Senior Indenture"), among Publishing, the Guarantor and Fleet
National Bank of Connecticut, as trustee (the "Trustee").

   The interest rate and certain other terms of the Securities and the purchase
price of the Securities to be paid by the Underwriters shall be agreed upon by
Publishing, the Guarantor and the Underwriters and such agreement shall be set
forth in a separate written instrument substantially in the form of Exhibit I
hereto (the "Price Determination Agreement").  The Price Determination
Agreement may take the form of an exchange of any standard form of written
telecommunication among Publishing, the Guarantor and the Underwriters and
shall specify such applicable information as is indicated in Exhibit A hereto.
The offering of the Securities will be governed by this Agreement, as
supplemented by the Price Determination Agreement.  From and after the date of
the execution and delivery of the Price Determination Agreement, this Agreement
shall be deemed to incorporate, and all references herein to "this Agreement"
or "herein" shall be deemed to include, the Price Determination Agreement.

   Concurrently with the execution of this Agreement, Publishing, the Guarantor
and Merrill Lynch, Donaldson, Lufkin & Jenrette Securities Corporation ("DLJ"),
TD, Bear, Stearns & Co. Inc. ("Bear Stearns") and CIBC are entering into a
senior subordinated note purchase agreement (the "Senior Subordinated Note
Purchase Agreement") pursuant to which Publishing will issue and sell to
Merrill Lynch, DLJ, TD, Bear Stearns and CIBC $290,000,000 aggregate principal
amount of Publishing's 9-1/4% Senior Subordinated Notes due 2007 (the "Senior
Subordinated Notes").  The pricing terms for the Senior Subordinated Notes to
be sold pursuant to the Senior Subordinated Notes Purchase Agreement shall be
set forth in a separate agreement (the "Senior Subordinated Notes Price
Determination Agreement"), the form of which will be attached to the Senior
Subordinated Notes Purchase Agreement.

   Publishing and the Guarantor have prepared and filed with the Securities and
Exchange Commission (the "Commission") a registration statement on Form S-3
(No. 333-17113) and a related preliminary prospectus for the registration of
the Securities under the Securities Act of 1933 (the "1933 Act"), have filed
such amendments thereto, if any, and such amended preliminary prospectuses as
may have been required to the date hereof, and will file such additional
amendments thereto and such amended


<PAGE>   3
                                                                           - 3 -


prospectuses as may hereafter be required.  The term "Registration Statement"
as used in this Agreement means the registration statement (including all
financial schedules and exhibits), as amended at the time it becomes effective,
and as thereafter amended by post-effective amendment, and any registration
statement and any amendments thereto filed pursuant to Rule 462(b) of the 1933
Act relating to the offering covered by the initial registration statement (the
"Rule 462(b) Registration Statement").  The term "Prospectuses" as used in this
Agreement means the prospectuses in the forms included in the Registration
Statement, or, if the prospectuses included in the Registration Statement omit
information in reliance on Rule 430A under the 1933 Act and such information is
included in prospectuses filed with the Commission pursuant to Rule 424(b)
under the 1933 Act, the term "Prospectuses" as used in this Agreement means the
prospectuses in the forms included in the Registration Statement as
supplemented by the addition of the Rule 430A information contained in the
prospectuses filed with the Commission pursuant to Rule 424(b).

   Publishing and the Guarantor understand that the Underwriters propose to
make a public offering of the Securities as soon as the Underwriters deem
advisable after the Registration Statement becomes effective and the Price
Determination Agreement has been executed and delivered.

   Publishing hereby confirms its engagement of Merrill Lynch, Pierce, Fenner &
Smith Incorporated as, and Merrill Lynch, Pierce, Fenner & Smith Incorporated
hereby confirms its agreement with the Company to render services as, a
"qualified independent underwriter" within the meaning of Rule 2720 of the
By-laws of the National Association of Securities Dealers, Inc. with respect to
the offering and sale of the Securities.  Merrill Lynch, Pierce, Fenner & Smith
Incorporated, solely in its capacity as qualified independent underwriter and
not otherwise is referred to herein as the "Independent Underwriter".

   SECTION 1.  Representations and Warranties.  (a)  Publishing and the
Guarantor jointly and severally represent and warrant to the Underwriters as of
the date hereof and as of the date of the Price Determination Agreement (such
latter date





<PAGE>   4
                                                                           - 4 -


being hereinafter referred to as the "Representation Date") as follows:

   (i)  The Registration Statement in the form in which it became or becomes
  effective and also in such form as it may be when any post-effective
  amendment thereto or any Rule 462(b) Registration Statement or amendment
  thereto shall become effective and the Prospectus and any supplement or
  amendment thereto when filed with the Commission under Rule 424(b) under the
  1933 Act, complied or will comply in all material respects with the
  provisions of the 1933 Act and did not or will not at any such times contain
  an untrue statement of a material fact or omit to state a material fact
  required to be stated therein or necessary to make the statements therein not
  misleading, except that this representation and warranty does not apply to
  statements in or omissions from the Registration Statement or the Prospectus
  made in reliance upon and in conformity with information relating to the
  Underwriters furnished to Publishing and the Guarantor in writing by or on
  behalf of the Underwriters through you expressly for use therein.

   (ii)  All the outstanding shares of common stock of Publishing and the
  Guarantor have been duly authorized and validly issued, are fully paid and
  nonassessable and are free of any preemptive or similar rights; and the
  authorized capital stock of Publishing and the Guarantor conforms to the
  description thereof in the Registration Statement and the Prospectus.  Except
  as described in the Prospectus, there are no outstanding options, warrants or
  other rights issued by Publishing or the Guarantor calling for the issuance
  of, nor any written agreement entered into by Publishing or the Guarantor or
  oral commitments of Publishing or the Guarantor to issue, any shares of
  capital stock or any other security of Publishing or the Guarantor or any
  security convertible into or exchangeable or exercisable for capital stock or
  any other security of Publishing or the Guarantor.

   (iii)  Publishing and the Guarantor are corporations duly incorporated and
  validly existing in good standing under the laws of the State of Delaware
  with corporate power and authority to own, lease and operate their properties
  and to conduct their business as described in the Registration Statement and
  the Prospectus.





<PAGE>   5
                                                                           - 5 -



   (iv)  The only significant subsidiaries (as defined in the 1933 Act) of
  Publishing and the Guarantor are the subsidiaries listed in Schedule II
  hereto (each a "Subsidiary" and collectively the "Subsidiaries").  Each
  Subsidiary is a corporation duly incorporated, validly existing and in good
  standing in the jurisdiction of its incorporation, with corporate power and
  authority to own, lease and operate its properties and to conduct its
  business as described in the Registration Statement and the Prospectus, and
  is duly qualified as a foreign corporation for the transaction of business in
  and is in good standing under the laws of each other jurisdiction where the
  nature of its properties or the conduct of its business requires such
  qualification, except where the failure so to qualify does not have a
  material adverse effect on the condition (financial or other), business,
  properties, net worth or results of operations of such Subsidiary; all the
  outstanding shares of capital stock of each of the Subsidiaries have been
  duly authorized and validly issued, are fully paid and nonassessable, and all
  shares of the capital stock of the Subsidiaries that are owned directly or
  indirectly by Publishing or the Guarantor are owned free and clear of any
  lien, adverse claim, security interest, equity, or other encumbrance, except,
  to the extent set forth or described in the Registration Statement and the
  Prospectus, currently existing liens, claims and security interests of
  creditors and liens, claims and security interests pursuant to the terms of
  the FDTH Credit Facility, the Publishing Credit Facility and the contemplated
  New Bank Credit Facility (as defined).

   (v)  There are no legal or governmental proceedings pending or, to the
  knowledge of Publishing or the Guarantor, threatened, against Publishing or
  the Guarantor or any of the Subsidiaries, or to which Publishing or the
  Guarantor or any of the Subsidiaries, or to which any of their respective
  properties is subject, that are required to be described in the Registration
  Statement or the Prospectus but are not described as required, or which might
  have a material adverse effect on the condition (financial or other),
  business, properties, net worth or results of operation of Publishing, the
  Guarantor and their subsidiaries considered as one enterprise, or which might
  materially and adversely affect the properties or assets thereof or which
  might materially and adversely affect the consummation of this





<PAGE>   6
                                                                           - 6 -


  Agreement; all pending legal or governmental proceedings to which Publishing
  or the Guarantor or any of the Subsidiaries is a party or of which any of
  their respective property or assets is the subject which are not described in
  the Registration Statement, including ordinary routine litigation incidental
  to the business, are, considered in the aggregate, not material; and there
  are no agreements, contracts, indentures, leases or other instruments that
  are required to be described in the Registration Statement or the Prospectus
  or to be filed as an exhibit to the Registration Statement that are not
  described or filed as required by the 1933 Act.

   (vi)  Except as set forth in the Prospectus, neither Publishing, the
  Guarantor nor any of the Subsidiaries (A) is in violation of its certificate
  or articles of incorporation or by-laws, or other organizational documents,
  (B) is in violation of any law, ordinance, administrative or governmental
  rule or regulation applicable to Publishing or the Guarantor or any of the
  Subsidiaries or of any decree of any court or governmental agency or body
  having jurisdiction over Publishing or the Guarantor or any of the
  Subsidiaries, or (C) is in default in any material respect in the performance
  of any obligation, agreement or condition contained in any bond, debenture,
  note or any other evidence of indebtedness or in any material agreement,
  indenture, lease or other instrument to which Publishing or the Guarantor or
  any of the Subsidiaries is a party or by which any of them or any of their
  respective properties may be bound, except, in the case of clause (B) with
  respect to the Subsidiaries, where such violation does not have a  material
  effect on the condition (financial or other), business, properties, net worth
  or results of operations of Publishing, the Guarantor and their subsidiaries
  considered as one enterprise.

   (vii)  Neither the issuance and sale of the Securities, the execution,
  delivery or performance of this Agreement and the Price Determination
  Agreement by Publishing or the Guarantor, nor the consummation by Publishing
  or the Guarantor of the transactions contemplated hereby (A) requires any
  consent, approval, authorization or other order of or registration or filing
  with, any court, regulatory body, administrative agency or other governmental
  body, agency or official (except such as may be required for





<PAGE>   7
                                                                           - 7 -


  the registration of the Securities under the 1933 Act and the Securities
  Exchange Act of 1934 (the "Exchange Act") and compliance with the securities
  or Blue Sky laws of various jurisdictions, both of which have been or will be
  effected in accordance with this Agreement) or violates or will violate the
  certificate or articles of incorporation or by-laws, or other organizational
  documents, of Publishing or the Guarantor or any of the Subsidiaries or (B)
  constitutes or will constitute a breach of, or a default under, any material
  agreement, indenture, lease or other instrument to which Publishing or the
  Guarantor or any of the Subsidiaries is a party or by which any of them or
  any of their respective properties may be bound (except where consents or
  waivers as to such default have been obtained prior to the time of the
  execution of the Price Determination Agreement (the "Pricing Time")), or
  violates or will violate any statute, law, regulation or judgment,
  injunction, order or decree applicable to Publishing or the Guarantor or any
  of the Subsidiaries or any of their respective properties, or will result in
  the creation or imposition of any lien, charge or encumbrance upon any
  property or assets of Publishing or the Guarantor or any of the Subsidiaries
  pursuant to the terms of any agreement or instrument to which any of them is
  a party or by which any of them may be bound or to which any of the property
  or assets of any of them is subject.

   (viii)  KPMG Peat Marwick LLP, who have certified or shall certify certain
  of the financial statements included in the Registration Statement and the
  Prospectus (or any amendment or supplement thereto), are independent public
  accountants as required by the Act.

   (ix)  The consolidated financial information for the Guarantor and the
  Restricted Group, together with related notes, included in the Registration
  Statement and the Prospectus (and any amendment or supplement thereto), (A)
  in the case of the historical financial statements present fairly the
  supplemental consolidated financial position and results of operations of the
  Guarantor and of the Restricted Group, and (B) in the case of the pro forma
  financial statements present fairly, on a pro forma basis, the pro forma
  supplemental consolidated financial position and results of operations of
  Publishing and its subsidiaries, including The Telegraph Group Limited ("The
  Telegraph") and





<PAGE>   8
                                                                           - 8 -


  Southam Inc. ("Southam"), in each case on the basis stated in the
  Registration Statement at the respective dates or for the respective periods
  to which they apply.  Such financial statements, pro forma financial
  statements and related notes have been prepared in accordance with U.S.
  generally accepted accounting principles consistently applied throughout the
  periods involved, except as disclosed therein; and the other financial and
  statistical information and data included in the Registration Statement and
  the Prospectus (and any amendment or supplement thereto) are accurately
  presented in all material respects and prepared on a basis consistent with
  such financial statements and the books and records of the Guarantor,
  Publishing and their subsidiaries.

   (x)  The execution and delivery of, and the performance by Publishing and
  the Guarantor of their obligations under, this Agreement and the Price
  Determination Agreement have been duly and validly authorized by Publishing
  and the Guarantor, and this Agreement and the Price Determination Agreement
  have been duly executed and delivered by Publishing and the Guarantor.

   (xi)  Except as disclosed in the Registration Statement and the Prospectus
  (or any amendment or supplement thereto), subsequent to the respective dates
  as of which such information is given in the Registration Statement and the
  Prospectus (or any amendment or supplement thereto), neither Publishing nor
  the Guarantor nor any of the Subsidiaries has incurred any liability or
  obligation, direct or contingent, or entered into any transaction, not in the
  ordinary course of business, that is material to the Publishing, the
  Guarantor and their subsidiaries considered as one enterprise, and there has
  not been any change in the capital stock, or material increase in the
  short-term debt or long-term debt, of Publishing or the Guarantor or any of
  the Subsidiaries, or any material adverse change, or any development
  involving, or which may reasonably be expected to involve, a prospective
  material adverse change, in the condition (financial or other), business, net
  worth or results of operations of Publishing, the Guarantor and their
  subsidiaries considered as one enterprise.

   (xii)  Each of Publishing, the Guarantor and the Subsidiaries has good and
  marketable title to all property


<PAGE>   9
                                                                           - 9 -


  (real and personal) described in the Prospectus as being owned by them
  (excluding properties owned by West Ferry Printers, Trafford Park Printers,
  or Southam), free and clear of all liens, claims, security interests or other
  encumbrances except to the extent set forth or described in the Registration
  Statement and the Prospectus or in a document filed as an exhibit to the
  Registration Statement or are not material to the business of Publishing, the
  Guarantor and their subsidiaries considered as one enterprise and all the
  property described in the Prospectus as being held under lease by each of
  Publishing, the Guarantor and the Subsidiaries is held by it under valid,
  subsisting and enforceable leases with such exceptions as are not material to
  the business of Publishing, the Guarantor and their subsidiaries considered
  as one enterprise and do not interfere with the use made and proposed to be
  made of such properties by Publishing and the Guarantor and their
  subsidiaries.

   (xiii)  Neither Publishing nor the Guarantor has distributed and, prior to
  the later to occur of (i) the Closing Date and (ii) completion of the
  distribution of the Securities, neither will distribute any offering material
  in connection with the offering and sale of the Securities other than the
  Registration Statement, the Prospectus or other materials, if any, permitted
  by the Act.

   (xiv)  Publishing, the Guarantor and each of the Subsidiaries has such
  governmental authorizations, approvals, orders, licenses, certificates,
  franchises and permits of and from all governmental or regulatory officials
  and bodies ("permits") as are necessary to own its respective properties and
  to conduct its business in the manner described in the Prospectus, with such
  exceptions as are not material to the business of Publishing, the Guarantor
  and the Subsidiaries considered as one enterprise and do not interfere with
  the use made and proposed to be made of such properties by Publishing, the
  Guarantor and the Subsidiaries or are otherwise disclosed; Publishing, the
  Guarantor and each of the Subsidiaries has fulfilled and performed all its
  material obligations with respect to such permits and no event has occurred
  which allows, or after notice or lapse of time would allow, revocation or
  termination thereof or results in any other material impairment of the rights
  of the holder of any such permit,





<PAGE>   10
                                                                          - 10 -


  with such exceptions as are not material to the business of Publishing and
  the Guarantor and their subsidiaries considered as one enterprise and do not
  interfere with the use made and proposed to be made of such properties by
  Publishing and the Guarantor and the Subsidiaries or are otherwise disclosed;
  and, except as described in the Prospectus, none of such permits contains any
  restriction that is materially burdensome to Publishing and the Guarantor and
  their subsidiaries considered as one enterprise.

   (xv)  Publishing and the Guarantor maintain a system of internal accounting
  controls sufficient to provide reasonable assurances that (i) transactions
  are executed in accordance with management's general or specific
  authorization; (ii) transactions are recorded as necessary to permit
  preparation of financial statements in conformity with generally accepted
  accounting principles and to maintain accountability for assets; (iii) access
  to assets is permitted only in accordance with management's general or
  specific authorization; and (iv) the recorded accountability for assets is
  compared with existing assets at reasonable intervals and appropriate action
  is taken with respect to any differences.

   (xvi)  To Publishing's or the Guarantor's knowledge, neither Publishing nor
  the Guarantor nor any of the Subsidiaries nor any employee or agent of
  Publishing, the Guarantor or any Subsidiary has made any payment of funds of
  Publishing, the Guarantor or any Subsidiary or received or retained any funds
  in violation of any law, rule or regulation, which payment, receipt or
  retention of funds is of a character required to be disclosed in the
  Prospectus.

   (xvii)  Except as described in the Registration Statement and the
  Prospectus, Publishing, the Guarantor and each of the Subsidiaries have filed
  all tax returns required to be filed, which returns are complete and correct,
  and neither Publishing, the Guarantor nor any Subsidiary is in default in the
  payment of any taxes which were payable pursuant to said returns or any
  assessments with respect thereto, with such exceptions as are not material to
  the financial position of Publishing, the Guarantor and their subsidiaries
  considered as one enterprise.





<PAGE>   11
                                                                          - 11 -


   (xviii)  Publishing, the Guarantor and the Subsidiaries own, or possess
  adequate rights to use, all patents, trademarks, service marks, trade names,
  copyrights, licenses, and rights described in the Prospectus as being owned
  by them or any of them or necessary for the conduct of their respective
  businesses, and neither Publishing nor the Guarantor is aware of any claim to
  the contrary or any challenge by any other person to the rights of
  Publishing, the Guarantor and the Subsidiaries with respect to the foregoing.

   (xix)  Neither Publishing nor the Guarantor is now, and after sale of the
  Securities to be sold by it hereunder and application of the net proceeds
  from such sale as described in the Prospectus under the caption "Use of
  Proceeds" will not be, an "investment company" within the meaning of the
  Investment Company Act of 1940, as amended.

   (xx)  Publishing and the Guarantor have complied with all provisions of
  Florida Statutes, Section  517.075, relating to issuers doing business with
  Cuba.

   (xxi)  The Indenture has been duly authorized by Publishing and the
  Guarantor, will be substantially in the form heretofore delivered to the
  Underwriters and, when duly executed and delivered by Publishing, the
  Guarantor and the Trustee, will have been duly qualified under the 1939 Act
  and will constitute a valid and binding obligation of Publishing and the
  Guarantor, enforceable against Publishing and the Guarantor in accordance
  with its terms, except as enforcement thereof may be limited by bankruptcy,
  insolvency, moratorium, fraudulent conveyance, reorganization or other
  similar laws affecting enforcement of creditors' rights generally and except
  as enforcement thereof is subject to general principles of equity (regardless
  of whether enforcement is considered in a proceeding in equity or at law);
  the Indenture conforms to the description thereof contained in the
  Prospectus; the Indenture and the form and issuance of the Securities
  thereunder comply with the provisions of the 1939 Act.

   (xxii)  The Securities have been duly authorized by Publishing and the
  Guarantor and, when executed, authenticated, issued and delivered in the
  manner provided for in the Indenture and sold and paid for as provided in





<PAGE>   12
                                                                          - 12 -


  this Agreement, the Securities will constitute valid and binding obligations
  of the Publishing and the Guarantor enforceable against Publishing and the
  Guarantor in accordance with their terms, except as enforcement thereof may
  be limited by bankruptcy, insolvency, moratorium, fraudulent conveyance,
  reorganization or other similar laws affecting enforcement of creditors'
  rights generally and except as enforcement thereof is subject to general
  principles of equity (regardless of whether enforcement is considered in a
  proceeding in equity or at law); the holders thereof will be entitled to the
  benefits of the Indenture; and the Indenture and the Securities conform to
  the descriptions thereof contained in the Prospectus.

   (xxiii)  No holder of any security of Publishing or the Guarantor nor any
  other person has any right, contractual or otherwise, to have any securities
  included in the Registration Statement or the right, because of the filing of
  the Registration Statement or consummation of the transactions contemplated
  by this Agreement, to require registration of any security of Publishing or
  the Guarantor under the Act.

   (xxiv)  Except as set forth in the Prospectus, no labor dispute with the
  employees of Publishing or the Guarantor or any of the Subsidiaries exists
  or, to the knowledge of Publishing or the Guarantor, is imminent, which might
  be expected to result in a material adverse effect on the condition
  (financial or other), business, properties, net worth or results of
  operations of Publishing, the Guarantor and their subsidiaries considered as
  one enterprise.

   (xxv)  Except as set forth in the Registration Statement and except as would
  not result in a material effect on the condition (financial or other),
  business, properties, net worth or results of operations of Publishing, the
  Guarantor and their subsidiaries considered as one enterprise and which would
  not materially and adversely affect the consummation of this Agreement, (i)
  to the knowledge of Publishing and the Guarantor after reasonable inquiry,
  neither Publishing nor the Guarantor is in violation of any applicable
  Federal, foreign, state or local environmental law or any applicable order of
  any governmental authority with respect thereto; (ii) neither Publishing nor
  the Guarantor is in violation of or subject to any existing, or





<PAGE>   13
                                                                          - 13 -


  pending or, to Publishing's and the Guarantor's knowledge, threatened action,
  suit, investigation, inquiry or proceeding by any governmental authority nor
  is Publishing or the Guarantor subject to any environmental claim by any
  citizens' group or to remedial obligations under any applicable Federal,
  foreign, state or local environmental law; (iii) Publishing, the Guarantor
  and the subsidiaries are in compliance with all permits or similar
  authorizations, if any, required to be obtained or filed in connection with
  their operations including, without limitation, emissions, discharges,
  treatment, storage, disposal or release of a Hazardous Material into the
  environment except where any noncompliance could not reasonably be expected
  to have a material adverse effect on the operations of Publishing, the
  Guarantor and the Subsidiaries; and (iv) to the knowledge of Publishing and
  the Guarantor after reasonable inquiry, no Hazardous Materials have been
  disposed of or released by Publishing or the Guarantor or the Subsidiaries
  at, under or on any property currently or formerly owned or operated by
  Publishing, the Guarantor or the Subsidiaries, except in accordance with
  applicable environmental laws.  The term "Hazardous Material" means any oil
  (including petroleum products, crude oil and any fraction thereof), chemical,
  contaminant, pollutant, solid or hazardous waste or material, or Hazardous
  Substance (as defined in Section 101(14) of the Comprehensive Environmental
  Response, Compensation and Liability Act and regulations thereunder), that is
  regulated as toxic or hazardous to human health or the environment under any
  Federal, foreign, state or local environmental law.

   (xxvi)  Publishing and the Guarantor and each other person or entity that,
  together with Publishing and the Guarantor, is treated as a single employer
  under Section 414 of the Internal Revenue Code of 1986, as amended (the
  "Code") (each such person or entity being an "ERISA Affiliate"), complies in
  all material respects with the Employee Retirement Income Security Act of
  1974, as amended ("ERISA"), and the Code with respect to each pension plan
  (as defined in Section 3(2) of ERISA) maintained by Publishing, the Guarantor
  or such ERISA Affiliate, and none of Publishing, the Guarantor or any of its
  ERISA Affiliates has incurred any material liability to any pension plan or
  to the Pension Benefit Guaranty Corporation that has not been fully paid as





<PAGE>   14
                                                                          - 14 -


  of the date hereof except as disclosed in the Registration Statement or
  Prospectus (or any amendment or supplement thereto).

   (xxvii)  Publishing and the Guarantor will apply the protion of the net
  proceeds of the Offering deposited in escrow for the purpose of redeeming, in
  each case at the first redemption date occurring in 1997, the DTH and FDTH
  Preference Shares held by third parties as described in the Prospectus, and
  for no other purpose.

   (b)  Any certificate signed by an officer of Publishing or the Guarantor and
delivered to the Underwriters or to counsel for the Underwriters shall be
deemed a representation and warranty by Publishing and the Guarantor to the
Underwriters as to the matters covered thereby.

   SECTION 2.  Sale and Delivery to Underwriters; Closing.  (a)  On the basis
of the representations and warranties herein contained, and subject to the
terms and conditions herein set forth, Publishing agrees to sell to the
Underwriters, and the Underwriters agree to purchase from Publishing, at the
purchase price set forth in the Price Determination Agreement, the Securities.

   (b)  If Publishing has elected not to rely upon Rule 430A under the 1933 Act
Regulations, the initial public offering price and the purchase price to be
paid by the Underwriters shall be agreed upon and set forth in the Price
Determination Agreement, dated the date hereof, and an amendment to the
Registration Statement containing such information will be filed with the
Commission, before the Registration Statement becomes effective.

   (c)  If Publishing has elected to rely upon Rule 430A under the 1933 Act
Regulations, the initial public offering price and the purchase price to be
paid by the Underwriters shall be agreed upon and set forth in the Price
Determination Agreement.  In the event that the Price Determination Agreement
has not been executed by the close of business on the fourth business day
following the date on which the Registration Statement becomes effective, this
Agreement shall terminate forthwith, without liability of any party to any
other party except that Sections 6, 7 and 8 shall remain in effect.


<PAGE>   15
                                                                          - 15 -


   (d)  Publishing will deliver the Securities to the Underwriters, at the
offices of Cravath, Swaine & Moore, 825 Eighth Avenue, New York, NY 10019, or
at such other place as shall be agreed upon by Publishing, the Guarantor and
the Underwriters, against payment of the gross purchase price by wire transfer
to Publishing in U.S. dollars, in funds immediately available to Publishing, at
10:00 a.m. either (i) on the third business day following the date upon which
the Publishing and the Guarantor shall have fulfilled all requirements which
under the 1933 Act must be fulfilled to qualify the Securities for distribution
and the Registration Statement shall have become effective or (ii) if
Publishing has elected to rely upon Rule 430A under the 1933 Act Regulations,
on the third business day after execution of the Price Determination Agreement,
or at such other time not later than ten full business days thereafter as the
Underwriters and Publishing determine (such time being herein referred to as
the "Closing Date").  The Securities so to be delivered will be in definitive,
fully registered form in such denominations ($1,000 principal amount or an
integral multiple thereof) and registered in such names as the Underwriters
shall request in writing at least two full business days prior to the Closing
Date, and will be made available for checking and packaging at the office of
the Trustee, not later than 10:00 a.m. on the business day prior to the Closing
Date.  Concurrently with the payment by the Underwriters of the gross purchase
price for the Securities in the manner described in this Section 2(d),
Publishing will pay to the Underwriters by certified or official bank check or
checks in U.S. dollars, in funds available the next succeeding business day
drawn to the order of Merrill Lynch, Pierce, Fenner & Smith Incorporated, North
Tower, World Financial Center, New York, New York 10281-1305, for the account
of the Underwriters, an amount equal to the underwriting commission applicable
to the Securities as described in the Price Determination Agreement.

   SECTION 3.  Covenants of Publishing and the Guarantor.  Publishing and the
Guarantor, jointly and severally, covenant with the Underwriters as follows:

   (a)  Publishing will notify the Underwriters immediately, and confirm the
notice in writing, (i) of the effectiveness of the Registration Statement and
any amendment thereto (including any posteffective amendment), (ii) of the
receipt of any comments from the Commission, (iii) of any request by the
Commission for any amendment to the Registration Statement





<PAGE>   16
                                                                          - 16 -


or any amendment or supplement to the Prospectus or for additional information,
and (iv) of the issuance by the Commission of any stop order suspending the
effectiveness of the Registration Statement or the initiation of any
proceedings for that purpose.  Publishing will make every reasonable effort to
prevent the issuance of any stop order and, if any stop order is issued, to
obtain the lifting thereof at the earliest possible moment.

   (b)  Publishing will furnish to the Underwriters, without charge, five true
and correct copies of the Registration Statement as originally filed with the
Commission and of each amendment thereto, including financial statements and
all exhibits to the Registration Statement, and of any Rule 462(b) Registration
Statement and any amendment thereto, and will also furnish to you, without
charge, such number of conformed copies of the Registration Statement as
originally filed and of each amendment thereto, but without exhibits, and of
any Rule 462(b) Registration Statement and any amendment thereto, as you may
reasonably request.

   (c)  Publishing will not (i) file any amendment to the Registration
Statement, any Rule 462(b) Registration Statement or amendment thereto, or make
any amendment or supplement to the Prospectuses of which you shall not
previously have been advised or to which you shall reasonably object in writing
after being so advised or (ii) so long as, in the written opinion of counsel
for the Underwriters (a copy of which shall be delivered to Publishing), a
Prospectus is required to be delivered in connection with sales by any
Underwriters or dealer, file any information, documents or reports pursuant to
the Exchange Act, without delivering a copy of such information, documents or
reports to you prior to such filing.

   (d)  Publishing will furnish to the Underwriters, from time to time during
the period when the Prospectus is required to be delivered under the 1933 Act
or the Securities Exchange Act of 1934 (the "1934 Act"), such number of copies
of the Prospectus (as amended or supplemented) as the Underwriters may
reasonably request for the purposes contemplated by the 1933 Act or the 1934
Act or the respective applicable rules and regulations of the Commission
thereunder.

   (e)  If any event shall occur as a result of which it is necessary, in the
opinion of counsel for the Underwriters, to





<PAGE>   17
                                                                          - 17 -


amend or supplement the Prospectus in order to make the Prospectus not
misleading, in the light of the circumstances existing at the time it is
delivered to a purchaser, Publishing will forthwith amend or supplement the
Prospectus (in form and substance satisfactory to counsel for the Underwriters
so that, as so amended or supplemented, the Prospectus will not include an
untrue statement of a material fact or omit to state a material fact necessary
in order to make the statements therein, in the light of the circumstances
existing at the time it is delivered to a purchaser, not misleading), and
Publishing will furnish to the Underwriters a reasonable number of copies of
such amendment or supplement.

   (f)  Publishing will endeavor, in cooperation with the Underwriters, to
qualify the Securities for offering and sale under the applicable securities
laws of such states and other jurisdictions of the United States as the
Underwriters may designate; provided, however, that Publishing shall not be
obligated to qualify as a foreign corporation in any jurisdiction in which it
is not so qualified.  In each jurisdiction in which the Securities have been so
qualified Publishing will file such statements and reports as may be required
by the laws of such jurisdiction to continue such qualification in effect for a
period of not less than one year from the effective date of the Registration
Statement.

   (g)  Publishing will make generally available to its security holders as
soon as practicable, but not later than 60 days after the close of the period
covered thereby, an earnings statement (in form complying with the provisions
of Rule 158 of the 1933 Act Regulations) covering a 12-month period beginning
not later than the first day of Publishing's fiscal quarter next following the
"effective date" (as defined in said Rule 158) of the Registration Statement.

   (h)  Publishing will use the net proceeds received by it from the sale of
the Securities in the manner specified in the Prospectus under "Use of
Proceeds".

   (i)  If, at the time that the Registration Statement becomes effective, any
information shall have been omitted therefrom in reliance upon Rule 430A of the
1933 Act Regulations, then immediately following the execution of the Price
Determination Agreement, Publishing will prepare, and file or transmit for
filing with the Commission in accordance with such





<PAGE>   18
                                                                          - 18 -


Rule 430A and Rule 424(b) of the 1933 Act Regulations, copies of an amended
Prospectus, or, if required by such Rule 430A, a post-effective amendment of
the Registration Statement (including an amended Prospectus), containing all
information so omitted.

   (j)  Except as provided in this Agreement, Publishing will not directly or
indirectly, offer, sell, grant any option to purchase or otherwise dispose of,
any debt security of Publishing which is publicly offered or sold pursuant to
Rule 144A of the 1933 Act Regulations for a period of 180 days after the date
of the Prospectus, without the prior written consent of Merrill Lynch.

   (k)  For a period of three years after the Closing Date the Guarantor will
furnish to the Underwriters copies of all reports and communications delivered
to the Guarantor's stockholders or to holders of the Securities as a class and
will also furnish copies of all reports (excluding exhibits) filed with the
Commission on Form 8-K, 10-Q and 10-K, and all other reports and information
furnished to its stockholders generally, at the time such reports are furnished
to stockholders generally.  For such period of time, the Guarantor will file
with the Commission such documents required to be filed with the Commission
pursuant to Sections 13(a) and 15(d) of the 1934 Act, whether or not the
Guarantor or Publishing has a class of securities registered under the 1934
Act.

   (l)  The Company will use reasonable efforts to effect the listing of the
Securities on the New York Stock Exchange on the date of the Price
Determination Agreement.

   SECTION 4.  Payment of Expenses.  Publishing will pay all expenses incident
to the performance of its obligations under this Agreement, including (i) the
printing and filing of the Registration Statement as originally filed, and of
each amendment thereto, (ii) the printing of this Agreement, the Price
Determination Agreement, the Indenture and any Legal Investment Survey, (iii)
the preparation, issuance and delivery of the certificates for the Securities
to the Underwriters, (iv) the fees and disbursements of Publishing's and the
Guarantor's counsel and accountants, (v) the qualification of the Securities
under securities laws in accordance with the provisions of Section 3(f),
including filing fees and the fee and the disbursements of counsel for the
Underwriters in connection therewith and in connection with the preparation of
the Blue Sky





<PAGE>   19
                                                                          - 19 -


Survey, (vi) the printing and delivery to the Underwriters of copies of the
Registration Statement as originally filed and of each amendment thereto, of
the preliminary prospectus, and of the Prospectus and any amendments or
supplements thereto, (vii) the printing and delivery to the Underwriters of
copies of the Blue Sky Survey, (viii) the filing fee of the National
Association of Securities Dealers, Inc., (ix) the fees and expenses of the
Trustee, including the fees and disbursements of counsel for the Trustee, in
connection with the Indenture and the Securities, and (x) any fees charged by
investment-rating agencies for the rating of the Securities.

   If this Agreement is terminated by the Underwriters in accordance with the
provisions of Section 5, Section 9(a) or Section 11, Publishing shall reimburse
the Underwriters for all of their out-of-pocket expenses, including the
reasonable fees and disbursements of counsel for the Underwriters.

   SECTION 5.  Conditions of the Underwriters' Obligations.  The obligations of
the Underwriters hereunder are subject to the accuracy of the representations
and warranties of Publishing and the Guarantor herein contained, to the
performance by Publishing and the Guarantor of their obligations hereunder, and
to the following further conditions:

   (a)  The Registration Statement shall have become effective not later than
9:30 a.m. on the date hereof, or, with the consent of the Underwriters, at a
later time and date, not later, however, than 9:30 a.m. on the first business
day following the date hereof or at such later time and date as may be approved
by the Underwriters; and at the Closing Date no stop order suspending the
effectiveness of the Registration Statement shall have been issued under the
1933 Act or proceedings therefor initiated or threatened by the Commission.  If
Publishing has elected to rely upon Rule 430A of the 1933 Act Regulations, the
price of the Securities and any price-related information previously omitted
from the effective Registration Statement pursuant to such Rule 430A shall have
been transmitted to the Commission for filing pursuant to Rule 424(b) of the
1933 Act Regulations within the prescribed time period, and prior to the
Closing Date Publishing shall have provided evidence satisfactory to the
Underwriters of such timely filing, or a post-effective amendment providing
such information shall have been promptly filed and declared effective in
accordance with the requirements of Rule 430A of the 1933 Act Regulations.





<PAGE>   20
                                                                          - 20 -



   (b)    At the Closing Date, there shall not have been, since the date hereof
or since the respective dates as of which information is given in the
Prospectus, any material adverse change in the condition, financial or
otherwise, or in the earnings, business affairs or business prospects of
Publishing and the Guarantor and their subsidiaries considered as one
enterprise, whether or not arising in the ordinary course of business, and the
Underwriters shall have received a certificate of the Chairman and Chief
Executive Officer of each of Publishing and the Guarantor and of the Vice
President of each of Publishing and the Guarantor, dated as of Closing Date, to
the effect that (i) there has been no such material adverse change, (ii) the
representations and warranties in Section 1(a) are true and correct with the
same force and effect as though expressly made at and as of the Closing Date,
(iii) Publishing and the Guarantor have complied with all agreements and
satisfied all conditions on their part to be performed or satisfied at or prior
to the Closing Date, and (iv) no stop order suspending the effectiveness of the
Registration Statement has been issued and no proceedings for that purpose have
been initiated or threatened by the Commission.  As used in this Section 5, the
term "Prospectus" means the Prospectus in the form first used to confirm sales
of Securities.

   (c)   You shall have received on the Closing Date an opinion of Kirkpatrick
& Lockhart LLP, counsel for Publishing and the Guarantor, dated the Closing
Date and addressed to you, to the effect that:

   (i)  Publishing, the Guarantor and each of the United States Subsidiaries
  (the "U.S. Subsidiaries") is a corporation duly incorporated and validly
  existing in good standing under the laws of the jurisdiction of its
  organization, with corporate power and authority to own, lease and operate
  its properties and conduct its business as described in the Registration
  Statement and the Prospectus (and any amendment or supplement thereto), and
  is duly qualified as a foreign corporation for the transaction of business in
  and is in good standing under the laws of each jurisdiction where the nature
  of its properties or the conduct of its business requires such qualification,
  except where the failure so to qualify would not have a material adverse
  effect on the condition (financial or otherwise), business, properties, net
  worth or results of operations of





<PAGE>   21
                                                                          - 21 -


  Publishing, the Guarantor and their subsidiaries, considered as one
  enterprise.

   (ii)  All the outstanding shares of capital stock of each of the U.S.
  Subsidiaries have been duly authorized and validly issued, are fully paid and
  nonassessable, and are owned of record by Publishing directly, or indirectly
  through one of the other U.S. Subsidiaries, and are not subject to any
  perfected security interest, or, to the best knowledge of such counsel after
  reasonable inquiry, any adverse claims within the meaning of the Uniform
  Commercial Code, except, to the extent set forth or described in the
  Registration Statement and the Prospectus, currently existing liens, claims
  and security interests of creditors and liens, claims and security interests
  pursuant to the terms of the FDTH Credit Facility, the Publishing Credit
  Facility and the contemplated New Bank Credit Facility (as defined).

   (iii)  The Registration Statement and all post-effective amendments, if any,
  have become effective under the 1933 Act, the Indenture has been duly
  qualified under the 1939 Act and, to the best knowledge of such counsel after
  reasonable inquiry, no stop order suspending the effectiveness of the
  Registration Statement has been issued and no proceedings for that purpose
  are pending before or contemplated by the Commission; and any required filing
  of the Prospectus pursuant to Rule 424(b) has been made in accordance with
  Rule 424(b).

   (iv)  Publishing and the Guarantor have corporate power and authority to
  enter into this Agreement and to issue, sell and deliver the Securities to
  the Underwriter as provided herein, and this Agreement has been duly
  authorized, executed and delivered by Publishing and the Guarantor.

   (v)  Neither Publishing, the Guarantor nor any of the U.S. Subsidiaries is
  in violation of its certificate or articles of incorporation or its
  respective by-laws or, to the best knowledge of such counsel after reasonable
  inquiry, is in default in the performance of any material obligation,
  agreement or condition contained in any bond, debenture, note or other
  evidence of indebtedness to which the Guarantor, Publishing or any U.S.
  Subsidiary is a party that


<PAGE>   22
                                                                          - 22 -


  is included as an exhibit to, or otherwise described or summarized in, the
  Registration Statement, except as may be disclosed in the Prospectus and
  except for defaults under existing indebtedness of Publishing, the Guarantor
  or any U.S. Subsidiary as to which consents or waivers have been obtained
  prior to the Pricing Time.

   (vi)  Neither the offer, sale or delivery of the Securities, the execution,
  delivery or performance of this Agreement or the Indenture, compliance by
  Publishing or the Guarantor with the provisions of this Agreement or the
  Indenture, nor consummation by Publishing or the Guarantor of the sale of the
  Securities contemplated hereby violates the certificate or articles of
  incorporation or by-laws, or other organizational documents, of Publishing or
  the Guarantor or any of the U.S. Subsidiaries or constitutes a breach of or
  default under any agreement, indenture, lease or other instrument to which
  Publishing, the Guarantor or any of the U.S. Subsidiaries is a party or by
  which any of them or any of their respective properties is bound (except for
  defaults under existing indebtedness of Publishing, the Guarantor or any U.S.
  subsidiary as to which consents or waivers have been obtained prior to the
  Pricing Time) and that is an exhibit to the Registration Statement, or is
  material and is known to such counsel after reasonable inquiry, or will
  result in the creation or imposition of any lien, charge or encumbrance upon
  any property or assets of Publishing, the Guarantor or any of the U.S.
  Subsidiaries, nor will any such action violate any existing law, regulation,
  ruling (assuming compliance with all applicable state securities and Blue Sky
  laws), judgment, injunction, order or decree known to such counsel after
  reasonable inquiry, that names Publishing, the Guarantor or any of the U.S.
  Subsidiaries and is specifically directed to any of them or any of their
  respective properties.

   (vii)  No consent, approval, authorization or other order of, or
  registration or filing with, any court, regulatory body, administrative
  agency or other governmental body, agency, or official is required on the
  part of Publishing or the Guarantor (except as have been obtained under the
  1933 Act, the Exchange Act, and the 1939 Act or such as may be required under
  state securities or Blue Sky laws governing the purchase and distribution of
  the Securities) for the valid issuance and sale of the Securities by
  Publishing to





<PAGE>   23
                                                                          - 23 -


  the Underwriters or the consummation by Publishing and the Guarantor of the
  other transactions set forth in this Agreement.

   (viii)  The Registration Statement and the Prospectus and any supplements or
  amendments thereto (except for the financial statements and the notes thereto
  and the schedules and other financial and statistical data included therein,
  as to which such counsel need not express any opinion) comply as to form in
  all material respects with the requirements of the 1933 Act.

   (ix)  Assuming that (A) Publishing and the Guarantor have all requisite
  corporate power and authority to execute, deliver and perform its obligations
  under the Securities and the Indenture, (B) the Securities have been duly
  authorized, executed and delivered by Publishing and the Guarantor, (C) the
  Indenture has been duly authorized, executed and delivered by Publishing and
  the Guarantor and the Trustees and (D) the Securities have been duly
  authenticated by one of the Trustees pursuant to the Indenture (which fact
  such counsel need not determine by an inspection of the Securities), the
  Securities and the Indenture each constitute valid and binding obligations of
  Publishing and the Guarantor, enforceable against Publishing and the
  Guarantor in accordance with their respective terms, in each case subject to
  applicable bankruptcy, insolvency, reorganization, moratorium, fraudulent
  conveyance or other similar laws affecting creditors' rights generally from
  time to time in effect; and the holders of the Securities are entitled to the
  benefits of the Indenture.  The enforceability of the obligations of
  Publishing and the Guarantor is also subject to general principles of equity
  (regardless of whether such enforceability is considered in a proceeding in
  equity or at law).

   (x)  To the best knowledge of such counsel after reasonable inquiry, (A)
  other than as described or contemplated in the Prospectus (or any supplement
  thereto), there are no legal or governmental proceedings pending or
  threatened against Publishing, the Guarantor or any of the U.S. Subsidiaries,
  or to which Publishing, the Guarantor or any of the U.S. Subsidiaries, or any
  of their property, is subject, which are required to be described in the
  Registration Statement or Prospectus (or any amendment or


<PAGE>   24
                                                                          - 24 -


  supplement thereto), and (B) there are no material agreements, contracts,
  indentures, leases or other instruments to which the Guarantor, Publishing or
  any U.S. Subsidiary is a party, that are required to be described in the
  Registration Statement or the Prospectus (or any amendment or supplement
  thereto) or to be filed as an exhibit to the Registration Statement that are
  not described or filed as required, as the case may be.

   (xi)  The statements in the Registration Statement and Prospectus, insofar
  as they are descriptions or summaries of contracts, agreements or other legal
  documents to which Publishing, the Guarantor or any U.S. Subsidiary is a
  party, or are statements of law or legal conclusions (other than matters of
  English, Canadian, Australian or Israeli law), are accurate in all material
  respects and present fairly the information required to be shown.

   (xii)  Except as described in the Prospectus, there is no holder of any
  security of Publishing or the Guarantor or, to the best knowledge of such
  counsel after reasonable inquiry, any other person who has the right,
  contractual or otherwise, to cause Publishing or the Guarantor to sell or
  otherwise issue to them, or to permit them to underwrite the sale of, the
  Securities or the right to have any securities of Publishing or the Guarantor
  included in the Registration Statement or the right, as a result of the
  filing of the Registration Statement, to require registration under the 1933
  Act of any securities of Publishing or the Guarantor.

   (xiii) At the Closing Date, Southam Inc. and Hollinger Eastern Publishing
  Inc. qualify as Subsidiaries of Publishing as defined in the Senior
  Indenture.

   (xiv)  Although counsel cannot opine as to factual matters, and the
  character of determinations involved in the registration process in such that
  counsel cannot pass upon and assume any responsibility for the accuracy or
  completeness of the information contained in the Registration Statement and
  the Prospectus, counsel shall advise the Underwriters that on the basis of
  its review of the Registration Statement and the Prospectus and its
  participation in the preparation thereof (relying as to materiality to a
  large extent upon the statements of officers and other representatives of the
  Company) that





<PAGE>   25
                                                                          - 25 -


  counsel has no reason to believe that (A) the Registration Statement (except
  for the financial statements and notes thereto and the schedules and other
  financial or statistical data included therein or omitted therefrom, as to
  which counsel need express no opinion), at the time the Registration
  Statement became effective, contained an untrue statement of a material fact
  or omitted to state any material fact required  to be stated therein or
  necessary to make the statements therein not misleading or (B) the Prospectus
  (except for the financial statements and notes thereto and the schedules and
  other financial or statistical data included therein or omitted therefrom, as
  to which counsel need express no opinion) at the time the Prospectus was
  issued, includes an untrue statement of a material fact or omitted state any
  material fact necessary in order to make the statements therein, in the light
  of the circumstances under which they were made, not misleading; also, that
  counsel has no reason to believe, based upon the procedures described above,
  that either the Registration Statement or the Prospectus (except for the
  financial statements and notes thereto and the schedules and other financial
  or statistical data included therein or omitted therefrom, as to which
  counsel need express no opinion) as of the date and time of delivery of
  counsel's opinion contain an untrue statement of a material fact or omit to
  state a material fact necessary to make the statements therein, in light of
  the circumstances in which they were made, not misleading.

   In rendering their opinion as aforesaid, counsel may rely upon an opinion or
opinions, each dated the Closing Date, of other counsel retained by them,
Publishing or the Guarantor as to laws of any jurisdiction other than the
United States, the Commonwealth of Pennsylvania or the Delaware General
Corporation Law, provided that (1) each such local counsel is acceptable to the
Underwriters, (2) such reliance is expressly authorized by each opinion so
relied upon and a copy of each such opinion is delivered to the Underwriters
and is, in form and substance, satisfactory to the Underwriters and their
counsel, and (3) counsel shall state in their opinion that they believe that
they and the Underwriters are justified in relying thereon.  Counsel may also
rely, to the extent they deem such reliance proper, as to matters of fact upon
certificates of officers of Publishing or the Guarantor and of government
officials.  Copies of all such certificates shall be furnished to counsel to
the





<PAGE>   26
                                                                          - 26 -


Underwriters on the Closing Date.  Such opinion may state that it is limited to
the laws of the Commonwealth of Pennsylvania (excluding the conflict of laws
rules), the Delaware Business Corporation Law and the Federal securities laws
of the United States, and that such counsel expresses no opinion as to any
other laws (except with respect to the Indenture, as to which such counsel will
express certain opinions under New York law) and further that such opinions are
being given as if the Purchase Agreement was governed by Pennsylvania law.

   (d)  You shall have received on the Closing Date an opinion of Clifford
Chance, special English counsel for the





<PAGE>   27
                                                                          - 27 -


Guarantor, dated the Closing Date and addressed to you, to the effect that:

     (i)  Each of DT Holdings Limited ("DTH"), First DT Holdings Limited
  ("FDTH") and Telegraph, is a company duly incorporated and validly existing
  under the laws of England, with corporate power and authority to own or lease
  its properties and to conduct its business as described in the Prospectus.

     (ii)  All the issued shares in the capital of DTH, FDTH and Telegraph have
  been duly authorized and validly issued credited as fully paid.

     (iii)  Neither the offer, sale or delivery of the Common Stock, the
  execution, delivery or performance of the Purchase Agreement, compliance by
  the Company with the provisions of the Purchase Agreement nor consummation by
  the Company of the transactions contemplated by the Purchase Agreement (i)
  violates the memorandum or articles of association of DTH, FDTH or Telegraph
  or (ii) constitutes a breach of or default by FDTH, DTH or Telegraph under
  any Scheduled Agreement (iii) nor does any such action violate any existing
  English law, regulation, judgment, injunction, order or decree known to such
  counsel that names DTH, FDTH or Telegraph or is specifically directed to DTH,
  FDTH or Telegraph or their properties in England and, in the case of this
  sub-paragraph (iii), would have a material adverse effect on the condition
  (financial or other) or business, properties, net worth or results of
  operations of the Company and its subsidiaries considered as one enterprise;

     (iv)  Argsub Limited is a company duly incorporated and validly existing
  under the laws of England, with corporate power and authority to own or lease
  its properties and to conduct its business as described in the Prospectus;
  all the preference shares in the capital of Argsub Limited of the series
  issued to DTH in exchange for the FDTH Preference Shares previously held by
  DTH have been duly authorized and validly issued credited as fully paid.

   In rendering their opinion as aforesaid, counsel's opinion shall be limited
to the laws of England; provided that such counsel may rely upon an opinion or
opinions, each dated the Closing Date, of other counsel retained by them or the
Company as


<PAGE>   28
                                                                          - 28 -


to laws of any jurisdiction other than England, provided that (1) each such
local counsel is acceptable to the Underwriters, (2) such reliance is expressly
authorized by each opinion so relied upon and a copy of each such opinion is
delivered to the Underwriters and is, in form and substance satisfactory to the
Underwriters and their counsel, and (3) counsel shall state in their opinion
that they believe that they and the Underwriters are justified in relying
thereon.

   (e)  You shall have received on the Closing Date an opinion of Tory Tory
DesLaurier & Binnington, special Canadian counsel for the Publishing, dated the
Closing Date and addressed to you, to the effect that:

     (i)  Southam Inc. is a corporation duly incorporated and validly existing
  under the laws of Canada, with corporate power and authority to own or lease
  its properties and to conduct its business as described in the Registration
  Statement and the Prospectus.

     (ii)  Neither the offer, sale or delivery of the Securities, the
  execution, delivery or performance of this Agreement, compliance by
  Publishing or the Guarantor with the provisions of this Agreement or the
  Indenture, nor consummation by Publishing or the Guarantor of the
  transactions contemplated hereby (i) violates the memorandum or articles of
  association of Southam Inc. or (ii)  violates any existing Canadian law,
  regulation, ruling, judgment, injunction, order or decree known to such
  counsel that names Southam Inc. or its properties in Canada and would, in the
  case of this clause (ii), have a material adverse effect on the condition
  (financial or other), business, properties, net worth or results of
  operations of Publishing, the Guarantor and their subsidiaries considered as
  one enterprise.

   In rendering their opinion as aforesaid, counsel's opinion shall be limited
to the laws of Canada; provided that such counsel may rely upon an opinion or
opinions, each dated the Closing Date, of other counsel retained by them or
Publishing as to laws of any jurisdiction other than Canada, provided that (1)
each such local counsel is acceptable to the Underwriters, (2) such reliance is
expressly authorized by each opinion so relied upon and a copy of each such
opinion is delivered to the Underwriters and is, in form and substance
satisfactory to the


<PAGE>   29
                                                                          - 29 -


Underwriters and their counsel, and (3) counsel shall state in their opinion
that they believe that they and the Underwriters are justified in relying
thereon.

   (f)  You shall have received letters addressed to you dated the date hereof
and the Closing Date from KPMG Peat Marwick, independent certified public
accountants for Publishing and the Guarantor, substantially in the forms
heretofore approved by you.

   (g)  You shall have received on the Closing Date an opinion of Cravath,
Swaine & Moore, counsel for the Underwriters, dated the Closing Date and
addressed to you, the Underwriters, as to such matters as you may reasonably
request.

   (h)  At the Closing Date and at each Date of Delivery, if any, counsel for
the Underwriters shall have been furnished with such documents and opinions as
they may require for the purpose of enabling them to pass upon the issuance and
sale of the Securities as herein contemplated and related actions referred to
in subparagraphs (h), (i) and (k) hereof, or in order to evidence the accuracy
of any of the representations or warranties, or the fulfillment of any of the
conditions, herein contained; and all proceedings taken by Publishing and the
Guarantor in connection with the issuance and sale of the Securities as herein
contemplated shall be satisfactory in form and substance to the Underwriters
and counsel for the Underwriters.

   (i)  At the Closing Date, Southam Inc. and Hollinger Eastern Publishing Inc.
shall qualify as Subsidiaries of Publishing pursuant to the terms of the Senior
Indenture.

   (j)  At the Closing Date, Publishing shall have issued a notice of
redemption with respect to each of the DTH and FDTH Preference Shares held by
third parties.

   (k)  At the Closing Date, Publishing shall deposit in escrow an amount
sufficient to pay the aggregate redemption price of the DTH and FDTH Preference
Shares held by third parties.

   SECTION 6.  Indemnification.  (a)  Publishing and the Guarantor agree,
jointly and severally, to indemnify and hold harmless the Underwriters and each
person, if any, who controls





<PAGE>   30
                                                                          - 30 -


the Underwriters within the meaning of Section 15 of the 1933 Act to the extent
and in the manner set forth in clauses (i), (ii) and (iii) below:

   (i) against any and all loss, liability, claim, damage and expense
  whatsoever, as incurred, arising out of any untrue statement or alleged
  untrue statement of a material fact contained in the Registration Statement
  (or any amendment thereto), including the information deemed to be part of
  the Registration Statement pursuant to Rule 430A of the 1933 Act Regulations,
  if applicable, and any information contained in a Rule 462(b) Registration
  Statement or any amendments thereto, or the omission or alleged omission
  therefrom of a material fact necessary to make the statements therein, in
  light of the circumstances under which they were made, not misleading or
  arising out of any untrue statement or alleged untrue statement of a material
  fact contained in any preliminary prospectus or the Prospectus (or any
  amendment or supplement thereto) or the omission or alleged omission
  therefrom of a material fact necessary in order to make the statements
  therein, in the light of the circumstances under which they were made, not
  misleading;

   (ii) against any and all loss, liability, claim, damage and expense
  whatsoever, as incurred, to the extent of the aggregate amount paid in
  settlement of any litigation, or any investigation or proceeding by any
  governmental agency or body, commenced or threatened, or of any claim
  whatsoever based upon any such untrue statement or omission, or any such
  alleged untrue statement or omission, if such settlement is effected with the
  written consent of Publishing and the Guarantor; and

   (iii) against any and all expense whatsoever, as incurred (including,
  subject to Section 6(c) hereof, the fees and disbursements of counsel chosen
  by the Underwriters, reasonably incurred in investigating, preparing or
  defending against any litigation, or any investigation or proceeding by any
  governmental agency or body, commenced or threatened, or any claim whatsoever
  based upon any such untrue statement or omission, or any such alleged untrue
  statement or omission, to the extent that any such expense is not paid under
  (i) and (ii) above;





<PAGE>   31
                                                                          - 31 -


provided, however, that this indemnity agreement shall not apply to any loss,
liability, claim, damage or expense to the extent arising out of any untrue
statement or omission or alleged untrue statement or omission made in reliance
upon and in conformity with written information furnished to Publishing or the
Guarantor by the Underwriters expressly for use in the Registration Statement
(or any amendment thereto) or any preliminary prospectus or the Prospectus (or
any amendment or supplement thereto); and the parties agree that the statements
set forth in the last paragraph on the cover page, the legends on the inside
cover page, and the statements in the second and fourth paragraphs (except for
the first sentence of the fourth paragraph) under the caption "Underwriting" in
the Prospectus constitute the only information so furnished.

   (b)  Publishing and the Guarantor also agree, jointly and severally, to
indemnify and hold harmless the Independent Underwriter and each person, if
any, who controls the Independent underwriter within the meaning of either
Section 15 of the 1993 Act or Section 20 of the 1934 Act, from and against any
and all losses, claims, damages, liabilities and judgements incurred as a
result of the Independent Underwriter's participation as a "qualified
independent underwriter" within the meaning of Schedule E to the By-laws of the
National Association of Securities Dealers, Inc. in connection with the
offering of the Securities, except for any losses, claims, damages, liabilities
and judgments resulting from the independent Underwriter or such controlling
person's willful misconduct or gross negligence.

   (c)  Each Underwriter severally agrees to indemnify and hold harmless
Publishing and the Guarantor, their directors, each of their officers who
signed the Registration Statement, and each person, if any, who controls
Publishing or the Guarantor within the meaning of Section 15 of the 1933 Act
against any and all loss, liability, claim, damage and expense described in the
indemnity contained in subsection (a) of this Section, as incurred, but only
with respect to untrue statements or omissions, or alleged untrue statements or
omissions made in the Registration Statement (or amendment thereto) or any
preliminary prospectus or the Prospectus (or any amendment or supplement
thereto) in reliance upon and in conformity with written information furnished
to Publishing or the Guarantor by the Underwriters expressly for use in the
Registration Statement (or any amendment thereto) or such preliminary
prospectus or the Prospectus (or any amendment or supplement thereto) and set
forth





<PAGE>   32
                                                                          - 32 -


in the last paragraph on the cover page, the stabilization legends on the
inside cover page, and the statements in the second and fourth paragraph
(except for the first sentence of the fourth paragraph) under the caption
"Underwriting" in the Prospectus.

   (d)  Each indemnified party shall give notice as promptly as reasonably
practicable to each indemnifying party of any action commenced against it in
respect of which indemnity may be sought hereunder, but failure to so notify an
indemnifying party shall not relieve such indemnifying party from any liability
which it may have otherwise than on account of this indemnity agreement.  An
indemnifying party may participate at its own expense in the defense of any
such action.  In no event shall the indemnifying parties be liable for fees and
expenses of more than one counsel (in addition to any local counsel) separate
from their own counsel for all indemnified parties in connection with any one
action or separate but similar or related actions in the same jurisdiction
arising out of the same general allegations or circumstances; provided, that,
if indemnity is sought pursuant to Section 6(b), then, in addition to such
counsel for the indemnified parties, the indemnifying party shall be liable for
the reasonable fees and expenses of not more than one separate counsel (in
addition to any necessary local counsel) for the Independent underwriter in its
capacity as a "qualified independent underwriter" and all persons, if any, who
control the Independent Underwriter within the meaning of Section 15 of the
1993 Act or Section 20 of the 1934 Act if, in the reasonable judgment of the
Independent Underwriter there may exist a conflict of interest between the
Independent Underwriter and the other indemnified parties.  In the case of any
such separate counsel for the Independent Underwriter and such control person
of the Independent Underwriter, such counsel shall be designated in writing by
the Independent Underwriter.

   SECTION 7.  Contribution.  In order to provide for just and equitable
contribution in circumstances in which an indemnity agreement provided for in
Section 6 is for any reason held to be unenforceable by the indemnified parties
although applicable in accordance with its terms, Publishing and the Guarantor
on the one hand and the Underwriters on the other hand shall contribute to the
aggregate losses, liabilities, claims, damages and expenses of the nature
contemplated by such indemnity incurred by Publishing and the Guarantor on the
one hand and the Underwriters on the other hand, as incurred, in such
proportions that (a) the





<PAGE>   33
                                                                          - 33 -


Underwriters are responsible for that portion represented by the percentage
that the underwriting commission appearing on the cover page of the Prospectus
bears to the aggregate stated principal amount appearing thereon, and (b)
Publishing and the Guarantor are responsible for the balance; provided,
however, that no person guilty of fraudulent misrepresentation (within the
meaning of Section 11(f) of the 1933 Act) shall be entitled to contribution
from any person who was not guilty of such fraudulent misrepresentation.  For
purposes of this Section, each person, if any, who controls the Underwriters
within the meaning of Section 15 of the 1933 Act shall have the same rights to
contribution as the Underwriters, and each director of each of Publishing and
the Guarantor, each officer of Publishing or the Guarantor who signed the
Registration Statement, and each person, if any, who controls Publishing or the
Guarantor within the meaning of Section 15 of the 1933 Act shall have the same
rights to contribution as Publishing or the Guarantor.

   Publishing, the Guarantor and the Underwriters agree that Merrill Lynch,
Pierce, Fenner 7 Smith Incorporated will not receive any additional benefits
hereunder for serving as the Independent Underwriter in connection with the
offering and sale of Securities.

   SECTION 8.  Representations, Warranties and Agreements to Survive Delivery.
All representations, warranties and agreements contained in this Agreement and
the Price Determination Agreement, or contained in certificates of officers of
Publishing or the Guarantor submitted pursuant hereto, shall remain operative
and in full force and effect, regardless of any investigation made by or on
behalf of any Underwriters or controlling person, or by or on behalf of
Publishing or the Guarantor, and shall survive delivery of the Securities to
the Underwriters.

   SECTION 9.  Termination of Agreement.  (a)  The Underwriters may terminate
this Agreement by notice to Publishing or the Guarantor at any time at or prior
to the Closing Date (i) if there has been, since the date of this Agreement or
since the respective date as of which information is given in the Prospectus,
any material adverse change in the condition, financial or otherwise, or in the
earnings, business affairs or business prospects of Publishing, the Guarantor
and their subsidiaries considered as one enterprise, whether or not arising in
the ordinary course of business, or (ii) if there has occurred





<PAGE>   34
                                                                          - 34 -


any outbreak of hostilities or escalation thereof or other calamity or crisis,
the effect of which on the financial markets of the United States is such as to
make it, in the judgment of the Underwriters, impracticable to market the
Securities or to enforce contracts for the sale of the Securities, or (iii) if
trading in the Common Stock of the Guarantor has been suspended by the
Commission, or if trading generally on either the American Stock Exchange or
the New York Stock Exchange has been suspended, or minimum or maximum prices
for trading have been fixed, or maximum ranges for prices for securities have
been required, by either of said Exchanges or by order of the Commission or any
other governmental authority, or if a banking moratorium has been declared by
either Federal or New York authorities.  Notice of such termination may be
given by telegram, telecopy or telephone and shall be subsequently confirmed by
letter.  As used in this Section 10(a), the term "Prospectus" means the
Prospectus in the form first used to confirm sales of the Securities.

   (b)  If this Agreement is terminated pursuant to this Section, such
termination shall be without liability of any party to any other party except
as provided in Section 4.  Notwithstanding any such termination, the provisions
of Sections 6 and 7 shall remain in effect.

   SECTION 10.  Default by One or More of the Underwriters.  If one or more of
the Underwriters shall fail at the Closing Date to purchase the Securities that
it or they are obligated to purchase pursuant to this Agreement (the "Defaulted
Securities"), you shall have the right, within 24 hours thereafter, to make
arrangements for one or more of the non-defaulting Underwriters, or any other
underwriters, to purchase all, but not less than all, of the Defaulted
Securities in such amounts as may be agreed upon and upon the terms set forth
in this Agreement; if, however, you have not completed such arrangements within
such 24-hour period, then:

   (a) if the number of Defaulted Securities does not exceed 10% of the
  aggregate principal amount of the Securities, the nondefaulting Underwriters
  shall be obligated to purchase the full amount thereof in the proportions
  that their respective Securities underwriting obligation proportions bear to
  the underwriting obligation proportions of all non-defaulting Underwriters,
  or





<PAGE>   35
                                                                          - 35 -


   (b) if the number of Defaulted Securities exceeds 10% of the aggregate
  principal amount of the Securities, this Agreement shall terminate without
  liability on the part of any nondefaulting Underwriters.

   No action taken pursuant to this Section 10 shall relieve any defaulting
Underwriter from liability in respect of its default.

   In the event of any such default that does not result in a termination of
this Agreement, either you or the Company shall have the right to postpone the
Closing Date for a period not exceeding seven days in order to effect any
required changes in the Registration Statement or Prospectus or in any other
documents or arrangements.  As used herein, the term "Underwriters" includes
any person substituted for an Underwriter under this Section 10.

   SECTION 11.  Default by Publishing.  If Publishing shall fail at the Closing
Date or at the Date of Delivery to sell and deliver the number of Securities
which it is obligated to sell hereunder, then this Agreement shall terminate
without any liability on the part of any non- defaulting party.

   No action taken pursuant to this Section shall relieve Publishing from
liability, if any, in respect of such default.

   SECTION 12.  Notices.  Unless otherwise specifically indicated herein, all
notices and other communications hereunder shall be in writing and shall be
deemed to have been duly given if mailed or transmitted by any standard form of
telecommunication.  Notices to the Underwriters shall be directed to Merrill
Lynch at Merrill Lynch World Headquarters, North Tower, World Financial Center,
New York, New York 10281, attention of Syndicate Operations; notices to
Publishing shall be directed to it at 401 North Wabash Avenue, Chicago,
Illinois 60611, attention of President or Secretary; and notices to the
Guarantor shall be directed to it at 401 North Wabash Avenue, Chicago, Illinois
60611, attention of President or Secretary.

   SECTION 13.  Parties.  This Agreement and the Price Determination Agreement
shall each inure to the benefit of and be binding upon the Underwriters and
Publishing and the Guarantor and their respective successors, heirs and legal
representatives.  Nothing expressed or mentioned in this Agreement or the Price





<PAGE>   36
                                                                          - 36 -


Determination Agreement is intended or shall be construed to give any person,
firm or corporation, other than the Underwriters and Publishing and the
Guarantor and their respective successors, heirs and legal representatives, and
the controlling persons and officers and directors referred to in Sections 6
and 7 hereof and their heirs and legal representatives, any legal or equitable
right, remedy or claim under or in respect of this Agreement or the Price
Determination Agreement or any provision herein or therein contained.  This
Agreement and the Price Determination Agreement and all conditions and
provisions hereof and thereof are intended to be for the sole and exclusive
benefit of the Underwriters, Publishing and the Guarantor and their respective
successors, heirs and legal representatives and said controlling persons and
officers and directors and their heirs and legal representatives, and for the
benefit of no other person, firm or corporation.  No purchaser of Securities
from the Underwriters shall be deemed to be a successor by reason merely of
such purchase.

   SECTION 14.  Governing Law and Time.  This Agreement and the Price
Determination Agreement shall be governed by and construed in accordance with
the laws of the State of New York applicable to agreements made and to be
performed in said State.  Specified times of day refer to New York City time.

   If the foregoing is in accordance with your understanding of our agreement,
please sign and return to Publishing and the Guarantor a counterpart hereof,
whereupon





<PAGE>   37
                                                                          - 37 -


this instrument, along with all counterparts, will become a binding agreement
among the Underwriters, Publishing and the Guarantor in accordance with its
terms.


                                    Very truly yours,

                                    HOLLINGER INTERNATIONAL PUBLISHING INC.

                                    by
                                       _____________________________
                                       Kenneth L. Serota
                                       Vice President and
                                       Secretary


                                    HOLLINGER INTERNATIONAL INC.

                                    by
                                       ____________________________
                                       Kenneth L. Serota
                                       Vice President and
                                       Secretary


<PAGE>   38
                                                                          - 38 -


Confirmed and accepted as of
  the date first above written:


MERRILL LYNCH & CO.
  Merrill Lynch, Pierce,
  Fenner & Smith Incorporated

CIBC WOOD GUNDY SECURITIES INC.

SCOTIA CAPITAL MARKETS (USA) INC.

TD SECURITIES (USA) INC.

By:  MERRILL LYNCH & CO.
       Merrill Lynch, Pierce,
       Fenner & Smith Incorporated


     by __________________________


<PAGE>   39
                                                                       Exhibit A
                            HOLLINGER INTERNATIONAL
                                PUBLISHING INC.
                            (a Delaware corporation)


                          HOLLINGER INTERNATIONAL INC.
                            (a Delaware corporation)



                                  $260,000,000

                          8-5/8% Senior Notes due 2005

                         PRICE DETERMINATION AGREEMENT





                                                                  March 12, 1997




MERRILL LYNCH & CO.
  Merrill Lynch, Pierce, Fenner & Smith Incorporated
CIBC WOOD GUNDY SECURITIES CORP.
SCOTIA CAPITAL MARKETS (USA) INC.
TD SECURITIES (USA) INC.
c/o MERRILL LYNCH & CO.
Merrill Lynch, Pierce, Fenner & Smith
  Incorporated
Merrill Lynch World Headquarters
North Tower
World Financial Center
New York, New York 10281-1201

Ladies and Gentlemen:

   Reference is made to the Purchase Agreement dated March 12, 1997 (the
"Purchase Agreement") among Hollinger International Publishing Inc., a Delaware
corporation ("Publishing"), Hollinger International Inc. (the





<PAGE>   40
                                                                           - 2 -


"Guarantor") and Merrill Lynch, Pierce, Fenner & Smith Incorporated, CIBC Wood
Gundy Securities Corp., Scotia Capital Markets (USA) Inc. and, and TD
Securities (USA) Inc. (the "Underwriters").  The Purchase Agreement provides
for the purchase by the Underwriters from Publishing, subject to the terms and
conditions set forth therein, of $260,000,000 aggregate principal amount of
Publishing's 8-5/8% Senior Notes due 2005 (the "Securities").  This Agreement
is the Price Determination Agreement referred to in the Purchase Agreement.

   Pursuant to Section 2 of the Purchase Agreement, the undersigned agrees with
the Underwriters as follows:

     1.  The initial public offering price of the Securities shall be 99.5% of
   the aggregate stated principal amount thereof, plus accrued interest from
   March 18, 1997 to the Closing Time.

     2.  The purchase price of the Securities to be paid by the several
   Underwriters shall be 97.25% of the aggregate stated principal amount
   thereof, plus accrued interest from March 18, 1997 to the Closing Time.

     3.  The interest rate to be borne by the Securities shall be 8-5/8% per
   annum.

     4.  The Securities will mature on March 15, 2005.

   Publishing and the Guarantor represent and warrant to each of the
Underwriters that the representations and warranties of Publishing and the
Guarantor set forth in Section 1(a) of the Purchase Agreement are accurate as
though expressly made at and as of the date hereof.

   THIS AGREEMENT SHALL BE GOVERNED BY THE LAWS OF THE STATE OF NEW YORK.

   If the foregoing is in accordance with your understanding of our agreement,
please sign and return to Publishing and the Guarantor a counterpart hereof,
whereupon this instrument along with all counterparts and together with the
Purchase Agreement shall be a binding agreement


<PAGE>   41
                                                                           - 3 -


among the Underwriters and Publishing and the Guarantor in accordance with its
terms and the terms of the Purchase Agreement.

Very truly yours,


HOLLINGER INTERNATIONAL PUBLISHING INC.


By____________________________
  Kenneth L. Serota
  Vice President and
  Secretary


HOLLINGER INTERNATIONAL INC.


By____________________________
  Kenneth L. Serota
  Vice President and
  Secretary


<PAGE>   42
                                                                           - 4 -


Confirmed and accepted as of
  the date first above written:


MERRILL LYNCH & CO.
  Merrill Lynch, Pierce, Fenner & Smith
              Incorporated

CIBC WOOD GUNDY SECURITIES CORP.

SCOTIA CAPITAL MARKETS (USA) INC.

TD SECURITIES (USA) INC.

By:  MERRILL LYNCH & CO.
       Merrill Lynch, Pierce, Fenner & Smith
                   Incorporated


     By____________________________


<PAGE>   43
                                   SCHEDULE I


<TABLE>
<CAPTION>
                                                              Principal Amount
                                                               of Securities
                     Underwriters                              to Be Purchased
                     ------------                              ---------------
 <S>                                                            <C>
 Merrill Lynch, Pierce, Fenner & Smith                          $104,000,000
      Incorporated  . . . . . . . . . . . . . . . . . . . . 

 CIBC Wood Gundy Securities Corp . . . . . . . . . . . . . .     104,000,000

 Scotia Capital Markets (USA) Inc. . . . . . . . . . . . . .      39,000,000

 TD Securities
   (USA) Inc.  . . . . . . . . . . . . . . . . . . . . . . .      13,000,000

 Total   . . . . . . . . . . . . . . . . . . . . . . . . . .    $260,000,000
                                                                ============
</TABLE>


<PAGE>   44
                                  SCHEDULE II


            Significant Subsidiaries of Hollinger International Inc.
                  and Hollinger International Publishing Inc.


 1. Hollinger International Publishing Inc. is incorporated in Delaware and is 
    a wholly owned subsidiary of Hollinger International Inc.

 2. The Sun-Times Company is incorporated in Delaware and is a wholly owned
    subsidiary of Hollinger International Publishing Inc.

 3. Chicago Sun-Times, Inc. is incorporated in Delaware and is a wholly owned
    subsidiary of The Sun-Times Company.

 4. American Publishing Company is incorporated in Delaware and is a wholly
    owned subsidiary of Hollinger International Publishing Inc.

 5. American Publishing (1991) Inc. is incorporated in Delaware and is a
    subsidiary of American Publishing Company.

 6. American Publishing Holdings Inc. is incorporated in Delaware and is a
    wholly owned subsidiary of American Publishing Company.

 7. APAC-95 Inc. is incorporated in Delaware and is a wholly owned subsidiary of
    American Publishing Company.

 8. TelHoldco Inc. is incorporated in Delaware and is a wholly owned subsidiary
    of Hollinger International Publishing Inc.

 9. DT Holdings Limited is an English company and is a wholly owned subsidiary
    (excluding preference shares) of Hollinger International Publishing Inc.

10. First DT Holdings Limited is an English company and is a wholly owned
    subsidiary (excluding preference shares) of DT Holdings Limited.


<PAGE>   45
                                                                           - 2 -


11. Telegraph Group Limited plc is an English company and a subsidiary of
    First DT Holdings Limited.

12. Southam Inc.

<PAGE>   1





                                                                    EXHIBIT 1.02

                    HOLLINGER INTERNATIONAL PUBLISHING INC.
                            (a Delaware corporation)

                          HOLLINGER INTERNATIONAL INC.
                            (a Delaware corporation)


                                  $290,000,000
                   9 1/4% Senior Subordinated Notes due 2007



                               PURCHASE AGREEMENT



                                                                  March 12, 1997


MERRILL LYNCH & CO.
   Merrill Lynch, Pierce, Fenner & Smith Incorporated
DONALDSON, LUFKIN & JENRETTE SECURITIES CORPORATION
BEAR, STEARNS & CO. INC.
CIBC WOOD GUNDY SECURITIES CORP.
TD SECURITIES (USA) INC.
c/o Merrill Lynch & Co.
   Merrill Lynch, Pierce, Fenner & Smith Incorporated
Merrill Lynch World Headquarters
North Tower
World Financial Center
New York, New York  10281-1201


Ladies and Gentlemen:

   Hollinger International Publishing Inc., a Delaware corporation
("Publishing"), and Hollinger International Inc., a Delaware corporation (the
"Guarantor"), confirm their agreement with Merrill Lynch, Pierce, Fenner &
Smith Incorporated ("Merrill Lynch"), Donaldson, Lufkin & Jenrette Securities
Corporation ("DLJ"), TD Securities (USA) Inc. ("TD"), Bear, Stearns & Co. Inc.
("Bear Stearns") and CIBC Wood Gundy Securities Corp. ("CIBC") (collectively,
the "Underwriters", which term shall also include any underwriter substituted
as hereinafter provided in Section 10), with respect to the sale by Publishing
and the purchase by the Underwriters, acting severally and not jointly, of
$290,000,000 (all dollar references herein are in U.S. dollars unless otherwise
specifically indicated) aggregate principal amount of Publishing's 9 1/4%
Senior Subordinated Notes due 2007 (the
<PAGE>   2
"Securities").  The Notes will be guaranteed by the Guarantor on a senior
subordinated basis.

   The aforesaid $290,000,000 aggregate principal amount of Securities are to
be issued pursuant to an Indenture to be dated as of March 18, 1997, as
amended, (the "Senior Subordinated Indenture"), among Publishing, the Guarantor
and Fleet National Bank of Connecticut, as trustee (the "Trustee").

   The interest rate and certain other terms of the Securities and the purchase
price of the Securities to be paid by the Underwriters shall be agreed upon by
Publishing, the Guarantor and the Underwriters and such agreement shall be set
forth in a separate written instrument substantially in the form of Exhibit I
hereto (the "Price Determination Agreement").  The Price Determination
Agreement may take the form of an exchange of any standard form of written
telecommunication among Publishing, the Guarantor and the Underwriters and
shall specify such applicable information as is indicated in Exhibit A hereto.
The offering of the Securities will be governed by this Agreement, as
supplemented by the Price Determination Agreement.  From and after the date of
the execution and delivery of the Price Determination Agreement, this Agreement
shall be deemed to incorporate, and all references herein to "this Agreement"
or "herein" shall be deemed to include, the Price Determination Agreement.

   Concurrently with the execution of this Agreement, Publishing, the Guarantor
and Merrill Lynch, CIBC, Scotia Capital Markets (USA) Inc.  ("Scotia") and TD
are entering into a senior note purchase agreement (the "Senior Note Purchase
Agreement") pursuant to which Publishing will issue and sell to Merrill Lynch,
CIBC, Scotia and TD $260,000,000 aggregate principal amount of Publishing's
8-5/8% Senior Notes due 2005 (the "Senior Notes").  The pricing terms for the
Senior Notes to be sold pursuant to the Senior Notes Purchase Agreement shall
be set forth in a separate agreement (the "Senior Notes Price Determination
Agreement"), the form of which will be attached to the Senior Notes Purchase
Agreement.

   Publishing and the Guarantor have prepared and filed with the Securities and
Exchange Commission (the "Commission") a registration statement on Form S-3
(No. 333-17113) and a related preliminary prospectus for the registration of
the Securities under the Securities Act of 1933 (the "1933 Act"), have filed
such amendments thereto, if any, and such amended preliminary prospectuses as
may have been required to the date hereof, and will file such additional
amendments thereto and such amended prospectuses as may hereafter be required.
The term "Registration Statement" as used in this Agreement means the
registration statement (including all financial schedules and exhibits), as
amended at the time it becomes effective, and as thereafter amended by
post-effective amendment, and any registration statement and any amendments
thereto filed





<PAGE>   3
                                                                               3


pursuant to Rule 462(b) of the 1933 Act relating to the offering covered by the
initial registration statement (the "Rule 462(b) Registration Statement").  The
term "Prospectuses" as used in this Agreement means the prospectuses in the
forms included in the Registration Statement, or, if the prospectuses included
in the Registration Statement omit information in reliance on Rule 430A under
the 1933 Act and such information is included in prospectuses filed with the
Commission pursuant to Rule 424(b) under the 1933 Act, the term "Prospectuses"
as used in this Agreement means the prospectuses in the forms included in the
Registration Statement as supplemented by the addition of the Rule 430A
information contained in the prospectuses filed with the Commission pursuant to
Rule 424(b).

   Publishing and the Guarantor understand that the Underwriters propose to
make a public offering of the Securities as soon as the Underwriters deem
advisable after the Registration Statement becomes effective and the Price
Determination Agreement has been executed and delivered.

   Publishing hereby confirms its engagement of Merrill Lynch, Pierce, Fenner &
Smith Incorporated as, and Merrill Lynch, Pierce, Fenner & Smith Incorporated
hereby confirms its agreement with the Company to render services as, a
"qualified independent underwriter" within the meaning of Rule 2720 of the
By-laws of the National Association of Securities Dealers, Inc. with respect to
the offering and sale of the Securities.  Merrill Lynch, Pierce, Fenner & Smith
Incorporated, solely in its capacity as qualified independent underwriter and
not otherwise is referred to herein as the "Independent Underwriter".

   SECTION 1.  Representations and Warranties.  (a)  Publishing and the
Guarantor jointly and severally represent and warrant to the Underwriters as of
the date hereof and as of the date of the Price Determination Agreement (such
latter date being hereinafter referred to as the "Representation Date") as
follows:

   (i)  The Registration Statement in the form in which it became or becomes
  effective and also in such form as it may be when any post-effective
  amendment thereto or any Rule 462(b) Registration Statement or amendment
  thereto shall become effective and the Prospectus and any supplement or
  amendment thereto when filed with the Commission under Rule 424(b) under the
  1933 Act, complied or will comply in all material respects with the
  provisions of the 1933 Act and did not or will not at any such times contain
  an untrue statement of a material fact or omit to state a





<PAGE>   4
                                                                               4


  material fact required to be stated therein or necessary to make the
  statements therein not misleading, except that this representation and
  warranty does not apply to statements in or omissions from the Registration
  Statement or the Prospectus made in reliance upon and in conformity with
  information relating to the Underwriters furnished to Publishing and the
  Guarantor in writing by or on behalf of the Underwriters through you
  expressly for use therein.

   (ii)  All the outstanding shares of common stock of Publishing and the
  Guarantor have been duly authorized and validly issued, are fully paid and
  nonassessable and are free of any preemptive or similar rights; and the
  authorized capital stock of Publishing and the Guarantor conforms to the
  description thereof in the Registration Statement and the Prospectus.  Except
  as described in the Prospectus, there are no outstanding options, warrants or
  other rights issued by Publishing or the Guarantor calling for the issuance
  of, nor any written agreement entered into by Publishing or the Guarantor or
  oral commitments of Publishing or the Guarantor to issue, any shares of
  capital stock or any other security of Publishing or the Guarantor or any
  security convertible into or exchangeable or exercisable for capital stock or
  any other security of Publishing or the Guarantor.

   (iii)  Publishing and the Guarantor are corporations duly incorporated and
  validly existing in good standing under the laws of the State of Delaware
  with corporate power and authority to own, lease and operate their properties
  and to conduct their business as described in the Registration Statement and
  the Prospectus.

   (iv)  The only significant subsidiaries (as defined in the 1933 Act) of
  Publishing and the Guarantor are the subsidiaries listed in Schedule II
  hereto (each a "Subsidiary" and collectively the "Subsidiaries").  Each
  Subsidiary is a corporation duly incorporated, validly existing and in good
  standing in the jurisdiction of its incorporation, with corporate power and
  authority to own, lease and operate its properties and to conduct its
  business as described in the Registration Statement and the Prospectus, and
  is duly qualified as a foreign corporation for the transaction of business in
  and is in good standing under the laws of each other jurisdiction where the
  nature of its properties or the conduct of its business requires such
  qualification, except where the failure so to qualify does not have a
  material adverse effect on the condition (financial or other), business,
  properties,





<PAGE>   5
                                                                               5


  net worth or results of operations of such Subsidiary; all the outstanding
  shares of capital stock of each of the Subsidiaries have been duly authorized
  and validly issued, are fully paid and nonassessable, and all shares of the
  capital stock of the Subsidiaries that are owned directly or indirectly by
  Publishing or the Guarantor are owned free and clear of any lien, adverse
  claim, security interest, equity, or other encumbrance, except, to the extent
  set forth or described in the Registration Statement and the Prospectus,
  currently existing liens, claims and security interests of creditors and
  liens, claims and security interests pursuant to the terms of the FDTH Credit
  Facility, the Publishing Credit Facility and the contemplated New Bank Credit
  Facility (as defined).

   (v)  There are no legal or governmental proceedings pending or, to the
  knowledge of Publishing or the Guarantor, threatened, against Publishing or
  the Guarantor or any of the Subsidiaries, or to which Publishing or the
  Guarantor or any of the Subsidiaries, or to which any of their respective
  properties is subject, that are required to be described in the Registration
  Statement or the Prospectus but are not described as required, or which might
  have a material adverse effect on the condition (financial or other),
  business, properties, net worth or results of operation of Publishing, the
  Guarantor and their subsidiaries considered as one enterprise, or which might
  materially and adversely affect the properties or assets thereof or which
  might materially and adversely affect the consummation of this Agreement; all
  pending legal or governmental proceedings to which Publishing or the
  Guarantor or any of the Subsidiaries is a party or of which any of their
  respective property or assets is the subject which are not described in the
  Registration Statement, including ordinary routine litigation incidental to
  the business, are, considered in the aggregate, not material; and there are
  no agreements, contracts, indentures, leases or other instruments that are
  required to be described in the Registration Statement or the Prospectus or
  to be filed as an exhibit to the Registration Statement that are not
  described or filed as required by the 1933 Act.

   (vi)  Except as set forth in the Prospectus, neither Publishing, the
  Guarantor nor any of the Subsidiaries (A) is in violation of its certificate
  or articles of incorporation or by-laws, or other organizational documents,
  (B) is in violation of any law, ordinance, administrative or governmental
  rule or regulation applicable to Publishing or the Guarantor or





<PAGE>   6
                                                                               6


  any of the Subsidiaries or of any decree of any court or governmental agency
  or body having jurisdiction over Publishing or the Guarantor or any of the
  Subsidiaries, or (C) is in default in any material respect in the performance
  of any obligation, agreement or condition contained in any bond, debenture,
  note or any other evidence of indebtedness or in any material agreement,
  indenture, lease or other instrument to which Publishing or the Guarantor or
  any of the Subsidiaries is a party or by which any of them or any of their
  respective properties may be bound, except, in the case of clause (B) with
  respect to the Subsidiaries, where such violation does not have a  material
  effect on the condition (financial or other), business, properties, net worth
  or results of operations of Publishing, the Guarantor and their subsidiaries
  considered as one enterprise.

   (vii)  Neither the issuance and sale of the Securities, the execution,
  delivery or performance of this Agreement and the Price Determination
  Agreement by Publishing or the Guarantor, nor the consummation by Publishing
  or the Guarantor of the transactions contemplated hereby (A) requires any
  consent, approval, authorization or other order of or registration or filing
  with, any court, regulatory body, administrative agency or other governmental
  body, agency or official (except such as may be required for the registration
  of the Securities under the 1933 Act and the Securities Exchange Act of 1934
  (the "Exchange Act") and compliance with the securities or Blue Sky laws of
  various jurisdictions, both of which have been or will be effected in
  accordance with this Agreement) or violates or will violate the certificate
  or articles of incorporation or by-laws, or other organizational documents,
  of Publishing or the Guarantor or any of the Subsidiaries or (B) constitutes
  or will constitute a breach of, or a default under, any material agreement,
  indenture, lease or other instrument to which Publishing or the Guarantor or
  any of the Subsidiaries is a party or by which any of them or any of their
  respective properties may be bound (except where consents or waivers as to
  such default have been obtained prior to the time of the execution of the
  Price Determination Agreement (the "Pricing Time")), or violates or will
  violate any statute, law, regulation or judgment, injunction, order or decree
  applicable to Publishing or the Guarantor or any of the Subsidiaries or any
  of their respective properties, or will result in the creation or imposition
  of any lien, charge or encumbrance upon any property or assets of Publishing
  or the Guarantor or any of the Subsidiaries pursuant to





<PAGE>   7
                                                                               7


  the terms of any agreement or instrument to which any of them is a party or
  by which any of them may be bound or to which any of the property or assets
  of any of them is subject.

   (viii)  KPMG Peat Marwick LLP, who have certified or shall certify certain
  of the financial statements included in the Registration Statement and the
  Prospectus (or any amendment or supplement thereto), are independent public
  accountants as required by the Act.

   (ix)  The consolidated financial information for the Guarantor and the
  Restricted Group, together with related notes, included in the Registration
  Statement and the Prospectus (and any amendment or supplement thereto), (A)
  in the case of the historical financial statements present fairly the
  consolidated financial position and results of operations of the Guarantor
  and of the Restricted Group, and (B) in the case of the pro forma financial
  statements present fairly, on a pro forma basis, the pro forma supplemental
  consolidated financial position and results of operations of Publishing and
  its subsidiaries, including The Telegraph Group Limited ("The Telegraph") and
  Southam Inc.  ("Southam"), in each case on the basis stated in the
  Registration Statement at the respective dates or for the respective periods
  to which they apply.  Such financial statements, pro forma financial
  statements and related notes have been prepared in accordance with U.S.
  generally accepted accounting principles consistently applied throughout the
  periods involved, except as disclosed therein; and the other financial and
  statistical information and data included in the Registration Statement and
  the Prospectus (and any amendment or supplement thereto) are accurately
  presented in all material respects and prepared on a basis consistent with
  such financial statements and the books and records of the Guarantor,
  Publishing and their subsidiaries.

   (x)  The execution and delivery of, and the performance by Publishing and
  the Guarantor of their obligations under, this Agreement and the Price
  Determination Agreement have been duly and validly authorized by Publishing
  and the Guarantor, and this Agreement and the Price Determination Agreement
  have been duly executed and delivered by Publishing and the Guarantor.

(xi)  Except as disclosed in the Registration Statement and the Prospectus (or
any amendment or





<PAGE>   8
                                                                               8


  supplement thereto), subsequent to the respective dates as of which such
  information is given in the Registration Statement and the Prospectus (or any
  amendment or supplement thereto), neither Publishing nor the Guarantor nor
  any of the Subsidiaries has incurred any liability or obligation, direct or
  contingent, or entered into any transaction, not in the ordinary course of
  business, that is material to the Publishing, the Guarantor and their
  subsidiaries considered as one enterprise, and there has not been any change
  in the capital stock, or material increase in the short-term debt or
  long-term debt, of Publishing or the Guarantor or any of the Subsidiaries, or
  any material adverse change, or any development involving, or which may
  reasonably be expected to involve, a prospective material adverse change, in
  the condition (financial or other), business, net worth or results of
  operations of Publishing, the Guarantor and their subsidiaries considered as
  one enterprise.

   (xii)  Each of Publishing, the Guarantor and the Subsidiaries has good and
  marketable title to all property (real and personal) described in the
  Prospectus as being owned by them (excluding properties owned by West Ferry
  Printers, Trafford Park Printers, or Southam), free and clear of all liens,
  claims, security interests or other encumbrances except to the extent set
  forth or described in the Registration Statement and the Prospectus or in a
  document filed as an exhibit to the Registration Statement or are not
  material to the business of Publishing, the Guarantor and their subsidiaries
  considered as one enterprise and all the property described in the Prospectus
  as being held under lease by each of Publishing, the Guarantor and the
  Subsidiaries is held by it under valid, subsisting and enforceable leases
  with such exceptions as are not material to the business of Publishing, the
  Guarantor and their subsidiaries considered as one enterprise and do not
  interfere with the use made and proposed to be made of such properties by
  Publishing and the Guarantor and their subsidiaries.

   (xiii)  Neither Publishing nor the Guarantor has distributed and, prior to
  the later to occur of (i) the Closing Date and (ii) completion of the
  distribution of the Securities, neither will distribute any offering material
  in connection with the offering and sale of the Securities other than the
  Registration Statement, the Prospectus or other materials, if any, permitted
  by the Act.





<PAGE>   9
                                                                               9


   (xiv)  Publishing, the Guarantor and each of the Subsidiaries has such
  governmental authorizations, approvals, orders, licenses, certificates,
  franchises and permits of and from all governmental or regulatory officials
  and bodies ("permits") as are necessary to own its respective properties and
  to conduct its business in the manner described in the Prospectus, with such
  exceptions as are not material to the business of Publishing, the Guarantor
  and the Subsidiaries considered as one enterprise and do not interfere with
  the use made and proposed to be made of such properties by Publishing, the
  Guarantor and the Subsidiaries or are otherwise disclosed; Publishing, the
  Guarantor and each of the Subsidiaries has fulfilled and performed all its
  material obligations with respect to such permits and no event has occurred
  which allows, or after notice or lapse of time would allow, revocation or
  termination thereof or results in any other material impairment of the rights
  of the holder of any such permit, with such exceptions as are not material to
  the business of Publishing and the Guarantor and their subsidiaries
  considered as one enterprise and do not interfere with the use made and
  proposed to be made of such properties by Publishing and the Guarantor and
  the Subsidiaries or are otherwise disclosed; and, except as described in the
  Prospectus, none of such permits contains any restriction that is materially
  burdensome to Publishing and the Guarantor and their subsidiaries considered
  as one enterprise.

   (xv)  Publishing and the Guarantor maintain a system of internal accounting
  controls sufficient to provide reasonable assurances that (i) transactions
  are executed in accordance with management's general or specific
  authorization; (ii) transactions are recorded as necessary to permit
  preparation of financial statements in conformity with generally accepted
  accounting principles and to maintain accountability for assets; (iii) access
  to assets is permitted only in accordance with management's general or
  specific authorization; and (iv) the recorded accountability for assets is
  compared with existing assets at reasonable intervals and appropriate action
  is taken with respect to any differences.

   (xvi)  To Publishing's or the Guarantor's knowledge, neither Publishing nor
  the Guarantor nor any of the Subsidiaries nor any employee or agent of
  Publishing, the Guarantor or any Subsidiary has made any payment of funds of
  Publishing, the Guarantor or any Subsidiary or received or retained any funds
  in violation of any law, rule or regulation, which payment, receipt or
  retention





<PAGE>   10
                                                                              10


  of funds is of a character required to be disclosed in the Prospectus.

   (xvii)  Except as described in the Registration Statement and the
  Prospectus, Publishing, the Guarantor and each of the Subsidiaries have filed
  all tax returns required to be filed, which returns are complete and correct,
  and neither Publishing, the Guarantor nor any Subsidiary is in default in the
  payment of any taxes which were payable pursuant to said returns or any
  assessments with respect thereto, with such exceptions as are not material to
  the financial position of Publishing, the Guarantor and their subsidiaries
  considered as one enterprise.

   (xviii)  Publishing, the Guarantor and the Subsidiaries own, or possess
  adequate rights to use, all patents, trademarks, service marks, trade names,
  copyrights, licenses, and rights described in the Prospectus as being owned
  by them or any of them or necessary for the conduct of their respective
  businesses, and neither Publishing nor the Guarantor is aware of any claim to
  the contrary or any challenge by any other person to the rights of
  Publishing, the Guarantor and the Subsidiaries with respect to the foregoing.

   (xix)  Neither Publishing nor the Guarantor is now, and after sale of the
  Securities to be sold by it hereunder and application of the net proceeds
  from such sale as described in the Prospectus under the caption "Use of
  Proceeds" will not be, an "investment company" within the meaning of the
  Investment Company Act of 1940, as amended.

   (xx)  Publishing and the Guarantor have complied with all provisions of
  Florida Statutes, Section  517.075, relating to issuers doing business with
  Cuba.

   (xxi)  The Indenture has been duly authorized by Publishing and the
  Guarantor, will be substantially in the form heretofore delivered to the
  Underwriters and, when duly executed and delivered by Publishing, the
  Guarantor and the Trustee, will have been duly qualified under the 1939 Act
  and will constitute a valid and binding obligation of Publishing and the
  Guarantor, enforceable against Publishing and the Guarantor in accordance
  with its terms, except as enforcement thereof may be limited by bankruptcy,
  insolvency, moratorium, fraudulent conveyance, reorganization or other
  similar laws affecting enforcement of creditors' rights generally and except





<PAGE>   11
                                                                              11


  as enforcement thereof is subject to general principles of equity (regardless
  of whether enforcement is considered in a proceeding in equity or at law);
  the Indenture conforms to the description thereof contained in the
  Prospectus; the Indenture and the form and issuance of the Securities
  thereunder comply with the provisions of the 1939 Act.

   (xxii)  The Securities have been duly authorized by Publishing and the
  Guarantor and, when executed, authenticated, issued and delivered in the
  manner provided for in the Indenture and sold and paid for as provided in
  this Agreement, the Securities will constitute valid and binding obligations
  of the Publishing and the Guarantor enforceable against Publishing and the
  Guarantor in accordance with their terms, except as enforcement thereof may
  be limited by bankruptcy, insolvency, moratorium, fraudulent conveyance,
  reorganization or other similar laws affecting enforcement of creditors'
  rights generally and except as enforcement thereof is subject to general
  principles of equity (regardless of whether enforcement is considered in a
  proceeding in equity or at law); the holders thereof will be entitled to the
  benefits of the Indenture; and the Indenture and the Securities conform to
  the descriptions thereof contained in the Prospectus.

   (xxiii)  No holder of any security of Publishing or the Guarantor nor any
  other person has any right, contractual or otherwise, to have any securities
  included in the Registration Statement or the right, because of the filing of
  the Registration Statement or consummation of the transactions contemplated
  by this Agreement, to require registration of any security of Publishing or
  the Guarantor under the Act.

   (xxiv)  Except as set forth in the Prospectus, no labor dispute with the
  employees of Publishing or the Guarantor or any of the Subsidiaries exists
  or, to the knowledge of Publishing or the Guarantor, is imminent, which might
  be expected to result in a material adverse effect on the condition
  (financial or other), business, properties, net worth or results of
  operations of Publishing, the Guarantor and their subsidiaries considered as
  one enterprise.

   (xxv)  Except as set forth in the Registration Statement and except as would
  not result in a material effect on the condition (financial or other),
  business, properties, net worth or results of operations of Publishing, the
  Guarantor and their subsidiaries





<PAGE>   12
                                                                              12


  considered as one enterprise and which would not materially and adversely
  affect the consummation of this Agreement, (i) to the knowledge of Publishing
  and the Guarantor after reasonable inquiry, neither Publishing nor the
  Guarantor is in violation of any applicable Federal, foreign, state or local
  environmental law or any applicable order of any governmental authority with
  respect thereto; (ii) neither Publishing nor the Guarantor is in violation of
  or subject to any existing, or pending or, to Publishing's and the
  Guarantor's knowledge, threatened action, suit, investigation, inquiry or
  proceeding by any governmental authority nor is Publishing or the Guarantor
  subject to any environmental claim by any citizens' group or to remedial
  obligations under any applicable Federal, foreign, state or local
  environmental law; (iii) Publishing, the Guarantor and the subsidiaries are
  in compliance with all permits or similar authorizations, if any, required to
  be obtained or filed in connection with their operations including, without
  limitation, emissions, discharges, treatment, storage, disposal or release of
  a Hazardous Material into the environment except where any noncompliance
  could not reasonably be expected to have a material adverse effect on the
  operations of Publishing, the Guarantor and the Subsidiaries; and (iv) to the
  knowledge of Publishing and the Guarantor after reasonable inquiry, no
  Hazardous Materials have been disposed of or released by Publishing or the
  Guarantor or the Subsidiaries at, under or on any property currently or
  formerly owned or operated by Publishing, the Guarantor or the Subsidiaries,
  except in accordance with applicable environmental laws.  The term "Hazardous
  Material" means any oil (including petroleum products, crude oil and any
  fraction thereof), chemical, contaminant, pollutant, solid or hazardous waste
  or material, or Hazardous Substance (as defined in Section 101(14) of the
  Comprehensive Environmental Response, Compensation and Liability Act and
  regulations thereunder), that is regulated as toxic or hazardous to human
  health or the environment under any Federal, foreign, state or local
  environmental law.

   (xxvi)  Publishing and the Guarantor and each other person or entity that,
  together with Publishing and the Guarantor, is treated as a single employer
  under Section 414 of the Internal Revenue Code of 1986, as amended (the
  "Code") (each such person or entity being an "ERISA Affiliate"), complies in
  all material respects with the Employee Retirement Income Security Act of
  1974, as amended ("ERISA"), and the Code with





<PAGE>   13
                                                                              13


  respect to each pension plan (as defined in Section 3(2) of ERISA) maintained
  by Publishing, the Guarantor or such ERISA Affiliate, and none of Publishing,
  the Guarantor or any of its ERISA Affiliates has incurred any material
  liability to any pension plan or to the Pension Benefit Guaranty Corporation
  that has not been fully paid as of the date hereof except as disclosed in the
  Registration Statement or Prospectus (or any amendment or supplement
  thereto).

    (xxvii)  Publishing and the Guarantor will apply the protion of the net
  proceeds of the Offering deposited in escrow for the purpose of redeeming, in
  each case at the first redemption date occurring in 1997, the DTH and FDTH
  Preference Shares held by third parties as described in the Prospectus, and
  for no other purpose.

   (b)  Any certificate signed by an officer of Publishing or the Guarantor and
delivered to the Underwriters or to counsel for the Underwriters shall be
deemed a representation and warranty by Publishing and the Guarantor to the
Underwriters as to the matters covered thereby.

   SECTION 2.  Sale and Delivery to Underwriters; Closing.  (a)  On the basis
of the representations and warranties herein contained, and subject to the
terms and conditions herein set forth, Publishing agrees to sell to the
Underwriters, and the Underwriters agree to purchase from Publishing, at the
purchase price set forth in the Price Determination Agreement, the Securities.

   (b)  If Publishing has elected not to rely upon Rule 430A under the 1933 Act
Regulations, the initial public offering price and the purchase price to be
paid by the Underwriters shall be agreed upon and set forth in the Price
Determination Agreement, dated the date hereof, and an amendment to the
Registration Statement containing such information will be filed with the
Commission, before the Registration Statement becomes effective.

   (c)  If Publishing has elected to rely upon Rule 430A under the 1933 Act
Regulations, the initial public offering price and the purchase price to be
paid by the Underwriters shall be agreed upon and set forth in the Price
Determination Agreement.  In the event that the Price Determination Agreement
has not been executed by the close of business on the fourth business day
following the date on which the Registration Statement becomes effective, this
Agreement shall terminate forthwith, without liability of





<PAGE>   14
                                                                              14


any party to any other party except that Sections 6, 7 and 8 shall remain in
effect.

   (d)  Publishing will deliver the Securities to the Underwriters, at the
offices of Cravath, Swaine & Moore, 825 Eighth Avenue, New York, NY 10019, or
at such other place as shall be agreed upon by Publishing, the Guarantor and
the Underwriters, against payment of the gross purchase price by wire transfer
to Publishing in U.S. dollars, in funds immediately available to Publishing, at
10:00 a.m. either (i) on the third business day following the date upon which
the Publishing and the Guarantor shall have fulfilled all requirements which
under the 1933 Act must be fulfilled to qualify the Securities for distribution
and the Registration Statement shall have become effective or (ii) if
Publishing has elected to rely upon Rule 430A under the 1933 Act Regulations,
on the third business day after execution of the Price Determination Agreement,
or at such other time not later than ten full business days thereafter as the
Underwriters and Publishing determine (such time being herein referred to as
the "Closing Date").  The Securities so to be delivered will be in definitive,
fully registered form in such denominations ($1,000 principal amount or an
integral multiple thereof) and registered in such names as the Underwriters
shall request in writing at least two full business days prior to the Closing
Date, and will be made available for checking and packaging at the office of
the Trustee, not later than 10:00 a.m. on the business day prior to the Closing
Date.  Concurrently with the payment by the Underwriters of the gross purchase
price for the Securities in the manner described in this Section 2(d),
Publishing will pay to the Underwriters by certified or official bank check or
checks in U.S. dollars, in funds available the next succeeding business day
drawn to the order of Merrill Lynch, Pierce, Fenner & Smith Incorporated, North
Tower, World Financial Center, New York, New York 10281-1305, for the account
of the Underwriters, an amount equal to the underwriting commission applicable
to the Securities as described in the Price Determination Agreement.

   SECTION 3.  Covenants of Publishing and the Guarantor.  Publishing and the
Guarantor, jointly and severally, covenant with the Underwriters as follows:

   (a)  Publishing will notify the Underwriters immediately, and confirm the
notice in writing, (i) of the effectiveness of the Registration Statement and
any amendment thereto (including any posteffective amendment), (ii) of the
receipt of any comments from the Commission, (iii) of any request by the
Commission for any amendment to the Registration Statement or any amendment or
supplement to





<PAGE>   15
                                                                              15


the Prospectus or for additional information, and (iv) of the issuance by the
Commission of any stop order suspending the effectiveness of the Registration
Statement or the initiation of any proceedings for that purpose.  Publishing
will make every reasonable effort to prevent the issuance of any stop order
and, if any stop order is issued, to obtain the lifting thereof at the earliest
possible moment.

   (b)  Publishing will furnish to the Underwriters, without charge, five true
and correct copies of the Registration Statement as originally filed with the
Commission and of each amendment thereto, including financial statements and
all exhibits to the Registration Statement, and of any Rule 462(b) Registration
Statement and any amendment thereto, and will also furnish to you, without
charge, such number of conformed copies of the Registration Statement as
originally filed and of each amendment thereto, but without exhibits, and of
any Rule 462(b) Registration Statement and any amendment thereto, as you may
reasonably request.

   (c)  Publishing will not (i) file any amendment to the Registration
Statement, any Rule 462(b) Registration Statement or amendment thereto, or make
any amendment or supplement to the Prospectuses of which you shall not
previously have been advised or to which you shall reasonably object in writing
after being so advised or (ii) so long as, in the written opinion of counsel
for the Underwriters (a copy of which shall be delivered to Publishing), a
Prospectus is required to be delivered in connection with sales by any
Underwriters or dealer, file any information, documents or reports pursuant to
the Exchange Act, without delivering a copy of such information, documents or
reports to you prior to such filing.

   (d)  Publishing will furnish to the Underwriters, from time to time during
the period when the Prospectus is required to be delivered under the 1933 Act
or the Securities Exchange Act of 1934 (the "1934 Act"), such number of copies
of the Prospectus (as amended or supplemented) as the Underwriters may
reasonably request for the purposes contemplated by the 1933 Act or the 1934
Act or the respective applicable rules and regulations of the Commission
thereunder.

   (e)  If any event shall occur as a result of which it is necessary, in the
opinion of counsel for the Underwriters, to amend or supplement the Prospectus
in order to make the Prospectus not misleading, in the light of the
circumstances existing at the time it is delivered to a purchaser, Publishing
will forthwith amend or supplement the Prospectus (in form and substance
satisfactory to counsel





<PAGE>   16
                                                                              16


for the Underwriters so that, as so amended or supplemented, the Prospectus
will not include an untrue statement of a material fact or omit to state a
material fact necessary in order to make the statements therein, in the light
of the circumstances existing at the time it is delivered to a purchaser, not
misleading), and Publishing will furnish to the Underwriters a reasonable
number of copies of such amendment or supplement.

   (f)  Publishing will endeavor, in cooperation with the Underwriters, to
qualify the Securities for offering and sale under the applicable securities
laws of such states and other jurisdictions of the United States as the
Underwriters may designate; provided, however, that Publishing shall not be
obligated to qualify as a foreign corporation in any jurisdiction in which it
is not so qualified.  In each jurisdiction in which the Securities have been so
qualified Publishing will file such statements and reports as may be required
by the laws of such jurisdiction to continue such qualification in effect for a
period of not less than one year from the effective date of the Registration
Statement.

   (g)  Publishing will make generally available to its security holders as
soon as practicable, but not later than 60 days after the close of the period
covered thereby, an earnings statement (in form complying with the provisions
of Rule 158 of the 1933 Act Regulations) covering a 12-month period beginning
not later than the first day of Publishing's fiscal quarter next following the
"effective date" (as defined in said Rule 158) of the Registration Statement.

   (h)  Publishing will use the net proceeds received by it from the sale of
the Securities in the manner specified in the Prospectus under "Use of
Proceeds".

   (i)  If, at the time that the Registration Statement becomes effective, any
information shall have been omitted therefrom in reliance upon Rule 430A of the
1933 Act Regulations, then immediately following the execution of the Price
Determination Agreement, Publishing will prepare, and file or transmit for
filing with the Commission in accordance with such Rule 430A and Rule 424(b) of
the 1933 Act Regulations, copies of an amended Prospectus, or, if required by
such Rule 430A, a post-effective amendment of the Registration Statement
(including an amended Prospectus), containing all information so omitted.

   (j)  Except as provided in this Agreement, Publishing will not directly or
indirectly, offer, sell, grant any option to purchase or otherwise dispose of,
any debt security of Publishing which is publicly offered or





<PAGE>   17
                                                                              17


sold pursuant to Rule 144A of the 1933 Act Regulations for a period of 180 days
after the date of the Prospectus, without the prior written consent of Merrill
Lynch.

   (k)  For a period of three years after the Closing Date the Guarantor will
furnish to the Underwriters copies of all reports and communications delivered
to the Guarantor's stockholders or to holders of the Securities as a class and
will also furnish copies of all reports (excluding exhibits) filed with the
Commission on Form 8-K, 10-Q and 10-K, and all other reports and information
furnished to its stockholders generally, at the time such reports are furnished
to stockholders generally.  For such period of time, the Guarantor will file
with the Commission such documents required to be filed with the Commission
pursuant to Sections 13(a) and 15(d) of the 1934 Act, whether or not the
Guarantor or Publishing has a class of securities registered under the 1934
Act.

   (l)  The Company will use reasonable efforts to effect the listing of the
Securities on the New York Stock Exchange on the date of the Price
Determination Agreement.

   SECTION 4.  Payment of Expenses.  Publishing will pay all expenses incident
to the performance of its obligations under this Agreement, including (i) the
printing and filing of the Registration Statement as originally filed, and of
each amendment thereto, (ii) the printing of this Agreement, the Price
Determination Agreement, the Indenture and any Legal Investment Survey, (iii)
the preparation, issuance and delivery of the certificates for the Securities
to the Underwriters, (iv) the fees and disbursements of Publishing's and the
Guarantor's counsel and accountants, (v) the qualification of the Securities
under securities laws in accordance with the provisions of Section 3(f),
including filing fees and the fee and the disbursements of counsel for the
Underwriters in connection therewith and in connection with the preparation of
the Blue Sky Survey, (vi) the printing and delivery to the Underwriters of
copies of the Registration Statement as originally filed and of each amendment
thereto, of the preliminary prospectus, and of the Prospectus and any
amendments or supplements thereto, (vii) the printing and delivery to the
Underwriters of copies of the Blue Sky Survey, (viii) the filing fee of the
National Association of Securities Dealers, Inc., (ix) the fees and expenses of
the Trustee, including the fees and disbursements of counsel for the Trustee,
in connection with the Indenture and the Securities, and (x) any fees charged
by investment-rating agencies for the rating of the Securities.





<PAGE>   18
                                                                              18


   If this Agreement is terminated by the Underwriters in accordance with the
provisions of Section 5, Section 9(a) or Section 11, Publishing shall reimburse
the Underwriters for all of their out-of-pocket expenses, including the
reasonable fees and disbursements of counsel for the Underwriters.

   SECTION 5.  Conditions of the Underwriters' Obligations.  The obligations of
the Underwriters hereunder are subject to the accuracy of the representations
and warranties of Publishing and the Guarantor herein contained, to the
performance by Publishing and the Guarantor of their obligations hereunder, and
to the following further conditions:

   (a)  The Registration Statement shall have become effective not later than
9:30 a.m. on the date hereof, or, with the consent of the Underwriters, at a
later time and date, not later, however, than 9:30 a.m. on the first business
day following the date hereof or at such later time and date as may be approved
by the Underwriters; and at the Closing Date no stop order suspending the
effectiveness of the Registration Statement shall have been issued under the
1933 Act or proceedings therefor initiated or threatened by the Commission.  If
Publishing has elected to rely upon Rule 430A of the 1933 Act Regulations, the
price of the Securities and any price-related information previously omitted
from the effective Registration Statement pursuant to such Rule 430A shall have
been transmitted to the Commission for filing pursuant to Rule 424(b) of the
1933 Act Regulations within the prescribed time period, and prior to the
Closing Date Publishing shall have provided evidence satisfactory to the
Underwriters of such timely filing, or a post-effective amendment providing
such information shall have been promptly filed and declared effective in
accordance with the requirements of Rule 430A of the 1933 Act Regulations.

   (b)    At the Closing Date, there shall not have been, since the date hereof
or since the respective dates as of which information is given in the
Prospectus, any material adverse change in the condition, financial or
otherwise, or in the earnings, business affairs or business prospects of
Publishing and the Guarantor and their subsidiaries considered as one
enterprise, whether or not arising in the ordinary course of business, and the
Underwriters shall have received a certificate of the Chairman and Chief
Executive Officer of each of Publishing and the Guarantor and of the Vice
President of each of Publishing and the Guarantor, dated as of Closing Date, to
the effect that (i) there has been no such material adverse change, (ii) the
representations and warranties in





<PAGE>   19
                                                                              19


Section 1(a) are true and correct with the same force and effect as though
expressly made at and as of the Closing Date, (iii) Publishing and the
Guarantor have complied with all agreements and satisfied all conditions on
their part to be performed or satisfied at or prior to the Closing Date, and
(iv) no stop order suspending the effectiveness of the Registration Statement
has been issued and no proceedings for that purpose have been initiated or
threatened by the Commission.  As used in this Section 5, the term "Prospectus"
means the Prospectus in the form first used to confirm sales of Securities.

   (c)   You shall have received on the Closing Date an opinion of Kirkpatrick
& Lockhart LLP, counsel for Publishing and the Guarantor, dated the Closing
Date and addressed to you, to the effect that:

   (i)  Publishing, the Guarantor and each of the United States Subsidiaries
  (the "U.S. Subsidiaries") is a corporation duly incorporated and validly
  existing in good standing under the laws of the jurisdiction of its
  organization, with corporate power and authority to own, lease and operate
  its properties and conduct its business as described in the Registration
  Statement and the Prospectus (and any amendment or supplement thereto), and
  is duly qualified as a foreign corporation for the transaction of business in
  and is in good standing under the laws of each jurisdiction where the nature
  of its properties or the conduct of its business requires such qualification,
  except where the failure so to qualify would not have a material adverse
  effect on the condition (financial or otherwise), business, properties, net
  worth or results of operations of Publishing, the Guarantor and their
  subsidiaries, considered as one enterprise.

   (ii)  All the outstanding shares of capital stock of each of the U.S.
  Subsidiaries have been duly authorized and validly issued, are fully paid and
  nonassessable, and are owned of record by Publishing directly, or indirectly
  through one of the other U.S. Subsidiaries, and are not subject to any
  perfected security interest, or, to the best knowledge of such counsel after
  reasonable inquiry, any adverse claims within the meaning of the Uniform
  Commercial Code, except, to the extent set forth or described in the
  Registration Statement and the Prospectus, currently existing liens, claims
  and security interests of creditors and liens, claims and security interests
  pursuant to the terms of the FDTH Credit Facility, the Publishing Credit
  Facility and the contemplated New Bank Credit Facility (as defined).





<PAGE>   20
                                                                              20



   (iii)  The Registration Statement and all post-effective amendments, if any,
  have become effective under the 1933 Act, the Indenture has been duly
  qualified under the 1939 Act and, to the best knowledge of such counsel after
  reasonable inquiry, no stop order suspending the effectiveness of the
  Registration Statement has been issued and no proceedings for that purpose
  are pending before or contemplated by the Commission; and any required filing
  of the Prospectus pursuant to Rule 424(b) has been made in accordance with
  Rule 424(b).

   (iv)  Publishing and the Guarantor have corporate power and authority to
  enter into this Agreement and to issue, sell and deliver the Securities to
  the Underwriter as provided herein, and this Agreement has been duly
  authorized, executed and delivered by Publishing and the Guarantor.

   (v)  Neither Publishing, the Guarantor nor any of the U.S. Subsidiaries is
  in violation of its certificate or articles of incorporation or its
  respective by-laws or, to the best knowledge of such counsel after reasonable
  inquiry, is in default in the performance of any material obligation,
  agreement or condition contained in any bond, debenture, note or other
  evidence of indebtedness to which the Guarantor, Publishing or any U.S.
  Subsidiary is a party that is included as an exhibit to, or otherwise
  described or summarized in, the Registration Statement, except as may be
  disclosed in the Prospectus and except for defaults under existing
  indebtedness of Publishing, the Guarantor or any U.S. Subsidiary as to which
  consents or waivers have been obtained prior to the Pricing Time.

   (vi)  Neither the offer, sale or delivery of the Securities, the execution,
  delivery or performance of this Agreement or the Indenture, compliance by
  Publishing or the Guarantor with the provisions of this Agreement or the
  Indenture, nor consummation by Publishing or the Guarantor of the sale of the
  Securities contemplated hereby violates the certificate or articles of
  incorporation or by-laws, or other organizational documents, of Publishing or
  the Guarantor or any of the U.S. Subsidiaries or constitutes a breach of or
  default under any agreement, indenture, lease or other instrument to which
  Publishing, the Guarantor or any of the U.S. Subsidiaries is a party or by
  which any of them or any of their respective properties is bound (except for
  defaults under existing indebtedness of Publishing, the





<PAGE>   21
                                                                              21


  Guarantor or any U.S. subsidiary as to which consents or waivers have been
  obtained prior to the Pricing Time) and that is an exhibit to the
  Registration Statement, or is material and is known to such counsel after
  reasonable inquiry, or will result in the creation or imposition of any lien,
  charge or encumbrance upon any property or assets of Publishing, the
  Guarantor or any of the U.S. Subsidiaries, nor will any such action violate
  any existing law, regulation, ruling (assuming compliance with all applicable
  state securities and Blue Sky laws), judgment, injunction, order or decree
  known to such counsel after reasonable inquiry, that names Publishing, the
  Guarantor or any of the U.S.  Subsidiaries and is specifically directed to
  any of them or any of their respective properties.

   (vii)  No consent, approval, authorization or other order of, or
  registration or filing with, any court, regulatory body, administrative
  agency or other governmental body, agency, or official is required on the
  part of Publishing or the Guarantor (except as have been obtained under the
  1933 Act, the Exchange Act, and the 1939 Act or such as may be required under
  state securities or Blue Sky laws governing the purchase and distribution of
  the Securities) for the valid issuance and sale of the Securities by
  Publishing to the Underwriters or the consummation by Publishing and the
  Guarantor of the other transactions set forth in this Agreement.

   (viii)  The Registration Statement and the Prospectus and any supplements or
  amendments thereto (except for the financial statements and the notes thereto
  and the schedules and other financial and statistical data included therein,
  as to which such counsel need not express any opinion) comply as to form in
  all material respects with the requirements of the 1933 Act.

   (ix)  Assuming that (A) Publishing and the Guarantor have all requisite
  corporate power and authority to execute, deliver and perform its obligations
  under the Securities and the Indenture, (B) the Securities have been duly
  authorized, executed and delivered by Publishing and the Guarantor, (C) the
  Indenture has been duly authorized, executed and delivered by Publishing and
  the Guarantor and the Trustees and (D) the Securities have been duly
  authenticated by one of the Trustees pursuant to the Indenture (which fact
  such counsel need not determine by an inspection of the Securities), the
  Securities and the Indenture each constitute valid and binding





<PAGE>   22
                                                                              22


  obligations of Publishing and the Guarantor, enforceable against Publishing
  and the Guarantor in accordance with their respective terms, in each case
  subject to applicable bankruptcy, insolvency, reorganization, moratorium,
  fraudulent conveyance or other similar laws affecting creditors' rights
  generally from time to time in effect; and the holders of the Securities are
  entitled to the benefits of the Indenture.  The enforceability of the
  obligations of Publishing and the Guarantor is also subject to general
  principles of equity (regardless of whether such enforceability is considered
  in a proceeding in equity or at law).

   (x)  To the best knowledge of such counsel after reasonable inquiry, (A)
  other than as described or contemplated in the Prospectus (or any supplement
  thereto), there are no legal or governmental proceedings pending or
  threatened against Publishing, the Guarantor or any of the U.S. Subsidiaries,
  or to which Publishing, the Guarantor or any of the U.S. Subsidiaries, or any
  of their property, is subject, which are required to be described in the
  Registration Statement or Prospectus (or any amendment or supplement
  thereto), and (B) there are no material agreements, contracts, indentures,
  leases or other instruments to which the Guarantor, Publishing or any U.S.
  Subsidiary is a party, that are required to be described in the Registration
  Statement or the Prospectus (or any amendment or supplement thereto) or to be
  filed as an exhibit to the Registration Statement that are not described or
  filed as required, as the case may be.

   (xi)  The statements in the Registration Statement and Prospectus, insofar
  as they are descriptions or summaries of contracts, agreements or other legal
  documents to which Publishing, the Guarantor or any U.S. Subsidiary is a
  party, or are statements of law or legal conclusions (other than matters of
  English, Canadian, Australian or Israeli law), are accurate in all material
  respects and present fairly the information required to be shown.

   (xii)  Except as described in the Prospectus, there is no holder of any
  security of Publishing or the Guarantor or, to the best knowledge of such
  counsel after reasonable inquiry, any other person who has the right,
  contractual or otherwise, to cause Publishing or the Guarantor to sell or
  otherwise issue to them, or to permit them to underwrite the sale of, the
  Securities or the right to have any securities of Publishing or the Guarantor
  included in the Registration Statement or





<PAGE>   23
                                                                              23


  the right, as a result of the filing of the Registration Statement, to
  require registration under the 1933 Act of any securities of Publishing or
  the Guarantor.

   (xiii)  At the Closing Date, Southam Inc. and Hollinger Eastern Publishing
  Inc. qualify as Subsidiaries as defined in the Senior Subordinated Indenture.

   (xiv)  Although counsel cannot opine as to factual matters, and the
  character of determinations involved in the registration process in such that
  counsel cannot pass upon and assume any responsibility for the accuracy or
  completeness of the information contained in the Registration Statement and
  the Prospectus, counsel shall advise the Underwriters that on the basis of
  its review of the Registration Statement and the Prospectus and its
  participation in the preparation thereof (relying as to materiality to a
  large extent upon the statements of officers and other representatives of the
  Company) that counsel has no reason to believe that (A) the Registration
  Statement (except for the financial statements and notes thereto and the
  schedules and other financial or statistical data included therein or omitted
  therefrom, as to which counsel need express no opinion), at the time the
  Registration Statement became effective, contained an untrue statement of a
  material fact or omitted to state any material fact required  to be stated
  therein or necessary to make the statements therein not misleading or (B) the
  Prospectus (except for the financial statements and notes thereto and the
  schedules and other financial or statistical data included therein or omitted
  therefrom, as to which counsel need express no opinion) at the time the
  Prospectus was issued, includes an untrue statement of a material fact or
  omitted state any material fact necessary in order to make the statements
  therein, in the light of the circumstances under which they were made, not
  misleading; also, that counsel has no reason to believe, based upon the
  procedures described above, that either the Registration Statement or the
  Prospectus (except for the financial statements and notes thereto and the
  schedules and other financial or statistical data included therein or omitted
  therefrom, as to which counsel need express no opinion) as of the date and
  time of delivery of counsel's opinion contain an untrue statement of a
  material fact or omit to state a material fact necessary to make the
  statements therein, in light of the circumstances in which they were made,
  not misleading.





<PAGE>   24
                                                                              24


   In rendering their opinion as aforesaid, counsel may rely upon an opinion or
opinions, each dated the Closing Date, of other counsel retained by them,
Publishing or the Guarantor as to laws of any jurisdiction other than the
United States, the Commonwealth of Pennsylvania or the Delaware General
Corporation Law, provided that (1) each such local counsel is acceptable to the
Underwriters, (2) such reliance is expressly authorized by each opinion so
relied upon and a copy of each such opinion is delivered to the Underwriters
and is, in form and substance, satisfactory to the Underwriters and their
counsel, and (3) counsel shall state in their opinion that they believe that
they and the Underwriters are justified in relying thereon.  Counsel may also
rely, to the extent they deem such reliance proper, as to matters of fact upon
certificates of officers of Publishing or the Guarantor and of government
officials.  Copies of all such certificates shall be furnished to counsel to
the Underwriters on the Closing Date.  Such opinion may state that it is
limited to the laws of the Commonwealth of Pennsylvania (excluding the conflict
of laws rules), the Delaware Business Corporation Law and the Federal
securities laws of the United States, and that such counsel expresses no
opinion as to any other laws (except with respect to the Indenture, as to which
such counsel will express certain opinions under New York law) and further that
such opinions are being given as if the Purchase Agreement was governed by
Pennsylvania law.

   (d)  You shall have received on the Closing Date an opinion of Clifford
Chance, special English counsel for the Guarantor, dated the Closing Date and
addressed to you, to the effect that:

   (i)  Each of Publishing's subsidiaries, DT Holdings Limited ("DTH"), First
  DT Holdings Limited ("FDTH") and The Telegraph, is a corporation duly
  incorporated and validly existing under the laws of England, with corporate
  power and authority to own or lease its properties and to conduct its
  business as described in the Registration Statement and the Prospectus.

   (ii)  All the issued shares in the capital of DTH, FDTH and The Telegraph
  have been duly authorized, validly issued and credited as fully paid.

   (iii)  Neither the offer, sale or delivery of the Securities, the
  execution, delivery or performance of this Agreement, compliance by
  Publishing or the Guarantor with the provisions of this Agreement or the
  Indenture, nor consummation by Publishing or the Guarantor of the
  transactions contemplated hereby


<PAGE>   25
                                                                              25


  (i) violates the memorandum or articles of association of DTH, FDTH or The
  Telegraph or (ii) constitutes a breach of or default by FDTH, DTH or The
  Telegraph under any agreement listed on Schedule III hereto to which DTH,
  FDTH or The Telegraph is a party or by which they are bound, or is material
  and is known to such counsel, or (iii) violates any existing English law,
  regulation, ruling, judgment, injunction, order or decree known to such
  counsel that names DTH, FDTH or The Telegraph or is specifically directed to
  DTH, FDTH or The Telegraph or their properties in England and would, in the
  case of this clause (iii), have a material adverse effect on the condition
  (financial or other), business, properties, net worth or results of
  operations of Publishing, the Guarantor and their subsidiaries considered as
  one enterprise.

   (iv)  The statements in the Registration Statement and Prospectus with
  respect to DTH, FDTH and The Telegraph and English law, insofar as they are
  descriptions of agreements listed on Schedule III hereto or are statements of
  law or legal conclusions with respect thereto, are accurate in all material
  respects and present fairly the information required to be shown.

   (v)  Argsub Limited is a corporation duly incorporated and validly existing
  under the laws of England, with corporate power and authority to own or lease
  its properties and to conduct its business as described in the Prospectus;
  all the issued preference shares in the capital of Argsub Limited of the
  series issued to DTH in exchange for the FDTH Preference Shares previously
  held by DTH have been duly authorized and validly issued.

   In rendering their opinion as aforesaid, counsel's opinion shall be limited
to the laws of England; provided that such counsel may rely upon an opinion or
opinions, each dated the Closing Date, of other counsel retained by them or
Publishing as to laws of any jurisdiction other than England, provided that (1)
each such local counsel is acceptable to the Underwriters, (2) such reliance is
expressly authorized by each opinion so relied upon and a copy of each such
opinion is delivered to the Underwriters and is, in form and substance
satisfactory to the Underwriters and their counsel, and (3) counsel shall state
in their opinion that they believe that they and the Underwriters are justified
in relying thereon.

   (d)  You shall have received on the Closing Date an opinion of Tory Tory
DesLauriers & Binnington,        ],


<PAGE>   26
                                                                              26


special Canadian counsel for the Publishing, dated the Closing Date and
addressed to you, to the effect that:

    (i)  Southam Inc. is a corporation duly incorporated and validly existing
  under the laws of Canada, with corporate power and authority to own or lease
  its properties and to conduct its business as described in the Registration
  Statement and the Prospectus.

    (ii)  Neither the offer, sale or delivery of the Securities, the
  execution, delivery or performance of this Agreement, compliance by
  Publishing or the Guarantor with the provisions of this Agreement or the
  Indenture, nor consummation by Publishing or the Guarantor of the
  transactions contemplated hereby (i) violates the memorandum or articles of
  association of Southam Inc. or (ii)  violates any existing Canadian law,
  regulation, ruling, judgment, injunction, order or decree known to such
  counsel that names Southam Inc. or its properties in Canada and would, in the
  case of this clause (ii), have a material adverse effect on the condition
  (financial or other), business, properties, net worth or results of
  operations of Publishing, the Guarantor and their subsidiaries considered as
  one enterprise.

   In rendering their opinion as aforesaid, counsel's opinion shall be limited
to the laws of Canada; provided that such counsel may rely upon an opinion or
opinions, each dated the Closing Date, of other counsel retained by them or
Publishing as to laws of any jurisdiction other than Canada, provided that (1)
each such local counsel is acceptable to the Underwriters, (2) such reliance is
expressly authorized by each opinion so relied upon and a copy of each such
opinion is delivered to the Underwriters and is, in form and substance
satisfactory to the Underwriters and their counsel, and (3) counsel shall state
in their opinion that they believe that they and the Underwriters are justified
in relying thereon.

   (f)  You shall have received letters addressed to you dated the date hereof
and the Closing Date from KPMG Peat Marwick, independent certified public
accountants for Publishing and the Guarantor, substantially in the forms
heretofore approved by you.

   (g)  You shall have received on the Closing Date an opinion of Cravath,
Swaine & Moore, counsel for the Underwriters, dated the Closing Date and
addressed to you, the Underwriters, as to such matters as you may reasonably
request.


<PAGE>   27
                                                                              27



   (h)  At the Closing Date and at each Date of Delivery, if any, counsel for
the Underwriters shall have been furnished with such documents and opinions as
they may require for the purpose of enabling them to pass upon the issuance and
sale of the Securities as herein contemplated and related actions referred to
in subparagraphs (h), (i) and (k) hereof, or in order to evidence the accuracy
of any of the representations or warranties, or the fulfillment of any of the
conditions, herein contained; and all proceedings taken by Publishing and the
Guarantor in connection with the issuance and sale of the Securities as herein
contemplated shall be satisfactory in form and substance to the Underwriters
and counsel for the Underwriters.

   (i)  At the Closing Date, Southam Inc. and Hollinger Eastern Publishing Inc.
shall qualify as Subsidiaries as defined in the Senior Subordinated Indenture.

   (j)  At the Closing Date, Publishing shall have issued a notice of
redemption with respect to each of the DTH and FDTH Preference Shares held by
third parties.

   (k)  At the Closing Date, Publishing shall deposit in escrow an amount
sufficient to pay the aggregate redemption price of the DTH and FDTH Preference
Shares held by third parties.

   SECTION 6.  Indemnification.  (a)  Publishing and the Guarantor agree,
jointly and severally, to indemnify and hold harmless the Underwriters and each
person, if any, who controls the Underwriters within the meaning of Section 15
of the 1933 Act to the extent and in the manner set forth in clauses (i), (ii)
and (iii) below:

   (i) against any and all loss, liability, claim, damage and expense
  whatsoever, as incurred, arising out of any untrue statement or alleged
  untrue statement of a material fact contained in the Registration Statement
  (or any amendment thereto), including the information deemed to be part of
  the Registration Statement pursuant to Rule 430A of the 1933 Act Regulations,
  if applicable, and any information contained in a Rule 462(b) Registration
  Statement or any amendments thereto, or the omission or alleged omission
  therefrom of a material fact necessary to make the statements therein, in
  light of the circumstances under which they were made, not misleading or
  arising out of any untrue statement or alleged untrue statement of a material
  fact contained in any preliminary prospectus or the Prospectus (or any
  amendment or supplement thereto) or the omission or alleged omission
  therefrom of a





<PAGE>   28
                                                                              28


  material fact necessary in order to make the statements therein, in the light
  of the circumstances under which they were made, not misleading;

   (ii) against any and all loss, liability, claim, damage and expense
  whatsoever, as incurred, to the extent of the aggregate amount paid in
  settlement of any litigation, or any investigation or proceeding by any
  governmental agency or body, commenced or threatened, or of any claim
  whatsoever based upon any such untrue statement or omission, or any such
  alleged untrue statement or omission, if such settlement is effected with the
  written consent of Publishing and the Guarantor; and

   (iii) against any and all expense whatsoever, as incurred (including,
  subject to Section 6(c) hereof, the fees and disbursements of counsel chosen
  by the Underwriters, reasonably incurred in investigating, preparing or
  defending against any litigation, or any investigation or proceeding by any
  governmental agency or body, commenced or threatened, or any claim whatsoever
  based upon any such untrue statement or omission, or any such alleged untrue
  statement or omission, to the extent that any such expense is not paid under
  (i) and (ii) above;

provided, however, that this indemnity agreement shall not apply to any loss,
liability, claim, damage or expense to the extent arising out of any untrue
statement or omission or alleged untrue statement or omission made in reliance
upon and in conformity with written information furnished to Publishing or the
Guarantor by the Underwriters expressly for use in the Registration Statement
(or any amendment thereto) or any preliminary prospectus or the Prospectus (or
any amendment or supplement thereto); and the parties agree that the statements
set forth in the last paragraph on the cover page, the legends on the inside
cover page, and the statements in the second and fourth paragraphs (except for
the first sentence of the fourth paragraph) under the caption "Underwriting" in
the Prospectus constitute the only information so furnished.

   (b)  Publishing and the Guarantor also agree, jointly and severally, to
indemnify and hold harmless the Independent Underwriter and each person, if
any, who controls the Independent underwriter within the meaning of either
Section 15 of the 1993 Act or Section 20 of the 1934 Act, from and against any
and all losses, claims, damages, liabilities and judgements incurred as a
result of the Independent Underwriter's participation as a "qualified
independent underwriter" within the meaning of Schedule E to





<PAGE>   29
                                                                              29


the By-laws of the National Association of Securities Dealers, Inc. in
connection with the offering of the Securities, except for any losses, claims,
damages, liabilities and judgments resulting from the independent Underwriter
or such controlling person's willful misconduct or gross negligence.

   (c)  Each Underwriter severally agrees to indemnify and hold harmless
Publishing and the Guarantor, their directors, each of their officers who
signed the Registration Statement, and each person, if any, who controls
Publishing or the Guarantor within the meaning of Section 15 of the 1933 Act
against any and all loss, liability, claim, damage and expense described in the
indemnity contained in subsection (a) of this Section, as incurred, but only
with respect to untrue statements or omissions, or alleged untrue statements or
omissions made in the Registration Statement (or amendment thereto) or any
preliminary prospectus or the Prospectus (or any amendment or supplement
thereto) in reliance upon and in conformity with written information furnished
to Publishing or the Guarantor by the Underwriters expressly for use in the
Registration Statement (or any amendment thereto) or such preliminary
prospectus or the Prospectus (or any amendment or supplement thereto) and set
forth in the last paragraph on the cover page, the stabilization legends on the
inside cover page, and the statements in the second and fourth paragraph
(except for the first sentence of the fourth paragraph) under the caption
"Underwriting" in the Prospectus.

   (d)  Each indemnified party shall give notice as promptly as reasonably
practicable to each indemnifying party of any action commenced against it in
respect of which indemnity may be sought hereunder, but failure to so notify an
indemnifying party shall not relieve such indemnifying party from any liability
which it may have otherwise than on account of this indemnity agreement.  An
indemnifying party may participate at its own expense in the defense of any
such action.  In no event shall the indemnifying parties be liable for fees and
expenses of more than one counsel (in addition to any local counsel) separate
from their own counsel for all indemnified parties in connection with any one
action or separate but similar or related actions in the same jurisdiction
arising out of the same general allegations or circumstances; provided, that,
if indemnity is sought pursuant to Section 6(b), then, in addition to such
counsel for the indemnified parties, the indemnifying party shall be liable for
the reasonable fees and expenses of not more than one separate counsel (in
addition to any necessary local counsel) for the Independent underwriter in its
capacity as a "qualified independent underwriter" and





<PAGE>   30
                                                                              30


all persons, if any, who control the Independent Underwriter within the meaning
of Section 15 of the 1993 Act or Section 20 of the 1934 Act if, in the
reasonable judgment of the Independent Underwriter there may exist a conflict
of interest between the Independent Underwriter and the other indemnified
parties.  In the case of any such separate counsel for the Independent
Underwriter and such control person of the Independent Underwriter, such
counsel shall be designated in writing by the Independent Underwriter.

   SECTION 7.  Contribution.  In order to provide for just and equitable
contribution in circumstances in which an indemnity agreement provided for in
Section 6 is for any reason held to be unenforceable by the indemnified parties
although applicable in accordance with its terms, Publishing and the Guarantor
on the one hand and the Underwriters on the other hand shall contribute to the
aggregate losses, liabilities, claims, damages and expenses of the nature
contemplated by such indemnity incurred by Publishing and the Guarantor on the
one hand and the Underwriters on the other hand, as incurred, in such
proportions that (a) the Underwriters are responsible for that portion
represented by the percentage that the underwriting commission appearing on the
cover page of the Prospectus bears to the aggregate stated principal amount
appearing thereon, and (b) Publishing and the Guarantor are responsible for the
balance; provided, however, that no person guilty of fraudulent
misrepresentation (within the meaning of Section 11(f) of the 1933 Act) shall
be entitled to contribution from any person who was not guilty of such
fraudulent misrepresentation.  For purposes of this Section, each person, if
any, who controls the Underwriters within the meaning of Section 15 of the 1933
Act shall have the same rights to contribution as the Underwriters, and each
director of each of Publishing and the Guarantor, each officer of Publishing or
the Guarantor who signed the Registration Statement, and each person, if any,
who controls Publishing or the Guarantor within the meaning of Section 15 of
the 1933 Act shall have the same rights to contribution as Publishing or the
Guarantor.

   Publishing, the Guarantor and the Underwriters agree that Merrill Lynch,
Pierce, Fenner 7 Smith Incorporated will not receive any additional benefits
hereunder for serving as the Independent Underwriter in connection with the
offering and sale of Securities.

   SECTION 8.  Representations, Warranties and Agreements to Survive Delivery.
All representations, warranties and agreements contained in this Agreement and
the Price Determination Agreement, or contained in certificates of officers of
Publishing or the Guarantor





<PAGE>   31
                                                                              31


submitted pursuant hereto, shall remain operative and in full force and effect,
regardless of any investigation made by or on behalf of any Underwriters or
controlling person, or by or on behalf of Publishing or the Guarantor, and
shall survive delivery of the Securities to the Underwriters.

   SECTION 9.  Termination of Agreement.  (a)  The Underwriters may terminate
this Agreement by notice to Publishing or the Guarantor at any time at or prior
to the Closing Date (i) if there has been, since the date of this Agreement or
since the respective date as of which information is given in the Prospectus,
any material adverse change in the condition, financial or otherwise, or in the
earnings, business affairs or business prospects of Publishing, the Guarantor
and their subsidiaries considered as one enterprise, whether or not arising in
the ordinary course of business, or (ii) if there has occurred any outbreak of
hostilities or escalation thereof or other calamity or crisis, the effect of
which on the financial markets of the United States is such as to make it, in
the judgment of the Underwriters, impracticable to market the Securities or to
enforce contracts for the sale of the Securities, or (iii) if trading in the
Common Stock of the Guarantor has been suspended by the Commission, or if
trading generally on either the American Stock Exchange or the New York Stock
Exchange has been suspended, or minimum or maximum prices for trading have been
fixed, or maximum ranges for prices for securities have been required, by
either of said Exchanges or by order of the Commission or any other
governmental authority, or if a banking moratorium has been declared by either
Federal or New York authorities.  Notice of such termination may be given by
telegram, telecopy or telephone and shall be subsequently confirmed by letter.
As used in this Section 10(a), the term "Prospectus" means the Prospectus in
the form first used to confirm sales of the Securities.

   (b)  If this Agreement is terminated pursuant to this Section, such
termination shall be without liability of any party to any other party except
as provided in Section 4.  Notwithstanding any such termination, the provisions
of Sections 6 and 7 shall remain in effect.

   SECTION 10.  Default by One or More of the Underwriters.  If one or more of
the Underwriters shall fail at the Closing Date to purchase the Securities that
it or they are obligated to purchase pursuant to this Agreement (the "Defaulted
Securities"), you shall have the right, within 24 hours thereafter, to make
arrangements for one or more of the non-defaulting Underwriters, or any other
underwriters, to purchase all, but not less than all, of the Defaulted
Securities in such amounts as may be agreed upon





<PAGE>   32
                                                                              32


and upon the terms set forth in this Agreement; if, however, you have not
completed such arrangements within such 24-hour period, then:

   (a) if the number of Defaulted Securities does not exceed 10% of the
  aggregate principal amount of the Securities, the nondefaulting Underwriters
  shall be obligated to purchase the full amount thereof in the proportions
  that their respective Securities underwriting obligation proportions bear to
  the underwriting obligation proportions of all non-defaulting Underwriters,
  or

   (b) if the number of Defaulted Securities exceeds 10% of the aggregate
  principal amount of the Securities, this Agreement shall terminate without
  liability on the part of any nondefaulting Underwriters.

   No action taken pursuant to this Section 10 shall relieve any defaulting
Underwriter from liability in respect of its default.

   In the event of any such default that does not result in a termination of
this Agreement, either you or the Company shall have the right to postpone the
Closing Date for a period not exceeding seven days in order to effect any
required changes in the Registration Statement or Prospectus or in any other
documents or arrangements.  As used herein, the term "Underwriters" includes
any person substituted for an Underwriter under this Section 10.

   SECTION 11.  Default by Publishing.  If Publishing shall fail at the Closing
Date or at the Date of Delivery to sell and deliver the number of Securities
which it is obligated to sell hereunder, then this Agreement shall terminate
without any liability on the part of any non-defaulting party.

   No action taken pursuant to this Section shall relieve Publishing from
liability, if any, in respect of such default.

   SECTION 12.  Notices.  Unless otherwise specifically indicated herein, all
notices and other communications hereunder shall be in writing and shall be
deemed to have been duly given if mailed or transmitted by any standard form of
telecommunication.  Notices to the Underwriters shall be directed to Merrill
Lynch at Merrill Lynch World Headquarters, North Tower, World Financial Center,
New York, New York 10281, attention of Syndicate Operations; notices to
Publishing shall be directed to it at


<PAGE>   33
                                                                              33


401 North Wabash Avenue, Chicago, Illinois 60611, attention of President or
Secretary; and notices to the Guarantor shall be directed to it at 401 North
Wabash Avenue, Chicago, Illinois 60611, attention of President or Secretary.

   SECTION 13.  Parties.  This Agreement and the Price Determination Agreement
shall each inure to the benefit of and be binding upon the Underwriters and
Publishing and the Guarantor and their respective successors, heirs and legal
representatives.  Nothing expressed or mentioned in this Agreement or the Price
Determination Agreement is intended or shall be construed to give any person,
firm or corporation, other than the Underwriters and Publishing and the
Guarantor and their respective successors, heirs and legal representatives, and
the controlling persons and officers and directors referred to in Sections 6
and 7 hereof and their heirs and legal representatives, any legal or equitable
right, remedy or claim under or in respect of this Agreement or the Price
Determination Agreement or any provision herein or therein contained.  This
Agreement and the Price Determination Agreement and all conditions and
provisions hereof and thereof are intended to be for the sole and exclusive
benefit of the Underwriters, Publishing and the Guarantor and their respective
successors, heirs and legal representatives and said controlling persons and
officers and directors and their heirs and legal representatives, and for the
benefit of no other person, firm or corporation.  No purchaser of Securities
from the Underwriters shall be deemed to be a successor by reason merely of
such purchase.

   SECTION 14.  Governing Law and Time.  This Agreement and the Price
Determination Agreement shall be governed by and construed in accordance with
the laws of the State of New York applicable to agreements made and to be
performed in said State.  Specified times of day refer to New York City time.

   If the foregoing is in accordance with your understanding of our agreement,
please sign and return to Publishing and the Guarantor a counterpart hereof,
whereupon





<PAGE>   34
                                                                              34


this instrument, along with all counterparts, will become a binding agreement
among the Underwriters, Publishing and the Guarantor in accordance with its
terms.


                                     Very truly yours,

                                     HOLLINGER INTERNATIONAL PUBLISHING INC.

                                     by
                                        ___________________________________
                                        Kenneth L. Serota
                                        Vice President and
                                        Secretary



                                     HOLLINGER INTERNATIONAL INC.
                
                                     by
                                        ___________________________________
                                        Kenneth L. Serota
                                        Vice President and
                                        Secretary


<PAGE>   35
                                                                              35


Confirmed and accepted as of
  the date first above written:


MERRILL LYNCH & CO.
  Merrill Lynch, Pierce,
  Fenner & Smith Incorporated

DONALDSON, LUFKIN & JENRETTE
  SECURITIES CORPORATION

TD SECURITIES (USA) INC.

BEAR, STEARNS & CO. INC.

CIBC WOOD GUNDY SECURITIES CORP.

By:  MERRILL LYNCH & CO.
       Merrill Lynch, Pierce,
       Fenner & Smith Incorporated


     by ___________________________


<PAGE>   36
                                                                       Exhibit A
                            HOLLINGER INTERNATIONAL
                                PUBLISHING INC.
                            (a Delaware corporation)


                          HOLLINGER INTERNATIONAL INC.
                            (a Delaware corporation)



                                  $290,000,000
                   9-1/4% Senior Subordinated Notes due 2007

                         PRICE DETERMINATION AGREEMENT





                                                                  March 12, 1997




MERRILL LYNCH & CO.
  Merrill Lynch, Pierce, Fenner & Smith
Incorporated
DONALDSON, LUFKIN & JENRETTE SECURITIES
  CORPORATION
TD SECURITIES (USA) INC.
BEAR, STEARNS & CO. INC.
CIBC WOOD GUNDY SECURITIES INC.
c/o MERRILL LYNCH & CO.
Merrill Lynch, Pierce, Fenner & Smith
  Incorporated
Merrill Lynch World Headquarters
North Tower
World Financial Center
New York, New York 10281-1201

Ladies and Gentlemen:

   Reference is made to the Purchase Agreement dated March 12, 1997 (the
"Purchase Agreement") among Hollinger International Publishing Inc., a Delaware
corporation ("Publishing"), Hollinger International Inc. (the "Guarantor") and
Merrill Lynch & Co., Merrill Lynch, Pierce,





<PAGE>   37
                                                                               2


Fenner & Smith Incorporated, Donaldson, Lufkin & Jenrette Securities
Corporation, TD Securities (USA) Inc., Bear, Stearns & Co. Inc. and CIBC Wood
Gundy Securities Corp. (the "Underwriters").  The Purchase Agreement provides
for the purchase by the Underwriters from Publishing, subject to the terms and
conditions set forth therein, of $290,000,000 aggregate principal amount of
Publishing's 9-1/4% Senior Subordinated Notes due 2007 (the "Securities").
This Agreement is the Price Determination Agreement referred to in the Purchase
Agreement.

   Pursuant to Section 2 of the Purchase Agreement, the undersigned agrees with
the Underwriters as follows:

     1.  The initial public offering price of the Securities shall be 96.358%
   of the aggregate stated principal amount thereof, plus accrued interest from
   March 18, 1997 to the Closing Time.

     2.  The purchase price of the Securities to be paid by the several
   Underwriters shall be 96.608% of the aggregate stated principal amount
   thereof, plus accrued interest from March 18, 1997 to the Closing Time.

     3.  The interest rate to be borne by the Securities shall be 9-1/4% per
   annum.

     4.  The Securities will mature on March 15, 2007.

     5.  The optional redemption prices (to be supplied on page S-41 of the
   Prospectus (and correspondingly in the Indenture)) shall be equal to the
   percentage of the principal amount set forth below if redeemed during the
   12-month period beginning March 12, 1997 for the years indicated:

<TABLE>
<CAPTION>
                                              Redemption
               Year                              Price  
               ----                            ---------
               <S>                             <C>
               2002                            104.625%

               2003                            103.083%

               2004                            101.541%
</TABLE>


<PAGE>   38
                                                                               3


   and thereafter at 100% of the principal amount, together in the case of any
   such redemption with accrued and unpaid interest to the redemption date.

   Publishing and the Guarantor represent and warrant to each of the
Underwriters that the representations and warranties of Publishing and the
Guarantor set forth in Section 1(a) of the Purchase Agreement are accurate as
though expressly made at and as of the date hereof.

   THIS AGREEMENT SHALL BE GOVERNED BY THE LAWS OF THE STATE OF NEW YORK.

   If the foregoing is in accordance with your understanding of our agreement,
please sign and return to Publishing and the Guarantor a counterpart hereof,
whereupon this instrument along with all counterparts and together with the
Purchase Agreement shall be a binding agreement among the Underwriters and
Publishing and the Guarantor in accordance with its terms and the terms of the
Purchase Agreement.

                                        Very truly yours,


                                        HOLLINGER INTERNATIONAL PUBLISHING INC.


                                        By____________________________
                                          Kenneth L. Serota
                                          Vice President and
                                          Secretary


                                        HOLLINGER INTERNATIONAL INC.


                                        By____________________________
                                          Kenneth L. Serota
                                          Vice President and
                                          Secretary


<PAGE>   39
                                                                               4


Confirmed and accepted as of
  the date first above written:


MERRILL LYNCH & CO.
  Merrill Lynch, Pierce, Fenner & Smith
              Incorporated

DONALDSON, LUFKIN & JENRETTE
  SECURITIES CORPORATION

TD SECURITIES (USA) INC.

BEAR, STEARNS & CO. INC.

CIBC WOOD GUNDY SECURITIES CORP.

By:  MERRILL LYNCH & CO.
       Merrill Lynch, Pierce, Fenner & Smith
                   Incorporated


     By______________________________________


<PAGE>   40
                                   SCHEDULE I


<TABLE>
<CAPTION>
                                                                Principal Amount
                                                                 of Securities
                    Underwriters                                to Be Purchased 
                    ------------                                ----------------
 <S>                                                              <C> 
 Merrill Lynch, Pierce, Fenner & Smith Incorporated  . . . .      $145,000,000

 Donaldson, Lufkin, Jenrette
   Securities Corporation  . . . . . . . . . . . . . . . . .        43,500,000

 TD Securities
   (USA) Inc.  . . . . . . . . . . . . . . . . . . . . . . .        43,500,000

 Bear, Stearns & Co. Inc.  . . . . . . . . . . . . . . . . .        29,000,000

 CIBC Wood Gundy Securities Corp.. . . . . . . . . . . . . .        29,000,000


 Total . . . . . . . . . . . . . . . . . . . . . . . . . . .      $290,000,000
                                                                  ============
</TABLE>


<PAGE>   41
                                  SCHEDULE II


            Significant Subsidiaries of Hollinger International Inc.
                  and Hollinger International Publishing Inc.

 
 1. Hollinger International Publishing Inc. is incorporated in Delaware and 
    is a wholly owned subsidiary of Hollinger International Inc.

 2. The Sun-Times Company is incorporated in Delaware and is a wholly owned
    subsidiary of Hollinger International Publishing Inc.

 3. Chicago Sun-Times, Inc. is incorporated in Delaware and is a wholly owned
    subsidiary of The Sun-Times Company.

 4. American Publishing Company is incorporated in Delaware and is a wholly
    owned subsidiary of Hollinger International Publishing Inc.

 5. American Publishing (1991) Inc. is incorporated in Delaware and is a
    subsidiary of American Publishing Company.

 6. American Publishing Holdings Inc. is incorporated in Delaware and is a
    wholly owned subsidiary of American Publishing Company.

 7. APAC-95 Inc. is incorporated in Delaware and is a wholly owned subsidiary of
    American Publishing Company.

 8. TelHoldco Inc. is incorporated in Delaware and is a wholly owned subsidiary
    of Hollinger International Publishing Inc.

 9. DT Holdings Limited is an English company and is a wholly owned subsidiary
    (excluding preference shares) of Hollinger International Publishing Inc.

10. First DT Holdings Limited is an English company and is a wholly owned
    subsidiary (excluding preference shares) of DT Holdings Limited.

11. Telegraph Group Limited plc is an English company and a subsidiary of
    First DT Holdings Limited.

12. Southam Inc.

<PAGE>   1





                                                                    EXHIBIT 4.01





                    HOLLINGER INTERNATIONAL PUBLISHING INC.

                          8-5/8% Senior Notes due 2005


                         Unconditionally Guaranteed by

                          HOLLINGER INTERNATIONAL INC.

                        ________________________________


                                   INDENTURE


                           Dated as of March 18, 1997


                        _______________________________


                              FLEET NATIONAL BANK,

                                    Trustee
<PAGE>   2



                               TABLE OF CONTENTS

<TABLE>
<CAPTION>
                                                                                                       Page
                                                                                                       ----
<S>                                                                                                      <C>
PARTIES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  1
RECITALS  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  1

                                                 ARTICLE I

                           Definitions and Other Provisions of General Application
                           -------------------------------------------------------

SECTION 1.01.  Definitions  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  2
SECTION 1.02.  Other Definitions  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36
SECTION 1.03.  Compliance Certificates and Opinions   . . . . . . . . . . . . . . . . . . . . . . . . . 37
SECTION 1.04.  Form of Documents Delivered to Trustee   . . . . . . . . . . . . . . . . . . . . . . . . 38
SECTION 1.05.  Acts of Holders  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
SECTION 1.06.  Notices, etc., to Trustee and Publishing   . . . . . . . . . . . . . . . . . . . . . . . 40
SECTION 1.07.  Notice to Holders; Waiver  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40
SECTION 1.08.  Conflict with Trust Indenture Act  . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
SECTION 1.09.  Effect of Headings and Table of Contents   . . . . . . . . . . . . . . . . . . . . . . . 41
SECTION 1.10.  Successors and Assigns   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
SECTION 1.11.  Separability Clause  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
SECTION 1.12.  Benefits of Indenture  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
SECTION 1.13.  Governing Law  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
SECTION 1.14.  Legal Holidays   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
SECTION 1.15.  Schedules  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42
SECTION 1.16.  Counterparts   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42


                                                 ARTICLE II

                                               Security Forms
                                               --------------

SECTION 2.01.  Forms Generally  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42
SECTION 2.02.  Forms of Securities  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42
SECTION 2.03.  Form of Trustee's Certificate
  of Authentication . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43
SECTION 2.04.  Form of Guarantee of Hollinger
  International . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43
SECTION 2.05.  Securities Issuable in the Form
  of a Global Security  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44
</TABLE>
<PAGE>   3

<TABLE>
<CAPTION>
                                                                                                      PAGE
                                                                                                      ----
<S>                                                                                                     <C>
                                          ARTICLE III

                                         The Securities
                                         --------------

SECTION 3.01.  General Title; General Limitations;
  Issuable in Series; Terms of
  Particular Series . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
SECTION 3.02.  Denominations  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
SECTION 3.03.  Execution, Authentication, Delivery
  and Dating  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
SECTION 3.04.  Temporary Securities   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51
SECTION 3.05.  Registration, Registration of Transfer
  and Exchange  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51
SECTION 3.06.  Mutilated, Destroyed, Lost and
  Stolen Securities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53
SECTION 3.07.  Payment of Interest; Interest
  Rights Preserved  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 54
SECTION 3.08  Persons Deemed Owners . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
SECTION 3.09.  Cancellation   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
SECTION 3.10.  Computation of Interest  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56
SECTION 3.11.  Delayed Issuance of Securities   . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56


                                               ARTICLE IV

                                   Defeasance and Covenant Defeasance
                                   ----------------------------------

SECTION 4.01.  Publishing's Option to Effect
  Defeasance or Covenant Defeasance . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57
SECTION 4.02.  Defeasance and Discharge   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57
SECTION 4.03.  Covenant Defeasance  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
SECTION 4.04.  Conditions to Defeasance or
  Covenant Defeasance . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
SECTION 4.05.  Deposited Money and U.S. Government
  Obligations to Be Held in Trust; Other Miscellaneous Provisions . . . . . . . . . . . . . . . . . . . 61
SECTION 4.06.  Reinstatement  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61
</TABLE>


                                       ii
<PAGE>   4



<TABLE>
<CAPTION>
                                                                                                      PAGE
                                                                                                      ----
<S>                                                                                                     <C>
                                              ARTICLE V

                                              Remedies
                                              --------

SECTION 5.01.  Events of Default  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 62
SECTION 5.02.  Acceleration of Maturity; Rescission
  and Annulment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
SECTION 5.03.  Collection of Indebtedness and Suits
  for Enforcement by Trustee  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66
SECTION 5.04.  Trustee May File Proofs of Claim   . . . . . . . . . . . . . . . . . . . . . . . . . . . 66
SECTION 5.05.  Trustee May Enforce Claims Without
  Possession of Securities  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67
SECTION 5.06.  Application of Money Collected   . . . . . . . . . . . . . . . . . . . . . . . . . . . . 68
SECTION 5.07.  Limitation on Suits  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 68
SECTION 5.08.  Unconditional Right of Holders
  to Receive Principal, Premium
  and Interest  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69
SECTION 5.09.  Restoration of Rights and Remedies   . . . . . . . . . . . . . . . . . . . . . . . . . . 69
SECTION 5.10.  Rights and Remedies Cumulative   . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69
SECTION 5.11.  Delay or Omission Not Waiver   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70
SECTION 5.12.  Control by Holders   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70
SECTION 5.13.  Waiver of Past Defaults  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70
SECTION 5.14.  Undertaking for Costs  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71
SECTION 5.15.  Waiver of Stay, Extension or Usury Laws  . . . . . . . . . . . . . . . . . . . . . . . . 71
SECTION 5.16.  Remedies Subject to Applicable Law   . . . . . . . . . . . . . . . . . . . . . . . . . . 71


                                               ARTICLE VI

                                               The Trustee
                                               -----------

SECTION 6.01.  Duties of Trustee  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 72
SECTION 6.02.  Notice of Defaults   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
SECTION 6.03.  Certain Rights of Trustee  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
SECTION 6.04.  Trustee Not Responsible for Recitals,
  Dispositions of Securities or Application of Proceeds Thereof . . . . . . . . . . . . . . . . . . . . 75
SECTION 6.05.  Trustee and Agents May Hold Securities; Collections; etc.  . . . . . . . . . . . . . . . 75
SECTION 6.06.  Money Held in Trust  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
SECTION 6.07.  Compensation and Indemnification of
  Trustee and Its Prior Claim . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 76
SECTION 6.08.  Conflicting Interests  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
SECTION 6.09.  Corporate Trustee Required; Eligibility  . . . . . . . . . . . . . . . . . . . . . . . . 77
SECTION 6.10.  Resignation and Removal; Appointment
  of Successor Trustee  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
SECTION 6.11.  Acceptance of Appointment by Successor   . . . . . . . . . . . . . . . . . . . . . . . . 79
SECTION 6.12.  Merger, Conversion, Consolidation or
  Succession to Business  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80
</TABLE>


                                      iii
<PAGE>   5



<TABLE>
<CAPTION>
                                                                                                      PAGE
                                                                                                      ----
<S>                                                                                                     <C>
SECTION 6.13.  Preferential Collection of Claims Against Publishing  . . . . , . . . . . . . . . . . . . 81


                                                ARTICLE VII

                           Holders' Lists and Reports by Trustee and Publishing
                           ----------------------------------------------------

SECTION 7.01.  Publishing to Furnish Trustee Names and
  Addresses of Holders  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81
SECTION 7.02.  Disclosure of Names and Addresses
  of Holders  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81
SECTION 7.03.  Reports by Trustee   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82
SECTION 7.04.  Reports by Publishing  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82


                                            ARTICLE VIII

                               Consolidation, Merger, Sale of Assets
                               -------------------------------------

SECTION 8.01.  Publishing May Merge, Consolidate,
  etc., Only on Certain Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 83
SECTION 8.02.  Successor Substituted  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85


                                              ARTICLE IX

                                        Supplemental Indentures
                                        -----------------------

SECTION 9.01.  Supplemental Indentures and
  Agreements Without Consent of Holders . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86
SECTION 9.02.  Supplemental Indentures and
  Agreements with Consent of Holders  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88
SECTION 9.03.  Execution of Supplemental Indentures and Agreements  . . . . . . . . . . . . . . . . . . 89
SECTION 9.04.  Effect of Supplemental Indentures  . . . . . . . . . . . . . . . . . . . . . . . . . . . 90
SECTION 9.05.  Conformity with Trust Indenture Act  . . . . . . . . . . . . . . . . . . . . . . . . . . 90
SECTION 9.06.  Reference in Securities to
  Supplemental Indentures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 90
SECTION 9.07.  Record Date  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 90


                                             ARTICLE X

                                             Covenants
                                             ---------

SECTION 10.01. Payment of Principal, Premium
  and Interest  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 91
SECTION 10.02. Maintenance of Office or Agency  . . . . . . . . . . . . . . . . . . . . . . . . . . . . 91
SECTION 10.03. Money for Security Payments
  To Be Held in Trust . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 91

</TABLE>


                                       iv
<PAGE>   6



<TABLE>
<CAPTION>
                                                                                                      PAGE
                                                                                                      ----
<S>                                                                                                    <C>
SECTION 10.04. Corporate Existence  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93
SECTION 10.05. Payment of Taxes and Other Claims  . . . . . . . . . . . . . . . . . . . . . . . . . . . 93
SECTION 10.06. Maintenance of Properties  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94
SECTION 10.07. Insurance  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94
SECTION 10.08. Limitation on Indebtedness   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94
SECTION 10.09. Limitation on Restricted Payments  . . . . . . . . . . . . . . . . . . . . . . . . . . . 95
SECTION 10.10. Limitation on Transactions
  with Affiliates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  101
SECTION 10.11. Limitation on Liens  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  102
SECTION 10.12. Limitation on Issuances of Guarantees
  of Indebtedness . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  103
SECTION 10.13. Limitation on Sale of Assets   . . . . . . . . . . . . . . . . . . . . . . . . . . . .  104
SECTION 10.14. Purchase of Securities upon a
  Change of Control . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  110
SECTION 10.15. Limitation on Issuance and Sale
  of Capital Stock of Restricted
  Subsidiaries  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  114
SECTION 10.16. Limitation on Dividends and Other
  Payment Restrictions Affecting
  Restricted Subsidiaries . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  116
SECTION 10.17. Provision of Financial Statements  . . . . . . . . . . . . . . . . . . . . . . . . . .  116
SECTION 10.18. Statement by Officers as to Default  . . . . . . . . . . . . . . . . . . . . . . . . .  117
SECTION 10.19. Waiver of Certain Covenants  . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  118
SECTION 10.20. Limitation on the Designation of
  Additional Restricted or Unrestricted Subsidiaries  . . . . . . . . . . . . . . . . . . . . . . . .  118


                                        ARTICLE XI

                                   Redemption of Securities
                                  ------------------------


                                         ARTICLE XII

                                    Satisfaction and Discharge
                                    --------------------------

SECTION 12.01  Satisfaction and Discharge of Indenture  . . . . . . . . . . . . . . . . . . . . . . .  118
SECTION 12.02. Application of Trust Money   . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  120


                                          ARTICLE XIII

                                            Guarantee
                                            ---------

SECTION 13.01. Hollinger International Guarantee  . . . . . . . . . . . . . . . . . . . . . . . . . .  120
SECTION 13.02. Continuing Guarantee; No Right
  of Set-Off; Independent Obligation  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  120
SECTION 13.03. Guarantee Absolute   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  121
SECTION 13.04. Right to Demand Full Performance   . . . . . . . . . . . . . . . . . . . . . . . . . .  124
</TABLE>


                                       v
<PAGE>   7



<TABLE>
<CAPTION>
                                                                                                      PAGE
                                                                                                      ----
<S>                                                                                                    <C>
SECTION 13.05. Waivers  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  124
SECTION 13.06. Hollinger International Remains
  Obligated in Event Publishing Is
  No Longer Obligated to Discharge
  Indenture Obligations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  125
SECTION 13.07. Waiver of Rights   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  125
SECTION 13.08. Guarantee Is in Addition to
  Other Security  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  125
SECTION 13.09. Release of Security Interests  . . . . . . . . . . . . . . . . . . . . . . . . . . . .  125
SECTION 13.10. No Bar to Further Actions  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  126
SECTION 13.11. Failure to Exercise Rights Shall
  Not Operate as a Waiver; No Suspension of Remedies  . . . . . . . . . . . . . . . . . . . . . . . .  126
SECTION 13.12. Trustee's Duties; Notice to Trustee  . . . . . . . . . . . . . . . . . . . . . . . . .  126
SECTION 13.13. Successors and Assigns   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  127
SECTION 13.14. Release of Guarantee   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  127
SECTION 13.15. Execution of Guarantee   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  128
SECTION 13.16. Payment Permitted by Hollinger
  International if No Default . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  128

SIGNATURES AND SEALS  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .  129

ACKNOWLEDGEMENTS

SCHEDULE I  Permitted Indebtedness
</TABLE>


                                       vi
<PAGE>   8




                             CROSS-REFERENCE TABLE

<TABLE>
<CAPTION>
TIA SECTION                                                                      INDENTURE SECTION
- -----------                                                                      -----------------
<S>  <C>                                                                               <C>
310  (a)(1)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.09
     (a)(2)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.09
     (a)(5)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.11; 6.12
     (b)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.08; 6.10
311  (a)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.13
     (b)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.13
312  (a)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          7.01
     (c)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          7.02
313  (a)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          7.03
     (c)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          7.03
314  (a)(1)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          7.04(a)
     (a)(2)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          7.04(b)
     (a)(3)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          7.04(c)
     (a)(4)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          10.18
     (c)(1)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          1.03
     (c)(2)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          1.03
     (e)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          1.03
315  (a)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.01(b)
     (b)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.02
     (c)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.01(a)
     (d)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          6.01(c)
     (e)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          5.14
316  (a) (last sentence)  . . . . . . . . . . . . . . . . . . . . . . . . . .          1.01 ("Outstanding")
     (a)(1)(A)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          5.12
     (a)(1)(B)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          5.13
     (b)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          5.08
     (c)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          9.07
317  (a)(1)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          5.03
     (a)(2)   . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          5.04
     (b)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          10.03
318  (a)  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          1.08
</TABLE>

______________________

Note:   This Cross-Reference Table shall not, for any purpose, be deemed to 
        be a part of the Indenture.


                                      vii
<PAGE>   9
                                  SENIOR INDENTURE, dated as of March 18, 1997,
                          among HOLLINGER INTERNATIONAL PUBLISHING INC., a
                          Delaware corporation (as more fully defined below,
                          "Publishing"), HOLLINGER INTERNATIONAL INC., a
                          Delaware corporation (as more fully defined below,
                          "Hollinger International") and FLEET NATIONAL BANK,
                          as trustee (the "Trustee").


                             RECITALS OF PUBLISHING

                 Publishing has duly authorized the execution and delivery of
this Indenture to provide for the issuance of its senior debentures, notes,
bonds or other evidences of indebtedness, to be issued in one or more series
pursuant to Article III hereof or a supplemental indenture (each a "Series" and
collectively the "Securities").

                 Hollinger International has duly authorized the issuance of a
guarantee (the "Guarantee") of the Securities, of substantially the tenor as
hereinafter set forth, and to provide therefor, Hollinger International has
duly authorized the execution and delivery of this Indenture in its capacity as
Guarantor hereunder.

                 This Indenture is subject to, and shall be governed by, the
provisions of the Trust Indenture Act that are required to be part of and to
govern indentures qualified under the Trust Indenture Act; and

                 All acts and things necessary have been done to make (i) the
Securities, when executed by Publishing and authenticated and delivered
hereunder and duly issued by Publishing, the valid obligations of Publishing
and (ii) this Indenture a valid agreement of Publishing and Hollinger
International in accordance with the terms of this Indenture.


                 NOW, THEREFORE, in consideration of the premises and the
purchase of the Securities by the Holders thereof,

<PAGE>   10

                                                                              2

it is mutually covenanted and agreed, for the equal and proportionate benefit of
all Holders of the Securities, as follows:


                                   ARTICLE I

            Definitions and Other Provisions of General Application

                 SECTION 1.01.  Definitions.  For all purposes of this
Indenture, except as otherwise expressly provided or unless the context
otherwise requires:

                 (a) the terms defined in this Article have the meanings
         assigned to them in this Article, and include the plural as well as
         the singular;

                 (b) all other terms used herein which are defined in the Trust
         Indenture Act, either directly or by reference therein, have the
         meanings assigned to them therein;

                 (c) all accounting terms not otherwise defined herein have the
         meanings assigned to them in accordance with GAAP;

                 (d) the words "herein", "hereof" and "hereunder" and other
         words of similar import refer to this Indenture as a whole and not to
         any particular Article, Section or other subdivision; and

                 (e) all references to $, US$, dollars or United States dollars
         shall refer to the lawful currency of the United States of America.

                 The following terms shall have the meanings set forth in this
Section:

                 "Acceleration Right" means a right, which at the time is
immediately exercisable (without further notice or lapse of time), by the
holders or a trustee to cause the acceleration of the maturity of Indebtedness
of Publishing or a Restricted Subsidiary having an aggregate principal amount
outstanding of at least $5,000,000; provided that this definition shall exclude
the rights of the holders of the existing preference shares of DTH and FDTH to
require that Restricted Subsidiaries or Affiliates purchase those shares
pursuant to the terms of the governing instruments or existing agreements
relating to such preference shares existing on January 1, 1997.

                 "Acquired Indebtedness" means Indebtedness of a Person
(including an Unrestricted Subsidiary) (i) existing at the time such Person
becomes a Restricted Subsidiary or (ii) assumed in connection with the
acquisition of assets from such Person, in each case, other than Indebtedness
Incurred in connection with, or in contemplation of, such Person becoming a
Restricted Subsidiary or such acquisition.

<PAGE>   11

                                                                              3

Acquired Indebtedness will be deemed to be Incurred on the date of the related 
acquisition of assets from any Person or the date the acquired Person becomes 
a Restricted Subsidiary.

                 "Affiliate" means, with respect to any specified Person, (i)
any other Person directly or indirectly controlling or controlled by or under
direct or indirect common control with such specified Person or (ii) any other
Person that owns, directly or indirectly, 10% or more of such Person's equity
ownership or Voting Stock or any officer or director of any such Person or
other Person or with respect to any natural Person, any person having a
relationship with such Person by blood, marriage or adoption not more remote
than first cousin.  For the purposes of this definition, "control" when used
with respect to any specified Person means the power to direct the management
and policies of such Person directly or indirectly, whether through ownership
of voting securities, by contract or otherwise; and the terms "controlling" and
"controlled" have meanings correlative to the foregoing.

                 "Agent" means the administrative agent under the New Bank
Credit Facility, and its successors and assigns in such capacity.

                 "Amortization Expense" of any Person means, for any period,
amounts recognized during such period as (i) amortization of goodwill or (ii)
amortization of any other intangible assets with an original life of ten years
or more, in each case in accordance with GAAP and to the extent reflected in
the Consolidated Net Income of Publishing and the Restricted Subsidiaries;
provided, however, that in determining the aggregate cumulative Amortization
Expense of Publishing and its Restricted Subsidiaries for purposes of Section
10.09 following the date on which both of The Telegraph and Southam are
Restricted Subsidiaries, the Amortization Expense of Restricted Subsidiaries
that are not Wholly Owned Restricted Subsidiaries shall be determined in
accordance with the actual percentage of Publishing's common equity in such
Restricted Subsidiary on the date of the transaction necessitating the
determination (thus, for example, in the case of a Restricted Subsidiary in
which Publishing owns a 51% common equity interest on the date of the
Restricted Payment, 51% of such Restricted Subsidiary's Amortization Expense
would be included in the calculation of the aggregate cumulative Amortization
Expense of Publishing and the Restricted Subsidiaries).

                 "AP-91" means American Publishing (1991) Inc., a wholly owned,
indirect Subsidiary.

<PAGE>   12

                                                                             4

                 "AP-91 Senior Notes" means the $150 million in senior secured
notes issued by AP-91 which are held by 19 insurance companies.

                 "Argsub" means a wholly owned subsidiary of Argus.

                 "Argsub Preferred" means Preferred Stock of any Argsub issued
to and held by DTH or FDTH.

                 "Argus" means Argus Corporation Limited, a Canadian
corporation, so long as such corporation is controlled by Hon. Conrad M.  Black
or his heirs, executors and legal representatives and his Affiliates.

                 "Asset Sale" means any sale, issuance, conveyance, transfer,
lease or other disposition (including, without limitation, by way of merger,
consolidation or sale and leaseback transaction but not the grant of a pledge
or security interest) (collectively, a "transfer"), directly or indirectly, in
one or a series of related transactions, of (i) any Capital Stock of any
Restricted Subsidiary; (ii) all or substantially all of the properties and
assets of any division or line of business of Publishing or any of its
Restricted Subsidiaries; or (iii) any other properties or assets (other than
cash) of Publishing or any Restricted Subsidiary, other than in the ordinary
course of business.  For the purposes of this definition, the term "Asset Sale"
shall not include any transfer of properties and assets (A) that is governed by
the provisions of Article VIII, (B) from any Restricted Subsidiary to
Publishing in accordance with the terms of this Indenture, (C) having a market
value of less than $1,000,000 (it being understood that if the market value of
the properties or assets being transferred exceeds $1,000,000, the entire value
and not just the portion in excess of $1,000,000 shall be deemed to have been
the subject of an Asset Sale), (D) which are obsolete (in the case of
equipment) to Publishing's and its Restricted Subsidiaries' businesses,
(E) to any Wholly Owned Restricted Subsidiary (or, provided that both the
Telegraph and Southam are Restricted Subsidiaries, a Restricted Subsidiary),
(F) from any Wholly Owned Restricted Subsidiary to any other Wholly Owned
Restricted Subsidiary (or, provided that both The Telegraph and Southam are
Restricted Subsidiaries, from a Restricted Subsidiary to a Restricted
Subsidiary), (G) consisting of any transfer of HTH common shares to Hollinger
Inc. pursuant to the provisions of the HTH/FDTH Share Exchange Agreement, (H)
by Southam, provided that (i) Southam is a Restricted Subsidiary; (ii) Southam
is a Public Entity at the time of such sale of assets and (iii) the proceeds of
such sale of assets are not paid as a dividend or distribution of Southam's
equity capital; provided, however, that any issuance by Southam of its Capital
Stock shall be subject to the requirements of Section 10.15(b)(i), and (I) any
issuance of Mirror

<PAGE>   13

                                                                               5
Preferred so long as the conditions set forth in the definition of Mirror
Preferred are satisfied.

                 "Average Life to Stated Maturity" means, as of the date of
determination with respect to any Indebtedness, the quotient obtained by
dividing (i) the sum of the products of (a) the number of years from the date
of determination to the date or dates of each successive scheduled principal
payment of such Indebtedness multiplied by (b) the amount of each such
principal payment by (ii) the sum of all such principal payments.

                 "Bankruptcy Law" means Title 11 of the United States Code, as
amended, or any similar United States federal or state or foreign law relating
to bankruptcy, insolvency, receivership, winding-up, liquidation,
reorganization or relief of debtors or any amendment to, succession to or
change in any such law.

                 "Board of Directors" means the board of directors of 
Publishing or any duly authorized committee of such board.

                 "Board Resolution" means a copy of a resolution certified by
the Secretary or an Assistant Secretary of Publishing to have been duly adopted
by such Board of Directors and to be in full force and effect on the date of
such certification, and delivered to the Trustee.

                 "Business Day" means each Monday, Tuesday, Wednesday, Thursday
and Friday which is not a day on which banking institutions in The City of New
York, or the city in which the principal corporate trust office of the Trustee
is located (initially Hartford, Connecticut), are authorized or obligated by
law or executive order to close.

                 "Business Opportunities Agreement" means the Business
Opportunities Agreement dated as of February 7, 1996, between Hollinger Inc.
and Hollinger International and any amendment, modification, or supplement
thereto or restatement thereof and any similar agreements entered into after
the date of the original issuance of the Securities in accordance with the
terms of this Indenture.

                 "Capital Lease Obligation" of any Person means any obligation
of such Person and its subsidiaries on a consolidated basis under any capital
lease of real or personal property which, in accordance with GAAP, has been
recorded as a capitalized lease obligation.

                 "Capital Stock" of any Person means any and all shares,
interests, participations or other equivalents (however designated) of such
Person's capital stock.

<PAGE>   14

                                                                             6

                 "Cash Equivalents" means (i) any evidence of Indebtedness 
with a maturity of 180 days or less issued or directly and fully guaranteed 
or insured by the United States of America or any agency or instrumentality
thereof (provided that the full faith and credit of the United States of
America is pledged in support thereof); (ii) certificates of deposit or
acceptances with a maturity of 180 days or less of any financial institution
that is a member of the Federal Reserve System having combined capital and
surplus and undivided profits of not less than $500,000,000; (iii) commercial
paper with a maturity of 180 days or less issued by a corporation that is not
an Affiliate of Publishing organized under the laws of any state of the United
States or the District of Columbia and rated A-1 (or higher) according to S&P
or P-1 (or higher) according to Moody's or at least an equivalent rating
category of another nationally recognized securities rating agency; (iv) any
money market deposit accounts issued or offered by a domestic commercial bank
having capital and surplus in excess of $500,000,000; and (v) repurchase
agreements and reverse repurchase agreements relating to marketable direct
obligations issued or unconditionally guaranteed by the government of the
United States of America or issued by any agency thereof and backed by the full
faith and credit of the United States of America, in each case maturing within
180 days from the date of acquisition; provided that the terms of such
agreements comply with the guidelines set forth in the Federal Financial
Agreements of Depository Institutions with Securities Dealers and Others, as
adopted by the Comptroller of the Currency on October 31, 1985.

                 "Change of Control" means the occurrence of any of the
following:

                 (a) there is a report filed on Schedule 13D, 14D-1 or 14D-1F
(or any successor schedule, form or report) pursuant to the Exchange Act,
disclosing that any person (for purposes of this definition, as the term
"person" is used in Section 13(d)(3) or Section 14(d)(2) of the Exchange Act or
any successor provision to either of the foregoing), other than any person
consisting solely of Conrad M. Black (or his heirs, executors or legal
representatives) and his Affiliates, has become the beneficial owner (as the
term "beneficial owner" is defined under Rule 13d-3 or any successor rule or
regulation promulgated under the Exchange Act) of Voting Stock representing 50%
or more of the total voting power attached to all Voting Stock of Hollinger
Inc., Hollinger International or Publishing then outstanding; provided,
however, that a person shall not be deemed to be the beneficial owner of, or to
own beneficially, (i) any securities tendered pursuant to a tender or exchange
offer made by or on behalf of such person or any of such person's Affiliates
until such tendered securities are accepted for purchase or exchange 
thereunder, or (ii) any securities if

<PAGE>   15

                                                                             7

such beneficial ownership (A) arises solely as a result of a revocable proxy
delivered in response to a proxy or consent solicitation made pursuant to
applicable law, and (B) is not also then reportable on Schedule 13D (or any
successor schedule) under the Exchange Act;

                 (b) there is a report filed or required to be filed with any
securities commission or securities regulatory authority in Canada, disclosing
that any offeror (as the term "offeror" is defined in Section 89(1) of
Securities Act (Ontario) for the purpose of Section 101 of such Securities Act
or any successor provision of the foregoing) other than any person consisting
solely of Conrad M. Black (or his heirs, executors or legal representatives)
and his Affiliates, has acquired beneficial ownership (within the meaning of
the Securities Act (Ontario)) of, or the power to exercise control or direction
over, or securities convertible into, any voting or equity shares of Hollinger
Inc. that together with such offeror's securities (as the term "offeror's
securities" is defined in Section 89(1) of the Securities Act (Ontario) or any
successor provision thereto in relation to the voting or equity shares of
Hollinger Inc.), would constitute Voting Stock of Hollinger Inc. representing
50% or more of the total voting power attached to all Voting Stock of Hollinger
Inc. then outstanding;

                 (c) Hollinger International shall cease to own, directly or
indirectly, 100% of the Voting Stock of Publishing;

                 (d) there is consummated a consolidation (involving a business
combination) or merger of Publishing or Hollinger International, as the case
may be, (i) in which Publishing or Hollinger International, as the case may be,
is not the continuing or surviving corporation or (ii) pursuant to which any
Voting Stock of Publishing or Hollinger International, as the case may be,
would be reclassified, changed or converted into or exchanged for cash,
securities or other property, other than (in each case) a consolidation or
merger of Publishing or Hollinger International, as the case may be, in which
the holders of the Voting Stock of Publishing or Hollinger International, as
the case may be, immediately prior to the consolidation or merger have,
directly or indirectly, 50% or more of the Voting Stock of the continuing or
surviving corporation immediately after such transaction; or

                 (e) Conrad M. Black (or his heirs, executors and legal
representatives) and his Affiliates cease to beneficially own and control the
voting of, directly or indirectly, Voting Stock of Publishing or Hollinger
International representing a greater percentage of the total voting power
attached to the Voting Stock of Publishing or Hollinger International than the
percentage beneficially

<PAGE>   16

                                                                               8

owned and controlled, directly or indirectly, by any other single shareholder
of Publishing or Hollinger International together with its Affiliates
(a "Designated Transaction") and there shall occur a Rating Decline.

                 "Code" means the Internal Revenue Code of 1986, as amended.

                 "Collateral" means any property, assets, proceeds or other
items that may be pledged as security for the Securities, whether pursuant to
Section 10.11 or otherwise.

                 "Commission" means the Securities and Exchange Commission, as
from time to time constituted, created under the Exchange Act, or if at any
time after the execution of this Indenture such Commission is not existing and
performing the duties now assigned to it under the Trust Indenture Act, then
the body performing such duties at such time.

                 "Consolidated Assets" means, with respect to Publishing, the
total assets shown on the balance sheet of Publishing and its Restricted
Subsidiaries, as determined on a consolidated basis in accordance with GAAP, as
of Publishing's latest full fiscal quarter.

                 "Consolidated Cash Flow Ratio" means, as at any date of
determination, the ratio of (i) the aggregate amount of Indebtedness of
Publishing and the Restricted Subsidiaries on a Consolidated basis outstanding
as at such date to (ii) the Operating Cash Flow of Publishing and the
Restricted Subsidiaries (determined on a Consolidated basis) for the most
recently completed period of four consecutive fiscal quarters of Publishing;
provided (a) that once both of The Telegraph and Southam are Restricted
Subsidiaries, for the purpose of determining the Consolidated Cash Flow Ratio,
the Indebtedness and Operating Cash Flow of Restricted Subsidiaries that are
not Wholly Owned Restricted Subsidiaries shall be determined in accordance with
the actual percentage of Publishing's common equity interest in such Restricted
Subsidiary on the date of determination of the Consolidated Cash Flow Ratio
(thus, for example, in the case of a Restricted Subsidiary in which Publishing
owns a 51% common equity interest, 51% each of such Restricted Subsidiary's
Indebtedness and Operating Cash Flow would be included in the calculation of
Publishing's aggregate Indebtedness and Operating Cash Flow, respectively); and
provided further that (i) so long as Southam is a Restricted Subsidiary and
(ii) until such time as Southam is not a Public Entity, the portion of
Operating Cash Flow represented by Southam Operating Cash Flow shall not exceed
thirty-three and one third percent (33 1/3%) and, to the extent Southam Cash
Flow represents greater than thirty-three and one third percent (33 1/3%) of
Operating Cash Flow, such excess shall be deducted from Operating Cash Flow and
(b) that, so


<PAGE>   17

                                                                              9

long as any Southam shares owned by Publishing or a Restricted Subsidiary are
pledged, directly or indirectly, to secure Indebtedness other than Indebtedness
by Publishing or a Restricted Subsidiary, the equity interest in Southam
represented by such shares shall be excluded for purposes of calculating the
percentage of Southam's Indebtedness and Operating Cash Flow to be included in
determining Publishing's aggregate Indebtedness and Operating Cash Flow on a
Consolidated basis.

                 "Consolidated Net Income (Loss)" of Publishing and the
Restricted Subsidiaries means, for any period, the Consolidated net income (or
loss (and treating a loss as a negative number)) of Publishing and the
Restricted Subsidiaries for such period as determined in accordance with GAAP,
adjusted by (a) excluding, without duplication, to the extent included in
calculating such Consolidated Net Income (or Loss), (i) all extraordinary gains
and losses, (ii) the portion of Consolidated net income (or loss) of Publishing
and its Restricted Subsidiaries allocable to Investments in unconsolidated
Persons (other than Unrestricted Subsidiaries) to the extent that cash
dividends or distributions have not actually been received by such Person or
one of its Restricted Subsidiaries, (iii) the portion of Consolidated net
income (or loss) of Publishing and its Restricted Subsidiaries allocable to
Publishing's Unrestricted Subsidiaries (or to payments received therefrom),
(iv) net income (or loss) of a Person combined with Publishing or any of its
subsidiaries on a "pooling of interests" basis attributable to any period prior
to the date of combination, (v) any gain or loss, net of taxes, realized upon
the termination of any employee pension benefit plan, (vi) aggregate net gains
and losses (less all fees and expenses relating thereto) in respect of
dispositions of assets (including without limitation sales of shares of
Unrestricted Subsidiaries or unconsolidated Persons and noncash writeoffs of
assets (provided that there are no continuing cash expenses related to such
writeoffs)) other than in the ordinary course of business, (vii) any income,
gain or loss resulting from the issuance, sale or redemption of Mirror Preferred
or Argsub Preferred, (viii) the net income of any Restricted Subsidiary to the
extent that the declaration of dividends or similar distributions by that
Restricted Subsidiary of that income is not at the time permitted, directly or
indirectly, by operation of the terms of its charter or any agreement, 
instrument, judgment, decree, order, statute, rule or governmental regulations 
applicable to that Restricted Subsidiary or its stockholders; provided, 
however, that the foregoing shall not apply to the net income of AP-91 
relating to the business of AP-91, as conducted as of the date of this 
Indenture on account of restrictions on AP-91 in agreements as in effect on 
the date of this Indenture, or restrictions permitted under clauses (iii) and 
(iv) of Section 10.16 (to the extent such clauses are applicable at the time of

<PAGE>   18


                                                                            10

determination), (ix) any restoration to income of any contingency reserve,
except to the extent that provision for such reserve was made out of income
accrued at any time following the date of this Indenture, (x) any net gain from
the collection of proceeds of life insurance policies, (xi) any gain arising
from the acquisition of any securities, or the extinguishment, under GAAP, of
any Indebtedness of Publishing or one of its Restricted Subsidiaries, (xii)
aggregate net gains or losses relating to foreign currency transactions or
translations and (xiii) redundancy costs relating to the permanent elimination
of jobs, provided that the amount of such expenses are certified by Publishing's
independent accountants, and (b) subtracting, without duplication, the aggregate
amount of dividends on Preferred Stock of Restricted Subsidiaries to the extent
that such Preferred Stock is included as Indebtedness in the calculation of
Publishing's Consolidated Cash Flow Ratio.  In calculating the Operating Cash
Flow of Publishing and its Restricted Subsidiaries, the Consolidated Net Income
of Restricted Subsidiaries that are not Wholly Owned Restricted Subsidiaries
will be included only to the extent of Publishing's common equity interest in
such Restricted Subsidiaries.

                 "Consolidated Net Worth" means the common and preferred
stockholders' equity of Publishing and its Restricted Subsidiaries (exclusive
of any redeemable capital stock), as determined on a Consolidated basis and in
accordance with GAAP.

                 "Consolidated Tangible Assets" means the total assets
appearing on a Consolidated balance sheet of Publishing and its Restricted
Subsidiaries less, without duplication, each of the following:  (i) all
applicable depreciation, amortization and other valuation reserves, (ii) all
other intangible assets and deferred charges, (iii) deferred income tax assets
(to the extent recorded as an asset) and (iv) all investments in unconsolidated
subsidiaries (including all Unrestricted Subsidiaries).

                 "Consolidation" means, with respect to any Person, the
consolidation of the accounts of such Person and each of its subsidiaries if
and to the extent the accounts of such Person and each of its subsidiaries
would normally be consolidated with those of such Person, all in accordance
with GAAP; provided, however, that the accounts of any Unrestricted Subsidiary
shall not be consolidated with Publishing but instead the interest of
Publishing or any Restricted Subsidiary therein will be accounted for as an
investment.  The term "Consolidated" shall have a correlative meaning.

                 "Corporate Trust Office" means the office of the Trustee or an
affiliate or agent thereof at which at any particular time the corporate trust
business for the


<PAGE>   19

                                                                            11

purposes of this Indenture shall be principally administered, which office at 
the date of execution of this Indenture is located at 777 Main Street, 
Hartford, Connecticut 06115-2001.

                 "CST Real Estate" means the real estate, including land,
building and fixtures, located at 401 North Wabash Avenue, Chicago, Illinois, 
where Publishing currently maintains its headquarters, and all improvements 
thereon.

                 "CST Real Estate Transaction" means the sale or other
disposition (other than to an Affiliate) of all or any portion of the interest
of Publishing or a Restricted Subsidiary in the CST Real Estate.

                 "Currency Agreements" means one or more of the following
agreements which shall be entered into with one or more financial institutions:
foreign exchange contracts, currency swap agreements or other similar
agreements or arrangements designed to protect against fluctuations in currency
values.

                 "Default" means any event which is, or after notice or passage
of time or both would be, an Event of Default.

                 "DTH" means DT Holdings Limited, a corporation under the laws
of England and its successors and assigns.

                 "ERISA" means the Employee Retirement Income Security Act of
1974, as amended.

                 "Event of Default" has the meaning specified in Article V.

                 "Exchange Act" means the Securities Exchange Act of 1934, as
amended.

                 "Extraordinary Cash Dividend" means in respect of the Southam
Interests:

                 (i) a cash dividend in respect of a particular calendar year   
        representing the excess, if any, of (A) the aggregate of all    cash
        dividends delcared and paid on such securities during the calendar year
        over (B) the greatest of (x) 200% of the aggregate of all cash
        dividends declared and paid on such securities during the immediately
        preceding calendar year; (y) 300% of the average of the aggregate of
        all cash dividends declared and paid on such securities during the
        immediately preceding three calendar years; and (z) 100% of the
        aggregate consolidated net income of the issuer of such securities,
        before extraordinary items, for its immediately preceding fiscal year;
        and
<PAGE>   20

                                                                             12


                (ii) any cash dividend declared by Southam on its common shares
        which the directors of Southam by resolution determine to be
        extraordinary, taking into account the amount of the dividend, the
        effect of the dividend on the market value of such securities after
        payment thereof, the form of payment, the financial position of
        Southam, economic conditions, business practices and such other factors
        as the directors of Southam consider to be relevant.

                 "FDTH" means First DT Holdings Limited, a corporation under
the laws of England and its successors and assigns.

                 "FDTH Credit Facility" means the credit agreement dated as of
May 30, 1996, among FDTH, the financial institutions party thereto and The
Toronto-Dominion Bank, as issuing bank and Agent, as such agreement may be
amended, renewed, extended, substituted, refinanced, restructured, replaced,
supplemented or otherwise modified from time to time (including, without
limitation, any successive renewals, extensions, substitutions, refinancings,
restructurings, replacements, supplementations or other modifications of the
foregoing that increase the aggregate amount of borrowings outstanding or the
aggregate commitments of the lenders thereunder).

                 "Foreign Subsidiary Indebtedness" means Indebtedness Incurred
by a non-U.S. domiciled Subsidiary that has no material U.S.  operations.

                 "Generally Accepted Accounting Principles" or "GAAP" means
generally accepted accounting principles in the United States, consistently
applied, which are in effect on the date of this Indenture.

                 "Global Security" means a Security evidencing all or part of
the Securities of any Series and issued to a Depository in accordance with
Section 3.03 hereof and bearing the legend prescribed in Section 2.05 hereof.

                 "Guarantee" means the guarantee by Hollinger International
and, if the context requires, by any Restricted Subsidiary Guarantor of the
Indenture Obligations.

                 "Guaranteed Debt" of any Person means, without duplication,
all Indebtedness of any other Person referred to in the definition of
Indebtedness guaranteed directly or indirectly in any manner by such Person, or
in effect guaranteed directly or indirectly by such Person through an agreement
(i) to pay or purchase such Indebtedness or to advance or supply funds for the 
payment or purchase of such Indebtedness (or to indemnify another Person for t
he costs thereof), (ii) to purchase, sell or lease (as lessee or 

<PAGE>   21

                                                                             13

lessor) property, or to purchase or sell services, primarily for the
purpose of enabling the debtor to make payment of such Indebtedness or to
assure the holder of such Indebtedness against loss, (iii) to supply funds to,
or in any other manner invest in, the debtor (including any agreement to pay
for property or services without requiring that such property be received or
such services be rendered), (iv) to maintain working capital or equity capital
of the debtor, or otherwise to maintain the net worth, solvency or other
financial condition of the debtor or (v) otherwise to assure a creditor against
loss, provided that the term "guarantee" shall not include endorsements for
collection or deposit, in either case in the ordinary course of business.

                 "Guarantor" means any guarantor of the Securities in accordance
with the terms of this Indenture, including Hollinger International.

                "Holder" means a Person in whose name a Security is registered
in the Security Register.

                 "Hollinger Eastern" means Hollinger Eastern Publishing Inc., a
Canadian corporation, and its successors and assigns.

                 "Hollinger Inc. Transaction" means the transaction, in all
material respects as announced publicly on January 7, 1997, by which Hollinger
Inc. is to transfer, directly or indirectly, to Hollinger Eastern certain of
its owned Canadian publishing interests for an aggregate consideration not to
exceed $382 million, subject to working capital adjustments and currency
exchange adjustments.

                 "Hollinger International" means Hollinger International Inc.,
a corporation incorporated under the laws of Delaware and a Guarantor of the
Indenture Obligations, until a successor Person shall have become such pursuant
to Article VIII of this Indenture and thereafter "Hollinger International"
shall mean such successor Person.

                 "Hollinger International/Hollinger Eastern Interests" means
Preferred Stock of any Person (or other Capital Stock convertible or
exchangeable into Preferred Stock of such Person) which holds the voting
interests of Hollinger Eastern which are owned by Hollinger International
and its Subsidiaries as of the date that Hollinger Eastern is designated as a
Restricted Subsidiary.

                 "Hollinger International Guarantee" means the unsecured,
senior guarantee of the Securities provided by Hollinger International.

<PAGE>   22


                                                                            14

                 "HTH" means Hollingers-Telegraph Holdings Inc., corporation
continued under the laws of Alberta, and its successors and assigns.

                 "HTH/FDTH Share Exchange Agreement" means the share exchange
agreement dated as of July 19, 1995, between Hollinger Inc. and FDTH, as
amended, supplemented or otherwise modified from to time.

                 "Incur" means create, issue, assume, guarantee or otherwise in
any manner become directly or indirectly liable for or with respect to or
otherwise incur.

                 "Indebtedness" means, with respect to any Person, without
duplication, (i) all indebtedness of such Person for borrowed money or for the
deferred purchase price of property or services (or other obligations to former
owners of acquired businesses), excluding any trade payables and other accrued
current liabilities arising in the ordinary course of business, but including,
without limitation, all obligations, contingent or otherwise, of such Person in
connection with any letters of credit issued under letter of credit facilities,
acceptance facilities or other similar facilities and in connection with any
agreement to purchase, redeem, exchange, convert or otherwise acquire for value
any Capital Stock of such Person, or any warrants, rights or options to acquire
such Capital Stock, now or hereafter outstanding, (ii) all obligations of such
Person evidenced by bonds, notes, debentures or other similar instruments,
(iii) all indebtedness created or arising under any conditional sale or other
title retention agreement with respect to property acquired by such Person
(even if the rights and remedies of the seller or lender under such agreement
in the event of default are limited to repossession or sale of such property),
but excluding trade payables arising in the ordinary course of business, (iv)
all obligations under Interest Rate Agreements and Currency Agreements of such
Person, (v) all Capital Lease Obligations of such Person, (vi) all Indebtedness
referred to in clauses (i) through (v) above of other Persons and all dividends
of other Persons, the payment of which is secured by (or for which the holder
of such Indebtedness has an existing right, contingent or otherwise, to be
secured by) any Lien, upon or with respect to property (including, without
limitation, accounts and contract rights) owned by such Person, even though 
such Person has not assumed or become liable for the payment of such
Indebtedness, (vii) all Guaranteed Debt of such Person, (viii) all Redeemable
Capital Stock and (without duplication) all Preferred Stock of Restricted
Subsidiaries other than (a) Mirror Preferred, provided that such Mirror
Preferred continues to qualify as such under the definition thereof, (b) the
Hollinger International/Hollinger Eastern Interests, provided that Hollinger
International grants a security interest, pari passu in right of payment 
with the 

<PAGE>   23


                                                                            15  

Securities, in such Hollinger International/Hollinger Eastern Interests as
security for its guarantee of the Securities, which security interest, in
either case, shall be subordinate to any security interest in the Hollinger
International/Hollinger Eastern Interests that may be granted under the New
Bank Credit Facility and (c) Preferred Stock held by Restricted Subsidiaries or
Publishing, in each case valued at the greater of its voluntary or involuntary
maximum fixed repurchase price plus accrued and unpaid dividends and (ix) any
amendment, supplement, modification, deferral, renewal, extension, refunding or
refinancing of any Indebtedness of the types referred to in clauses (i) through
(viii) above; provided, however, that this definition shall not apply to
Indebtedness represented by Southam-Linked Debentures which are secured,
directly or indirectly, by shares of Southam, which are owned directly or
indirectly by Publishing.  For purposes hereof, the "maximum fixed repurchase
price" of any Redeemable Capital Stock or Preferred Stock which does not have a
fixed repurchase price shall be calculated in accordance with the terms of such
Redeemable Capital Stock or Preferred Stock as if such Redeemable Capital Stock
or Preferred Stock were purchased on any date on which Indebtedness shall be
required to be determined pursuant to this Indenture, and if such price is
based upon, or measured by, the fair market value of such Redeemable Capital
Stock or Preferred Stock, such fair market value to be determined in good faith
by the Board of Directors of such Person.

                 "Indenture" means this instrument as originally executed
(including all exhibits and schedules thereto) and as it may from time to time
be supplemented or amended by one or more indentures supplemental hereto
entered into pursuant to the applicable provisions hereof and shall include the
terms of particular Series of Securities established as contemplated by Section
3.01.

                 "Indenture Obligations" means the obligations of Publishing
under this Indenture or under the Securities to pay principal of, premium, if
any, and interest when due and payable, and all other amounts due or to become
due under or in connection with this Indenture and the Securities, and the
performance of all other obligations to the Trustee, the Paying Agent and the
holders under this Indenture and the Securities, according to the terms
thereof.

                 "Independent Committee" means a committee of the board of
directors of Publishing whose membership meets the requirements of the New York
Stock Exchange applicable to audit committees as in effect on the date of
original issuance of the Securities or a committee of the board of directors of
Publishing whose membership satisfies any more restrictive requirements of
independence of any securities exchange or market on which Publishing's or
Hollinger International's equity securities are traded or listed.

<PAGE>   24


                                                                             16

                 "Independent Director" means a member of the board of
directors of a Person that is not an officer, employee or former officer or
employee of such Person or one of its Affiliates and, with respect to any
transaction or series of related transactions, a member of the board of
directors who does not have any material direct or indirect financial interest
in or with respect to such transaction or series of related transactions
(including for such purpose the interest of any other Person with respect to
whom such director is also a director, officer or employee).

                 "Interest Payment Date" means the Stated Maturity of a regular
installment of interest on the Securities or the Special Payment Date with
respect to Defaulted Interest.

                 "Interest Rate Agreements" means one or more of the following
agreements which shall be entered into from time to time with one or more
financial institutions:  interest rate protection agreements (including,
without limitation, interest rate swaps, caps, floors, collars and similar
agreements) and/or other types of interest rate hedging agreements.

                 "Investment" means, with respect to any Person, directly or
indirectly, any advance, loan (including guarantees), or other extension of
credit or capital contribution to (by means of any transfer of cash or other
property to others or any payment for property or services for the account or
use of others), or any purchase, acquisition or ownership by such Person of any
Capital Stock, bonds, notes, debentures or other securities issued or owned by,
any other Person and all other items that are or would be classified as 
investments on a balance sheet prepared in accordance with GAAP.

                 "Lien" means any mortgage, charge, pledge, lien (statutory or
otherwise), security interest, hypothecation or other encumbrance upon or with
respect to any property of any kind, real or personal, movable or immovable,
now owned or hereafter acquired.

                 "Marketable Security" means any common stock, debt security or
other security of a Person which is (or will, upon distribution thereof, be)
listed on the NYSE, the American Stock Exchange or any national securities
exchange registered under Section 6 of the Securities Exchange Act of 1934, as
amended, or approved for quotation in the Nasdaq National Market or any similar
system of automated dissemination of quotations of securities prices in the
United States or for which there is a recognized market maker or trading
market.

                 "Material Restricted Subsidiary" means each Restricted
Subsidiary of Publishing which (i) for the most recent fiscal year of
Publishing accounted for more than 5% 

<PAGE>   25

                                                                            17

of the Consolidated revenues of Publishing and its Restricted Subsidiaries or 
(ii) at the end of such fiscal year was the owner (beneficial or otherwise) of 
more than 5% of the Consolidated Assets of Publishing and its Restricted 
Subsidiaries, all as shown on Publishing's Consolidated financial statements 
for such fiscal year.

                 "Maturity" when used with respect to any Security means the
date on which the principal of such Security becomes due and payable as therein
provided or as provided in this Indenture, whether at Stated Maturity, the
Purchase Date or the Redemption Date and whether by declaration of
acceleration, Offer in respect of Excess Proceeds, Change of Control, call for
redemption or otherwise.

                 "Media Business" means the business of the broadcast of radio
or television broadcasting, cable and satellite programs (including national,
regional or local radio, television, cable and satellite programs).

                 "Mirror Preferred" means Preferred Stock of DTH or FDTH
currently held by or hereafter issued to an Argsub (i) having terms (including,
without limitation, terms with respect to liquidation, redemption and
dividends) identical to those contained in Argsub Preferred issued or
transferred simultaneously with such Argsub's acquisition of such DTH or
FDTH Preferred Stock in equivalent amounts to DTH or FDTH, as the case may be,
and (ii) in respect of which no cash payments are or have been made by the
issuer thereof, except for cash payments in respect of certain Mirror Preferred
directly from FDTH to DTH at the direction of Argsub; provided that, at such
time as (x) the foregoing clauses (i) and (ii) are no longer satisfied, (y) the
issuer of any Argsub Preferred Incurs any Indebtedness or other liability other
than tax liabilities or pursuant to such Argsub Preferred or acquires any other
assets other than the Mirror Preferred, or (z) the holder of any Mirror
Preferred transfers such stock other than to a Wholly Owned Restricted
Subsidiary, then (1) an Event of Default will occur under the Indenture and (2)
such Preferred Stock of FDTH held by Argsub will be deemed to be Redeemable
Capital Stock that is Incurred on such date; and provided further, that in the
event that the Mirror Preferred have not been redeemed, retracted, transferred
to DTH or otherwise canceled without the payment of cash (except for cash
payments in respect of certain Mirror Preferred directly to DTH) on or before
July 1, 1997, then such Preferred Stock shall be treated as Indebtedness for
the purposes of Section 10.08.

                 "Net Cash Proceeds" means (a) with respect to any Asset Sale
by any Person, the proceeds thereof in the form of cash or cash equivalents
including payments of principal and interest in respect of deferred payment
obligations when received in the form of, or stock or other assets when
disposed of for, cash or cash equivalents (except to the 

<PAGE>   26

                                                                            18

extent that such obligations are financed or sold with recourse to Publishing 
or any Restricted Subsidiary) net of (i) brokerage commissions and other 
reasonable fees and expenses (including fees and expenses of counsel and
investment bankers) related to such Asset Sale, (ii) provisions for all taxes
payable as a result of such Asset Sale, (iii) payments made to retire
indebtedness where payment of such indebtedness is secured by the assets or
properties the subject of such Asset Sale, (iv) amounts required to be paid to
any Person (other than Publishing or any Restricted Subsidiary) owning a
beneficial interest in the assets subject to the Asset Sale and (v) appropriate
amounts to be provided by Publishing or any Restricted Subsidiary, as the case
may be, as a reserve, in accordance with GAAP, against any liabilities
associated with such Asset Sale and retained by Publishing or any Restricted
Subsidiary, as the case may be, after such Asset Sale, including, without
limitation, pension and other post-employment benefit liabilities, liabilities
related to environmental matters and liabilities under any indemnification
obligations associated with such Asset Sale, all as determined and reflected 
in an Officers' Certificate delivered to the Trustee and (b) with respect to 
any issuance or sale of Capital Stock or options, warrants or rights to 
purchase Capital Stock, or debt securities or Capital Stock that have been
converted into or exchanged for Capital Stock, as referred to in Section 10.09,
the proceeds of such issuance or sale in the form of cash or cash equivalents,
including payments in respect of deferred payment obligations when received in
the form of, or stock or other assets when disposed of for, cash or cash
equivalents (except to the extent that such obligations are financed or sold
with recourse to Publishing or any Restricted Subsidiary), net of attorneys'
fees, accountants' fees and brokerage, consultation, underwriting and other
fees and expenses actually incurred in connection with such issuance or sale
and net of taxes paid or payable as a result thereof.

                 "New Bank Credit Facility" means the credit agreement dated as
of May 30, 1996, among Publishing, the financial institutions party thereto and
The Toronto-Dominion Bank, as issuing bank and the Agent, as such agreement may
be amended, renewed, extended, substituted, refinanced, restructured, replaced,
supplemented or otherwise modified from time to time (including, without
limitation, any successive renewals, extensions, substitutions, refinancings,
restructurings, replacements, supplementations or other modifications of the
foregoing that increase the aggregate amount of borrowings outstanding or the
aggregate commitments of the lenders thereunder).

                 "Newspaper Business" means the business of publishing and
distributing (including distributing by electronic means) newspapers, magazines
and other paid or 

<PAGE>   27


                                                                             19

free publications having national, regional, local or targeted markets, 
including publications having limited or no news or editorial content such as 
shoppers or other "total market coverage" publications and similar publications.

                 "Officers' Certificate" means a certificate signed by the
Chairman of the Board, Vice Chairman, President or a Vice President (regardless
of Vice Presidential designation), and by the Treasurer, Secretary or an
Assistant Secretary, of Publishing, in form and substance reasonably
satisfactory to, and delivered to, the Trustee.

                 "Operating Cash Flow" means, for any period, an amount equal
to the Consolidated Net Income of Publishing and the Restricted Subsidiaries
for such period, plus, to the extent deducted in calculating such Consolidated 
Net Income, (a) interest expense and other financing costs and expenses, 
(b) dividends paid on any Preferred Stock of Restricted Subsidiaries to the 
extent such Preferred Stock is included as Indebtedness in the calculation of 
Publishing's Consolidated Cash Flow Ratio, (c) depreciation and amortization 
and (d) all taxes, whether or not deferred, applicable to such period.

                 For purposes of calculating Operating Cash Flow for the four
fiscal quarters most recently completed prior to any date on which an action is
taken that requires a calculation of the Consolidated Cash Flow Ratio, (a) any
Person that is a Restricted Subsidiary on such date (or would become a
Restricted Subsidiary in connection with the transaction that requires the
determination of such ratio) shall be deemed to have been a Restricted
Subsidiary at all times during such period, (b) any Person that is not a
Restricted Subsidiary on such date (or would cease to be a Restricted
Subsidiary in connection with the transaction that requires the determination
of such ratio) shall be deemed not to have been a Restricted Subsidiary at any
time during such period, (c) if Publishing or any Restricted Subsidiary shall
have in any manner acquired or disposed of any operating business (including
without limitation acquisitions accounted for on a "pooling of interests" or
"as if pooling of interests" basis) during or subsequent to such period, such
calculation shall be made on a pro forma basis on the assumption that such
acquisition or disposition has been completed on the first day of such period
and (d) in the case of a Restricted Subsidiary that is not a Wholly Owned
Restricted Subsidiary, the determination of the percentage of the Operating
Cash Flow of such Restricted Subsidiary that is to be included in the
calculation of Publishing's Consolidated Cash Flow Ratio shall be made on a pro
forma basis on the assumption that the percentage of Publishing's common equity
interest in such Restricted Subsidiary on the date of determination (it being
understood, in the case of foregoing clause (c), that if 

<PAGE>   28


                                                                           20

such pro forma calculations shall have been made in accordance with Regulation 
S-X under the Exchange Act, such method of calculation (but not necessarily 
the adjustments) shall be presumed to be acceptable) (it being further 
understood that the foregoing clause (d) shall not be operative until such 
time as both of The Telegraph and Southam shall be Restricted Subsidiaries).

                 "Opinion of Counsel" means a written opinion of counsel, in
form and substance reasonably satisfactory to the Trustee, who may be counsel
for Publishing or the Trustee, and who shall be reasonably acceptable to the 
Trustee, including but not limited to an Opinion of Independent Counsel.

                 "Opinion of Independent Counsel" means a written opinion, in
form and substance reasonably satisfactory to the Trustee, by someone who is
not an employee or former employee of Publishing and who shall be reasonably
acceptable to the Trustee.

                 "Original Issue Discount Security" means (i) any Security
which provides for an amount less than the principal amount thereof to be due
and payable upon a declaration of acceleration of the Maturity thereof, and
(ii) any other Security which is issued with "original issue discount" within
the meaning of Section 1273(a) of the Internal Revenue Code of 1986, as
amended, and the regulations thereunder.

                 "Outstanding" when used with respect to Securities means, as
of the date of determination, all Securities theretofore authenticated and
delivered under this Indenture, except:

                 (a) Securities theretofore cancelled by the Trustee or
         delivered to the Trustee for cancellation;

                 (b) Securities, or portions thereof, for whose payment or
         redemption money in the necessary amount has been theretofore
         irrevocably deposited with the Trustee or any Paying Agent (other than
         Publishing) in trust or set aside and segregated in trust by
         Publishing (if Publishing shall act as its own Paying Agent) for the
         Holders of such Securities; provided that if such Securities are to be
         redeemed, notice of such redemption has been duly given pursuant to
         this Indenture or provision therefor reasonably satisfactory to the
         Trustee has been made;

                 (c) Securities, except to the extent provided in Sections 4.02
         and 4.03, with respect to which Publishing has effected defeasance or
         covenant defeasance as provided in Article IV; and


<PAGE>   29

                                                                              21
                 (d) Securities in exchange for or in lieu of which other
         Securities have been authenticated and delivered pursuant to this
         Indenture, other than any such Securities in respect of which there
         shall have been presented to the Trustee and Publishing proof
         reasonably satisfactory to each of them that such Securities are held
         by a bona fide purchaser in whose hands the Securities are valid
         obligations of Publishing; provided, however, that in determining
         whether the Holders of the requisite principal amount of Outstanding
         Securities have given any request, demand, authorization, direction,
         notice, consent or waiver hereunder, Securities owned by Publishing or
         any other obligor upon the Securities or any Affiliate of Publishing or
         such other obligor shall be disregarded and deemed not to be
         Outstanding, except that, in determining whether the Trustee shall be
         protected in relying upon any such request, demand, authorization,
         direction, notice, consent or waiver, only Securities which the Trustee
         actually knows to be so owned shall be so disregarded.  Securities so
         owned which have been pledged in good faith may be regarded as
         Outstanding if the pledgee establishes to the reasonable satisfaction
         of the Trustee the pledgee's right so to act with respect to such
         Securities and that the pledgee is not Publishing or any other obligor
         upon the Securities or any Affiliate of Publishing or such other
         obligor.

                 "Pari Passu Guarantor Indebtedness" means any Indebtedness of
any Guarantor that is pari passu in right of payment with such Guarantor's
Guarantee.

                 "Pari Passu Indebtedness" means any Indebtedness of Publishing
that is pari passu in right of payment with the Securities.

                 "Paying Agent" means any Person authorized by Publishing to
pay the principal, premium, if any, or interest on any Securities on behalf of
Publishing.  The Company initially authorizes the Trustee to act as Paying
Agent for the Securities on its behalf.  The Company may at any time and from
time to time authorize one or more Persons to act as Paying Agent in addition
to or in place of the Trustee with respect to any Series of Securities issued
under this Indenture.

                 "Permitted Indebtedness" means the following:

                 (i) Indebtedness of Publishing or Foreign Subsidiary
         Indebtedness under the New Bank Credit Facility in an aggregate
         principal amount at any one time outstanding not to exceed $150
         million; and once both of The Telegraph and Southam are Restricted
         Subsidiaries, $250 million; and, once the Hollinger Inc. Transaction
         closes, $475 million; provided, 

<PAGE>   30

                                                                              22

         however, that Indebtedness under the New Bank Credit Facility may not 
         be Incurred under this paragraph for purposes of purchasing or 
         otherwise acquiring the Capital Stock or a substantial portion of the 
         assets of another Person (including the minority interest in Southam 
         but excluding acquisitions of inventory, equipment and similar assets 
         in the ordinary course of business) unless, immediately after giving 
         effect to such transaction on a pro forma basis, Publishing could 
         Incur $1.00 of additional Indebtedness (other than Permitted 
         Indebtedness) under Section 10.08;

                 (ii) once Southam is a Restricted Subsidiary and until such
         time as Southam is not a Public Entity, Indebtedness of Southam;
         provided that the Southam Cash Flow Ratio for the four full fiscal
         quarters immediately preceding the Incurrence of such Indebtedness
         taken as one period is not greater than 4.0:1.0 (for purposes of
         determining the Southam Cash Flow Ratio for any period, pro forma
         effect shall be given to (i) the Incurrence of such Indebtedness and
         (if applicable) the application of the net proceeds therefrom,
         including to refinance other Indebtedness, as if such Indebtedness was
         Incurred, and the application of such proceeds occurred, at the
         beginning of such four-quarter period; (ii) the Incurrence, repayment
         or retirement of any other Indebtedness by Southam or any of its
         Restricted Subsidiaries since the first day of such four-quarter
         period as if such Indebtedness was Incurred, repaid or retired at the
         beginning of such four-quarter period; (iii) in the case of Acquired
         Indebtedness, the related acquisition (as if such acquisition had been
         consummated on the first day of such four-quarter period); and (iv)
         any acquisition or disposition by Southam or any of its Restricted
         Subsidiaries of any company or any business or any assets out of the
         ordinary course of business, whether by merger, stock purchase or sale
         or asset purchase or sale or any related repayment of Indebtedness, in
         each case since the first day of such four-quarter period, as if such
         acquisition or disposition had been consummated on the first day of
         such four-quarter period); provided, however, that Southam may not
         Incur Indebtedness under this paragraph for purposes of purchasing or
         otherwise acquiring the Capital Stock or a substantial portion of the
         assets of another Person (including the minority interest in Southam
         but excluding acquisitions of inventory, equipment and similar assets
         in the ordinary course of business) unless, immediately after giving
         effect to such transaction on a pro forma basis, Publishing could
         Incur $1.00 of additional Indebtedness (other than Permitted
         Indebtedness) under Section 10.08;

<PAGE>   31

                                                                             23

                 (iii) guarantees by, and Liens on the property of, any
         Restricted Subsidiary guaranteeing or securing Indebtedness of
         Publishing or Foreign Subsidiary Indebtedness under the New Bank
         Credit Facility, and provided that both of The Telegraph and Southam
         are Restricted Subsidiaries, guarantees of and Liens securing the FDTH
         Credit Facility, which guarantees or Liens are in existence on the
         date of this Indenture or on the date which they become Restricted
         Subsidiaries or guarantees that are otherwise permitted under Section
         10.12;

                 (iv) Indebtedness of Publishing pursuant to the Securities
         issued on the date of this Indenture and Indebtedness of any
         Restricted Subsidiary constituting a Guarantee of the Securities;

                 (v) Indebtedness of Publishing or any Restricted Subsidiary
         outstanding on the date of this Indenture and listed on Schedule I
         hereto;

                 (vi) Indebtedness (a) of Publishing owing to a Wholly Owned
         Restricted Subsidiary or, provided that both of The Telegraph and
         Southam are Restricted Subsidiaries, a Restricted Subsidiary, or (b) of
         a Wholly Owned Restricted Subsidiary owing to Publishing or another
         Wholly Owned Restricted Subsidiary or, provided that both of The
         Telegraph and Southam are Restricted Subsidiaries, a Restricted
         Subsidiary owing to another Restricted Subsidiary or Publishing;
         provided that any such Indebtedness is made pursuant to an intercompany
         note setting forth the principal amount, interest rate and payment
         dates, the maturity or similar terms, and, in the case of Indebtedness
         of Publishing owing to a Wholly Owned Restricted Subsidiary or a
         Restricted Subsidiary, as the case may be, is subordinated in right of
         payment from and after such time as the Securities shall become due and
         payable (whether at Stated Maturity, acceleration or otherwise) to the
         payment and performance of Publishing's obligations under the
         Securities; provided further, that (x) any disposition, pledge or
         transfer of any such Indebtedness to a Person (other than (A) to
         Publishing or a Wholly Owned Restricted Subsidiary or, provided that
         both of The Telegraph and Southam are Restricted Subsidiaries, a
         Restricted Subsidiary or (B) a pledge of such Indebtedness to secure
         Indebtedness existing at such time under, and pursuant to the terms of,
         the New Bank Credit Facility or the AP-91 Senior Notes and provided
         that both of The Telegraph and Southam are Restricted Subsidiaries, the
         FDTH Credit Facility and the Southam credit facilities existing on
         January 1, 1997, as amended), will be deemed to be an Incurrence of
         such Indebtedness by the obligor not permitted by this clause (vi) 
         and (y) any 
<PAGE>   32

                                                                              24

         transaction pursuant to which any Wholly Owned Restricted Subsidiary
         (or, provided that both of The Telegraph and Southam are Restricted
         Subsidiaries, a Restricted Subsidiary), that has Indebtedness owing to
         Publishing or any other Wholly Owned Restricted Subsidiary (or,
         provided that both of The Telegraph and Southam are Restricted
         Subsidiaries, any other Restricted Subsidiary), ceases to be a Wholly
         Owned Restricted Subsidiary or, provided that both of The Telegraph and
         Southam are Restricted Subsidiaries, a Restricted Subsidiary, will be
         deemed to be the Incurrence of Indebtedness by Publishing or such other
         Restricted Subsidiary that is not permitted by this clause (vi);

                 (vii) obligations of Publishing or any Restricted Subsidiary
         pursuant to Interest Rate Agreements or Currency Agreements designed
         to protect Publishing or any Restricted Subsidiary against
         fluctuations in interest rates or currency exchange rates in respect
         of Indebtedness of Publishing or any of its Restricted Subsidiaries or
         changes in dividend rates in respect of preference shares of DTH, the
         notional amount of which (in the case of Interest Rate Agreements) and
         the notional or exchange amount of which (in the case of Currency
         Agreements) do not exceed the aggregate principal amount of such
         Indebtedness or of such preference shares of DTH, as the case may be;

                 (viii) guarantees by Restricted Subsidiaries of Pari Passu
         Indebtedness of Publishing otherwise permitted to be Incurred in
         accordance with the provisions of Section 10.08;

                 (ix) Indebtedness of Publishing or a Restricted Subsidiary
         Incurred to finance a new printing plant for the Chicago Sun-Times and
         the liabilities directly associated therewith (collectively, the "CST
         Printing Plant") in an aggregate amount not in excess of the lesser of
         (x) $75,000,000 and (y) the aggregate amount needed to finance the CST
         Printing Plant and associated financing costs;

                 (x) letter of credit reimbursement obligations Incurred by
         Publishing or a Restricted Subsidiary in the ordinary course of
         business to support workers' compensation insurance obligations to the
         extent that such obligations are recorded on the balance sheet of the
         issuer;

                 (xi) any renewals, extensions, substitutions, refundings,
         refinancings or replacements (collectively, a "refinancing") of any
         Indebtedness Incurred pursuant to the ratio test set forth in
         paragraph (a) of Section 10.08, or described in paragraphs (i), (ii),
         (iii), 
<PAGE>   33
                                                                              25

         (iv), (viii), (ix) and (xii) of this definition of "Permitted
         Indebtedness" by Publishing or by the obligor of such Permitted
         Indebtedness, including any successive refinancings, so long as such
         refinancing does not increase the aggregate principal amount of
         Indebtedness represented thereby and such refinancing does not reduce
         the Average Life to Stated Maturity or the Stated Maturity of such
         Indebtedness and (B) any such refinancing Indebtedness shall not be
         senior in right of payment to the Indebtedness so refinanced;

                 (xii) provided that both of The Telegraph and Southam are
         Restricted Subsidiaries, Indebtedness of Publishing or any Restricted
         Subsidiary in an aggregate amount at any time outstanding not to
         exceed $25 million in respect of purchase money obligations, provided
         such Indebtedness (a) is Incurred within 180 days of the purchase of
         the relevant assets, (b) does not exceed the actual purchase price of
         such assets and (c) any related Liens do not extend to any assets
         other than those being purchased; and

                 (xiii) provided that both of The Telegraph and Southam are
         Restricted Subsidiaries, Indebtedness of Publishing or any Restricted
         Subsidiary in an aggregate principal amount at any time outstanding
         not to exceed $10 million.

                 "Permitted Investment" means any of the following provided
that, in the case of clauses (vii), (viii), (ix), (x) and (xi), (a) no Default
or Event of Default shall have occurred and be continuing, (b) no holders of
any other Indebtedness of Publishing or any Restricted Subsidiary shall have an
Acceleration Right and (c) immediately before and immediately after giving
effect to such Investment, on a pro forma basis, Publishing could Incur $1.00 
of additional Indebtedness (other than Permitted Indebtedness) under the 
provisions described in Section 10.08 of this Indenture:

                 (i) Investments in any Wholly Owned Restricted Subsidiary (or,
         provided that both of The Telegraph and Southam are Restricted
         Subsidiaries, a Restricted Subsidiary) or Publishing or Investments in
         a Person, if as a result of such Investment (A) such Person becomes a
         Wholly Owned Restricted Subsidiary (or, provided both of The Telegraph
         and Southam are Restricted Subsidiaries, a Restricted Subsidiary), or
         (B) such Person is merged, consolidated or amalgamated with or into,
         or transfers or conveys substantially all of its assets to, or is
         liquidated into, Publishing or any Wholly Owned Restricted Subsidiary
         (or, provided that both of The Telegraph and Southam are Restricted
         Subsidiaries, a Restricted Subsidiary);

                 (ii) Investments in the Securities;
<PAGE>   34

                                                                              26

                 (iii) Indebtedness owing to a Wholly Owned Restricted
         Subsidiary or, provided that both of The Telegraph and Southam are
         Restricted Subsidiaries, a Restricted Subsidiary, in each case as
         described under clause (vi) of the definition of "Permitted
         Indebtedness";

                 (iv) Temporary Cash Investments;

                 (v) Investments acquired by Publishing or any Subsidiary in
         connection with an Asset Sale permitted under Section 10.13 to the
         extent such Investments are non-cash consideration as permitted under
         such covenant;

                 (vi) Investments in existence on the date of this Indenture;

                 (vii) Investments in or in Persons owning Newspaper Business
         or Media Business assets (including Investments in Unrestricted
         Subsidiaries but excluding Investments in Affiliates that control
         Publishing) in an aggregate amount following the date of this
         Indenture not in excess of the greater of (i) $40,000,000 or (ii) 25%
         of the aggregate cumulative cash dividends or distributions received
         by Publishing and its Restricted Subsidiaries from any of Publishing's
         Unrestricted Subsidiaries received during the period (treated as a
         single accounting period) after the date of this Indenture and prior to
         the date of the Permitted Investment; provided, however, that for
         purposes of this clause (vii), cash dividends or distributions shall
         not include the Southam Dividend Amount or any cash dividends or
         distributions received by Publishing or any Wholly Owned Restricted
         Subsidiary in accordance with Section 10.09(b)(iv);

                 (viii) provided that The Telegraph is a Restricted Subsidiary,
         Investments in West Ferry Printers and Trafford Park Printers to cover
         The Telegraph's share of operating losses associated with the printing
         of newspapers and to finance capital expenditures related to the
         printing business; provided that at time of any such Investment,
         neither West Ferry Printers nor Trafford Park Printers shall be
         engaged in any business other than the business of printing
         newspapers, periodicals and similar media;

                 (ix) Investments by Southam in Newspaper Businesses and Media
         Businesses and Media Businesses in Canada; provided that (i) Southam
         is at the time a Restricted Subsidiary, (ii) Southam is at the time a
         Public Entity and (iii) the Investment is not made in an Affiliate of
         Southam (other than a Subsidiary of Southam); and provided further
         that, unless such Investment by Southam otherwise qualifies as a
         Permitted 
<PAGE>   35

                                                                              27

         Investment under this definition (other than pursuant to this clause
         (ix)), such Investment will constitute a Restricted Payment under
         Section 10.09;

                 (x) Investments by DTH or FDTH in Argsub Preferred, provided
         that (x) the issuer of such Argsub Preferred simultaneously makes an
         Investment in Mirror Preferred of DTH or FDTH, as the case may be, in
         an equivalent amount and (y) such Mirror Preferred continues to
         qualify as such under the definition thereof; and

                 (xi) in addition to the Investments described in clauses (i)
         through (x) of this definition of "Permitted Investments," Investments
         in any Restricted Subsidiary, Unrestricted Subsidiary or in any joint
         venture or other entity in an amount not to exceed $10,000,000 in the
         aggregate since the date of this Indenture; provided that so long as
         The Telegraph is a Restricted Subsidiary, the loan of $6,000,000 from
         Publishing to FDTH prior to the time The Telegraph became a Restricted
         Subsidiary shall not count against the $10,000,000 amount provided for
         in this clause (xi).

                 "Permitted Real Estate Sale" means any Asset Sale not
involving an Affiliate of Publishing consisting of the sale of any printing or
distribution facility (including the associated real property and the
improvements and fixtures forming a part thereof) (other than the CST Real
Estate) formerly used by Publishing or a Restricted Subsidiary in the
production of newspapers and related publications (or acquired by one of them
as part of the acquisition of a Newspaper Business whether or not used by
Publishing) and that after such Asset Sale will not be used for the production
of any newspaper or related publication of Publishing or a Restricted
Subsidiary, provided that the aggregate value (as determined by the Board of
Directors of Publishing) of all such Asset Sales completed within any twelve
month period shall not exceed $5,000,000 (it being understood that this
definition does not include, among other things, any Asset Sale consisting of
the sale of any printing or distribution facility in connection with the sale
by Publishing or any Restricted Subsidiary of any Newspaper Business).

                 "Permitted Subsidiary Indebtedness" means Indebtedness of the
Restricted Subsidiaries, taken as a whole, with an aggregate principal amount
outstanding (calculated exclusive of the AP-91 Senior Notes) not in excess of
the greater of (x) $40,000,000 and (y) 10% of Consolidated Tangible Assets
measured as of the most recent fiscal quarter.
<PAGE>   36

                                                                              28

                 "Person" means any individual, corporation, limited liability
company, limited or general partnership, joint venture, association, joint
stock company, trust, unincorporated organization or government or any agency
or political subdivisions thereof.

                 "Predecessor Security" of any particular Security means every
previous Security evidencing all or a portion of the same debt as that
evidenced by such particular Security; and, for the purposes of this
definition, any Security authenticated and delivered under Section 3.06 in
exchange for a mutilated Security or in lieu of a lost, destroyed or stolen
Security shall be deemed to evidence the same debt as the mutilated, lost,
destroyed or stolen Security.

                 "Preferred Stock" means, with respect to any Person, any
Capital Stock of any class or classes (however designated) which is preferred
as to the payment of dividends or distributions, or as to the distribution of
assets upon any voluntary or involuntary liquidation or dissolution of such
Person, over the Capital Stock of any other class in such Person, provided that
this definition shall not include Mirror Preferred provided that such Mirror
Preferred continues to qualify as such under the definition thereof.

                 "Public Debt" means any notes, bonds or debentures or other
evidence of Indebtedness issued in the public markets or the market for
securities sold pursuant to Rule 144A under the Securities Act of 1933.

                 "Public Entity" means an entity (x) in which the equity
interest of Hollinger International and its Affiliates does not exceed 80%, (y)
in which the market value of the Capital Stock held by nonaffiliates exceeds
$100,000,000 and (z) the Capital Stock of which is traded on a recognized
national securities exchange in the United States or a prescribed securities
exchange in Canada.

                 "Publishing" means Hollinger International Publishing Inc., a
corporation incorporated under the laws of Delaware, until a successor Person
shall have become such pursuant to Article VIII of this Indenture and
thereafter "Publishing" shall mean such successor Person.  To the extent
necessary to comply with the requirements of the provisions of Trust Indenture
Act Sections 310 through 317 as they are applicable to Publishing, the term
"Publishing" shall include any other obligor with respect to the Securities for
purposes of complying with such provisions, including any Guarantor.

                 "Publishing Request" or "Publishing Order" means a written
request or order signed in the name of Publishing by any one of its Chairman of
the Board, its Vice Chairman, its President or a Vice President (regardless of
Vice 

<PAGE>   37

                                                                              29

Presidential designation), and by any one of its Treasurer, an Assistant
Treasurer, its Secretary or an Assistant Secretary, and in form and substance
reasonably satisfactory to the Trustee and delivered to the Trustee.

                 "Qualified Capital Stock" of any Person means any and all
Capital Stock of such Person other than Redeemable Capital Stock.

                 "Rating Agency" means Standard & Poor's Corporation and its
successors ("S&P"), and Moody's Investors Service, Inc. and its successors
("Moody's"), or if S&P and Moody's or both shall not make a rating of the
Securities publicly available, a nationally recognized United States
statistical rating agency or agencies, substituted for S&P or Moody's or both,
as the case may be.

                 "Rating Category" means each major rating category symbolized
by (a) in the case of S&P, AAA, AA, A, BBB, BB, B, CCC, CC and C and each such
Rating Category shall include pluses or minuses ("gradations") modifying such
capital letters; and (b) in the case of Moody's, Aaa, Aa, A, Baa, Ba, B, Caa,
Ca and C and each such Rating Category shall include added numerals such as 1,
2 or 3 ("gradations") modifying such letters.

                 "Rating Decline" means an event that will be deemed to have
occurred if, on any date within the period (the "Rating Period") beginning on
the date (the "Reference Date") of the earlier to occur of (A) the first public
announcement by Publishing or any other Person of an intention to effect any
Designated Transaction and (B) the occurrence of such Designated Transaction,
and ending on the date 90 days thereafter, either of the following events has
occurred:  (1) the Securities of any Series (or any other securities of
Publishing which are rated by a Rating Agency on the date which is 61 days
prior to the Reference Date (the "Rating Date")) shall be rated by any Rating
Agency at any time during the Rating Period at a rating which is lower than the
rating of the Securities of such Series (or such other securities of
Publishing, as the case may be) by such Rating Agency on the Rating Date by one
or more gradations (including gradations within Rating Categories as well as
between Rating Categories) or (2) any Rating Agency shall have withdrawn its
rating of the Securities of any Series (or such other securities of Publishing,
as the case may be) during the Rating Period.

                 "Redeemable Capital Stock" means any Capital Stock that,
either by its terms or by the terms of any security into which it is
convertible or exchangeable or otherwise, is, or upon the happening of an event
or passage of time would be, required to be redeemed prior to any Stated
Maturity of the principal of the Securities or is redeemable at the option of
the holder thereof at any time prior to any 

<PAGE>   38

                                                                              30

such Stated Maturity, or is convertible into or exchangeable for debt 
securities at any time prior to any such Stated Maturity at the option of the 
holder thereof; provided that this definition shall not include Mirror 
Preferred provided that such Mirror Preferred continues to qualify as such 
under the definition thereof.

                 "Redemption Date" when used with respect to any Security to be
redeemed pursuant to any provision in this Indenture means the date fixed for
such redemption by or pursuant to this Indenture.

                 "Redemption Price" when used with respect to any Security to
be redeemed pursuant to any provision in this Indenture means the price at
which it is to be redeemed pursuant to this Indenture.

                 "Regular Record Date" for the interest payable on any Interest
Payment Date relating to a particular Series means the date specified in the
Board Resolution or supplemental indenture relating to such Series.

                 "Responsible Officer" when used with respect to the Trustee
means any officer assigned to the Corporate Trust Division of the Trustee or
any agent of the Trustee appointed hereunder, including the president, any vice
president, any assistant vice president, the secretary, any assistant
secretary, the treasurer, any assistant treasurer, any trust officer or
assistant trust officer or any other officer of the Trustee customarily
performing functions similar to those performed by any of the above designated
functions similar to those performed by any of the above designated officers or
any other officer appointed hereunder to whom any corporate trust matter is
referred because of his or her knowledge of and familiarity with the particular
subject.

                 "Restricted Subsidiary" means, initially, each Subsidiary of
Publishing existing on the date of this Indenture, other than DTH and its
Subsidiaries, and any other Subsidiary designated from time to time by the
Board of Directors of Publishing as a "Restricted Subsidiary" in accordance
with Section 10.20 of this Indenture.

                 "Restricted Subsidiary Guarantor" means each Subsidiary of
Publishing that is required to issue a Guarantee of the Securities under the
terms of this Indenture.

                 "Scheme of Arrangement" means the acquisition by FDTH of the
publicly held shares in The Telegraph not owned by FDTH or any of its
Affiliates effected by way of a "Scheme of Arrangement under Section 425 of the
Companies Act 1985 of England.
<PAGE>   39
                                                                              31

                 "Securities" has the meaning specified in the first recital of
this Indenture.

                 "Securities Act" means the Securities Act of 1933, as amended.

                 "Senior Subordinated Securities" means the securities, and any
series thereof, issued under the Senior Subordinated Securities Indenture.

                 "Senior Subordinated Securities Indenture" means the Senior
Subordinated Indenture, dated as of             , among Publishing, Hollinger
International and Fleet National Bank of Connecticut, as Trustee.

                 "Series" means any series of debentures, notes, bonds or other
evidences of indebtedness issued pursuant to Article III hereof or a
supplemental indenture.

                 "Series A Preferred Shares" means the Series A Redeemable
Convertible Preferred Stock of Hollinger International, as in effect on the
date of this Indenture.

                 "Services Agreement" means the Services Agreement dated as of
February 7, 1996, as amended in connection with the offering of the Securities,
among Hollinger International, Publishing and Hollinger Inc., and as the same
may be further amended in accordance with the terms of this Indenture.

                 "Southam" means Southam Inc., a corporation continued under
the laws of Canada.

                 "Southam Cash Flow" means, for any period, an  amount equal to
the Southam Net Income for such period, plus, to the extent deducted in
calculating such Southam Net Income, (a) interest expense and other financing
costs and expenses, (b) dividends paid on any Preferred Stock of Restricted
Subsidiaries of Southam to the extent such Preferred Stock is included as
Indebtedness in the calculation of the Southam Cash Flow Ratio, (c)
depreciation and amortization, and (d) all taxes, whether or not deferred,
applicable to such period.

                 For purposes of calculating Southam Cash Flow for the four
fiscal quarters most recently completed prior to any date on which an action is
taken that requires a calculation of the Southam Cash Flow Ratio, (a) any
Person that is a Restricted Subsidiary of Southam on such date (or would become
a Restricted Subsidiary of Southam in connection with the transaction that
requires the determination of such ratio) shall be deemed to have been a
Restricted Subsidiary of Southam at all times during such period, (b) any
Person that is not a Restricted Subsidiary of Southam on such date (or would
cease to be a Restricted 
<PAGE>   40


                                                                              32

Subsidiary of Southam in connection with the transaction that requires the
determination of such ratio) shall be deemed not to have been a Restricted
Subsidiary of Southam at any time during such period; (c) if Southam or any of
its Restricted Subsidiaries shall have in any manner acquired or disposed of 
any operating business during or subsequent to such period, such calculation 
shall be made on a pro forma basis on the assumption that such acquisition or
disposition has been completed on the first day of such period; and (d) in 
the case of a Restricted Subsidiary that is not a Wholly Owned Restricted
Subsidiary, the determination of the percentage of the Operating Cash Flow of
such Restricted Subsidiary that is to be included in the calculation of the
Consolidated Publishing's Consolidated Cash Flow Ratio shall be made on a pro
forma basis on the assumption that the percentage of Publishing's common equity
interest in such Restricted Subsidiary on the first day of such period was
equivalent to its common equity interest on the date of the determination (it
being understood, in the case of the foregoing clause (c), that if such pro
forma calculations have been made in accordance with Regulation S-X under the
Exchange Act, such method of calculation (but not necessarily the adjustments)
shall be presumed to be acceptable).

                 "Southam Cash Flow Ratio" means, as at any date of
determination, the ratio of (i) the aggregate amount of Indebtedness of Southam
and its Restricted Subsidiaries outstanding as at such date to (ii) the Southam
Cash Flow (determined on a Consolidated basis for Southam and its Restricted
Subsidiaries) for the most recently completed period of four consecutive fiscal
quarters of Southam, provided that once Southam is a Restricted Subsidiary, for
the purpose of determining the Southam Cash Flow Ratio, the Indebtedness and
Southam Cash Flow of Restricted Subsidiaries of Southam that are not Wholly
Owned Restricted Subsidiaries of Southam will be determined in accordance with
the actual percentage of Southam's common equity interest in such Restricted
Subsidiary on the date of determination of the Southam Cash Flow ratio (thus,
for example, in the case of a Restricted Subsidiary of Southam in which Southam
owns a 51% common equity interest, 51% each of such Restricted Subsidiary's
indebtedness and Southam Cash Flow would be included in the calculation of
Southam's aggregate Indebtedness and the aggregate of Southam Cash Flow,
respectively).

                 "Southam Dividend Amount" means the lesser of (x) the
aggregate amount paid or payable by the Guarantor since the date of this
Indenture in respect of regularly scheduled periodic dividends on the Series A
Preferred and (y) the aggregate amount of the Southam Interests Dividends 
received by Publishing since the date of this Indenture on account of its 
ownership interest (whether direct or indirect) in Southam.
<PAGE>   41

                                                                              33

                 "Southam Interests" means 7,395,000 Southam common shares held
by Hollinger International or its subsidiaries; provided, however, that if
Southam shall pay a dividend, or make a distribution, on its common shares in
the form of capital stock of the same or another corporation, or subdivide its
outstanding common shares into a greater number of common shares, or combine
its outstanding common shares into a smaller number of common shares, or effect
a reorganization or reclassification of its Capital Stock, or amalgamate, enter
into an arrangement or consolidation or merge with or into another entity
(other than an amalgamation, arrangement, consolidation or merger which does
not result in a reclassification or change of the outstanding common shares of
Southam), the "Southam Interests" shall thereafter include any securities
distributed with respect to any such shares or into which any such shares shall
be converted, changed or reclassified or for which any such shares shall be
exchanged.

                 "Southam Interests Dividend" means a dividend or other
distribution paid on or with respect to the Southam Interests on or prior to
the earlier of (i) the redemption date for the redemption of all the Series A
Preferred Shares outstanding as of such redemption date or (ii) the date of
final distribution to the holders of the Series A Preferred Shares of the full
preferential amount provided under the terms thereof; provided, however, that
the term "Southam Interests Dividend" does not mean or include (x) any part of
any dividend or distribution that is payable otherwise than in cash or that
constitutes an Extraordinary Cash Dividend as applied to the Southam Interests,
or (y) any dividend or distribution on or with respect to the 7,395,000 Southam
common shares held by Publishing or its subsidiaries.

                 "Southam-Linked Debentures" means the debentures of Hollinger
Inc. in the original principal amount of Cdn.$125,000,000 due November 1, 1998.

                 "Southam Net Income (Loss)" means, for any period, the
Consolidated net income (or loss) (and treating a loss as a negative number)) of
Southam and its Restricted Subsidiaries for such period as determined in
accordance with GAAP, adjusted by (a) excluding, without duplication, to the
extent included in calculating such Consolidated net income (or loss), (i) all
extraordinary gains and losses, (ii) the portion of Consolidated net income (or
loss) of Southam and its Restricted Subsidiaries allocable to Investments in
unconsolidated Persons (other than Unrestricted Subsidiaries) to the extent that
cash dividends or distributions have not actually been received by such Southam
or one of its Restricted Subsidiaries, (iii) the portion of Consolidated net
income (or loss) of Southam and its Restricted Subsidiaries allocable to
Southam's Unrestricted Subsidiaries (or to payments received therefrom), (iv)
net income (or loss) of a Person combined 
<PAGE>   42

                                                                              34

with Southam or any of its Subsidiaries on a "pooling of interests" basis
attributable to any period prior to the date of combination, (v) any gain or
loss, net of taxes, realized upon the termination of any employee pension
benefit plan, (vi) aggregate net gains and losses (less all fees and expenses
relating thereto) in respect of dispositions of assets (including without
limitation sales of shares of Unrestricted Subsidiaries or unconsolidated
Persons and noncash writeoffs of assets (provided that there are no continuing
cash expenses related to such writeoffs)) other than in the ordinary course of
business, (vii) the net income of any Restricted Subsidiary to the extent that
the declaration of dividends or similar distributions by that Restricted
Subsidiary of that income is not at time permitted, directly or indirectly, by
operation of the terms of its charter or any agreement, instrument, judgment,
decree, order, statute, rule or governmental regulations applicable to that
Restricted Subsidiary or its stockholders; provided, however, that the foregoing
shall not apply to the restrictions permitted under clause (iv) of Section 10.16
(to the extent such clause is applicable at the time of determination), (viii)
any restoration to income of any contingency reserve, except to the extent that
provision for such reserve was made out of income accrued at any time following
the date of the Indenture, (ix) any net gain from the collection of proceeds of
life insurance policies, (x) any gain arising from the acquisition of any
securities, or the extinguishment, under GAAP, of any Indebtedness of Southam or
one of its Restricted Subsidiaries, (xi) aggregate net gains or losses relating
to foreign currency transactions or translations, (xii) redundancy costs
relating to the permanent elimination of jobs, provided that the amount of such
expenses are certified by Southam's independent accountants and (b) subtracting,
without duplication, the aggregate amount of dividends on Preferred Stock of
Restricted Subsidiaries of Southam (i) to the extent such Preferred Stock is not
equivalent to Common Stock for purposes of the payment of dividends and (ii) to
the extent that such Preferred Stock is included as Indebtedness in the
calculation of the Southam Cash Flow Ratio.

                 "Special Record Date" for the payment of any Defaulted
Interest means a date fixed by the Trustee pursuant to Section 3.07.

                 "Stated Maturity" when used with respect to any Indebtedness
or any installment of interest thereon, means the dates specified in such
Indebtedness as the fixed date on which the principal of such Indebtedness or
such installment of interest, as the case may be, is due and payable.

<PAGE>   43

                                                                             35

                 "Subordinated Guarantor Indebtedness" means Indebtedness of a
Guarantor subordinated in right of payment to such Guarantor's Guarantee.

                 "Subordinated Indebtedness" means (i) in the case of any
person other than Publishing, Indebtedness of such person that is expressly
subordinate in right of payment to any other Indebtedness of such Person
pursuant to a written agreement, and (ii) in the case of Publishing,
Indebtedness of Publishing that is expressly subordinate in right of payment to
the Senior Securities.

                 "Subsidiary" means any Person a majority of the equity
ownership of the Voting Stock of which is at the time owned, directly or
indirectly, by Publishing or by one or more Subsidiaries, or by Publishing and
one or more other Subsidiaries; provided that, notwithstanding the foregoing,
(i) Southam will be a Subsidiary so long as majority of the Voting Stock of
Southam is held by a Person in which, directly or indirectly, (x) 50% of the
Voting Stock is held by Publishing and the remainder is held by Hollinger Inc.
and (y) 100% of the nonvoting Capital Stock is held by Publishing, and (ii)
Hollinger Eastern will be a Subsidiary so long as 50% of its Voting Stock is
held, directly or indirectly, by Publishing and the remainder is held, directly
or indirectly, by Hollinger Inc.

                 "Tax Sharing Agreement" means an agreement providing for the
payment of amounts in lieu of income taxes among Publishing and other companies
with which it forms a single consolidated tax group.

                 "The Telegraph" means Telegraph Group Limited (formerly The
Telegraph plc), a corporation under the laws of England.

                 "Temporary Cash Investments" means (i) any evidence of
Indebtedness, maturing not more than one year after the date of acquisition,
issued by the United States of America, or an instrumentality or agency
thereof, and guaranteed fully as to principal, premium, if any, and interest by
the United States of America, (ii) any certificate of deposit, maturing not
more than one year after the date of acquisition, issued by, or time deposit of
the Trustee or a commercial banking institution that is a member of the Federal
Reserve System and that has combined capital and surplus and undivided profits
of not less than $500,000,000, whose debt has a rating, at the time as of which
any investment therein is made, of "P-1" (or higher) according to Moody's or
"A-1" (or higher") according to S&P, (iii) commercial paper, maturing not more
than one year after the date of acquisition, issued by a corporation (other
than an Affiliate or Restricted Subsidiary of Publishing) organized and
existing under the laws of the United States of America with a rating, at the
time as of 

<PAGE>   44
                                                                              36


which any investment therein is made, of "P-1" (or higher according to Moody's 
or "A-1" (or higher) according to S&P, (iv) any money market deposit accounts 
issued or offered by the Trustee or a domestic commercial bank having capital 
and surplus in excess of $500,000,000.

                 "Trustee" means the Person named as the "Trustee" in the first
paragraph of this Indenture, until a successor Trustee shall have become such
pursuant to the applicable provisions of this Indenture, and thereafter
"Trustee" shall mean such successor Trustee.  If at any time there is more than
one such Person, "Trustee" as used with respect to the Securities of any Series
shall mean the Trustee with respect to Securities of that Series.

                 "Trust Indenture Act" means the Trust Indenture Act of 1939,
as amended.

                 "Unrestricted Subsidiary" means any Subsidiary that is not a
Restricted Subsidiary, including any Restricted Subsidiary that becomes an
Unrestricted Subsidiary in accordance with Section 10.20 of this Indenture;
provided, however, that a Person may not be designated as an Unrestricted
Subsidiary unless (i) the creditors of such Person have no direct or indirect
recourse (including, but not limited to, recourse with respect to the payment
of principal or interest on Indebtedness of such Subsidiary) to Publishing or a
Restricted Subsidiary and (ii) a default by such Person on any of its
Indebtedness will not result in, or permit any holder of Indebtedness of
Publishing or a Restricted Subsidiary to declare, a default on such 
Indebtedness of Publishing or a Restricted Subsidiary or cause the payment 
thereof to be accelerated or payable prior to its Stated Maturity.  Any
subsidiary of an Unrestricted Subsidiary shall be an Unrestricted Subsidiary
for purposes of this Indenture.

                 "Voting Stock" means stock of the class or classes pursuant to
which the holders thereof have the general voting power under ordinary
circumstances to elect at least a majority of the board of directors, managers
or trustees of a corporation (irrespective of whether or not at the time stock
of any other class or classes shall have or might have voting power by reason
of the happening of any contingency).

                 "Wholly Owned Restricted Subsidiary" means a Restricted
Subsidiary all the outstanding Capital Stock (other than directors' qualifying
shares) of which are owned by Publishing or another Wholly Owned Restricted
Subsidiary or, in the case of a Restricted Subsidiary of Southam, all the
outstanding Capital Stock (other than directors' qualifying shares) of which
are owned by Southam or another Wholly Owned Restricted Subsidiary of Southam.

                 SECTION 1.02.  Other Definitions.
<PAGE>   45
                                                                             37

                                                                Defined in
Term                                                              Section  
- ----                                                            ----------
"Act"                                                              1.05
"Change of Control Offer"                                         10.14
"Change of Control Purchase Date"                                 10.14
"Change of Control Purchase Notice"                               10.14
"Change of Control Purchase Price"                                10.14
"covenant defeasance"                                              4.03
"Defaulted Interest"                                               3.07
"defeasance"                                                       4.02
"Defeasance Redemption Date"                                       4.04
"Defeased Securities"                                              4.01
"Deficiency"                                                      10.13
"Excess Proceeds"                                                 10.13
"Excluded Indebtedness                                            10.11
"Initial Blockage Period"                                         12.03
"Note Amount"                                                     10.13
"Offer"                                                           10.13
"Offered Price"                                                   10.13
"Pari Passu Debt Amount"                                          10.13
"Pari Passu Offer"                                                10.13
"Payment Blockage Period"                                         12.03
"Permitted Payment"                                               10.09
"Purchase Date"                                                   10.13
"refinancing"                                                     10.09
"Required Filing Dates"                                           10.17
"Restricted Payments"                                             10.09
"Security Register"                                                3.05
"Security Registrar"                                               3.05
"Senior Representative"                                           12.03
"Senior Subordinated Securities Offer"                            11.13
"Special Payment Date"                                             3.07
"Surviving Entity"                                                 8.01
"U.S. Government Obligations"                                      4.04

                 SECTION 1.03.  Compliance Certificates and Opinions.  Upon any
application or request by Publishing to the Trustee to take any action under
any provision of this Indenture, Publishing shall furnish to the Trustee an
Officers' Certificate to the effect that all conditions precedent, if any,
provided for in this Indenture (including any covenant compliance with which
constitutes a condition precedent) relating to the proposed action have been
complied with and an Opinion of Counsel to the effect that in the opinion of
such counsel all such conditions precedent, if any, have been complied with,
except that, in the case of any such application or request as to which the
furnishing of any certificates and/or opinions is specifically required by any
provision of this Indenture relating to such particular application or request,
no additional certificate or opinion need be furnished.
<PAGE>   46

                                                                             38

                 Every certificate or Opinion of Counsel with respect to
compliance with a condition or covenant provided for in this Indenture shall
include:

                 (a) a statement to the effect that each individual or firm
         signing such certificate or opinion has read and understands such
         covenant or condition and the definitions herein relating thereto;

                 (b) a brief statement as to the nature and scope of the
         examination or investigation upon which the statements or opinions
         contained in such certificate or opinion are based;

                 (c) a statement to the effect that, in the opinion of each
         such individual or such firm, he has made such examination or
         investigation as is necessary to enable him or them to express an
         informed opinion as to whether or not such covenant or condition has
         been complied with; and

                 (d) a statement as to whether, in the opinion of each such 
         individual or such firm, such condition or covenant has been complied 
         with.

                 SECTION 1.04.  Form of Documents Delivered to Trustee.  In any
case where several matters are required to be certified by, or covered by an
opinion of, any specified Person, it is not necessary that all such matters be
certified by, or covered by the opinion of, only one such Person, or that they
be so certified or covered by only one document, but one such Person may
certify or give an opinion with respect to some matters and one or more other
such Persons as to other matters, and any such Person may certify or give an
opinion as to such matters in one or several documents.

                 Any certificate or opinion of an officer of Publishing may be
based, insofar as it relates to legal matters, upon a certificate or opinion
of, or representations by, counsel, unless such officer knows, or in the
exercise of reasonable care should know, that the certificate or opinion or
representations with respect to the matters upon which his certificate or
opinion is based are erroneous.  Any certificate or opinion of such an officer
or of counsel may be based, insofar as it relates to factual matters, upon a
certificate or opinion of, or representations by, an officer or officers of
Publishing with respect to such factual matters and which contains a statement
to the effect that the information with respect to such factual matters is in
the possession of Publishing, unless such officer or counsel knows that the
certificate or opinion or representations with respect to such matters are
erroneous.  Opinions of Counsel required to be delivered to the Trustee may
have qualifications customary for opinions 
<PAGE>   47

                                                                              39

of the type required and counsel delivering such Opinions of Counsel may rely 
on certificates of Publishing or government or other officials customary for
opinions of the type required, including certificates certifying as to matters
of fact, including that various financial covenants have been complied with.

                 Where any Person is required to make, give or execute two or
more applications, requests, consents, certificates, statements, opinions or
other instruments under this Indenture, they may, but need not, be consolidated
and form one instrument.

                 SECTION 1.05.  Acts of Holders.  (a)  Any request, demand,
authorization, direction, notice, consent, waiver or other action provided by
this Indenture to be given or taken by Holders of any Series may be embodied 
in and evidenced by one or more instruments of substantially similar tenor 
signed by such Holders in person or by an agent duly appointed in writing; 
and, except as herein otherwise expressly provided, such action shall become 
effective when such instrument or instruments are delivered to the Trustee 
and, where it is hereby expressly required, to Publishing. Such instrument or
instruments (and the action embodied therein and evidenced thereby) are herein
sometimes referred to as the "Act" of the Holders signing such instrument 
or instruments.  Proof of execution of any such instrument or of a writing
appointing any such agent shall be sufficient for any purpose of this Indenture
and conclusive in favor of the Trustee and Publishing, if made in the manner
provided in this Section.

                 (b)  The ownership of Securities shall be proved by the
Security Register.

                 (c)  Any request, demand, authorization, direction, notice,
consent, waiver or other Act by the Holder of any Security shall bind every
future Holder of the same Security or the Holder of every Security issued upon
the transfer thereof or in exchange therefor or in lieu thereof, in respect of
anything done, suffered or omitted to be done by the Trustee, any Paying Agent
or Publishing in reliance thereon, whether or not notation of such action is
made upon such Security.

                 (d)  The fact and date of the execution by any Person of any
such instrument or writing may be proved by the affidavit of a witness of such
execution or by a certificate of a notary public or other officer authorized by
law to take acknowledgments of deeds, certifying that the individual signing
such instrument or writing acknowledged to him the execution thereof.  Where
such execution is by a signer acting in a capacity other than his individual
capacity, such certificate of affidavit shall also constitute sufficient proof
of his authority.  The fact and 
<PAGE>   48
                                                                              40

date of the execution of any such instrument or writing, or the authority of 
the Person executing the same, may also be proved in any other manner which 
the Trustee deems sufficient.

                 SECTION 1.06.  Notices, etc., to Trustee and Publishing.  Any
request, demand, authorization, direction, notice, consent, waiver or Act of 
Holders or other document provided or permitted by this Indenture to be made 
upon, given or furnished to, or filed with:

                 (a) the Trustee by any Holder or by Publishing shall be
         sufficient for every purpose hereunder if made, given, furnished or
         filed, in writing, by first-class mail postage prepaid (return receipt
         requested) or delivered in person or by recognized overnight courier
         to or with the Trustee at its Corporate Trust Office, Attention:
         Corporate Trust Division, or at any other address furnished in writing
         prior thereto to the Holders and Publishing by the Trustee; or

                 (b) Publishing or Hollinger International shall be sufficient
         for every purpose (except as provided in Section 5.01(c)) hereunder if
         in writing and mailed, first-class postage prepaid or delivered by
         recognized overnight courier, to Publishing, addressed to it at: 401
         North Wabash Avenue, Chicago, IL 60611  Attn: General Counsel or to
         Hollinger International, addressed to it at: 401 North Wabash Avenue,
         Chicago, IL 60611  Attn: General Counsel, or at any other address
         previously furnished in writing to the Trustee by Publishing or
         Hollinger International, as the case may be.

                 SECTION 1.07.  Notice to Holders; Waiver.  Where this
Indenture or the Securities of any Series provide for notice to Holders of any
event, such notice shall be sufficiently given (unless otherwise herein
expressly provided) if in writing and mailed, first-class postage prepaid, to
each Holder affected by such event, at such Holder's address as it appears in
the Security Register, not later than the latest date, and not earlier than the
earliest date, prescribed for the giving of such notice.  In any case where
notice to Holders is given by mail, neither the failure to mail such notice,
nor any defect in any notice so mailed, to any particular Holder shall affect
the sufficiency of such notice with respect to other Holders.  Any notice when
mailed to a Holder in the aforesaid manner shall be conclusively deemed to have
been received by such Holder whether or not actually received by such Holder.
Where this Indenture or the Securities of any Series provide for notice in any
manner, such notice may be waived in writing by the Person entitled to receive
such notice, either before or after the event, and such waiver shall be the
equivalent of such notice.  Waivers of notice by Holders 
<PAGE>   49

                                                                              41

shall be filed with the Trustee, but such filing shall not be a condition 
precedent to the validity of any action taken in reliance upon such waiver.

                 In case by reason of the suspension of regular mail service or
by reason of any other cause, it shall be impracticable to mail notice of any
event as required by any provision of this Indenture, then any method of giving
such notice as shall be reasonably satisfactory to the Trustee or Publishing,
as applicable, shall be deemed to be a sufficient giving of such notice.

                 SECTION 1.08.  Conflict with Trust Indenture Act.  If any
provision hereof limits, qualifies or conflicts with any provision of the Trust
Indenture Act or another provision which is required or deemed to be included
in this Indenture by any of the provisions of the Trust Indenture Act, the
provision or requirement of the Trust Indenture Act shall control.  If any
provision of this Indenture modifies or excludes any provision of the Trust
Indenture Act that may be so modified or excluded, such provision of the Trust
Indenture Act shall be deemed to apply to this Indenture as so modified or to
be excluded, as the case may be.

                 SECTION 1.09.  Effect of Headings and Table of Contents.  The
Article and Section headings herein and the Table of Contents are for
convenience only and shall not affect the construction hereof.

                 SECTION 1.10.  Successors and Assigns.  All covenants and
agreements in this Indenture by Publishing or any Guarantor shall bind its
successors and assigns, whether so expressed or not.

                 SECTION 1.11.  Separability Clause.  In case any provision in
this Indenture or in the Securities of any Series shall be invalid, illegal or
unenforceable, the validity, legality and enforceability of the remaining
provisions shall not in any way be affected or impaired thereby.

                 SECTION 1.12.  Benefits of Indenture.  Nothing in this
Indenture or in the Securities, express or implied, shall give to any Person
(other than the parties hereto and their successors hereunder, any Paying Agent
and the Holders) any benefit or any legal or equitable right, remedy or claim
under this Indenture.

                 SECTION 1.13.  GOVERNING LAW.  THIS INDENTURE AND THE
SECURITIES SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE LAWS 
OF THE STATE OF NEW YORK (WITHOUT GIVING EFFECT TO THE CONFLICT OF LAWS 
PRINCIPLES THEREOF).

                 SECTION 1.14.  Legal Holidays.  In any case where any Interest
Payment Date, Redemption Date or Stated 
<PAGE>   50

                                                                             42

Maturity of any Security shall not be a Business Day, then (notwithstanding 
any other provision of this Indenture or of the Securities) payment of 
interest or principal or premium, if any, need not be made on such date, but 
may be made on the next succeeding Business Day with the same force and effect 
as if made on the Interest Payment Date or Redemption Date, or at Maturity or 
the Stated Maturity, and no interest shall accrue with respect to such payment 
for the period from and after such Interest Payment Date, Redemption Date, 
Maturity or Stated Maturity, as the case may be, to the next succeeding 
Business Day.

                 SECTION 1.15.  Schedules.  All schedules attached hereto are
by this reference made a part with the same effect as if herein set forth in
full.

                 SECTION 1.16.  Counterparts.  This Indenture may be executed
in any number of counterparts, each of which shall be an original; but such
counterparts shall together constitute but one and the same instrument.


                                   ARTICLE II

                                 Security Forms

                 SECTION 2.01.  Forms Generally.  The Securities and the
Trustee's certificate of authentication thereof shall be in substantially the
forms set forth in this Article II, with such appropriate insertions,
omissions, substitutions and other variations as are required or permitted by
this Indenture and may have such letters, numbers or other marks of
identification and such legends or endorsements placed thereon as may be
required to comply with the rules of any securities exchange, any
organizational document or governing instrument or applicable law or as may,
consistently herewith, be determined by the officers executing such Securities,
as evidenced by their execution of the Securities.  Any portion of the text of
any Security may be set forth on the reverse thereof, with an appropriate
reference thereto on the face of the Security.

                 The definitive Securities shall be printed, lithographed or 
engraved or produced by any combination of these methods or may be produced in 
any other manner permitted by the rules of any securities exchange on which the
Securities may be listed, all as determined by the officers executing such
Securities, as evidenced by their execution of such Securities.

                 SECTION 2.02.  Forms of Securities.  Each Security shall be in
one of the forms approved from time to time by or pursuant to a Board
Resolution, or established in one or more indentures supplemental hereto.
Prior to the delivery 
<PAGE>   51
                                                                              43

of a Security to the Trustee for authentication in any form approved by or
pursuant to a Board Resolution, Publishing shall deliver to the Trustee the
Board Resolution by or pursuant to which such form of Security has been
approved, which Board Resolution shall have attached thereto a true and correct
copy of the form of Security which has been approved thereby or, if a Board
Resolution authorizes a specific officer or officers to approve of form of
Security, a certificate of such officer or officers approving the form of
Security attached thereto.  Any form of Security approved by or pursuant to a
Board Resolution must be acceptable as to form to the Trustee, such acceptance
to be evidenced by the Trustee's authentication of Securities in that form or a
certificate signed by a Responsible Officer of the Trustee and delivered to
Publishing.

                 SECTION 2.03.  Form of Trustee's Certificate of
Authentication.  The Trustee's certificate of authentication shall be included
on the form of the face of the Securities substantially in the following form:

                    TRUSTEE'S CERTIFICATE OF AUTHENTICATION.

                 This is one of the Securities referred to in the
within-mentioned Indenture.

                                    FLEET NATIONAL BANK, as Trustee

                                    by ___________________________________
                                       Authorized Signatory


                  SECTION 2.04.    Form of Guarantee of Hollinger International.

                 The form of Guarantee of Hollinger International shall be set
forth on the Securities substantially as follows:

                   GUARANTEE OF HOLLINGER INTERNATIONAL INC.

                 For value received, HOLLINGER INTERNATIONAL INC., a Delaware
corporation, hereby absolutely, unconditionally and irrevocably guarantees to
the holder of this Security and the Trustee, as if Hollinger International were
the principal debtor, the punctual payment of principal of, premium, if any,
and interest on this Security in the amounts and at the time when due and
interest on the overdue principal and interest, if any, of this Security, if
lawful, and the payment or performance of all other obligations of Publishing
under the Indenture or the Securities, to the holder of this Security and the
Trustee, all in accordance with and subject to the terms and limitations of
this 

<PAGE>   52

                                                                              44

Security and Article Fourteen of the Indenture.  This Guarantee will not 
become effective until the Trustee duly executes the certificate of
authentication on this Security.

                                         HOLLINGER INTERNATIONAL INC.


Attest:__________________________        By_______________________________
                                           Authorized Signatory

                 SECTION 2.05.  Securities Issuable in the Form of a Global
Security.  (a)  If Publishing shall establish pursuant to Sections 2.02 and
3.01 that the Securities of a particular Series are to be issued in whole or in
part in the form of one or more Global Securities, then Publishing shall
execute and the Trustee or its agent shall, in accordance with Section 3.03 and
any order by Publishing delivered to the Trustee or its agent thereunder,
authenticate and deliver, such Global Security or Securities, which (i) shall
represent, and shall be denominated in an amount equal to the aggregate
principal amount of, the Outstanding Securities of such Series to be
represented by such Global Security or Securities, or such portion thereof as
Publishing shall specify in such order, (ii) shall be registered in the name of
the Depository for such Global Security or Securities or its nominee, (iii)
shall be delivered by the Trustee or its agent to the Depository or pursuant to
the Depository's instruction and (iv) shall bear a legend substantially to the
following effect:  "Unless this certificate is presented by an authorized
representative of the Depository to Issuer or its agent for registration of 
transfer, exchange, or payment, and any certificate issued is registered in 
the name of the nominee of the Depository or in such other name as is requested
by an authorized representative of the Depository (and any payment is made to 
the nominee of the Depository or to such other entity as is requested by an 
authorized representative of the Depository), ANY TRANSFER, PLEDGE, OR OTHER 
USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL inasmuch as 
the registered owner hereof, the nominee of the Depository, has an interest 
herein."

                 (b)  Notwithstanding any other provision of this Section 2.05
or of Section 3.05, and subject to the provisions of paragraph (c) below,
unless the terms of a Global Security expressly permit such Global Security to
be exchanged in whole or in part for individual Securities, a Global Security
may be transferred, in whole but not in part and in the manner provided in
Section 3.05, only to a nominee of the Depository for such Global Security, or
to the Depository, or a successor Depository for such Global Security selected
or approved by Publishing, or to a nominee of such successor Depository.
<PAGE>   53
                                                                              45

                 (c)  (i)  If at any time the Depository for a Global Security
notifies Publishing that it is unwilling or unable to continue as Depository
for such Global Security or if at any time the Depository for the Securities
for such Series shall no longer be eligible or in good standing under the
Securities Exchange Act of 1934, as amended, or other applicable statute or
regulation, Publishing shall appoint a successor Depository with respect to
such Global Security.  If a successor Depository for such Global Security is
not appointed by Publishing within 90 days after Publishing receives such
notice or becomes aware of such ineligibility, Publishing will execute, and the
Trustee or its agent, upon receipt of a request by Publishing for the
authentication and delivery of individual Securities of such Series in exchange
for such Global Security, will authenticate and deliver, individual Securities
of such Series of like tenor and terms in an aggregate principal amount equal
to the principal amount of the Global Security in exchange for such Global
Security.

                 (ii)  Publishing may at any time and in its sole discretion
determine that the Securities of any Series or portion thereof issued or
issuable in the form of one or more Global Securities shall no longer be
represented by such Global Security or Securities.  In such event Publishing 
will execute, and the Trustee, upon receipt of a Company Request for
the authentication and delivery of individual Securities of such Series in
exchange in whole or in part for such Global Security, will authenticate and
deliver individual Securities of such Series of like tenor and terms in
definitive form in an aggregate principal amount equal to the principal amount
of such Global Security or Securities representing such Series or portion
thereof in exchange for such Global Security or Securities.

                 (iii)  If specified by Publishing pursuant to Sections 2.02
and 3.01 with respect to Securities issued or issuable in the form of a Global
Security, the Depository for such Global Security may surrender such Global
Security in exchange in whole or in part for individual Securities of such
Series of like tenor and terms in definitive form on such terms as are
acceptable to Publishing and such Depository.  Thereupon Publishing shall
execute, and the Trustee or its agent shall authenticate and deliver, without
service charge, (1) to each Person specified by such Depository a new Security
or Securities of the same Series of like tenor and terms and of any authorized
denomination as requested by such Person in aggregate principal amount equal to
and in exchange for such Person's beneficial interest as specified by such
Depository in the Global Security; and (2) to such Depository a new Global
Security of like tenor and terms and in an authorized denomination equal to the
difference, if any, between the principal amount of the surrendered Global
Security and the aggregate principal amount of Securities delivered to Holders
thereof.
<PAGE>   54
                                                                              46

                 (iv)  In any exchange provided for in any of the preceding
three paragraphs, Publishing will execute and the Trustee or its agent will
authenticate and deliver individual Securities in definitive registered form in
authorized denominations.  Upon the exchange of the entire principal amount of
a Global Security for individual Securities, such Global Security shall be
cancelled by the Trustee or its agent.  Except as provided in the preceding
paragraph, Securities issued in exchange for a Global Security pursuant to this
Section shall be registered in such names and in such authorized denominations
as the Depository for such Global Security, pursuant to instructions from its
direct or indirect participants or otherwise, shall instruct the Trustee or the
Security Registrar.  The Trustee or the Security Registrar shall deliver at its
Corporate Trust Office such Securities to the Persons in whose names such
Securities are so registered.

                                  ARTICLE III

                                 The Securities

                 SECTION 3.01.  General Title; General Limitations; Issuable in
Series; Terms of Particular Series.  The aggregate principal amount of
Securities which may be authenticated and delivered under this Indenture is not
limited.

                 The Securities may be issued in one or more Series as from
time to time may be authorized by the Board of Directors.  There shall be
established in or pursuant to a Board Resolution or in a supplemental
indenture, subject to Section 3.11, prior to the issuance of Securities of any
such Series:

                 (1) the title of the Securities of such Series (which shall
         distinguish the Securities of such Series from Securities of any other
         Series);

                 (2) any limit upon the aggregate principal amount of the
         Securities of such Series which may be authenticated and delivered
         under this Indenture (except for Securities authenticated and
         delivered upon registration of transfer of, or in exchange for, or in
         lieu of, other Securities of such Series pursuant to Section 3.04,
         3.05, 3.06, 9.06, and 11.08 and except for any Securities which,
         pursuant to Section 3.03, are deemed never to have been authenticated
         and delivered hereunder);

                 (3) the Person to whom any interest on a Security of such
         Series shall be payable, if other than the Person in whose name that
         Security (or one or more 
<PAGE>   55

                                                                              47

         Predecessor Securities) is registered at the close of business on the 
         Regular Record Date for such interest;

                 (4) the date or dates on which the principal of the Securities
         of such Series is payable;

                 (5) the rate or rates at which the Securities of such Series
         shall bear interest, if any, the date or dates from which such
         interest shall accrue, the Interest Payment Dates on which any such
         interest shall be payable and the Regular Record Date for any interest
         payable on any Interest Payment Date;

                 (6) the place or places where the principal of and any 
         premium and interest on Securities of such Series shall be payable;

                 (7) the price or prices at which the Securities of such Series
         shall be issued;

                 (8) the period or periods within which the Redemption Price or
         Prices at which and the terms and conditions upon which Securities of
         such Series may be redeemed or repaid, as the case may be, in whole or
         in part, at the option of Publishing or the Holder;

                 (9) the obligation, if any, of Publishing to purchase
         Securities of such Series pursuant to any sinking fund or analogous
         provisions or at the option of a Holder thereof and the period or
         periods within which, the price or prices at which and the terms and
         conditions upon which Securities of such Series shall be purchased, in
         whole or in part, pursuant to such obligation;

                 (10) provisions, if any, with regard to the conversion or
         exchange of the Securities of such Series, at the option of the
         Holders thereof or the Company, as the case may be, for or into new
         Securities of a different Series, Common Stock or other securities
         and, if the Securities of such Series are convertible into Common
         Stock or other Marketable Securities, the Conversion Price therefor;

                 (11) any terms applicable to Securities of such Series issued
         at an issue price below their stated principal amount, including the
         issue price thereof and the rate or rates at which such original issue
         discount will occur;

                 (12) if other than denominations of $1,000 and any integral
         multiple thereof, the denominations in which Securities of such Series
         shall be issuable;
<PAGE>   56

                                                                             48

                 (13) if other than U.S. dollars, the currency or currencies or
         units based on or related to currencies in which the Securities of
         such Series shall be denominated and in which payments of principal
         of, and any premium and interest on, such Securities shall or may be
         payable;

                 (14) if the amount of payments of principal of (and premium, 
         if any)  or interest, if any, on the Securities of such Series may be 
         determined with reference to an index based on a coin or currency 
         (including a composite currency) other than that in which the 
         Securities are stated to be payable, the manner in which such amounts 
         shall be determined;

                 (15) if the principal of (and premium, if any) or interest, if
         any, on the Securities of such Series are to be payable, at the
         election of Publishing or a Holder thereof, in a coin or currency
         (including a composite currency) other than that in which the
         Securities are stated to be payable, the period or periods within
         which, and the terms and conditions upon which, such election may be
         made;

                 (16) the portion of the principal amount of Securities of the
         Series, if other than the principal amount thereof, which shall be
         payable upon declaration of acceleration of the Maturity thereof
         pursuant to Section 5.02 or provable in bankruptcy pursuant to Section
         5.04;

                 (17) any Event of Default with respect to the Securities of
         such Series, if not set forth herein, and any additions, deletions or
         other changes to the Events of Default set forth herein that shall be
         applicable to the Securities of such Series;

                 (18) any special United States Federal income tax 
         considerations applicable to the Securities of such Series;

                 (19) if the Securities of such Series shall be issued in whole
         or in part in the form of a Global Security or Securities, the terms
         and conditions, if any, upon which such Global Security or Securities
         may be exchanged in whole or in part for other individual Securities;
         and the Depository for such Global Security or Securities; and

                 (20) any other terms of such Series,

all upon such terms as may be determined in or pursuant to such Board
Resolution or supplemental indenture with respect to such Series.
<PAGE>   57

                                                                             49

                 The form of the Securities of each Series shall be established
pursuant to the provisions of this Indenture in or pursuant to the Board 
Resolution or in the supplemental indenture creating such Series.  The 
Securities of each Series shall be distinguished from the Securities of each 
other Series in such manner, reasonably satisfactory to the Trustee, as the 
Board of Directors may determine.

                 Unless otherwise provided with respect to Securities of a
particular Series, the Securities of any Series may only be issuable in
registered form, without coupons.

                 Any terms or provisions in respect of the Securities of any
Series issued under this Indenture may be determined pursuant to this Section
by providing for the method by which such terms or provisions shall be
determined.

                 SECTION 3.02.  Denominations.  The Securities of each Series
shall be issuable in such denominations and currency as shall be provided in
the provisions of this Indenture or in or pursuant to the Board Resolution or
the supplemental indenture creating such Series.  In the absence of any such
provisions with respect to the Securities of any Series, the Securities of that
Series shall be issuable only in fully registered form in denominations of
$1,000 and any integral multiple thereof.

                 The Securities shall be redeemable as provided in Article XI.

                 At the election of Publishing, the entire indebtedness on the
Securities or certain of Publishing's obligations and covenants and certain
Events of Default thereunder may be defeased as provided in Article IV.

                 SECTION 3.03.  Execution, Authentication, Delivery and Dating.
The Securities shall be executed on behalf of Publishing by one of its Chairman
of the Board, Vice-Chairman, President or one of its Vice Presidents under its
corporate seal reproduced thereon attested by its Secretary or one of its
Assistant Secretaries.  The signature of any of these officers on the
Securities may be manual or facsimile.

                 Securities bearing the manual or facsimile signatures of
individuals who were at any time the proper officers of Publishing shall bind
Publishing, notwithstanding that such individuals or any of them have
ceased to hold such offices prior to the authentication and delivery of such
Securities or did not hold such offices on the date of such Securities.
<PAGE>   58

                                                                             50

                 At any time and from time to time after the execution and
delivery of this Indenture, Publishing may deliver Securities executed by
Publishing to the Trustee for authentication, together with a Publishing Order
for the authentication and delivery of such Securities; and the Trustee in
accordance with such Company Order shall authenticate and deliver such
Securities as provided in this Indenture and not otherwise.

                 Each Security shall be dated the date of its authentication.

                 No Security shall be entitled to any benefit under this
Indenture or be valid or obligatory for any purpose unless there appears on
such Security a certificate of authentication substantially in the form
provided for herein duly executed by the Trustee by manual signature of an
authorized signatory, and such certificate upon any Security shall be
conclusive evidence, and the only evidence, that such Security has been duly
authenticated and delivered hereunder and is entitled to the benefits of this
Indenture.

                 In case Publishing, pursuant to Article VIII, shall be
consolidated or merged with or into any other Person or shall sell, convey,
assign, transfer, lease or otherwise dispose of substantially all of its
properties and assets to any Person, and the successor Person resulting from
such consolidation, or surviving such merger, or into which Publishing shall
have been merged or consolidated, or the successor Person which shall have
received a conveyance, transfer, lease or other disposition as aforesaid, shall
have executed an indenture supplemental hereto with the Trustee pursuant to
Article VIII, any of the Securities authenticated or delivered prior to such
consolidation, merger, conveyance, transfer, lease or other disposition may,
from time to time, at the request of the successor Person, be exchanged for
other Securities executed in the name of the successor Person with such changes
in phraseology and form as may be appropriate, but otherwise in substance of
like tenor as the Securities surrendered for such exchange and of like
principal amount; and the Trustee, upon a Publishing Request of the successor
Person, shall authenticate and deliver Securities as specified in such request
for the purpose of such exchange.  If Securities shall at any time be
authenticated and delivered in any new name of a successor Person pursuant to
this Section in exchange or substitution for or upon registration of transfer 
of any Securities, such successor Person, at the option of a Holder but without
expense to such Holder, shall provide for the exchange of all Securities at the
time Outstanding held by such Holder for Securities authenticated and delivered
in such new name.

                 The Trustee may appoint an authenticating agent reasonably
acceptable to Publishing to authenticate 
<PAGE>   59

                                                                             51

Securities on behalf of the Trustee.  Unless limited by the terms of such 
appointment, an authenticating agent may authenticate Securities whenever the 
Trustee may do so.  Each reference in this Indenture to authentication by the 
Trustee includes authentication by such agent.  An authenticating agent has 
the same rights as any Security Registrar or Paying Agent to deal with 
Publishing and its Affiliates.

                 SECTION 3.04.  Temporary Securities.  Pending the preparation
of definitive Securities of any Series, Publishing may execute, and upon a
Publishing Order the Trustee shall authenticate and deliver, temporary
Securities which are printed, lithographed, typewritten or otherwise produced,
in any authorized denomination, substantially of the tenor of the definitive
Securities in lieu of which they are issued and with such appropriate
insertions, omissions, substitutions and other variations as the officers
executing such Securities may determine, as conclusively evidenced by their
execution of such Securities.

                 If temporary Securities of any Series are issued, Publishing
will cause definitive Securities to be prepared without unreasonable delay.
After the preparation of definitive Securities, the temporary Securities shall
be exchangeable for definitive Securities upon surrender of the temporary
Securities at the office or agency of Publishing designated for such purpose
pursuant to Section 10.02 (or in accordance with Section 3.03, in the case of
the initial Securities), without charge to the Holders thereof.  Upon surrender
for cancellation of any one or more temporary Securities, Publishing shall
execute and upon a Publishing Order the Trustee shall authenticate and deliver
in exchange therefor a like principal amount of definitive Securities of such
Series of authorized denominations.  Until so exchanged the temporary
Securities of such Series shall in all respects be entitled to the same
benefits under this Indenture as definitive Securities.

                 SECTION 3.05.  Registration, Registration of Transfer and
Exchange.  Publishing shall cause to be kept at the Corporate Trust Office of
the Trustee, or such other office as the Trustee may designate, a register (the
register maintained in such office and in any other office or agency designated
pursuant to Section 10.02 being herein sometimes referred to as the "Security
Register") in which, subject to such reasonable regulations as the Security
Registrar may prescribe, Publishing shall provide for the registration of
Securities, or of Securities of a particular Series, and of transfers of
Securities or of Securities of such Series.  The Trustee or an agent thereof or
of Publishing shall initially be the "Security Registrar" for the purpose of
registering Securities and transfers of Securities as herein provided.
Publishing may appoint one or 
<PAGE>   60

                                                                             52

more co-registrars, but there shall be only one Security Register per Series 
of Securities.

                 Upon surrender for registration of transfer of any Security at
the office or agency of Publishing designated pursuant to Section 10.02,
Publishing shall execute, and the Trustee shall authenticate and deliver, in
the name of the designated transferee or transferees, one or more new
Securities of such Series of any authorized denomination or denominations, of a
like aggregate principal amount.

                 At the option of the Holder, Securities may be exchanged for
other Securities of any authorized denomination or denominations, of a like
aggregate principal amount, upon surrender of the Securities to be exchanged at
such office or agency.  Whenever any Securities are so surrendered for
exchange, Publishing shall execute, and the Trustee shall authenticate and
deliver, the Securities which the Holder making the exchange is entitled to
receive.

                 All Securities issued upon any registration of transfer or
exchange of Securities shall be the valid obligations of Publishing, evidencing
the same Indebtedness, and entitled to the same benefits under this Indenture,
as the Securities surrendered upon such registration of transfer or exchange.

                 Every Security presented or surrendered for registration of
transfer, or for exchange or redemption, shall (if so required by Publishing or
the Trustee) be duly endorsed, or be accompanied by a written instrument of
transfer in form satisfactory to Publishing, the Trustee and the Security
Registrar, duly executed by the Holder thereof or such Holder's attorney duly
authorized in writing.


                 No service charge shall be made to a Holder for any
registration of, transfer, exchange or redemption of Securities, but Publishing
or the Trustee may require payment of a sum sufficient to pay all or other
governmental charges that may be imposed in connection with any registration
of, transfer, exchange or redemption of Securities, other than exchanges
pursuant to Section 3.03 3.04, 3.06, 9.06, 10.14, 10.15 or 11.08 not involving
any transfer.

                 Publishing shall not be required (a) to issue, register the
transfer of or exchange any Security of any Series during a period beginning 
at the opening of business (i) 15 days before the mailing of a notice of
redemption of the Securities selected for redemption under Section 11.04 and
ending at the close of business on the day of such mailing or (ii) 15 days
before an Interest Payment Date and ending on the close of business on the
Interest Payment Date, or (b) to register the transfer of or exchange any
Security so selected for redemption in whole or in part, 
<PAGE>   61

                                                                             53

except the unredeemed portion of Securities being redeemed in part.

                 None of Publishing, the Trustee, any agent of the Trustee, any
Paying Agent or the Security Registrar will have any responsibility or
liability for any aspect of the records relating to or payments made on account
of beneficial ownership interests of a Global Security or for maintaining,
supervising or reviewing any records relating to such beneficial ownership
interests.

                 SECTION 3.06.  Mutilated, Destroyed, Lost and Stolen
Securities.  If (a) any mutilated Security is surrendered to the Trustee, or
(b) Publishing and the Trustee receive evidence to their satisfaction of the
destruction, loss or theft of any Security, and there is delivered to
Publishing or the Trustee, such security and/or indemnity, in each case as may
be required by them to save each of them harmless, then, in the absence of
notice to Publishing or the Trustee that such Security has been acquired by a
bona fide purchaser, Publishing shall execute and upon receipt of a Publishing
Request the Trustee shall authenticate and deliver, in exchange for any such
mutilated Security or in lieu of any such destroyed, lost or stolen Security, a
replacement Security of like tenor and principal amount, bearing a number not
contemporaneously outstanding.

                 In case any such mutilated, destroyed, lost or stolen Security
has become or is about to become due and payable, Publishing in its discretion 
may, instead of issuing a replacement Security, pay such Security.

                 Upon the issuance of any replacement Securities under this
Section, Publishing may require the payment of a sum sufficient to pay all
documentary, stamp or similar issue or transfer taxes or other governmental
charge that may be imposed in relation thereto and any other expenses
(including the fees and expenses of the Trustee and its agents and counsel)
connected therewith.

                 Every replacement Security issued pursuant to this Section in
lieu of any destroyed, lost or stolen Security shall constitute an original
additional contractual obligation of Publishing, whether or not the destroyed,
lost or stolen Security shall be at any time enforceable by anyone, and shall
be entitled to all benefits of this Indenture equally and proportionately with
any and all other Securities of the same Series duly issued hereunder.

                 The provisions of this Section are exclusive and shall
preclude (to the extent lawful) all other rights and remedies with respect to
the replacement or payment of mutilated, destroyed, lost or stolen Securities.
<PAGE>   62

                                                                              54

                SECTION 3.07.  Payment of Interest; Interest Rights Preserved.
Interest on any Security which is payable, and is punctually paid or duly
provided for, on the Stated Maturity of such interest shall be paid to the
Person in whose name that Security is registered at the close of business on
the Regular Record Date for such interest payment.

                 Any interest on any Security which is payable, but is not paid
or duly provided for on the Stated Maturity of such interest (or within 15 days
after the Stated Maturity of such interest) and interest on such defaulted
interest at the then applicable interest rate borne by the Securities, to the
extent lawful (such defaulted interest and interest thereon herein collectively
called "Defaulted Interest") shall forthwith cease to be payable to the Holder
in whose name such Security is registered as of the Regular Record Date; and
such Defaulted Interest may be paid by Publishing, at its election in each
case, as provided in Subsection (a) or (b) below:

                 (a)  Publishing may elect to make payment of any Defaulted
         Interest to the Persons in whose names the Securities are registered
         at the close of business on a Special Record Date for the payment of 
         such Defaulted Interest, which shall be fixed in the following manner.

                 Publishing shall notify the Trustee in writing of the amount
         of Defaulted Interest proposed to be paid on each Security and the
         date of the proposed payment (the "Special Payment Date"), and at the
         same time Publishing shall irrevocably deposit with the Trustee an
         amount of money equal to the aggregate amount proposed to be paid in
         respect of such Defaulted Interest or shall make arrangements
         satisfactory to the Trustee for such deposit prior to the Special
         Payment Date, such money when deposited to be held in trust for the
         benefit of the Persons entitled to such Defaulted Interest as in this
         Subsection provided.  Such notice shall be received by the Trustee no
         less than 30 days prior to the Special Payment Date.  Thereupon the
         Trustee shall fix a Special Record Date for the payment of such
         Defaulted Interest which Special Record Date shall be not more than 15
         days and not less than 10 days prior to the Special Payment Date and
         not less than 10 days after the receipt by the Trustee of the notice
         of the proposed payment.  The Trustee shall promptly notify Publishing
         in writing of such Special Record Date.  In the name and at the
         expense of Publishing, the Trustee shall cause notice of the proposed
         payment of such Defaulted Interest and the Special Record Date and
         Special Payment Date therefor to be mailed, certified or registered
         (return receipt requested) first-class postage prepaid, to each Holder
         at his address as it appears in the Security Register, 
<PAGE>   63

                                                                             55

         not less than 10 days prior to such Special Record Date.  Notice of 
         the Proposed payment of such Defaulted Interest and the Special Record 
         Date therefor having been so mailed, such Defaulted Interest shall be 
         paid to the Persons in whose names the Securities are registered on 
         such Special Record Date and shall no longer be payable pursuant to the
         following Subsection (b).

                 (b)  Publishing may make payment to the Persons in whose name
         the Securities are registered at the close of business on the Special
         Record Date of any Defaulted Interest in any other lawful manner not
         inconsistent with the requirements of any securities exchange on which
         the Securities may be listed, and upon such notice as may be required
         by such exchange, unless, after written notice given by Publishing to
         the Trustee of the proposed payment pursuant to this Subsection, such
         manner of payment shall not be deemed practicable by the Trustee 
         (acting reasonably).  The Trustee shall give prompt written notice to 
         Publishing of any such determination.

                 Subject to the foregoing provisions of this Section 3.07, each
Security delivered under this Indenture upon registration of transfer of or in
exchange for or in lieu of any other Security shall carry the rights to
interest accrued and unpaid, and to accrue, which were carried by such other
Security.

                 SECTION 3.08.  Persons Deemed Owners.  Prior to due
presentment of a Security for registration of transfer, Publishing, the Trustee
and any agent of Publishing or the Trustee may treat the Person in whose name
any Security is registered on the Security Register as the owner of such
Security for the purpose of receiving payment of principal of, premium, if any,
and (subject to Section 3.07) interest on such Security and for all other
purposes whatsoever, whether or not such Security is overdue, and none of
Publishing, the Trustee or any agent of Publishing or the Trustee shall be
affected by notice to the contrary.

                 None of the Company, the Trustee, any Paying Agent or the
Security Registrar will have any responsibility or liability for any aspect of
the records relating to or payments made on account of beneficial ownership
interests in a Global Security or for maintaining, supervising or reviewing any
records relating to such beneficial ownership interests.

                 SECTION 3.09.  Cancellation.  All Securities surrendered for
payment, purchase, redemption, registration of transfer or exchange shall be
delivered to the Trustee and, if not already canceled, shall be promptly
canceled by it.  Publishing or any Restricted Subsidiary may at any time
<PAGE>   64

                                                                             56

deliver to the Trustee for cancellation any Securities previously authenticated
and delivered hereunder which Publishing or any such Restricted Subsidiary may
have acquired in any manner whatsoever, and all Securities so delivered shall
upon receipt of a Publishing Order be promptly canceled by the Trustee.  No
Securities shall be authenticated in lieu of or in exchange for any Securities
canceled as provided in this Section, except as expressly permitted by this
Indenture.  All canceled securities held by the Trustee shall, unless by a
Publishing Order received by the Trustee prior to such destruction Publishing
shall direct that the canceled Securities be returned to it, be destroyed in
accordance with its customary procedures and certification of their destruction
delivered to Publishing. The Trustee shall provide Publishing a list of all 
Securities that have been canceled from time to time as requested by Publishing.

                 SECTION 3.10.  Computation of Interest.  Unless otherwise
provided as contemplated in Section 3.01, interest on the Securities shall be
computed on the basis of a 360-day year of twelve 30-day months.

                 SECTION 3.11.  Delayed Issuance of Securities.
Notwithstanding any contrary provision herein, if all Securities of a Series
are not to be originally issued at one time, it shall not be necessary for
Publishing to deliver to the Trustee an Officers' Certificate, Board
Resolution, supplemental indenture or Opinion of Counsel otherwise required
pursuant to Sections 1.03, 2.02, 3.01 and 3.03 at or prior to the time of
authentication of each Security of such Series if such documents are delivered
to the Trustee or its agent at or prior to the authentication upon original
issuance of the first Security of such Series to be issued; provided that any
subsequent request by Publishing to the Trustee to authenticate Securities of
such Series upon original issuance shall constitute a representation and
warranty by Publishing that as of the date of such request, the statements made
in the Officers' Certificate or other certificates delivered pursuant to
Sections 1.02 and 2.02 shall be true and correct as if made on such date.

                 An Officers' Certificate or Board Resolution or supplemental
indenture delivered by Publishing to the Trustee in the circumstances set forth
in the preceding paragraph may provide that Securities which are the subject
thereof will be authenticated and delivered by the Trustee or its agent on
original issue from time to time in the aggregate principal amount, if any,
established for such Series pursuant to such procedures acceptable to the
Trustee as may be specified from time to time upon the telephonic, electronic
or written order of Persons designated in such Officers' Certificate,
supplemental indenture or Board Resolution (any such telephonic or electronic
instructions 
<PAGE>   65

                                                                             57

to be promptly confirmed in writing by such Persons) and that such Persons 
are authorized to determine, consistent with such Officers' Certificate,
supplemental indenture or Board Resolution, such terms and conditions of said
Securities as are specified in such Officers' Certificate, supplemental
indenture or Board Resolution.


                                   ARTICLE IV

                       Defeasance and Covenant Defeasance

                 SECTION 4.01.  Publishing's Option To Effect Defeasance or
Covenant Defeasance.  Publishing may, at its option by Board Resolution, at any
time, with respect to any Series of Securities, elect to have either Section
4.02 or Section 4.03 be applied to all of the Outstanding Securities of such
Series (the "Defeased Securities"), upon compliance with the conditions set
forth below in this Article IV.

                 SECTION 4.02.  Defeasance and Discharge.  Upon Publishing's
exercise under Section 4.01 of the option applicable to this Section 4.02,
Publishing shall be deemed to have been discharged from its obligations with
respect to the Defeased Securities on the date the conditions set forth below
are satisfied (hereinafter, "defeasance") and each Guarantor shall be deemed to
be discharged from its obligations with respect to its Guarantee relating to
the Defeased Securities.  For this purpose, such defeasance means that
Publishing shall be deemed to have paid and discharged the entire indebtedness
represented by the Defeased Securities, which shall thereafter be deemed to be
"Outstanding" only for the purposes of Section 4.05 and the other Sections of
this Indenture referred to in (a) and (b) below, and to have satisfied all its
other obligations under such Securities and this Indenture insofar as such
Securities are concerned (and the Trustee, at the expense of Publishing and
upon written request, shall execute proper instruments acknowledging the same),
except for the following which shall survive until otherwise terminated or
discharged hereunder:  (a) the rights of Holders of Defeased Securities to
receive, solely from the trust fund described in Section 4.04 and as more fully
set forth in such Section, payments in respect of the principal of, premium, if
any, and interest on such Securities when such payments are due, (b)
Publishing's obligations with respect to such Defeased Securities under
Sections 3.04, 3.05, 3.06, 10.02 and 10.03, (c) the rights, powers, trusts,
duties, indemnities and immunities of the Trustee hereunder, and (d) this
Article IV.  Subject to compliance with this Article IV, Publishing may
exercise its option under this Section 4.02 notwithstanding the prior exercise
of its option under Section 4.03 with respect to the Securities.
<PAGE>   66

                                                                             58

                 SECTION 4.03.  Covenant Defeasance.  Upon Publishing's
exercise under Section 4.01 of the option applicable to this Section 4.03,
Publishing shall be released from its obligations under any covenant or
provision contained in Sections 10.05 through 10.18, inclusive, and Sections
13.16 through 13.27 shall not apply, with respect to the Defeased Securities on
and after the date the conditions set forth below are satisfied (hereinafter,
"covenant defeasance"), and the Defeased Securities shall thereafter be deemed
to be not "Outstanding" for the purposes of any direction, waiver, consent or
declaration or Act of Holders (and the consequences of any thereof) in
connection with such covenants and provisions, but shall continue to be deemed
"Outstanding" for all other purposes hereunder.  For this purpose, such
covenant defeasance means that, with respect to the Defeased Securities,
Publishing may omit to comply with and shall have no liability in respect of
any term, condition or limitation set forth in any such Section or Article,
whether directly or indirectly, by reason of any reference elsewhere herein or
in such Defeased Securities to any such Section or Article or by reason of any
reference in any such Section or Article to any other provision herein or in
any other document and such omission to comply shall not constitute a Default
or an Event of Default under Section 5.01(c), (d) or (f) but, except as
specified above, the remainder of this Indenture and such Defeased Securities
shall be unaffected thereby.

                 SECTION 4.04.  Conditions to Defeasance or Covenant
Defeasance.  The following shall be the conditions to application of either
Section 4.02 or Section 4.03 to the Defeased Securities:

                 (1)  Publishing shall irrevocably have deposited or caused to
be deposited with the Trustee as trust funds in trust for the purpose of making
the following payments, specifically pledged as security for, and dedicated
solely to, the benefit of the Holders of such Series of Securities, (a) United
States dollars in an amount, (b) U.S. Government Obligations which through the
scheduled payment of principal and interest in respect thereof in accordance
with their terms will provide, not later than one day before the due date of
any payment, money in an amount, or (c) a combination thereof, in such amounts
as will be sufficient, as reflected in the written report of a nationally
recognized firm of independent public accountants or a nationally recognized
investment banking firm delivered to the Trustee, to pay and discharge (and
which shall be applied by the Trustee to pay and discharge) the principal of,
premium, if any, and interest on, the Defeased Securities on (x) the Stated
Maturity thereof or (y) any date selected by Publishing on which the Defeased
Securities may be redeemed in whole at the option of Publishing (such date 
being referred to as the "Defeasance Redemption Date"), 

<PAGE>   67

                                                                             59

if (in the case of clause (y)) when electing either defeasance or covenant
defeasance, Publishing has delivered to the Trustee an irrevocable notice to
redeem all of the outstanding Securities of such Series on the Defeasance
Redemption Date) of such principal or installment of interest; provided that the
Trustee (or such qualifying trustee) shall have been irrevocably instructed to
apply such United States dollars or the proceeds of such U.S. Government
Obligations to said payments with respect to the Securities of such Series.  For
this purpose, "U.S. Government Obligations" means securities that are (i) direct
obligations of the United States of America for the timely payment of which its
full faith and credit is pledged or (ii) obligations of a Person controlled or
supervised by and acting as an agency or instrumentality of the United States of
America the timely payment of which is unconditionally guaranteed as a full
faith and credit obligation by the United States of America, which, in either
case, are not callable or redeemable at the option of the issuer thereof, and
shall also include a depository receipt issued by a bank (as defined in Section
3(a)(2) of the Securities Act), as custodian with respect to any such U.S.
Government Obligation or a specific payment of principal of or interest on any
such U.S. Government Obligation held by such custodian for the account of the
holder of such depository receipt; provided that (except as required by law)
such custodian is not authorized to make any deduction from the amount payable
to the holder of such depository receipt from any amount received by the
custodian in respect of the U.S. Government Obligation or the specific payment
of principal of or interest on the U.S. Government Obligation evidenced by such
depository receipt.

                 (2)  In the case of an election under Section 4.02, Publishing
shall have delivered to the Trustee an Opinion of Independent Counsel in the
United States to the effect that (A) Publishing has received from, or there has
been published by, the Internal Revenue Service a ruling or (B) since the date
of this Indenture, there has been a change in the applicable Federal income tax
law, in either case to the effect that the Holders of the Outstanding
Securities of such Series will not recognize income, gain or loss for Federal
income tax purposes as a result of such defeasance and will be subject to
Federal income tax on the same amounts, in the same manner and at the same
times as would have been the case if such defeasance had not occurred.

                 (3)  In the case of an election under Section 4.03, Publishing
shall have delivered to the Trustee an Opinion of Independent Counsel in the
United States to the effect that the Holders of the Outstanding Securities of
such Series will not recognize income, gain or loss for Federal income tax
purposes as a result of such covenant defeasance and will be subject to federal
income tax on the 
<PAGE>   68

                                                                             60

same amounts, in the same manner and at the same times as would have been the 
case if such covenant defeasance had not occurred.

                 (4)  No Default or Event of Default shall have occurred and be
continuing on the date of such deposit or insofar as subsections 5.01(g) and
(h) are concerned, at any time during the period ending on the 121st day after
the date of deposit.

                 (5)  Such defeasance or covenant defeasance shall not cause
the Trustee to have a conflicting interest with respect to any securities of
Publishing.

                 (6)  Such defeasance or covenant defeasance shall not result
in a breach or violation of, or constitute a Default under, this Indenture or a
breach or violation of any provision of any agreement relating to any
Indebtedness.

                 (7)  Publishing shall have delivered to the Trustee an Opinion
of Independent Counsel in the United States to the effect that after the 121st
day following the deposit, the trust funds will not be subject to the effect of
any applicable bankruptcy, insolvency, reorganization or similar laws affecting
creditors' rights generally.

                 (8)  Publishing shall have delivered to the Trustee an
Officers' Certificate stating that the deposit was not made by Publishing with
the intent of preferring the holders of the Securities of such Series over the
other creditors of Publishing or with the intent of defeating, hindering,
delaying or defrauding creditors of Publishing.

                 (9)  No event or condition shall exist that would prevent
Publishing from making payments of the principal of, premium, if any, and
interest on the Securities of such Series on the date of such deposit or at any
time ending on the 121st day after the date of such deposit.

                 (10)  Publishing shall have delivered to the Trustee an
Officers' Certificate and an Opinion of Independent Counsel, each to the effect
that all conditions precedent provided for relating to either the defeasance
under Section 4.02 or the covenant defeasance under Section 4.03 (as the case
may be) have been complied with as contemplated by this Section 4.04.

                 Opinions of Counsel required to be delivered under this
Section may have qualifications customary for opinions of the type required and
counsel delivering such Opinions of Counsel may rely on certificates of
Publishing or government or other officials customary for opinions of the type
required, which certificates shall be limited to matters of fact, including
that various financial covenants have been complied with.
<PAGE>   69

                                                                             61

                 SECTION 4.05.  Deposited Money and U.S. Government Obligations
To Be Held in Trust; Other Miscellaneous Provisions.  Subject to the provisions
of the last paragraph of Section 10.03, all United States dollars and U.S.
Government Obligations (including the proceeds thereof) deposited with the
Trustee pursuant to Section 4.04 in respect of the Defeased Securities shall be
held in trust and applied by the Trustee, in accordance with the provisions of
such Series of Securities and this Indenture, to the payment, either directly
or through any Paying Agent as the Trustee may determine, to the Holders of
such Series of Securities of all sums due and to become due thereon in respect
of principal, premium, if any, and interest, but such money need not be
segregated from other funds except to the extent required by law.

                 Publishing shall fully pay and indemnify the Trustee against
any tax, fee or other charge imposed on or assessed against the U.S. Government
Obligations deposited pursuant to Section 4.04 or the principal and interest
received in respect thereof, other than any such tax, fee or other charge which
by law is for the account of the Holders of the Defeased Securities.

                 Anything in this Article IV to the contrary notwithstanding,
the Trustee shall deliver or pay to Publishing from time to time upon a
Publishing Request any United States dollars or U.S. Government Obligations
held by it as provided in Section 4.04 which, in the opinion of a nationally
recognized firm of independent public accountants or nationally recognized
investment banking firm expressed in a written report delivered to the Trustee,
are in excess of the amount thereof which would then be required to be
deposited to effect defeasance or covenant defeasance.  In the event of an
error in any calculation resulting in a withdrawal hereunder, Publishing shall
equal to the amount erroneously withdrawn as promptly as practicable after
becoming aware of such error.

                 SECTION 4.06.  Reinstatement.  If the Trustee or Paying Agent
is unable to apply any United States dollars or U.S. Government Obligations in
accordance with Section 4.02 or 4.03, as the case may be, by reason of any
order or judgment of any court or governmental authority enjoining, restraining
or otherwise prohibiting such application, then Publishing's obligations under
this Indenture and the Securities shall be revived and reinstated as though no
deposit had occurred pursuant to Section 4.02 or 4.03, as the case may be,
until such time as the Trustee or Paying Agent is permitted to apply all such
United States dollars or U.S. Government Obligations in accordance with Section
4.02 or 4.03, as the case may be; provided, however, that (a) if Publishing
makes any payment to the Trustee or Paying Agent of principal, premium, if any,
or interest on any Security following the reinstatement of its obligations, 
<PAGE>   70

                                                                             62

the Trustee or Paying Agent shall promptly pay any such amount to the Holders of
the Securities and Publishing shall be subrogated to the rights of the Holders
of such Securities to receive such payment from the United States dollars and
U.S. Government Obligations held by the Trustee or Paying Agent and (b) the
Trustee or Paying Agent shall return all such United States dollars and U.S.
Government Obligations to Publishing promptly after receiving a Publishing
Request therefor at any time, if the Trustee or Paying Agent receives written
notice from Publishing that such reinstatement of Publishing's obligations has
occurred and continues to be in effect at such time.


                                   ARTICLE V

                                    Remedies

                 SECTION 5.01.  Events of Default.  "Event of Default",
wherever used herein, means with respect to any Series of Securities any one of
the following events (whatever the reason for such Event of Default and whether
it shall be voluntary or involuntary or be effected by operation of law or
pursuant to any judgment, decree or order of any court or any order, rule or
regulation of any administrative or governmental body), unless such event is
either inapplicable to a particular Series or it is specifically modified in 
or pursuant to the supplemental indenture or Board Resolution creating such 
Series of Security or in the form of Security for such Series:

                 (a) there shall be a default in the payment of any interest on
         any Security of that Series when it becomes due and payable, and such
         default shall continue for a period of 30 days;

                 (b) there shall be a default in the payment of the principal
         of (or premium, if any, on) any Security of that Series when and as
         the same shall become due and payable at its Maturity (upon
         acceleration, optional or mandatory redemption, required repurchase or
         otherwise);

                 (c) (i) there shall be a default in the performance, or
         breach, of any covenant or agreement of Publishing under this
         Indenture (other than a default in the performance, or breach, of a
         covenant or agreement which is specifically dealt with in Section
         5.01(a) or (b) or in clauses (ii) or (iii) of this Section 5.01(c)),
         and such default or breach shall continue for a period of 30 days
         after written notice has been given, by certified mail, (x) to
         Publishing by the Trustee or (y) to Publishing and the Trustee by the
         Holders of at least 25% in aggregate principal amount of the
         Outstanding Securities; (ii) there shall be a 
<PAGE>   71

                                                                             63

         default in the performance or breach of the provisions of Article 
         VIII; or (iii) Publishing shall have failed to make or consummate a 
         Change of Control Offer in accordance with the provisions of 
         Section 10.14;

                 (d) one or more defaults shall have occurred under any
         agreements, indentures or instruments under which Publishing, any
         Guarantor or any Restricted Subsidiary then has outstanding
         Indebtedness in excess of $5,000,000 in the aggregate and, if not
         already matured at its final maturity in accordance with its terms,
         such Indebtedness shall have been accelerated;

                (e) any Guarantee relating to such Series shall for any reason
         cease  to be, or be assertied in writing by any Guarantor or
         Publishing not to be, in full force and effect, enforceable in
         accordance with its terms, except to the extent contemplated by the
         Indenture and any such Guarantee;
        
                (f) one or more final judgments, orders or decrees for  the
         payment of money in excess of $5,000,000, either individually or in
         the aggregate, shall be entered against Publishing, any Guarantor or
         any Restricted Subsidiary or any of their respective properties and
         shall not be discharged and either (i) enforcement proceedings shall
         have been commenced upon such judgment, order or decree or (ii) there
         shall have been a period of 60 consecutive days during which a stay of
         enforcement of such judgment or order, by reason of an appeal or
         otherwise, shall not be in effect;

                 (g) there shall have been the entry by a court of competent
         jurisdiction of (i) a decree or order for relief in respect of
         Publishing, any Guarantor or any Material Restricted Subsidiary in an
         involuntary case or proceeding under any applicable Bankruptcy Law or
         (ii) a decree or order adjudging Publishing, any Guarantor or any
         Material Restricted Subsidiary bankrupt or insolvent, or seeking
         reorganization, arrangement, adjustment or composition of or in
         respect of Publishing, any Guarantor or any Material Restricted
         Subsidiary under any applicable Federal or state law, or appointing a
         custodian, receiver, liquidator, assignee, trustee, sequestrator or
         similar official of Publishing, any Guarantor or any Material
         Restricted Subsidiary or of any substantial part of its property, or
         ordering the winding up or liquidation of its affairs, and any such
         decree or order for relief shall continue to be in effect, or any such
         other decree or order shall be unstayed and in effect, for a period of
         60 consecutive days;

<PAGE>   72

                                                                             64

                (h) (i) Publishing, any Guarantor or any Material Restricted
         Subsidiary commences a voluntary case or proceeding under any  
         applicable Bankruptcy Law or any other case or proceeding to be
         adjudicated bankrupt or insolvent, (ii) Publishing, any Guarantor or
         any Material Restricted Subsidiary consents to the entry of a decree
         or order for relief in respect of Publishing, any Guarantor or such
         Material Restricted Subsidiary in an involuntary case or proceeding
         under any applicable Bankruptcy Law or to the commencement of any
         bankruptcy or insolvency case or proceeding against it, (iii)
         Publishing, any Guarantor or any Material Restricted Subsidiary files
         a petition or answer or consent seeking reorganization or relief under
         any applicable Federal or state law, (iv) Publishing, any Guarantor or
         any Material Restricted Subsidiary (x) consents to the filing of such
         petition or the appointment of, or taking possession by, a custodian,
         receiver, liquidator, assignee, trustee, sequestrator or similar
         official of Publishing, any Guarantor or such Material Restricted
         Subsidiary or of any substantial part of its property, (y) makes an
         assignment for the benefit of creditors or (z) admits in writing its
         inability to pay its debts generally as they become due or (v)
         Publishing, any Guarantor or any Material Restricted Subsidiary takes
         any corporate action in furtherance of any such actions in this
         paragraph (h); or

                (i) any outstanding Mirror Preferred shall cease to qualify as
         Mirror Preferred under the definition thereof.

                 SECTION 5.02.  Acceleration of Maturity; Rescission and
Annulment.  If an Event of Default (other than an Event of Default specified in
Sections 5.01(g) and (h) with respect to Publishing) occurs and is continuing
with respect to any Series, the Trustee or the Holders of not less than 25% in
aggregate principal amount of the Outstanding Securities hereunder (each such
Series acting as a separate class) may, and the Trustee upon the request of the
Holders of not less than 25% in aggregate principal amount of the Outstanding
Securities of such Series shall, declare the principal amount (or, if the
Securities of such Series are Original Issue Discount Securities, such portion
of the principal amount as may be specified in the terms of that Series) of all
the Securities of such Series to be due and payable immediately in an amount
equal to the principal amount of the Securities of such Series, together with
accrued and unpaid interest, if any, to the date the Securities of such Series
shall have become due and payable, by a notice in writing to Publishing (and to
the Trustee, if given by Holders) and, if the New Bank Credit Facility is in
effect, to the Agent, and upon any such declaration such amount shall become
immediately due and payable.  If an 

<PAGE>   73

                                                                            65

Event of Default specified in Sections 5.01(g) or (h) (if  the Event of Default
under these paragraphs is with respect to all Series of Securities then
Outstanding) occurs with respect to Publishing and is continuing, then all the
Securities shall ipso facto become and be immediately due and payable, in an
amount equal to the principal amount of the Securities of any Series (or, if
any Securities are Original Issue Discount Securities, such portion of the
principal amount as may be specified in the terms thereof), together with
accrued and unpaid interest, if any, to the date the Securities become due and
payable, without any declaration or other act on the part of the Trustee or any
Holder.

                 At any time after such declaration or acceleration has been
made with respect to the Securities of any or all Series, as the case may be,
and before a judgment or decree for payment of the money due has been obtained
by the Trustee as provided hereinafter in this Article, the Holders of at least
a majority in aggregate principal amount of the Outstanding Securities of such
Series, by written notice to Publishing and the Trustee, may rescind and annul
such declaration and its consequences if:

                 (a) Publishing has paid or irrevocably deposited with the 
Trustee a sum sufficient to pay

                 (i) all sums paid or advanced by the Trustee under Section
         6.07 and the reasonable compensation, expenses, disbursements and
         advances of the Trustee, its agents and counsel;

                 (ii) all overdue interest on all Securities of such Series;

                 (iii) the principal and the premium, if any, on any Securities
         of such Series which have become due otherwise than by such
         declaration of acceleration and interest thereon at the rate or rates
         presented therefor by the terms of the Securities of such Series, to
         the extent that payment of such interest is lawful;

                 (iv) interest upon overdue interest at the rate or rates
         presented therefor by the terms of the Securities of such Series, to
         the extent that payment of such interest is lawful; and

                 (b) all Events of Default with respect to such Series of
Securities, other than the nonpayment of principal of the Securities of such
Series which have become due solely by such declaration of acceleration, have
been cured or waived as provided in Section 5.13.

No such rescission shall affect any subsequent Default or impair any right
consequent thereon.
<PAGE>   74

                                                                            66

                 SECTION 5.03.  Collection of Indebtedness and Suits for 
Enforcement by Trustee. Publishing covenants that if

                 (a) default is made in the payment of any interest on any
         Security of any Series when such interest becomes due and payable and
         such default continues for a period of 30 days, or

                 (b) default is made in the payment of the principal of (or
         premium, if any, on) any Security at the Stated Maturity (upon
         acceleration, optional or mandatory redemption, required repurchase or
         otherwise) thereof,

Publishing will, upon demand of the Trustee, pay to it, for the benefit of the
Holders of such Securities the whole amount then due and payable on such
Securities for principal and premium, if any, and interest, with interest upon
the overdue principal and premium, if any, and, to the extent that payment of
such interest shall be legally enforceable, upon overdue installments of
interest, at the rate or rates as may be presented therefor by the terms of any
such Security.

                 If Publishing fails to pay such amounts forthwith upon such
demand, the Trustee, in its own name and as trustee of an express trust, may
institute a judicial proceeding for the collection of the sums so due and
unpaid and may prosecute such proceeding to judgment or final decree, and may
enforce the same against Publishing or any other obligor upon the Securities of
such Series and collect the moneys adjudged or decreed to be payable in the
manner provided by law out of the property of Publishing or any other obligor
upon such Securities, wherever situated.

                 If an Event of Default with respect to any Series of
Securities occurs and is continuing, the Trustee may in its discretion proceed
to protect and enforce its rights and the rights of the Holders of Securities
of such Series under this Indenture by such appropriate private or judicial
proceedings as the Trustee shall deem most effectual to protect and enforce
such rights, whether for the specific enforcement of any covenant or agreement
in this Indenture or in aid of the exercise of any power granted herein or
therein, or to enforce any other proper remedy.

                 The rights and remedies under this Section 5.03 are in
addition to the other rights and remedies under this Article V or Article XIII.

                 SECTION 5.04.  Trustee May File Proofs of Claim.  In case of
the pendency of any receivership, insolvency, liquidation, bankruptcy,
reorganization, arrangement, adjustment, composition or other similar judicial
proceeding 
<PAGE>   75

                                                                             67

relative to Publishing or the property of Publishing, the Trustee 
(irrespective of whether the principal of the Securities shall then be due and
payable as therein expressed or by declaration or otherwise and irrespective of
whether the Trustee shall have made any demand on Publishing for the payment of
overdue principal or interest) shall be entitled and empowered, by intervention
in such proceeding or otherwise:

                 (a) to file and prove a claim for the whole amount of
         principal, and premium, if any, and interest owing and unpaid in
         respect of the Securities and to file such other papers or documents
         as may be necessary or advisable in order to have the claims of the
         Trustee (including any claim for the reasonable compensation,
         expenses, disbursements and advances of the Trustee, its agents and
         counsel) and of the Holders allowed in such judicial proceeding; and

                 (b) to collect and receive any moneys or other property
         payable or deliverable on any such claims and to distribute the same;

and any custodian, receiver, assignee, trustee, liquidator, sequestrator or
similar official in any such judicial proceeding is hereby authorized by each
Holder to make such payments to the Trustee and, in the event that the Trustee
shall consent to the making of such payments directly to the Holders, to pay
the Trustee any amount due it for the reasonable compensation, expenses,
disbursements and advances of the Trustee, its agents and counsel, and any
other amounts due the Trustee under Section 6.07.

                 Nothing herein contained shall be deemed to authorize the
Trustee to authorize or consent to or accept or adopt on behalf of any Holder
any plan of reorganization, arrangement, adjustment, composition or other
similar arrangement affecting the Securities or the rights of any Holder
thereof, or to authorize the Trustee to vote in respect of the claim of any
Holder in any such proceeding.

                 SECTION 5.05.  Trustee May Enforce Claims Without Possession
of Securities.  All rights of action and claims under this Indenture or the
Securities of any Series may be prosecuted and enforced by the Trustee without
the possession of any of the Securities of such Series or the production 
thereof in any proceeding relating thereto, and any such proceeding instituted 
by the Trustee shall be brought in its own name and as trustee of an express 
trust, and any recovery of judgment shall, after provision for the payment of 
the reasonable compensation, expenses, disbursements and advances of the 
Trustee, its agents and counsel, be for the ratable benefit of the Holders of 
the Securities of the Series in respect of which such judgment has been 
recovered.
<PAGE>   76

                                                                             68

                 SECTION 5.06.  Application of Money Collected.  Any money
collected by the Trustee with respect to a Series of Securities pursuant to
this Article or otherwise on behalf of the Holders or the Trustee pursuant to
this Article or through any proceeding or any arrangement or restructuring in
anticipation or in lieu of any proceeding contemplated by this Article shall be
applied, subject to applicable law, in the following order, at the date or
dates fixed by the Trustee and, in case of the distribution of such money on
account of principal, premium, if any, or interest, upon presentation of the
Securities of such Series and the notation thereon of the payment if only
partially paid and upon surrender thereof if fully paid:

                 FIRST:  To the payment of all amounts due the Trustee under
Section 6.07;

                 SECOND:  To the payment in full of the amounts then due and
unpaid upon the Securities of that Series for principal, premium, if any, and
interest, in respect of which or for the benefit of which such money has been
collected, ratably, without preference or priority of any kind, according to
the amounts due and payable on such Securities for principal, premium, if any,
and interest; and

                 THIRD:  The balance, if any, to the Person or Persons entitled
thereto as a court of competent jurisdiction shall direct, or to Publishing;
provided that all sums due and owing to the Holders and the Trustee have been
paid in full as required by this Indenture.

                 SECTION 5.07.  Limitation on Suits.  No Holder of any
Securities of any Series shall have any right to institute any proceeding,
judicial or otherwise, with respect to this Indenture or the Securities, or for
the appointment of a receiver or trustee, or for any other remedy hereunder, 
unless
                 (a) such Holder has previously given written notice to the
         Trustee of a continuing Event of Default with respect to Securities of
         such Series;

                 (b) the Holders of not less than 25% in principal amount of
         the Outstanding Securities of such Series shall have made written
         request to the Trustee to institute proceedings in respect of such
         Event of Default in its own name as Trustee hereunder;

                 (c) such Holder or Holders have offered, and if requested have
         provided, to the Trustee an indemnity satisfactory to the Trustee in
         its sole discretion against the costs, expenses and liabilities that
         may be incurred in compliance with such request;
<PAGE>   77

                                                                             69

                 (d) the Trustee for 60 days after its receipt of such notice,
         request and offer (and if requested, provision) of indemnity has
         failed to institute any such proceeding; and

                 (e) no direction inconsistent with such written request has
         been given to the Trustee during such 60-day period by the Holders of
         a majority in principal amount of the Outstanding Securities of such
         Series;

it being understood and intended that no one or more Holders of Securities of
such Series shall have any right in any manner whatever by virtue of, or by
availing of, any provision of this Indenture to affect, disturb or prejudice
the rights of any other Holders of such Series, or to obtain or to seek to
obtain priority or preference over any other Holders or to enforce any right
under this Indenture, except in the manner provided in this Indenture and for
the equal and ratable benefit of all the Holders of all Securities of such
Series.

                 SECTION 5.08.  Unconditional Right of Holders To Receive
Principal, Premium and Interest.  Notwithstanding any other provision in this
Indenture, the Holder of any Security shall have the right on the terms stated
herein, which is absolute and unconditional, to receive payment of the
principal of, premium, if any, and (subject to Section 3.07) interest on such
Security on the respective Stated Maturities expressed in such Security (or, in
the case of redemption, on the Redemption Date) and to institute suit for the 
enforcement of any such payment, and such rights shall not be impaired without 
the consent of such Holder.

                 SECTION 5.09.  Restoration of Rights and Remedies.  If the
Trustee or any Holder has instituted any proceeding to enforce any right or
remedy under this Indenture and such proceeding has been discontinued or
abandoned for any reason, or has been determined adversely to the Trustee or to
such Holder, then and in every such case, subject to any determination in such
proceeding, (a) Publishing, the Trustee and the Holders shall be restored
severally and respectively to their former positions hereunder, and (b)
thereafter all rights and remedies of the Trustee and the Holders shall
continue as though no such proceeding had been instituted.

                 SECTION 5.10.  Rights and Remedies Cumulative.  Except as
provided in Section 3.06, no right or remedy herein conferred upon or reserved
to the Trustee or to the Holders is intended to be exclusive of any other right
or remedy, and every right and remedy shall, to the extent permitted by law, be
cumulative and in addition to every other right and remedy given hereunder or
now or hereafter existing at law or in equity or otherwise.  The assertion or

<PAGE>   78

                                                                             70

employment of any right or remedy hereunder, or otherwise, shall not prevent
the concurrent assertion or employment of any other appropriate right or
remedy.

                 SECTION 5.11.  Delay or Omission Not Waiver.  No delay or
omission of the Trustee or of any Holder of any Security to exercise any right
or remedy accruing upon any Event of Default shall impair any such right or
remedy or constitute a waiver of any such Event of Default or an acquiescence
therein.  Every right and remedy given by this Article or by law to the Trustee
or to the Holders may be exercised from time to time, and as often as may be
deemed expedient, by the Trustee or by the Holders, as the case may be.

                 SECTION 5.12.  Control by Holders.  The Holders of not less
than a majority in aggregate principal amount of the Outstanding Securities of
any Series shall have the right to direct the time, method and place of
conducting any proceeding for any remedy available to the Trustee, or
exercising any trust or power conferred on the Trustee; provided that:

                 (a) such direction shall not be in conflict with any rule 
         of law or with this Indenture (including, without limitation, 
         Section 5.07) or expose the Trustee to personal liability; and

                 (b) subject to the provisions of Section 315 of the Trust
         Indenture Act, the Trustee may take any other action deemed proper by
         the Trustee which is not inconsistent with such direction.

                 SECTION 5.13.  Waiver of Past Defaults.  The Holders of not
less than a majority in aggregate principal amount of the Outstanding
Securities of any Series may on behalf of the Holders of all the Securities of
such Series waive any past Default hereunder and its consequences, except a
Default

                 (a) in the payment of the principal of, premium, if any, or
         interest on any Security of such Series, or

                 (b) in respect of a covenant or provision hereof which under
         Article IX cannot be modified or amended without the consent of the
         Holder of each Outstanding Security of such Series affected by such
         modification or amendment.

                 Upon any such waiver, such Default shall cease to exist, and
any Event of Default arising therefrom shall be deemed to have been cured, for
every purpose of this Indenture; but no such waiver shall extend to any
subsequent or other Default or impair any right consequent thereon.
<PAGE>   79

                                                                             71

                 SECTION 5.14.  Undertaking for Costs.  All parties to this
Indenture agree, and each Holder of any Security by his acceptance thereof
shall be deemed to have agreed, that any court may in its discretion require,
in any suit for the enforcement of any right or remedy under this Indenture, or
in any suit against the Trustee for any action taken, suffered or omitted by it
as Trustee, the filing by any party litigant in such suit of an undertaking to
pay the costs of such suit, and that such court may in its discretion assess
reasonable costs, including reasonable attorneys' fees, against any party
litigant in such suit, having due regard to the merits and good faith of the
claims or defenses made by such party litigant; but the provisions of this
Section shall not apply to any suit instituted by the Trustee, to any suit
instituted by any Holder, or group of Holders, holding in the aggregate more
than 10% in principal amount of the Outstanding Securities of any Series to
which the suit relates, or to any suit instituted by any Holder for the
enforcement of the payment of the principal of, premium, if any, or interest on
any Security on or after the respective Stated Maturities expressed in such 
Security (or, in the case of redemption, on or after the Redemption Date).

                 SECTION 5.15.  Waiver of Stay, Extension or Usury Laws.
Publishing (to the extent that it may lawfully do so) covenants that it will
not at any time insist upon, or plead, or in any manner whatsoever claim or
take the benefit or advantage of, any stay or extension law or any usury or
other similar law wherever enacted, now or at any time hereafter in force,
which would prohibit or forgive Publishing from paying all or any portion of
the principal of, premium, if any, or interest on the Securities contemplated
herein or in the Securities or which may affect the covenants or the
performance of this Indenture; and Publishing (to the extent that it may
lawfully do so) hereby expressly waives all benefit or advantage of any such
law, and covenants that it will not hinder, delay or impede the execution of
any power herein granted to the Trustee, but will suffer and permit the
execution of every such power as though no such law had been enacted.

                 SECTION 5.16.  Remedies Subject to Applicable Law.  All
rights, remedies and powers provided by this Article may be exercised only to
the extent that the exercise thereof does not violate any applicable provision
of law in the premises, and all the provisions of this Indenture are intended
to be subject to all applicable mandatory provisions of law which may be
controlling in the premises and to be limited to the extent necessary so that
they will not render this Indenture invalid, unenforceable or not entitled to
be recorded, registered or filed under the provisions of any applicable law.

<PAGE>   80
                                                                             72

                                   ARTICLE VI

                                  The Trustee

                 SECTION 6.01.  Duties of Trustee.  (a)  If a Default or an
Event of Default with respect to any Series of Securities actually known to the
Trustee has occurred and is continuing, the Trustee shall exercise such of the
rights and powers vested in it by this Indenture and use the same degree of
care and skill in its exercise thereof as a prudent person would exercise or
use under the circumstances in the conduct of his own affairs.  The Trustee
shall not be charged with knowledge of any Default or Event of Default
with respect to any Series of Securities, Asset Sale or Change of Control
unless written notice thereof shall have been delivered to a Responsible
Officer by Publishing or any other Person.

                 (b)  Except during the continuance of a Default or an Event of
Default with respect to any Series of Securities actually known to the Trustee:

                 (1) the Trustee need perform only those duties as are
         specifically set forth in this Indenture and no covenants or
         obligations shall be implied in this Indenture that are adverse to the
         Trustee; and

                 (2) in the absence of bad faith or wilful misconduct on its
         part, the Trustee may with respect to any Series of Securities,
         conclusively rely, as to the truth of the statements and the
         correctness of the opinions expressed therein, upon certificates or
         opinions furnished to the Trustee and conforming to the requirements
         of this Indenture.  However, the Trustee shall examine the
         certificates and opinions to determine whether or not they conform to
         the requirements of this Indenture.

                 (c)  The Trustee may not be relieved from liability for its
own negligent action, its own negligent failure to act, or its own wilful
misconduct, except that:

                 (1) this paragraph does not limit the effect of paragraph (b)
         of this Section 6.01;

                 (2) the Trustee shall not be liable for any error of judgment
         made in good faith by a Responsible Officer, unless it is proved that
         the Trustee was negligent in ascertaining the pertinent facts; and

                 (3) the Trustee shall not be liable with respect to any action
         it takes or omits to take in good faith in accordance with a direction
         of the Holders of a majority in principal amount of Outstanding
         Securities of any Series relating to the time, method and place of
<PAGE>   81

                                                                             73

         conducting any proceeding for any remedy available to the Trustee, or
         exercising any trust or power confirmed upon the Trustee under this
         Indenture.

                 (d)  No provision of this Indenture shall require the Trustee
to expend or risk its own funds or otherwise incur any loss, expense, fees or 
financial liability in the performance of any of its duties hereunder or in the 
exercise of any of its rights or powers if it   shall have reasonable grounds
for believing that repayment of such funds or adequate indemnity against
such risk or loss, expense, fees or financial liability is not reasonably
assured to it.

                 (e)  Whether or not therein expressly so provided, every
provision of this Indenture that in any way relates to the Trustee is subject
to paragraphs (a), (b), (c) and (d) of this Section 6.01.

                 (f)  The Trustee shall not be liable for interest on any money
or assets received by it except as the Trustee may agree with Publishing.
Assets held in trust by the Trustee need not be segregated from other assets
except to the extent required by law.

                 SECTION 6.02.  Notice of Defaults.  Within 30 days after a
Responsible Officer of the Trustee receives notice of the occurrence of any
Default with respect to Securities of any Series, the Trustee shall, at
Publishing's expense, transmit by mail to all Holders of such Series or any
other persons entitled to receive reports pursuant to Trust Indenture Act
Section 313(c), as their names and addresses appear in the Security Register,
notice of such Default, unless such Default shall have been cured or waived;
provided, however, that, except in the case of a Default in the payment of the
principal of, premium, if any, or interest on any Security, the Trustee shall
be protected in withholding such notice if and so long as a trust committee of
Responsible Officers of the Trustee in good faith determines that the
withholding of such notice is in the interest of the Holders of such Series.

                 SECTION 6.03.  Certain Rights of Trustee.  Subject to the
provisions of Trust Indenture Act Sections 315(a) through 315(d):

                 (a) the Trustee may rely conclusively and shall be protected
         in acting or refraining from acting upon any resolution, certificate,
         statement, instrument, opinion, report, notice, request, direction,
         consent, order, bond, debenture, note, other evidence of indebtedness
         or other paper or document believed by it to be genuine and to have
         been signed or presented by the proper party or parties;
<PAGE>   82

                                                                             74

                 (b) any request or direction of Publishing mentioned herein
         shall be sufficiently evidenced by a Publishing Request or Publishing
         Order and any resolution of the Board of Directors may be sufficiently
         evidenced by a Board Resolution;

                 (c) wherever in the administration of this Indenture the
         Trustee shall deem it desirable that a matter be proved or established
         prior to the taking, suffering or omitting any action hereunder, the
         Trustee (unless other evidence be herein specifically prescribed) in
         the absence of bad faith on its part, may rely conclusively, upon an
         Officers' Certificate and/or an Opinion of Counsel;

                 (d) the Trustee may consult with counsel and any written
         advice of such counsel or any Opinion of Counsel shall be full and
         complete authorization and protection in respect of any action taken,
         suffered or omitted by it hereunder in good faith and in reliance
         thereon in accordance with such advice or Opinion of Counsel;

                 (e) notwithstanding any other provisions contained in this
         Indenture, the Trustee shall be under no obligation to exercise any of
         the rights or powers vested in it by this Indenture at the request or
         direction of any of the Holders pursuant to this Indenture, unless
         such Holders shall have offered to the Trustee security or indemnity
         satisfactory to the Trustee in its sole discretion against the costs,
         expenses and liabilities which might be incurred therein or thereby in
         compliance with such request or direction;

                 (f) the Trustee shall not be liable for any action taken or
         omitted by it in good faith and believed by it to be authorized or
         within the discretion, rights or powers conferred upon it by this
         Indenture other than any liabilities arising out of the negligence or
         wilful misconduct of the Trustee;

                 (g) the Trustee shall not be bound to make any investigation
         into the facts or matters stated in any resolution, certificate,
         statement, instrument, opinion, report, notice, request, direction,
         consent, order, approval, appraisal, bond, debenture, note, coupon,
         security or other paper or document; but the Trustee in its discretion
         may make such further inquiry or investigation in accordance with any
         of the provisions of this Indenture into such facts or matters as it
         may see fit, and, if the Trustee shall determine to make such further
         inquiry or investigation, it shall be entitled to examine such 
         relevant books, records and 

<PAGE>   83

                                                                             75

         premises of Publishing as may be reasonable, personally or by agent 
         or attorney;

                 (h) the Trustee may execute any of the trusts or powers
         hereunder or perform any duties hereunder either directly or by or
         through agents or attorneys and the Trustee shall not be responsible
         for any misconduct or negligence on the part of any agent or attorney
         appointed with due care by it hereunder; and

                 (i) no provision of this Indenture shall require the Trustee
         to expend or risk its own funds or otherwise incur any financial
         liability in the performance of any of its duties hereunder, or in the
         exercise of any of its rights and powers.

                 SECTION 6.04.  Trustee Not Responsible for Recitals,
Dispositions of Securities or Application of Proceeds Thereof.  The recitals
contained herein and in the Securities, except the Trustee's certificates of
authentication, shall be taken as the statements of Publishing, and the Trustee
assumes no responsibility for their correctness.  The Trustee makes no
representations as to the validity or sufficiency of this Indenture or the
Securities, except that the Trustee represents that it is duly authorized to
execute and deliver this Indenture, authenticate the Securities and perform its
obligations hereunder and that the statements made by it in a Statement of
Eligibility and Qualification on Form T-1 supplied to Publishing are true and
accurate subject to the qualifications set forth therein.  The Trustee shall
not be accountable for the use or application by Publishing of Securities or
the proceeds thereof.

                 SECTION 6.05.  Trustee and Agents May Hold Securities;
Collections; etc.  The Trustee, any Paying Agent, Security Registrar or any
other agent of Publishing, in its individual or any other capacity, may become
the owner or pledgee of Securities, with the same rights it would have if it
were not the Trustee, Paying Agent, Security Registrar or such other agent and,
subject to Trust Indenture Act Sections 310 and 311, may otherwise deal with
Publishing and receive, collect, hold and retain collections from Publishing
with the same rights it would have if it were not the Trustee, Paying Agent,
Security Registrar or such other agent.


                 SECTION 6.06.  Money Held in Trust.  All moneys received by 
the Trustee shall, until used or applied as herein provided, be held in trust 
for the purposes for which they were received, but need not be segregated from 
other funds except to the extent required by mandatory provisions of law.  
Except for funds or securities deposited with the Trustee pursuant to 
Article IV, the Trustee shall only be required to invest moneys received by 
the Trustee, until 
<PAGE>   84

                                                                             76

used or applied as herein provided, in Temporary Cash  Investments in 
accordance with the directions of Publishing.

                 SECTION 6.07.  Compensation and Indemnification of Trustee and
Its Prior Claim.  Publishing covenants and agrees to pay to the Trustee from
time to time, and the Trustee shall be entitled to, reasonable compensation for
all services rendered by it hereunder (which, to the extent lawful, shall not be
limited by any provision of law in regard to the compensation of a trustee of an
express trust) and Publishing covenants and agrees to pay or reimburse the
Trustee and each predecessor Trustee upon its request for all reasonable
expenses, disbursements and advances incurred or made by or on behalf of it 
in accordance with any of the provisions of this Indenture (including the
reasonable compensation and the expenses and disbursements of its counsel and 
of all agents and other persons not regularly in its employ) except any such
expense, disbursement or advance as may arise from its negligence, bad faith or
wilful misconduct.  When the Trustee incurs expenses or renders services in
connection with an Event of Default specified in Section 5.01(g) or Section
5.01(h), the expenses (including the reasonable compensation and the expenses
and disbursements of its counsel) and the compensation for the services are
intended to constitute expenses of administration under any applicable Federal
or state bankruptcy, insolvency or other similar law.  Publishing also covenants
to indemnify the Trustee and each predecessor Trustee, and their respective
officers, agents and employees for, and to hold them harmless against, any
claim, loss, liability, tax, assessment or other governmental charge (other than
taxes applicable to the Trustee's compensation hereunder) or expense incurred
without negligence, bad faith or wilful misconduct on its part, arising out of
or in connection with the acceptance or administration of this Indenture or the
trusts hereunder and its duties hereunder, including enforcement of this Section
6.07 and also including any liability which the Trustee may incur as a result of
failure to withhold, pay or report any tax, assessment or other governmental
charge, and the costs and expenses of defending itself against or investigating
any claim of liability in the premises.  The obligations of Publishing under
this Section to compensate and indemnify the Trustee and each predecessor
Trustee and to pay or reimburse the Trustee and each predecessor Trustee for
expenses, disbursements and advances shall constitute an additional obligation
hereunder and shall survive the satisfaction and discharge of this Indenture and
the resignation or removal of the Trustee and each predecessor Trustee.  As
security for the performance of the obligations of Publishing under this
Section, the Trustee shall have a lien prior to the Securities upon all property
and funds held or collected by the Trustee as such, except funds held in trust
for the benefit of Holders of particular Securities.
<PAGE>   85

                                                                             77

                 SECTION 6.08.  Conflicting Interests.  The Trustee shall
comply with the provisions of Section 310(b) of the Trust Indenture Act.  In
determining whether the Trustee has a conflicting interest as defined in
Section 310(b) of the Trust Indenture Act with respect to the Securities of any
Series, there shall be excluded this Indenture with respect to Securities of
any particular Series of Securities other than that Series.  Nothing herein
shall prevent the Trustee from filing with the Commission the application
referred to in the second to last paragraph of Section 310(b) of the Trust
Indenture Act.

                 SECTION 6.09.  Corporate Trustee Required; Eligibility.  There
shall at all times be a Trustee hereunder which shall be eligible to act as
Trustee under the Trust Indenture Act Section 310(a)(1) and which shall have a
combined capital and surplus of at least $100,000,000, and have a Corporate
Trust Office in The City of New York to the extent there is such an institution
eligible and willing to serve.  If the Trustee does not have an office in the
City of New York, the Trustee shall appoint an agent in the City of New York
reasonably acceptable to Publishing to conduct any activities which the Trustee
is required under this Indenture to conduct in the City of New York.  The
Trustee may not rescind any such agency without the consent of Publishing,
which consent may not be unreasonably withheld, unless the Trustee appoints a
satisfactory replacement or has a Corporate Trust Office in the City of New
York.  If such corporation publishes reports of conditions at least annually,
pursuant to law or to the requirements of Federal, state, territorial or
District of Columbia supervising or examining authority, then for the purposes
of this Section, the combined capital and surplus of such corporation shall be
deemed to be its combined capital and surplus as set forth in its most recent
report of conditions so published.  If at any time the Trustee shall cease to 
be eligible in accordance with the provisions of this Section, the Trustee 
shall resign immediately in the manner and with the effect hereinafter 
specified in this Article.

                 SECTION 6.10.  Resignation and Removal; Appointment of
Successor Trustee.  (a)  No resignation or removal of the Trustee and no
appointment of a successor Trustee pursuant to this Article shall become
effective until the acceptance of appointment by the successor Trustee under
Section 6.11.

                 (b)  The Trustee, or any trustee or trustees hereafter
appointed, may at any time resign with respect to any Series of Securities by
giving written notice thereof to Publishing.  Upon receiving such notice of
resignation, Publishing shall use its best efforts to promptly appoint a
successor Trustee by Board Resolution or written instrument executed by
authority of the Board of Directors of 
<PAGE>   86

                                                                             78

Publishing, a copy of which shall be delivered to the resigning Trustee and a
copy to the successor Trustee.  If an instrument of acceptance by a successor
Trustee shall not have been delivered to the Trustee within 30 days after the
giving of such notice of resignation, the resigning Trustee may, or any Holder
who has been a bona fide Holder of a Security for at least six months may, on
behalf of himself and all others similarly situated, petition any court of
competent jurisdiction for the appointment of a successor Trustee.  Such court
may thereupon, after such notice, if any, as it may deem proper, appoint a
successor Trustee.

                 (c)  The Trustee may be removed with respect to any Series of
Securities at any time by an Act of the Holders of not less than a majority in
aggregate principal amount of the Outstanding Securities of that Series,
delivered to the Trustee and to Publishing.

                 (d)  If at any time:

                 (1) the Trustee shall fail to comply with the provisions of
         Trust Indenture Act Section 310(b) with respect to any Series of
         Securities after written request therefor by Publishing or by any
         Holder who has been a bona fide Holder of a Security for at least six
         months, or

                 (2) the Trustee shall cease to be eligible under Section 6.09
         with respect to any Series of Securities and shall fail to resign
         after written request therefor by Publishing or by any such Holder, or

                 (3) the Trustee shall become incapable of acting with respect
         to any Series of Securities or shall be adjudged a bankrupt or
         insolvent, or a receiver of the Trustee or of its property shall be
         appointed or any public officer shall take charge or control of the
         Trustee or of its property or affairs for the purpose of
         rehabilitation, conservation or liquidation,

then, in any case, (i) Publishing by a Board Resolution may remove the Trustee,
with respect to any Series of Securities or in the case of bankruptcy or
insolvency or receivership pursuant to clause (3) above, with respect to all
Series, or (ii) subject to Section 5.14, any Holder of any Security who has
been a bona fide Holder of a Security of such Series for at least six months
may, on behalf of himself and all others similarly situated, petition any court
of competent jurisdiction for the removal of the Trustee and the appointment of
a successor Trustee with respect to the Series, or in the case of bankruptcy or
insolvency or receivership pursuant to clause (3) above, with respect to all
Series.  Such court may thereupon, after such notice, if any, as it may deem
proper and prescribe, remove the Trustee and appoint a successor Trustee.
<PAGE>   87

                                                                             79

                 (e)  If the Trustee shall resign, be removed or become
incapable of acting with respect to any Series of Securities, or if a vacancy
shall occur in the office of Trustee with respect to any Series for any cause,
Publishing, by a Board Resolution or written instrument executed by authority
of the Board of Directors of Publishing, shall use its best efforts to promptly
appoint a successor Trustee for that Series of Securities and shall comply with
the applicable requirements of Section 6.11.  If, within one year after such
resignation, removal or incapability, or the occurrence of such vacancy,
Publishing or a court of competent jurisdiction has not appointed a successor
Trustee, a successor Trustee with respect to such Series of Securities shall be
appointed by Act of the Holders of a majority in principal amount of the
Outstanding Securities of such Series delivered to Publishing and the retiring
Trustee, and the successor Trustee so appointed shall, forthwith upon its
acceptance of such appointment, become the successor Trustee with respect to
such Series of Securities and supersede the successor Trustee appointed by
Publishing with respect to such Series of Securities.  If no successor Trustee
shall have been so appointed by Publishing or the Holders of such Series of
Securities and accepted appointment in the manner hereinafter provided, any
Holder of a Security who has been a bona fide Holder of a Security of that
Series for at least six months may, subject to Section 5.14, on behalf of 
himself and all other similarly situated, petition any court of competent 
jurisdiction for the appointment of a successor Trustee with respect to such 
Series.

                 (f)  Publishing shall give notice of each resignation and each
removal of the Trustee with respect to any Series and each appointment of a
successor Trustee with respect to any Series by mailing written notice of such
event by first-class mail, postage prepaid, to the Holders of Securities of
that Series as their names and addresses appear in the Security Register.  Each
notice shall include the name of the successor Trustee and the address of its
Corporate Trust Office or agent hereunder.

                 SECTION 6.11.  Acceptance of Appointment by Successor.  In
case of the appointment hereunder of a successor Trustee with respect to the
Securities, every such successor Trustee so appointed shall execute,
acknowledge and deliver to Publishing and to the retiring Trustee an instrument
accepting such appointment, and thereupon the resignation or removal of the
retiring Trustee shall become effective and such successor Trustee, without any
further act, deed or conveyance, shall become vested with all the rights,
powers, trusts and duties of the retiring Trustee under this Indenture with
respect to any such Series; but, nevertheless, on the written request of
Publishing or the successor Trustee, upon payment of its charges then unpaid,
such retiring Trustee shall pay over to the successor 
<PAGE>   88

                                                                             80

Trustee all moneys at the time held by it hereunder with respect to any such 
Series and shall execute and deliver an instrument transferring to such 
successor Trustee all such rights, powers, duties and obligations.

                 Upon request of any such successor Trustee, Publishing shall
execute any and all instruments for more fully and certainly vesting in and
confirming to such successor Trustee all such rights and powers.  Any Trustee
ceasing to act shall, nevertheless, retain a prior claim upon all property or
funds held or collected by such Trustee or such successor Trustee to secure any
amounts then due such Trustee pursuant to the provisions of Section 6.07.

                 No successor Trustee with respect to the Securities shall
accept appointment as provided in this Section 6.11 unless at the time of such
acceptance such successor Trustee shall be eligible to act as Trustee under the
provisions of Trust Indenture Act Section 310(a) and this Article VI and shall 
have a combined capital and surplus of at least $100,000,000 and have a 
Corporate Trust Office or an agent selected in accordance with Section 6.09 in 
the City of New York.

                 Upon acceptance of appointment by any successor Trustee as
provided in this Section 6.11, Publishing shall give notice thereof to the
Holders of the Securities of such Series, by mailing such notice to such
Holders at their addresses as they shall appear on the Security Register.  If
the acceptance of appointment is substantially contemporaneous with the
resignation, then the notice called for by the preceding sentence may be
combined with the notice called for by Section 6.10.  If Publishing fails to
give such notice within 10 days after acceptance of appointment by the
successor Trustee, the successor Trustee shall cause such notice to be given at
the expense of Publishing.

                 SECTION 6.12.  Merger, Conversion, Consolidation or Succession
to Business.  Any corporation into which the Trustee may be merged or converted
or with which it may be consolidated, or any corporation resulting from any
merger, conversion or consolidation to which the Trustee shall be a party, or
any corporation succeeding to all or substantially all of the corporate trust
business of the Trustee, shall be the successor of the Trustee hereunder,
without the execution or filing of any paper or any further act on the part of
any of the parties hereto; provided such corporation shall be eligible under
Trust Indenture Act Section 310(a) and this Article VI and shall have a
combined capital and surplus of at least $100,000,000.

                 In case at the time such successor to the Trustee shall
succeed to the trusts created by this Indenture any of the Securities shall
have been authenticated but not 
<PAGE>   89

                                                                             81

delivered, any such successor to the Trustee may adopt the certificate of  
authentication of any predecessor Trustee and deliver such Securities so
authenticated; and, in case at that time any of the Securities shall not have
been authenticated, any successor to the Trustee may authenticate such
Securities either in the name of any predecessor hereunder or in the name of
the successor Trustee.  In all such cases such certificates shall have the full
force and effect which this Indenture provides for the certificate of
authentication of the Trustee; provided that the right to adopt the certificate
of authentication of any predecessor Trustee or to authenticate Securities in
the name of any predecessor Trustee shall apply only to its successor or 
successors by merger, amalgamation, conversion or consolidation.

                 SECTION 6.13.  Preferential Collection of Claims Against
Publishing.  If and when the Trustee shall be or become a creditor of
Publishing, the Trustee shall be subject to the provisions of the Trust
Indenture Act regarding the collection of claims against Publishing.


                                  ARTICLE VII

              Holders' Lists and Reports by Trustee and Publishing

                 SECTION 7.01.  Publishing To Furnish Trustee Names and
Addresses of Holders.  Publishing will furnish or cause to be furnished to 
the Trustee:

                 (a) semiannually, not more than 10 days after each Regular
         Record Date, a list, in such form as the Trustee may reasonably
         require, of the names and addresses of the Holders of Securities of
         each Series as of such Regular Record Date; and

                 (b) at such other times as the Trustee may reasonably request
         in writing, within 30 days after receipt by Publishing of any such
         request, a list of similar form and content to that in subsection (a)
         hereof as of a date not more than 15 days prior to the time such list
         is furnished;

provided, however, that if and so long as the Trustee shall be the Security
Registrar for Securities of a Series, no such list need be furnished with
respect to such Series of Securities.

                 SECTION 7.02.  Disclosure of Names and Addresses of Holders.
Every Holder of Securities of any Series, by receiving and holding the same,
agrees with Publishing and the Trustee that neither Publishing nor the Trustee
or any agent of either of them shall be held accountable by reason of the
disclosure of any information as to the names and 
<PAGE>   90

                                                                             82

addresses of the Holders in accordance with Trust Indenture Act Section 312, 
regardless of the source from which such information was derived, and that the 
Trustee shall not be held accountable or liable by reason of mailing any 
material pursuant to a request made under Trust Indenture Act Section 312.

                  SECTION 7.03.  Reports by Trustee.  (a)  Within 60 days 
after May 15 of each year commencing with the first May 15 after the
issuance of Securities of any Series, the Trustee shall transmit by mail, at
Publishing's expense, to all Holders, as their names and addresses appear in
the Security Register, as provided in Trust Indenture Act Section 313(c), a
brief report dated as of such May 15 in accordance with and with respect to the
matters required by Trust Indenture Act Section 313(a).

                 (b)  The Trustee shall promptly transmit to Publishing a copy
of any report it transmits to Holders of such Series pursuant to this Section
7.03.

                 SECTION 7.04.  Reports by Publishing.  Publishing shall do the
following:

                 (a) file with the Trustee, in accordance with Section 10.17
hereof, and in any event within 30 days after Publishing is required to file
the same with the Commission, copies of the annual reports and of the
information, documents and other reports (or copies of such portions of any of
the foregoing as the Commission may from time to time by rules and regulations
prescribe) which Publishing is required to file with the Commission separately
or together with Hollinger International pursuant to Section 13 or Section
15(d) of the Exchange Act; or, if Publishing is not required to file
information, documents or reports pursuant to either of said Sections, then it
shall (i) deliver to the Trustee annual audited financial statements of
Publishing and its Restricted Subsidiaries, prepared on a Consolidated basis in
conformity with GAAP, within 120 days after the end of each fiscal year of
Publishing, and (ii) file with the Trustee and the Commission, in accordance
with, and so long as not prohibited by, the rules and regulations prescribed
from time to time by the Commission, such of the supplementary and periodic
information, documents and reports which may be required pursuant to Section 13
of the Exchange Act in respect of a security listed and registered on a
national securities exchange as may be prescribed from time to time in such
rules and regulations;

                 (b) file with the Trustee and the Commission, in accordance
with the rules and regulations prescribed from time to time by the Commission,
such additional information, documents and reports with respect to compliance
by Publishing with the conditions and covenants of this Indenture as is
required from time to time by such rules and 
<PAGE>   91

                                                                            83

regulations (including such rules and regulations, if any, referred to in 
Trust Indenture Act Section 314(a)); and

                 (c) transmit by mail to all Holders or any other persons
entitled to receive a report pursuant to Trust Indenture Act Section 313(c),
within 30 days after the filing thereof with the Trustee, in the manner and to
the extent provided in Trust Indenture Act Section 313(c), such summaries of
any information, documents and reports required to be filed by Publishing
pursuant to Section 10.17 hereunder and subsections (a) and (b) of this Section
as is required and not prohibited by rules and regulations prescribed from time
to time by the Commission.


                                  ARTICLE VIII

                     Consolidation, Merger, Sale of Assets

                 SECTION 8.01.  Publishing May Merge, Consolidate, etc., Only
on Certain Terms.  (a)  Publishing shall not, in a single transaction or a
series of related transactions, consolidate with or merge with or into any
other Person or sell, assign, convey, transfer, lease or otherwise dispose of
all or substantially all of its properties and assets to any Person or group of
affiliated Persons, or permit any of its Restricted Subsidiaries to enter into
any such transaction or transactions (other than, in the case of a Restricted
Subsidiary, such a consolidation, merger or transfer with or to one or more
Wholly Owned Restricted Subsidiaries) if such transaction or transactions, in
the aggregate, would result in a sale, assignment, conveyance, transfer, lease
or disposition of all or substantially all of the properties and assets of
Publishing and its Restricted Subsidiaries on a Consolidated basis to any other
Person or group of affiliated Persons, unless at the time and after giving
effect thereto:

                 (i) either (a) Publishing shall be the continuing corporation,
         or (b) the Person (if other than Publishing) formed by such
         consolidation or into which Publishing is merged or the Person which
         acquires by sale, assignment, conveyance, transfer, lease or
         disposition all or substantially all of the properties and assets of
         Publishing and its Restricted Subsidiaries on a Consolidated basis (the
         "Surviving Entity") shall be a corporation duly organized and validly
         existing under the laws of the United States of America, any state
         thereof or the District of Columbia and shall expressly assume, by a
         supplemental indenture hereto, executed and delivered to the Trustee,
         in form and substance reasonably satisfactory to the Trustee, all the
         obligations of Publishing under the Securities and this Indenture, and
         this Indenture shall remain in full force and effect;
<PAGE>   92

                                                                             84

                 (ii) immediately before and immediately after giving effect to
         such transaction on a pro forma basis, no Default or Event of Default
         shall have occurred and be continuing;

                 (iii) immediately after giving effect to the transaction on a
         pro forma basis, the Consolidated Net Worth of the Surviving Entity is
         not less than the Consolidated Net Worth of Publishing and the
         Restricted Subsidiaries immediately prior to the transaction;

                 (iv) immediately before and immediately after giving effect to
         such transaction on a pro forma basis (on the assumption that the
         transaction occurred on the first day of the four-quarter period
         immediately prior to the consummation of such transaction with the
         appropriate adjustments with respect to the transaction being included
         in such pro forma calculation), Publishing (or the Surviving Entity if
         Publishing is not the continuing obligor under this Indenture) could
         Incur $1.00 of additional Indebtedness under the provisions of Section
         10.08 (other than Permitted Indebtedness);

                 (v) if any of the property or assets of Publishing or any of
         its Restricted Subsidiaries would thereupon become subject to any
         Lien, the provisions of Section 10.12 are complied with; and

                 (vi) Publishing or the Surviving Entity shall have delivered,
         or caused to be delivered, to the Trustee, in form and substance
         reasonably satisfactory to the Trustee, an Officers' Certificate and
         an Opinion of Counsel, each to the effect that such consolidation,
         merger, transfer, sale, assignment, lease or other transaction and the
         supplemental indenture in respect thereof comply with the provisions
         described in this Section 8.01(a) and that all conditions precedent
         herein provided for in this Section 8.01(a) relating to such
         transaction have been complied with.

                 (b)  Neither Hollinger International nor any Restricted
Subsidiary Guarantor shall, and Publishing shall not permit a Restricted
Subsidiary Guarantor to, in a single transaction or series of related
transactions, consolidate with or merge with or into any other Person
(other than Publishing, Hollinger International or any other Restricted
Subsidiary Guarantor), or sell, assign, convey, transfer, lease or otherwise
dispose of all or substantially all of its properties and assets on a
Consolidated basis to any Person (other than Publishing, Hollinger
International or any other Restricted Subsidiary Guarantor) if such transaction
or transactions, in the aggregate, would result in a sale, assignment,
conveyance, transfer, lease or disposition of all or substantially all of the
properties 
<PAGE>   93

                                                                             85

and assets of such Guarantor to any other Person or group of affiliated 
Persons, unless at the time and after giving effect thereto:

                 (i) either (a) Hollinger International or such Restricted
Subsidiary Guarantor shall be the continuing corporation or (b) the Person (if
other than Hollinger International or such Restricted Subsidiary Guarantor)
formed by such consolidation or into which Hollinger International or such
Restricted Subsidiary Guarantor, as the case may be, is merged or the Person
which acquires by sale, assignment, conveyance, transfer, lease or disposition
all or substantially all of the properties and assets of Hollinger
International or such Restricted Subsidiary Guarantor shall be a corporation
duly organized and validly existing under the laws of the United States of
America, any state thereof or the District of Columbia and shall (except where
Hollinger International or such Restricted Subsidiary Guarantor is the
continuing corporation) expressly assume, by a supplemental indenture hereto,
executed and delivered to the Trustee, in form and substance reasonably
satisfactory to the Trustee, all the obligations of Hollinger International or
such Restricted Subsidiary Guarantor, as the case may be, under the Securities
and this Indenture, and this Indenture shall remain in full force and effect;

                 (ii) immediately before and immediately after giving effect to
such transaction on a pro forma basis, no Default or Event of Default shall
have occurred and be continuing; and

                 (iii) Hollinger International or such Restricted Subsidiary
Guarantor, as the case may be, shall have delivered, or caused to be delivered,
to the Trustee, in form and substance reasonably satisfactory to the Trustee,
an Officers' Certificate and an Opinion of Counsel, each stating that such
consolidation, merger, sale, assignment, conveyance, transfer, lease or other
transaction and the supplemental indenture in respect thereof comply with the
provisions described in this Section 8.01(b), and that all conditions precedent
herein provided for in this Section 8.01(a) relating to such transactions have
been complied with.

                 (c)  Notwithstanding anything in this Article Eight to the
contrary, any Guarantee by a Restricted Subsidiary of the Securities may be
released in accordance with the provisions of Section 10.13(c).

                 SECTION 8.02.  Successor Substituted.  Upon any consolidation
or merger, or any sale, assignment, conveyance, transfer, lease or disposition
of all or substantially all of the properties and assets on a Consolidated
basis of Publishing, Hollinger International or 
<PAGE>   94

                                                                             86

any Restricted Subsidiary Guarantor in accordance with Section 8.01 with  
respect to which Publishing, Hollinger International or such Restricted
Subsidiary Guarantor is not the continuing corporation, the successor Person
formed by such consolidation or into which Publishing, Hollinger International
or such Restricted Subsidiary Guarantor is merged or the successor Person to
which such sale, assignment, conveyance, transfer, lease or disposition is made
shall succeed to, and be substituted for, and may exercise every right and
power of, Publishing, Hollinger International or such Restricted Subsidiary
Guarantor, as the case may be, under this Indenture, with the same effect as if
such successor had been named as Publishing, Hollinger International or such
Restricted Subsidiary Guarantor, as the case may be, herein.  When a successor
assumes all the obligations and covenants of its predecessor under this
Indenture or the Securities, the predecessor shall be released from those
obligations and covenants; provided that, in the case of a transfer by lease,
the predecessor shall not be released from the payment of principal and
interest on the Securities or, in the case of Hollinger International or a
Restricted Subsidiary Guarantor, such Guarantee, as the case may be.

                 Any successor to Publishing described in the foregoing
paragraph may cause to be signed, and may issue either in its own name or in
the name of Publishing, any or all of the Securities issuable hereunder which
theretofore shall not have been signed by Publishing and delivered to the
Trustee; and, upon the order of such successor, instead of Publishing, and
subject to all the terms, conditions and limitations in this Indenture
prescribed, the Trustee shall authenticate and shall deliver any Securities
which previously shall have been signed and delivered by the officers of
Publishing to the Trustee for authentication, and any Securities which such 
successor thereafter shall cause to be signed and delivered to the Trustee for 
that purpose.  All the Securities so issued shall in all respects have the 
same legal rank and benefit under this Indenture as the Securities theretofore
or thereafter issued in accordance with the terms of this Indenture as though 
all of such Securities had been issued at the date of the execution of this 
Indenture.


                                   ARTICLE IX

                            Supplemental Indentures

                 SECTION 9.01.  Supplemental Indentures and Agreements Without
Consent of Holders.  Without the consent of any Holders of the Securities of
any Series, Publishing, each Guarantor and the Trustee, at any time and from
time to 
<PAGE>   95

                                                                             87

time, may enter into one or more indentures supplemental hereto, in form and 
substance reasonably satisfactory to the Trustee, for any of the following 
purposes:

                 (a) to evidence the succession of another Person to Publishing
         or any Guarantor, and the assumption by any such successor of the
         covenants of Publishing or such Guarantor, as the case may be, herein
         and in the Securities of any Series;

                 (b) to add to the covenants of Publishing or the Guarantors
         for the benefit of the Holders of the Securities of any or all Series
         (and if such covenants or the surrender of such right or power are to
         be for the benefit of less than all Series of Securities, stating that
         such covenants are expressly being included or such surrenders are
         expressly being made solely for the benefit of one or more specified
         Series), or to surrender any right or power conferred upon Publishing
         or the Guarantors in this Indenture or the Securities of any Series;

                 (c) to cure any ambiguity or to correct or supplement any
         provision in this Indenture or the Securities of any Series which may
         be defective or inconsistent with any other provision in this
         Indenture or the Securities;

                 (d) to comply with the requirements of the Commission in order
         to effect or maintain the qualification of this Indenture under the
         Trust Indenture Act, as contemplated by Section 9.05 or otherwise;

                 (e) to add a Guarantee of the Indenture Obligations;

                 (f) to evidence and provide the acceptance of the appointment
         of a successor Trustee hereunder;

                 (g) to mortgage, pledge, hypothecate or grant a security
         interest in favor of the Trustee for the benefit of the Holders as
         additional security, pursuant to the requirements of Section 10.12 or
         otherwise, for the payment and performance of the Indenture
         Obligations, in any property or assets, including any which are
         required to be mortgaged, pledged or hypothecated, or in which a
         security interest is required to be granted, to the Trustee pursuant
         to this Indenture or otherwise;

                 (h) to clarify or make any other provisions with respect to
         matters or questions arising under this Indenture or the Securities;
         provided that, in each 
<PAGE>   96

                                                                             88

         case, such clarification or provision thus made shall not adversely 
         affect the interests of the Holders; and

                 (i) to establish any form of Security, as provided in Article
         Two, and to provide for the issuance of any Series of Securities as
         provided in Article Three and to set forth the terms thereof, and/or
         to add to the rights of the Holders of the Securities of any Series.

                 SECTION 9.02.  Supplemental Indentures and Agreements with
Consent of Holders.  Except as permitted by Section 9.01, with the consent of
the Holders of not less than a majority in aggregate principal amount of the
Outstanding Securities of each Series affected by such supplemental indenture
or indentures, by Act of said Holders delivered to Publishing and the Trustee,
Publishing and each Guarantor (if a party thereto) and the Trustee may (i)
enter into an indenture or indentures supplemental hereto, in form and
substance reasonably satisfactory to the Trustee, for the purpose of adding any
provisions to or amending, modifying or changing in any manner or eliminating
any of the provisions of this Indenture or the Securities of each such Series
(including, but not limited to, for the purpose of modifying in any manner the
rights of the Holders of the Securities of each such Series under this
Indenture) or (ii) waive compliance with any provision in this Indenture or the
Securities of each such Series (other than waivers of past Defaults covered by 
Section 5.13 and waivers of covenants which are covered by Section 10.19); 
provided, however, that no such supplemental indenture, agreement or 
instrument shall, without the consent of the Holder of each Outstanding 
Securities of any Series affected thereby:

                 (a) change the Stated Maturity of the principal of, or any
         installment of interest on, any Securities of any Series or waive a
         default in the payment of the principal or interest on any Security of
         any Series or reduce the principal amount thereof or the rate of
         interest thereon or any premium payable upon the redemption thereof,
         or change the coin or currency in which the principal of any Security
         or any premium or the interest thereon is payable, or impair the right
         to institute suit for the enforcement of any such payment after the
         Stated Maturity thereof;

                 (b) amend, change or modify the obligation of Publishing to
         make and consummate a Change of Control Offer in the event of a Change
         of Control in accordance with Section 10.14, including amending,
         changing or modifying any of the provisions or definitions with
         respect thereto;

                 (c) reduce the percentage in principal amount of the
         Outstanding Securities of any Series, the consent of whose Holders is
         required for any such supplemental 
<PAGE>   97

                                                                            89

         indenture or the consent of whose Holders is required for any waiver 
         of compliance with certain provisions of this Indenture or certain 
         Defaults hereunder and their consequences provided for in this 
         Indenture;

                 (d) modify any of the provisions of this Section or Sections
         5.13 or 10.19, except to increase the percentage of Outstanding
         Securities of any Series required for such actions or to provide that
         certain other provisions of this Indenture cannot be modified or
         waived without the consent of the Holder of each Security affected
         thereby; or

                 (e) except as otherwise permitted under Article VIII, consent
         to the assignment or transfer by Publishing or any Guarantor of any of
         its rights and obligations under this Indenture.

                 A supplemental indenture which changes or eliminates any
covenant or other provision of this Indenture which has expressly been included
solely for the benefit of one or more particular Series of Securities, or which
modifies the rights of the Holders of Securities of such Series with respect to
such covenant or other provision, shall be deemed not to affect the rights under
this Indenture of the Holders of Securities of any other Series.

                 Upon the written request of Publishing, accompanied by a copy
of a Board Resolution authorizing the execution of any such supplemental
indenture, and upon the filing with the Trustee of evidence of the consent of
Holders as aforesaid, the Trustee shall join with Publishing in the execution
of such supplemental indenture.

                 It shall not be necessary for any Act of Holders under this
Section to approve the particular form of any proposed supplemental indenture
or agreement, but it shall be sufficient if such Act shall approve the
substance thereof.

                 SECTION 9.03.  Execution of Supplemental Indentures and
Agreements.  In executing, or accepting the additional trusts created by, any
supplemental indenture, agreement or instrument permitted by this Article or
the modifications thereby of the trusts created by this Indenture, the Trustee
shall be entitled to receive, and (subject to Trust Indenture Act Section
315(a) through 315(d) and Section 6.03 hereof) shall be fully protected in
relying upon, an Opinion of Counsel and an Officers' Certificate to the effect
that the execution of such supplemental indenture, agreement or instrument is
authorized or permitted by this Indenture.  The Trustee may, but shall not be
obligated to, enter into any such supplemental indenture, agreement or
instrument which 
<PAGE>   98

                                                                             90

affects the Trustee's own rights, duties or immunities under this Indenture 
or otherwise.

                 SECTION 9.04.  Effect of Supplemental Indentures.  Upon the
execution of any supplemental indenture under this Article, this Indenture
shall be modified in accordance therewith, and such supplemental indenture
shall form a part of this Indenture for all purposes; and every Holder of
Securities theretofore or thereafter authenticated and delivered hereunder
shall be bound thereby.

                 SECTION 9.05.  Conformity with Trust Indenture Act.  Every
supplemental indenture executed pursuant to this Article shall conform to the
requirements of the Trust Indenture Act as then in effect.

                 SECTION 9.06.  Reference in Securities to Supplemental
Indentures.  Securities authenticated and delivered after the execution of any
supplemental indenture pursuant to this Article IX may, and shall if required
by the Trustee, bear a notation in form approved by the Trustee as to any
matter provided for in such supplemental indenture.  If Publishing shall so
determine, new Securities modified so as to conform to any such supplemental
indenture, in the opinion of the Trustee and the Board of Directors, may be
prepared and executed by Publishing and authenticated and delivered by the
Trustee in exchange for Outstanding Securities.

                 SECTION 9.07.  Record Date.  If Publishing shall solicit from
the Holders of any Series of Securities any request, demand, authorization,
direction, notice, consent, waiver or other Act, Publishing may, but shall not
be obligated to, fix a record date for the purpose of determining the Holders
of such Series entitled to consent to any supplemental indenture, agreement or
instrument or any waiver, and shall promptly notify the Trustee of any such
record date.  If a record date is fixed, those Persons who were Holders of such
Series at such record date (or their duly designated proxies), and only those
Persons, shall be entitled to consent to such supplemental indenture, agreement
or instrument or waiver or to revoke any consent previously given, whether or
not such Persons continue to be Holders after such record date.  The record
date shall be a date no more than 30 days prior to the first solicitation of
Holders generally in connection therewith and no later than the date such
solicitation is completed.  No such consent shall be valid or effective for
more than six months after such record date.  Subject to applicable law, until
any supplemental indenture, agreement, instrument or waiver becomes effective,
or a consent to it by a Holder of a Security of such Series shall cease to be
valid and effective as set forth in the preceding sentence, such consent is a
continuing consent by the Holder and every 
<PAGE>   99

                                                                             91

subsequent Holder of a Security of such Series or portion of a Security of 
such Series that evidences the same debt as the consenting Holder's Security.


                                   ARTICLE X

                                   Covenants

                 SECTION 10.01.  Payment of Principal, Premium and Interest.
With respect to each Series of Securities, Publishing will duly and punctually
pay the principal of, premium, if any, and interest on such Securities in 
accordance with the terms of such Securities and this Indenture.

                 SECTION 10.02.  Maintenance of Office or Agency.  Publishing
will maintain in The City of New York an office or agency where Securities may
be presented or surrendered for payment, where Securities may be surrendered
for registration of transfer or exchange and where notices and demands to or
upon Publishing in respect of the Securities and this Indenture may be served.
The office of the Trustee at 14 Wall Street, Window #2, New York, New York
10005, shall be such office or agency of Publishing, unless Publishing shall
designate and maintain some other office or agency for one or more of such
purposes.  Publishing will give prompt written notice to the Trustee of any
change in the location of any such office or agency.  If at any time Publishing
shall fail to maintain any such required office or agency or shall fail to
furnish the Trustee with the address thereof, such presentations, surrenders,
notices and demands may be made or served at the Corporate Trust Office, and
Publishing hereby appoints the Trustee as its agent to receive all such
presentations, surrenders, notices and demands.

                 Publishing may from time to time designate one or more other
offices or agencies (in or outside of The City of New York) where the
Securities may be presented or surrendered for any or all such purposes, and
may from time to time rescind such designation; provided, however, that no such
designation or rescission shall in any manner relieve Publishing of its
obligation to maintain an office or agency in The City of New York for such
purposes.  Publishing will give prompt written notice to the Trustee of any
such designation or rescission and any change in the location of any such
office or agency.

                 SECTION 10.03.  Money for Security Payments To Be Held in
Trust.  Publishing will, on or before Noon, New York time, on each due date of
the principal of, premium, if any, or interest on, Securities with respect to
each Series of Securities, deposit with a Paying Agent (which shall not be
Publishing) a sum in same-day funds sufficient to pay the 
<PAGE>   100

                                                                             92

principal, premium, if any, or interest so becoming due, such sum to be held 
in trust for the benefit of the Persons entitled to such principal, premium or 
interest, and (unless such Paying Agent is the Trustee) Publishing will 
promptly notify the Trustee of such action or any failure so to act.

                 Publishing will cause each Paying Agent other than the Trustee
for any Series of Securities to execute and deliver to the Trustee an
instrument in which such Paying Agent shall agree with the Trustee, subject to
the provisions of this Section, that such Paying Agent will:

                 (a) hold all sums held by it for the payment of the principal
         of, premium, if any, or interest on Securities of such Series in trust
         for the benefit of the Persons entitled thereto until such sums shall
         be paid to such Persons or otherwise disposed of as herein provided;

                 (b) give the Trustee notice of any Default by Publishing (or
         any other obligor upon the Securities of such Series) in the making of
         any payment of principal, premium, if any, or interest on the
         Securities of such Series;

                 (c) at any time during the continuance of any such Default,
         upon the written request of the Trustee, forthwith pay to the Trustee
         all sums so held in trust by such Paying Agent; and

                 (d) acknowledge, accept and agree to comply in all aspects
         with the provisions of this Indenture relating to the duties, rights
         and liabilities of such Paying Agent.

                 Publishing may at any time, for the purpose of obtaining the
satisfaction and discharge of this Indenture with respect to any Series of
Securities or for any other purpose, by Publishing Order direct any Paying
Agent to pay to the Trustee all sums held in trust by such Paying Agent in
respect of each and every Series of Securities as to which it seeks to
discharge this Indenture or, if for any other purpose, all sums so held in
trust by Publishing in respect of all Securities, such sums to be held by the
Trustee upon the same trusts as those upon which such sums were held by such
Paying Agent; and, upon such payment by any Paying Agent to the Trustee, such
Paying Agent shall be released from all further liability with respect to such
money.

                 Any money deposited with the Trustee or any Paying Agent in
trust for the payment of the principal of, premium, if any, or interest on any
Security of any Series and remaining unclaimed for two years after such
principal and premium, if any, or interest has become due and payable 
<PAGE>   101

                                                                             93

shall promptly be paid to Publishing upon Publishing Request; and the
Holder of such Security shall thereafter, as an unsecured general creditor,
look only to Publishing for payment thereof, and all liability of the Trustee
or such Paying Agent with respect to such trust money, and all liability of
Publishing as trustee thereof, shall thereupon cease; provided, however, that
the Trustee or such Paying Agent, before being required to make any such
payment to Publishing, may at the expense of Publishing cause to be published
once, in The New York Times and The Wall Street Journal (national edition),
notice that such money remains unclaimed and that, after a date specified
therein, which shall not be less than 30 days from the date of such
notification or publication, any unclaimed balance of such money then remaining
will promptly be repaid to Publishing.

                 SECTION 10.04.  Corporate Existence.  Subject to Article VIII,
Publishing will do or cause to be done all things necessary to preserve and
keep in full force and effect its corporate existence and related rights and
franchises (charter and statutory) of Publishing and each Restricted
Subsidiary; provided, however, that Publishing shall not be required to
preserve any such right or franchise or the corporate existence of any such
Restricted Subsidiary if the Board of Directors of Publishing shall determine
that the preservation thereof is no longer desirable in the conduct of the
business of Publishing and its Restricted Subsidiaries as a whole and that the
loss thereof would not reasonably be expected to have a material adverse effect
on the ability of Publishing to perform its obligations hereunder; and provided
further, however, that the foregoing shall not prohibit a sale, transfer or
conveyance of a Restricted Subsidiary or any of its assets in compliance with
the terms of this Indenture.

                 SECTION 10.05.  Payment of Taxes and Other Claims.  Publishing
will pay or discharge or cause to be paid or discharged, on or before the date
the same shall become due and payable, (a) all material taxes, assessments and
governmental charges levied or imposed upon Publishing or any Restricted
Subsidiary shown to be due on any tax return of Publishing or any Restricted
Subsidiary or otherwise assessed or upon the income, profits or property of
Publishing or any Restricted Subsidiary and (b) all material lawful claims for
labor, materials and supplies, which, if unpaid, would by law become a Lien
upon the property of Publishing or any Restricted Subsidiary, except for any
Lien permitted to be Incurred under Section 10.11; provided, however, that
Publishing shall not be required to pay or discharge or cause to be paid or
discharged any such tax, assessment, charge or claim whose amount,
applicability or validity is being contested in good faith by appropriate 
proceedings properly instituted and diligently conducted and in respect of which
appropriate reserves (in the good-faith 
<PAGE>   102

                                                                             94

judgment of management of Publishing) are being maintained in accordance with 
GAAP consistently applied.

                 SECTION 10.06.  Maintenance of Properties.  Publishing will
cause all material properties owned by Publishing or any Restricted Subsidiary
or used or held for use in the conduct of its business or the business of any
Restricted Subsidiary to be maintained and kept in good condition, repair and
working order (ordinary wear and tear excepted) and supplied with all necessary
equipment and will cause to be made all necessary repairs, renewals,
replacements, betterments and improvements thereof, all as in the judgment of
Publishing may be consistent with sound business practice and reasonably
necessary so that the business carried on in connection therewith may be
properly and advantageously conducted at all times; provided, however, that
nothing in this Section 10.06 shall prevent Publishing from discontinuing the
maintenance of any of such properties if such discontinuance is, in the
judgment of Publishing, desirable in the conduct of the business of Publishing
and its Restricted Subsidiaries and not reasonably expected to have a material
adverse effect on the ability of Publishing to perform its obligations
hereunder.

                 SECTION 10.07.  Insurance.  Publishing will at all times keep
all of its and its Restricted Subsidiaries' properties which are of an
insurable nature reasonably self-insured or insured with insurers, believed by
Publishing to be responsible, against loss or damage to the extent that
property of similar character is usually so insured by corporations similarly
situated and owning like properties in the same general geographic areas in
which Publishing and its Restricted Subsidiaries operate, except where the
failure to do so would not reasonably be expected to have a material adverse
effect on the condition (financial or otherwise), earnings, business affairs or
prospects of Publishing and its Restricted Subsidiaries, taken as a whole.

                 SECTION 10.08.  Limitation on Indebtedness.  (a)  Publishing
will not, and will not permit any of its Restricted Subsidiaries to, Incur any
Indebtedness (including any Acquired Indebtedness but excluding any Permitted
Indebtedness) except for (x) Indebtedness of Publishing or (y) Indebtedness of
a Restricted Subsidiary constituting Acquired Indebtedness, Permitted
Subsidiary Indebtedness or Foreign Subsidiary Indebtedness, provided
that, in the case of the foregoing clauses (x) and (y), the Consolidated Cash
Flow Ratio for Publishing and the Restricted Subsidiaries for the four full
fiscal quarters immediately preceding the Incurrence of such Indebtedness taken
as one period is not greater than 6.0:1.0.  In addition (and without limiting
the foregoing requirement), unless both of The Telegraph and Southam are
Restricted Subsidiaries, Publishing shall not permit any Restricted 
<PAGE>   103

                                                                             95

Subsidiary to Incur any Indebtedness other than Acquired Indebtedness or 
Permitted Subsidiary Indebtedness.  For purposes of determining the 
Consolidated Cash Flow Ratio for any period, pro forma effect shall be given to
(i) the Incurrence of such Indebtedness and (if applicable) the application of
the net proceeds therefrom, including to refinance other Indebtedness, as if
such Indebtedness was Incurred, and the application of such proceeds occurred,
at the beginning of such four-quarter period; (ii) the Incurrence, repayment or
retirement of any other Indebtedness by Publishing and its Restricted
Subsidiaries since the first day of such four-quarter period as if such
Indebtedness was Incurred, repaid or retired at the beginning of such
four-quarter period; (iii) in the case of Acquired Indebtedness, the related
acquisition (as if such acquisition had been consummated on the first day of
such four-quarter period); and (iv) any acquisition or disposition by
Publishing and its Restricted Subsidiaries of any company or any business or
any assets out of the ordinary course of business, whether by merger, stock
purchase or sale or asset purchase or sale or any related repayment of
Indebtedness, in each case since the first day of such four-quarter period (as
if such acquisition or disposition had been consummated on the first day of
such four-quarter period).

                 (b) Prior to September 1, 1997, neither Publishing nor any
Restricted Subsidiary will issue any Public Debt  unless the aggregate
principal amount (or initial proceeds in the case of Public Debt sold with
"original issue discount" (within the meaning of Section 1273(a) of the
Internal Revenue Code of 1986, as amended)) of Public Debt so issued after the
date of this Indenture that is Pari Passu Indebtedness does not exceed the
aggregate principal amount (or initial proceeds in the case of Public Debt sold
with "original issue discount") of Public Debt so issued after the date of this
Indenture that is pari passu with or subordinated to the Securities.

                 SECTION 10.09.  Limitation on Restricted Payments.  (a)
Publishing will not, and will not permit any Restricted Subsidiary to, directly
or indirectly:

                 (i) declare or pay any dividend or make any other distribution
         or payment on or in respect of Publishing's Capital Stock (including
         dividends or distributions of the Capital Stock of any Subsidiary), or
         make any other payment to the direct or indirect holders (in their
         capacities as such) of Publishing's Capital Stock (other than (x)
         dividends or distributions payable in shares of Publishing's Qualified
         Capital Stock or in options, warrants or other rights to acquire such
         Qualified Capital Stock and (y) a dividend or distribution of up to
         $175 million payable to Hollinger International;
<PAGE>   104

                                                                             96

         provided that, simultaneously or in connection with such dividend or 
         distribution, Hollinger International contributes or transfers, 
         directly or indirectly, to Publishing all of the Capital Stock of 
         Hollinger Eastern then held by Hollinger International; and provided 
         further, that Hollinger Eastern then holds not less than 42% of the 
         voting interest of Southam);

                 (ii) purchase, redeem or otherwise acquire or retire for
         value, directly or indirectly, any Capital Stock of Publishing or any
         Capital Stock of any Affiliate of Publishing (other than Capital Stock
         of any Wholly Owned Restricted Subsidiary (or, provided that both of
         The Telegraph and Southam are Restricted Subsidiaries, Capital Stock
         of a Restricted Subsidiary) or Capital Stock of a Person that is, or
         immediately following such repurchase will become, a Wholly Owned
         Restricted Subsidiary (or, provided that both of The Telegraph and
         Southam are Restricted Subsidiaries, a Restricted Subsidiary)) or
         options, warrants or other rights to acquire such Capital Stock;

                 (iii) make any principal payment on, or repurchase, redeem,
         defease, retire or otherwise acquire for value, prior to any scheduled
         principal payment, sinking fund payment or maturity, any Subordinated
         Indebtedness (other than pursuant to Section 10.13(c));

                 (iv) declare or pay any dividend or distribution on any
         Capital Stock of any Restricted Subsidiary to any Person (other than
         (x) dividends and distributions on Preferred Stock of Restricted
         Subsidiaries or Mirror Preferred or (y) dividends and distributions
         made to any Person (other than a controlling Affiliate of
         Publishing or an Affiliate of such Affiliate (other than Publishing
         and any Restricted Subsidiary)) on a pro rata basis consistent with
         the ownership interests in such Capital Stock to the owners of such
         Capital Stock, except that, in the case of the Capital Stock of a
         Restricted Subsidiary that is a Guarantor, (i) no Default or Event of
         Default shall have occurred and be continuing; and (ii) no holders of
         any other Indebtedness of Publishing or any Restricted Subsidiary
         shall have an Acceleration Right);

                 (v) Incur, create or assume any guarantee of Indebtedness of
         any Affiliate of Publishing (other than a Wholly Owned Restricted
         Subsidiary of Publishing (or, provided that both of The Telegraph and
         Southam are Restricted Subsidiaries, a Restricted Subsidiary of
         Publishing)) except as permitted by Section 10.12;

                 (vi) make any Investment in any Person (other than any 
         Permitted Investments); or
<PAGE>   105
                                                                             97

                 (vii) designate any Restricted Subsidiary as an Unrestricted
         Subsidiary;

(any of the payments described in paragraphs (i) through (vii) above, other
than any such action that is a Permitted Payment (as defined below),
collectively, "Restricted Payments") unless at the time of and after giving
effect to the proposed Restricted Payment (the amount of any such Restricted
Payment, if other than cash, as determined by the Board of Directors, whose
determination shall be conclusive and evidenced by a Board Resolution), (1) no
Default or Event of Default shall have occurred and be continuing; (2) no
holders of any other Indebtedness of Publishing or any Restricted Subsidiary
shall have an Acceleration Right; (3) immediately before and immediately after
giving effect to such transaction on a pro forma basis, Publishing could Incur
$1.00 of additional Indebtedness (other than Permitted Indebtedness) under the
provisions of Section 10.08; and (4) the aggregate amount of all such
Restricted Payments declared or made after the date of this Indenture (provided
that, in the case of a Restricted Payment by a Restricted Subsidiary, such
Restricted Payment is calculated for the purposes of this paragraph (4) by
multiplying the amount of the Restricted Payment by the percentage of
Publishing's common equity interest in such Restricted Subsidiary at the time 
of such Restricted Payment but disregarding, in the case of Southam, common 
equity interests which are pledged to secure the Southam-Linked Debentures) 
does not exceed the sum of:

                 (A) 50% of the sum of (i) the aggregate cumulative
         Consolidated Net Income of Publishing and its Restricted Subsidiaries
         accrued during the period (treated as a single accounting period)
         beginning on the first day of Publishing's fiscal quarter commencing
         prior to the date of this Indenture and ending on the last day of
         Publishing's last fiscal quarter ending prior to the date of the
         Restricted Payment (or, if such aggregate cumulative Consolidated Net
         Income shall be a loss, 100% of such loss (treating a loss as a
         negative number)) and (ii) the aggregate cumulative Amortization
         Expense of Publishing and its Restricted Subsidiaries accrued during
         the period (treated as a single accounting period) beginning on the
         first day of Publishing's fiscal quarter commencing prior to the date
         of this Indenture and ending on the last day of Publishing's last
         fiscal quarter ending prior to the date of the Restricted Payment;

                 (B) 50% of the aggregate cumulative cash dividends or
         distributions received by Publishing and its Consolidated Restricted
         Subsidiaries from any of Publishing's Unrestricted Subsidiaries during
         the period (treated as a single accounting period) beginning on the
         first day of Publishing's fiscal 
<PAGE>   106

                                                                             98

        quarter commencing prior to the date of this Indenture and ending on 
        the last day of Publishing's last fiscal quarter ending prior
        to the date of the Restricted Payment; provided, however, that for
        purposes of this clause (B), cash dividends and distributions shall not
        include, without duplication, (x), prior to the time that Southam shall
        be a Restricted Subsidiary, cash dividends received by Publishing from
        Publishing's Unrestricted Subsidiaries not in excess of the Southam
        Dividend Amount, (y) cash dividends or distributions received by
        Publishing or any Wholly Owned Restricted Subsidiary in accordance with
        Section 10.09(b)(vii) or (z) dividends or distributions on any Argsub
        Preferred received by FDTH or DTH;

                 (C) the aggregate Net Cash Proceeds received after the date of
         this Indenture by Publishing from the issuance or sale (other than to
         any of its Restricted Subsidiaries) of its Qualified Capital Stock or
         any options, warrants or rights to purchase such Qualified Capital 
         Stock (except, in each case, to the extent such proceeds are used to 
         purchase, redeem or otherwise retire Capital Stock, Subordinated 
         Indebtedness or Pari Passu Indebtedness as set forth below);

                 (D) the aggregate Net Cash Proceeds received after the date of
         this Indenture by Publishing (other than from any of its Restricted
         Subsidiaries) upon the exercise of any options or warrants to purchase
         Qualified Capital Stock of Publishing;

                 (E) the aggregate Net Cash Proceeds received after the date of
         this Indenture by Publishing (other than from any of its Subsidiaries)
         from cash capital contributions made to Publishing;

                 (F) the aggregate amount by which any Indebtedness (other than
         Permitted Indebtedness) of Publishing or any Restricted Subsidiary is
         reduced after the date of this Indenture as a result of the conversion
         or exchange of debt securities or Redeemable Capital Stock of
         Publishing that has been converted into or exchanged for Qualified
         Capital Stock of Publishing to the extent such debt securities or
         Redeemable Capital Stock were originally sold for cash plus the
         aggregate Net Cash Proceeds received by Publishing at the time of any
         such conversion or exchange; and

                 (G) $25,000,000.

         (b)  Notwithstanding the foregoing, and, in the case of clauses (ii)
through (x) below, so long as (1) there is no Default or Event of Default
continuing and (2) no holders of any other Indebtedness of Publishing or any
Restricted Subsidiary have an Acceleration Right, the foregoing 
<PAGE>   107

                                                                             99

provisions will not prohibit the following actions (clauses (i) through (x) 
being referred to as "Permitted Payments"):

                 (i) the payment of any dividend or distribution within 60 days
         after the date of declaration thereof, if at such date of declaration
         such payment would be permitted by the provisions of paragraph (a) of
         this section and such payment will be deemed to have been paid on such
         date of declaration for purposes of the calculation required by
         paragraph (a) of this section;

                 (ii) the repurchase, redemption or other acquisition or
         retirement of any shares of Capital Stock of Publishing in exchange for
         (including any such exchange pursuant to the exercise of a conversion
         right or privilege in connection with which cash is paid in lieu of 
         the issuance of fractional shares or scrip), or out of the Net Cash
         Proceeds of a substantially concurrent issue and sale for cash (other
         than to a Restricted Subsidiary) of other Qualified Capital Stock of
         Publishing; provided that the Net Cash Proceeds from the issuance of
         such shares of Qualified Capital Stock are excluded from clauses (4)(D)
         and (4)(E) of paragraph (a) of this section;

                 (iii) any repurchase, redemption, defeasance, retirement or
         acquisition for value or payment of principal of any Subordinated
         Indebtedness in exchange for, or out of the net proceeds of, a
         substantially concurrent issuance and sale for cash (other than to any
         Restricted Subsidiary of Publishing) of any Qualified Capital Stock of
         Publishing; provided that the Net Cash Proceeds from the issuance of
         such Qualified Capital Stock are excluded from clauses (4)(D) and
         (4)(E) of paragraph (a) of this section;

                 (iv) the repurchase, redemption, defeasance, retirement,
         refinancing, acquisition for value or payment of principal of any
         Subordinated Indebtedness (other than Redeemable Capital Stock) (a
         "refinancing") through the issuance of new Subordinated Indebtedness
         of Publishing; provided that any such new Subordinated Indebtedness
         (1) shall be in a principal amount that does not exceed the principal
         amount so refinanced (or, if the Subordinated Indebtedness so
         refinanced provides for an amount less than the principal amount
         thereof to be due and payable upon a declaration or acceleration
         thereof, then such lesser amount as of the date of determination),
         plus the amount of any premium required to be paid in connection with
         such refinancing pursuant to the terms of such refinanced Indebtedness
         and any reasonable out-of-pocket expenses of Publishing incurred in
         connection with such refinancing; (2) has 
<PAGE>   108

                                                                            100

         an Average Life to Stated Maturity greater than the remaining Average 
         Life to Stated Maturity of the Securities; (3) has a Stated Maturity 
         for its final scheduled principal payment later than the Stated 
         Maturity for the final scheduled principal payment of the Securities; 
         and (4) is expressly subordinated in right of payment to the 
         Securities at least to the same extent as the Indebtedness to be 
         refinanced;

                 (v) dividends paid to Hollinger International after the date 
         of this Indenture to the extent not in excess of the Southam Dividend 
         Amount;

                 (vi) loans, advances, dividends or distributions by any
         Restricted Subsidiary to Publishing or any Wholly Owned Restricted
         Subsidiary and by FDTH or, to the extent it has received such funds
         directly or indirectly from FDTH, DTH or Publishing to Hollinger
         International for the purpose of redeeming shares of Series A
         Preferred Stock not exceeding in the aggregate any payments made by
         Hollinger Inc. to FDTH pursuant to the provisions of the HTH/FDTH
         Share Exchange Agreement;

                 (vii) loans, advances, dividends or distributions to Hollinger
         International in amounts not to exceed $1 million per year to permit
         Hollinger International to repurchase, redeem or otherwise acquire or
         retire any shares of its Capital Stock from employees, former
         employees or their estates upon disability, death, retirement or
         termination of employment;

                 (viii) tax payments pursuant to a Tax Sharing Agreement to the
         extent that the aggregate amount of such payments do not exceed the
         aggregate amount of the tax payments that Publishing and the
         Restricted Subsidiaries would have been required to make if they alone
         constituted a single consolidated tax group;

                 (ix) payments by Publishing or a Restricted Subsidiary in
         connection with the Scheme of Arrangement; and

                 (x) the issuance or redemption of or payment of distributions
         on Mirror Preferred, but only to the extent Argsub Preferred is
         simultaneously issued, redeemed or pays (or is deemed to pay)
         dividends, respectively, and only so long as no cash is transferred in
         any such transaction, except for cash payments in respect of certain
         Mirror Preferred made directly from FDTH to DTH at the direction of
         Argsub.

                 For purposes of this Section 10.09, if the Board of Directors
designates a Restricted Subsidiary as an Unrestricted Subsidiary, or a
Restricted Subsidiary is 
<PAGE>   109

                                                                           101

deemed to be so designated, a "Restricted Payment" shall be deemed to have 
been made in an amount equal to the fair value of the Investment of Publishing 
and its other Restricted Subsidiaries in such Restricted Subsidiary as
determined by the Board of Directors with the concurrence of a majority of the
Independent Directors (there being at least one Independent Director), whose
good faith determination shall be conclusive.  If a particular Restricted
Payment involves a non-cash payment, including a distribution of assets, then
such Restricted Payment shall be deemed to be in an amount equal to the fair
market value of the non-cash portion of such Restricted Payment as determined
by the Board of Directors, whose good faith determination shall be conclusive.

                 SECTION 10.10.  Limitation on Transactions with Affiliates.
(a)  Publishing will not, and will not permit any of its Restricted
Subsidiaries to, directly or indirectly, enter into or suffer to exist any
transaction or series of related transactions (including, without limitation,
the sale, purchase, exchange or lease of assets, property or services) with any
Affiliate of Publishing (other than Publishing or a Wholly Owned Restricted
Subsidiary, or, if both of The Telegraph and Southam are Restricted
Subsidiaries, a Restricted Subsidiary) unless (a) such transaction or series of
related transactions is on terms that are no less favorable to Publishing or
such Restricted Subsidiary, as the case may be, than would be available in a
comparable transaction in arm's-length dealings with an unrelated third party
and (b) with respect to any transaction or series of related transactions
involving aggregate payments in excess of $5,000,000, Publishing delivers an
Officers' Certificate to the Trustee certifying that such transaction or series
of related transactions complies with clause (a) above and such transaction or
series of related transactions has been approved by a majority of the
Independent Directors of the Board of Directors; provided that any transaction
or series of related transactions otherwise permitted under this paragraph
(other than any transaction or series of related transactions with respect to
the making of any Permitted Investment pursuant to clause (ix) of the
definition of "Permitted Investment" or any Restricted Payment permitted
pursuant to Section 10.09 pursuant to which Publishing or any Restricted
Subsidiary shall receive or render value exceeding $15,000,000 shall not be
permitted unless, prior to the consummation of any such transaction or series
of related transactions, Publishing shall have received an opinion, from an
independent nationally recognized investment banking firm or firm experienced
in the appraisal or similar review of similar types of transactions, that such
transaction is fair to Publishing from a financial point of view; provided
further, that this covenant shall not apply to (i) transactions or agreements
as in effect or securities outstanding on the date of this Indenture 
<PAGE>   110

                                                                            102 

(provided that any amendment to any existing agreement (including the
Services Agreement and the Business Opportunities Agreement), and any
transaction pursuant to the Business Opportunities Agreement, shall require
approval pursuant to this covenant; notwithstanding the foregoing, any
amendment to the Services Agreement or the Business Opportunities Agreement
shall require the approval of a majority of the Independent Directors); (ii)
directors' fees approved by the Board of Directors; (iii) any employee benefit
plan or arrangement entered into or made available to officers or other
employees of Publishing or the Restricted Subsidiaries in the ordinary course
of business; (iv) sales by Publishing and its Restricted Subsidiaries of their
products in the ordinary course of business on arm's-length terms; (v) tax
payments pursuant to a Tax Sharing Agreement to the extent that the aggregate
amount of such payments do not exceed the aggregate amount of the tax payments
that Publishing and the Restricted Subsidiaries would have been required to
make if they alone constituted a single consolidated tax group; (vi) loans,
advances, dividends or distributions by FDTH, DTH or Publishing to Hollinger
International in amounts and for the purpose permitted by Section 10.09(b)(v)
and (vii); (vii) payments made to Hollinger Inc. pursuant to the Services
Agreement that constitute the reimbursement for the fair value (as determined
by a majority of the Independent Directors serving on an Independent Committee)
of services received by Publishing or a Restricted Subsidiary consistent with
past practices; and (viii) the issuance or redemption, retraction or transfer
of or payment of dividends, distributions or other amounts on Mirror Preferred
by DTH or FDTH to an Argsub, but only to the extent that such Argsub
simultaneously, as the case may be, issues or redeems or pays dividends,
distributions or other amounts (or is deemed to have taken any such action) to
DTH or FDTH, in each case in equivalent amounts.

                 Section 10.11.  Limitation on Liens.  (a)  Publishing will
not, and will not permit any Restricted Subsidiary to Incur, affirm or suffer
to exist any Lien of any kind securing any pari passu Public Debt or
Subordinated Indebtedness of Publishing (including any assumption, guarantee or
other liability with respect thereto by any Restricted Subsidiary) upon any
property or assets (including any intercompany notes) of Publishing or any
Restricted Subsidiary owned on the date of this Indenture or acquired after the
date of this Indenture, or any income or profits therefrom, unless (i) in the
case of any Lien securing pari passu Public Debt, the Securities are secured
by a Lien on such property, assets or proceeds that is senior in priority to or
pari passu with such Lien and (ii) in the case of any Lien securing
Subordinated Indebtedness of Publishing, the Securities are secured by a Lien
on such property, assets or proceeds that is senior in priority to such Lien,
except for (x) any Lien securing 
<PAGE>   111

                                                                            103

Acquired Indebtedness created prior to (and not created in connection with, 
or in contemplation of) the issuance of such pari passu Public Debt or
the Incurrence of such Subordinated Indebtedness by Publishing or any
Restricted Subsidiary, in each case which Indebtedness is permitted under the
provisions of Section 10.08 (provided that any such Lien only extends to the
assets that were subject to such Lien securing such Acquired Indebtedness prior
to the related acquisition by Publishing or its Restricted Subsidiaries), and
(y) any Lien securing Indebtedness owing to Publishing or a Wholly Owned
Restricted Subsidiary by a Restricted Subsidiary.

                 (b)  Notwithstanding the foregoing, any security interest
granted by Publishing or any Restricted Subsidiary to secure the Securities
created pursuant to paragraph (a) above shall provide by its terms that such
security interest shall be automatically and unconditionally released and
discharged upon the release by the holders of the Indebtedness of Publishing or
any Restricted Subsidiary described in paragraph (a) above of their security
interest (including any deemed release upon payment in full of all obligations
under such Indebtedness), at a time when (A) no pari passu Public Debt or
Subordinated Indebtedness of Publishing or any Restricted Subsidiary has been
secured by such property or assets of Publishing or any such Restricted
Subsidiary or (B) the holders of all such pari passu Public Debt and
Subordinated Indebtedness which is secured by such property or assets of
Publishing or any such Restricted Subsidiary also release their security
interest in such property or assets (including any deemed release upon payment
in full of all obligations under such Indebtedness).

                 SECTION 10.12.  Limitation on Issuances of Guarantees of
Indebtedness.  (a)  Publishing will not permit any Restricted Subsidiary,
directly or indirectly, to guarantee, assume or in any other manner become
liable with respect to any Indebtedness of Publishing (other than pursuant to
the New Bank Credit Facility) unless such Restricted Subsidiary simultaneously
executes and delivers a supplemental indenture to this Indenture providing for
a senior guarantee of the Securities and if such Indebtedness of Publishing is
by its terms expressly subordinated to the Securities, any such assumption,
guarantee or other liability of such Restricted Subsidiary with respect to 
such Indebtedness shall be subordinated to such Restricted Subsidiary's 
guarantee to the same extent as such Indebtedness is subordinated to the 
Securities.

                 (b)  Notwithstanding the foregoing, any guarantee by a
Restricted Subsidiary of the Securities that is provided pursuant to the
foregoing paragraph or under the provisions of Section 10.15 may provide by its
terms that it shall be automatically and unconditionally released and
<PAGE>   112

                                                                            104

discharged (i) upon any sale, exchange or transfer, to any Person not an
Affiliate of Publishing, of all of Publishing's Capital Stock in, or all or
substantially all the assets of, such Restricted Subsidiary, which sale,
exchange or transfer is in compliance with this Indenture, (ii) if the
Restricted Subsidiary issuing such guarantee ceases to be a Restricted
Subsidiary or (iii) upon the release by the holders of the Indebtedness of
Publishing described in paragraph (a) above of their Guarantee by such
Restricted Subsidiary (including any deemed release upon payment in full of all
obligations under such Indebtedness), at a time when (A) no Indebtedness of
Publishing or any Restricted Subsidiary has been guaranteed by such Restricted
Subsidiary or (B) the holders of all such other Indebtedness which is
guaranteed by such Restricted Subsidiary also release their Guarantee by such
Restricted Subsidiary (including any deemed release upon payment in full of all
obligations under such Indebtedness).

                 SECTION 10.13.  Limitation on Sale of Assets.  (a)  Publishing
will not, and will not permit any of its Restricted Subsidiaries to, directly
or indirectly, consummate an Asset Sale unless (i) at least 80% of the proceeds
from such Asset Sale are received in cash (provided that the amount of (A) any
Pari Passu Indebtedness or Indebtedness of such Restricted Subsidiary that is
pari passu with any guarantee of the Securities (as shown on Publishing's or
such Restricted Subsidiaries' most recent balance sheet or in the notes
thereto) of Publishing or any such Restricted Subsidiary that is assumed by the
transferee of any asset in connection with any Asset Sale and (B) any deferred
payment obligations received by Publishing or any such Restricted Subsidiary as
proceeds of an Asset Sale that are concurrently with the Asset Sale converted
into cash without recourse to Publishing or any of its Restricted Subsidiaries
shall be deemed to be cash for purposes of this provision; provided further
that, for purposes of this clause (i), "cash" shall include any cash proceeds
received from the sale of securities received in an Asset Sale as long as at
the time of such Asset Sale, Publishing or its Restricted Subsidiary, as 
applicable, has entered into a legally binding agreement for the sale of such
securities and such securities are sold within 90 days of such Asset Sale; and
provided further that this clause (i) shall not apply to (x) Newspaper
Businesses received by Publishing or a Restricted Subsidiary from the transferee
as consideration for an Asset Sale (an "Asset Swap") so long as, immediately
before and immediately after giving effect to such transaction on a pro forma
basis, Publishing could Incur $1.00 of additional Indebtedness (other than
Permitted Indebtedness) under the provisions of Section 10.08, (y) a CST Real
Estate Transaction or (z) a Permitted Real Estate Sale)) and (ii) Publishing 
or such Restricted Subsidiary receives consideration at the time of such 
Asset Sale at least equal to the fair market value of the shares or assets 
<PAGE>   113

                                                                            105

sold (as determined by the Board of Directors of Publishing and evidenced by 
a board resolution).  The value of any properties or assets (other than cash) 
received pursuant to an Asset Sale shall be determined by the Board of 
Directors of Publishing and evidenced by a Board Resolution; provided that
if the value of the asset which is the subject of the Asset Sale is in excess
of $25,000,000, the value of the properties or assets received shall be
determined by an independent nationally recognized investment banking firm or
firm experienced in the appraisal or similar review of similar types of assets
(provided that for purposes of this sentence, any CST Real Estate Transaction
shall be deemed to involve an asset whose value exceeds $25,000,000).

                 (b)  If all or a portion of the Net Cash Proceeds of any Asset
Sale is not applied to permanently repay or otherwise permanently retire any
Pari Passu Indebtedness then outstanding as permitted or required by the terms
thereof, or if no such Pari Passu Indebtedness is then outstanding, Publishing
or a Restricted Subsidiary, as the case may be, may, within 12 months of the
Asset Sale, invest the Net Cash Proceeds in properties and assets that (as
determined by the Board of Directors) replace the properties and assets that
were the subject of the Asset Sale or in properties and assets that will be
used in the businesses of Publishing or its Restricted Subsidiaries existing on
the date of this Indenture or in businesses reasonably related thereto.  The
amount of such Net Cash Proceeds neither used to permanently repay or prepay
Pari Passu Indebtedness nor used or invested as set forth in this paragraph
constitutes "Excess Proceeds."

                 (c)  When the aggregate amount of Excess Proceeds equals or
exceeds $20,000,000, Publishing shall apply the Excess Proceeds to the
repayment of the Securities and any Pari Passu Indebtedness required to be 
repurchased under the instrument governing such Pari Passu Indebtedness as
follows:  (i) Publishing shall make an offer to purchase (an "Offer") from all
Holders in accordance with the procedures set forth in this Indenture in the
maximum principal amount (expressed as a multiple of $1,000) of Securities that
may be purchased out of an amount (the "Note Amount") equal to the product of
such Excess Proceeds multiplied by a fraction, the numerator of which is the
outstanding principal amount of the Securities, and the denominator of which is
the sum of the outstanding principal amount of the Securities and such Pari
Passu Indebtedness (subject to proration in the event such amount is less than
the aggregate Offered Price (as defined herein) of all Securities tendered) and
(ii) to the extent required by such Pari Passu Indebtedness to permanently
reduce the principal amount of such Pari Passu Indebtedness, Publishing shall
make an offer to purchase or otherwise repurchase or redeem Pari Passu
Indebtedness (a "Pari Passu Offer") in an amount (the "Pari Passu Debt Amount")
equal to the excess of the 
<PAGE>   114

                                                                            106

Excess Proceeds over the Note Amount; provided that in no event shall
the Pari Passu Debt Amount exceed the principal amount of such Pari Passu
Indebtedness plus the amount of any premium required to be paid to repurchase
such Pari Passu Indebtedness.  The offer price shall be payable in cash in an
amount equal to 100% of the principal amount of the Securities plus accrued and
unpaid interest, if any, to the date (the "Purchase Date") such Offer is
consummated (the "Offered Price"), in accordance with the procedures set forth
in this Indenture.  To the extent that the aggregate Offered Price of the
Securities tendered pursuant to the Offer is less than the Amount relating
thereto or the aggregate amount of Pari Passu Indebtedness that is purchased is
less than the Pari Passu Debt Amount (the amount of such shortfall, if any,
constituting a "Deficiency"), Publishing may then (i)(a) to the extent required
by the Senior Subordinated Securities Indenture, purchase Senior Subordinated
Securities tendered pursuant to an offer by Publishing for the Senior
Subordinated Securities (the "Senior Subordinated Securities Offer") at a
purchase price of 100% of their principal amount plus accrued interest to the
date of purchase in accordance with the procedures set forth in the Senior
Subordinated Securities Indenture and (b) to the extent required by the terms
of any other senior subordinated Indebtedness (other than Senior Subordinated
Securities) to permanently reduce the principal amount of such other senior
subordinated Indebtedness, make an offer to purchase or otherwise repurchase or
redeem such other senior subordinated Indebtedness, or (ii) use such Deficiency
in the business of Publishing and its Restricted Subsidiaries.  Upon completion
of the purchase of all Securities tendered pursuant to an Offer and repurchase 
of the Pari Passu Indebtedness pursuant to a Pari Passu Offer, the amount of 
Excess Proceeds, if any, shall be reset at zero.

                 (d)  Whenever the aggregate amount of Excess Proceeds received
by Publishing exceeds $20,000,000, such Excess Proceeds shall, prior to the
purchase of Securities, Pari Passu Indebtedness or any Senior Subordinated
Securities or Indebtedness described in paragraph (c) above, be set aside by
Publishing in a separate account pending (i) deposit with the depository or a
Paying Agent of the amount required to purchase the Securities or Pari Passu
Indebtedness tendered in an Offer or a Pari Passu Subordinated Offer, (ii)
delivery by Publishing of the Offered Price to the holders of the Securities or
Pari Passu Indebtedness tendered in an Offer or a Pari Passu Offer and (iii)
application, as set forth above, of Excess Proceeds in the business of
Publishing and its Restricted Subsidiaries.  Such Excess Proceeds may be
invested in Temporary Cash Investments; provided that the maturity date of any
such investment made after the amount of Excess Proceeds equals or exceeds
$20,000,000 shall not be later than the Purchase Date.  Publishing shall be
entitled to any interest or
<PAGE>   115

                                                                           107

dividends accrued, earned or paid on such Temporary Cash Investments; provided 
that Publishing shall not be entitled to such interest and shall not withdraw 
such interest from the separate account, if an Event of Default has occurred 
and is continuing.

                 (e)  If Publishing becomes obligated to make an Offer pursuant
to paragraph (c) above, the Securities shall be purchased by Publishing, at the
option of the Holder thereof, in whole or in part in integral multiples of
$1,000, on a date that is not earlier than 30 days and not later than 60 days
from the date the notice is given to Holders, or such later date as may be
necessary for Publishing to comply with the requirements under the Exchange
Act, subject to proration in the event the Note Amount is less than the
aggregate Offered Price of all Securities tendered.

                 (f)  Publishing shall comply with the applicable tender offer
rules, including Rule 14e-1 under the Exchange Act, and any other applicable
securities laws or regulations in connection with an Offer.

                 (g)  Publishing shall not, and shall not permit any 
Subsidiary to, create or permit to exist or become effective any restriction 
(other than restrictions existing under (i) Indebtedness as in effect on the 
date of this Indenture as such Indebtedness may be refinanced from time to 
time or (ii) any Pari Passu Indebtedness existing on the date of this Indenture 
or thereafter; provided, in each case, that such restrictions are no less 
favorable to the Holders than those existing on the date of this Indenture) 
that would expressly impair the ability of Publishing to make an Offer to 
purchase the Securities or, if such Offer is made, to pay for the Securities 
tendered for purchase.

                 (h)  Within 30 days after the date on which the amount of
Excess Proceeds equals or exceeds $20,000,000, Publishing shall send by
first-class mail, postage prepaid, to the Trustee and to each Holder of the
Securities of that Series, at such Holder's address appearing in the Security
Register, a notice stating or including:

                          A. that the Holder of such Series has the right to
                 require Publishing to repurchase, subject to proration, part
                 or all of such Holder's Securities at the Offered Price;

                          B. the Purchase Date;

                          C. the instructions a Holder of such Series must
                 follow in order to have its Securities purchased in accordance
                 with paragraph (c) of this Section; and
<PAGE>   116

                                                                           108

                          D. (i) the most recently filed Annual Report on Form
                 10-K (including audited consolidated financial statements) of
                 Publishing, the most recent subsequently filed Quarterly
                 Report on Form 10-Q, as applicable, and any Current Report on
                 Form 8-K of Publishing filed subsequent to such Quarterly
                 Report, other than Current Reports describing Asset Sales
                 otherwise described in the offering materials (or
                 corresponding successor reports) (or in the event Publishing
                 is not required to prepare any of the foregoing Forms, the
                 comparable information required pursuant to Section 10.17),
                 (ii) a description of material developments in Publishing's
                 business subsequent to the date of the latest of such Reports,
                 (iii) if material, appropriate pro forma financial
                 information, and (iv) such other information, if any,
                 concerning the business of Publishing and its Restricted
                 Subsidiaries which Publishing in good faith believes will 
                 enable such Holders to make an informed investment
                 decision regarding the Offer;

                          E. the Offered Price;

                          F. the names and addresses of the Paying Agent and 
                 the offices or agencies referred to in Section 10.02;

                          G. that Securities of such Series must be surrendered
                 at least three Business Days prior to the Purchase Date to the
                 Paying Agent or to an office or agency referred to in Section
                 10.02 to collect payment;

                          H. that any Securities of such Series not tendered
                 will continue to accrue interest and that unless Publishing
                 defaults in the payment of the purchase price, any Security
                 accepted for payment pursuant to the Offer shall cease to
                 accrue interest on and after the Purchase Date; and

                          I. the procedures for withdrawing a tender.

                 (i)  Holders electing to have Securities of such Series
purchased hereunder will be required to surrender such Securities at the
address specified in the notice at least three Business Days prior to the
Purchase Date.  Holders will be entitled to withdraw their election to have
their Securities purchased pursuant to this Section if Publishing receives, not
later than three Business Days prior to the Purchase Date, a telegram, telex,
facsimile transmission or letter setting forth (1) the name of the Holder, (2)
the certificate number of the Security in respect of which such notice of
withdrawal is being submitted, (3) the principal amount of the Security (which
<PAGE>   117

                                                                           109

shall be $1,000 or an integral multiple thereof) delivered for purchase by the
Holder as to which his election is to be withdrawn, (4) a statement that such
Holder is withdrawing such Holder's election to have such principal amount of
such Security purchased, and (5) the principal amount, if any, of such Security
(which shall be $1,000 or an integral multiple thereof) that remains subject to
the original notice of the Offer and that has been or will be delivered for
purchase by Publishing.

                 (j)  Publishing shall (i) not later than the Purchase Date,
accept for payment Securities of such Series or portions thereof tendered 
pursuant to the Offer, (ii) not later than 11:00 a.m. (New York time) on the 
Purchase Date, deposit with the Trustee or with a Paying Agent an amount of 
money in same day funds (or New York Clearing House funds if such deposit is
made prior to the Purchase Date) sufficient to pay the aggregate Offered Price
of all the Securities or portions thereof which are to be purchased on that
date and (iii) not later than 11:00 a.m. (New York time) on the Purchase Date,
deliver to the Paying Agent an Officers' Certificate stating the Securities or
portions thereof have been accepted for payment by Publishing.

                 The Trustee and the Paying Agent shall return to Publishing
any cash that remains unclaimed, together with interest, if any, thereon, held
by them for the payment of the Offered Price; provided, however, that, (x) to
the extent that the aggregate amount of cash deposited by Publishing with the
Trustee or a Paying Agent in respect of an Offer exceeds the aggregate Offered
Price of the Securities or portions thereof to be purchased, then the Trustee
or a Paying Agent shall hold such excess for Publishing and (y) unless
otherwise directed by Publishing in writing, promptly after the Business Day
following the Purchase Date the Trustee or a Paying Agent shall return any such
excess to Publishing together with interest or dividends, if any, thereon.

                 (k)  Securities of that Series to be purchased shall, on the
Purchase Date, become due and payable at the Offered Price and from and after
such date (unless Publishing shall default in the payment of the Offered Price)
such Securities shall cease to bear interest.  The Offered Price shall be paid
to such Holder promptly following the later of the Purchase Date and the time
of delivery of such Security to the relevant Paying Agent at the office of such
Paying Agent by the Holder thereof in the manner required.  Upon surrender of
any such Security for purchase in accordance with the foregoing provisions,
such Security shall be paid by Publishing at the Offered Price; provided,
however, that installments of interest whose Stated Maturity is on or prior to
the Purchase Date shall be payable to the Holders of such Securities, or one or
more Predecessor Securities, registered as such on the relevant 
<PAGE>   118

                                                                             110

Regular Record Dates according to the terms and the provisions of Section 3.07;
provided further that Securities of that Series to be purchased are subject 
to proration in the event the Excess Proceeds are less than the aggregate 
Offered Price of all Securities of such Series tendered for purchase,
with such adjustments as may be deemed appropriate by the Trustee so that only
Securities of such Series in denominations of $1,000 or integral multiples
thereof shall be purchased. If any Security of such Series tendered for
purchase in accordance with the terms of this Section shall not be so paid upon
surrender thereof by deposit of funds with the Trustee or a Paying Agent in
accordance with paragraph (j) above, the principal thereof (and premium, if
any, thereon) shall, until paid, bear interest from the Purchase Date at the
rate borne by such Security.  Any Security of such Series that is to be
purchased only in part shall be surrendered to a Paying Agent in accordance
with the terms of this Section at the office of such Paying Agent (with, if
Publishing or the Trustee so requires, due endorsement by, or a written
instrument of transfer in form satisfactory to Publishing and the Trustee duly
executed by, the Holder thereof or such Holder's attorney duly authorized in
writing), and Publishing shall execute and pursuant to a Publishing Order the
Trustee shall authenticate and deliver to the Holder of such Security, without
service charge, one or more new Securities of any authorized denomination as
requested by such Holder in an aggregate principal amount equal to, and in
exchange for, the portion of the principal amount of the Security so
surrendered that is not purchased.

                 SECTION 10.14.  Purchase of Securities upon a Change of
Control.  (a)  If a Change of Control shall occur at any time, then each Holder
with respect to Securities of any Series shall have the right to require that
Publishing purchase such Holder's Securities, pursuant to an offer described in
subsection (b) of this Section (a "Change of Control Offer"), in whole or in
part in integral multiples of $1,000, at a purchase price (the "Change of
Control Purchase Price") in cash in an amount equal to 101% of the principal
amount of such Securities, plus accrued and unpaid interest, if any, to the
date of purchase (the "Change of Control Purchase Date"), in accordance with
the procedures set forth in paragraphs (b), (c), (d) and (e) of this Section.

                 (b)  Within 30 days following any Change of Control,
Publishing shall notify the Trustee thereof and give written notice (a "Change
of Control Purchase Notice") of such Change of Control to each Holder by
first-class mail, postage prepaid, to the Trustee and to each Holder at his
address appearing in the Security Register, stating or including:

                 A. that a Change of Control has occurred, the date of such
         event, and that such Holder has the right to 
<PAGE>   119

                                                                           111

         require Publishing to repurchase such Holder's Securities at the 
         Change of Control Purchase Price;

                 B. the circumstances and relevant facts regarding such Change 
         of Control (including but not limited to information with respect to 
         pro forma historical income, cash flow and capitalization after giving
         effect to such Change of Control, if any);

                 C. that the Change of Control Offer is being made pursuant to
         Section 10.14(a) and that all Securities properly tendered pursuant to
         the Change of Control Offer will be accepted for payment at the Change
         of Control Offer Purchase Price;

                 D. the Change of Control Purchase Date, which shall be a
         Business Day no earlier than 30 days nor later than 60 days from the
         date such notice is mailed or such later date as may be necessary for
         Publishing to comply with the requirements under the Exchange Act;

                 E. (i) the most recently filed Annual Report on Form 10-K
         (including audited consolidated financial statements) of Publishing,
         the most recent subsequently filed Quarterly Report on Form 10-Q, as
         applicable, and any Current Report on Form 8-K of Publishing filed
         subsequent to such Quarterly Report (or in the event Publishing is not
         required to prepare any of the foregoing Forms, the comparable
         information required to be prepared by Publishing pursuant to Section
         10.17), (ii) a description of material developments in Publishing's
         business subsequent to the date of the latest of such reports and
         (iii) such other information, if any, concerning the business of
         Publishing and its Restricted Subsidiaries which Publishing in good
         faith believes will enable such Holders to make an informed investment
         decision regarding the Change of Control Offer;

                 F. the Change of Control Purchase Price;

                 G. the names and addresses of the Paying Agent and the offices
         or agencies referred to in Section 10.02;

                 H. that Securities of that Series must be surrendered at least
         three Business Days prior to the Change of Control Purchase Date to
         the Paying Agent at the Office of the Paying Agent or to an office or
         agency referred to in Section 10.02 to collect payment;

                 I. that the Change of Control Purchase Price for any Security 
         which has been properly tendered and not withdrawn will be paid 
         promptly following the Change of Control Purchase Date;
<PAGE>   120
                                                                           112

                 J. the procedures for withdrawing a tender of Securities and
         Change of Control Purchase Notice;

                 K. that any Security of such Series not tendered will 
         continue to accrue interest; and

                 L. that, unless Publishing defaults in the payment of the
         Change of Control Purchase Price, any Security of such Series accepted
         for payment pursuant to the Change of Control Offer shall cease to
         accrue interest after the Change of Control Purchase Date.

                 (c)  Upon receipt by Publishing of the proper tender of
Securities of such Series, each Holder of a Security in respect of which such
proper tender was made shall (unless the tender of such Security is properly
withdrawn) thereafter be entitled to receive solely the Change of Control
Purchase Price with respect to such Security.  Upon surrender of any such
Security for purchase in accordance with the foregoing provisions, such Security
shall be paid by Publishing at the Change of Control Purchase Price; provided,
however, that installments of interest whose Stated Maturity is on or prior to
the Change of Control Purchase Date shall be payable to the Holders of such
Securities, or one or more Predecessor Securities, registered as such on the
relevant Regular Record Dates according to the terms and the provisions of
Section 3.07.  If any Security tendered for purchase in accordance with the
provisions of this Section shall not be so paid upon surrender thereof by
deposit of funds with the Paying Agent in accordance with paragraph (d) below,
the principal thereof (and premium, if any, thereon) shall, until paid, bear
interest from the Change of Control Purchase Date at the rate borne by such
Security.  Holders electing to have Securities of such Series purchased will be
required to surrender such Securities to the Paying Agent at the address
specified in the notice at least three Business Days prior to the Change of
Control Purchase Date.  Any Security of such Series that is to be purchased only
in part shall be surrendered to a Paying Agent in accordance with the provisions
of this Section at the office of such Paying Agent (with, if Publishing or the
Trustee so requires, due endorsement by, or a written instrument of transfer in
form satisfactory to Publishing and the Trustee duly executed by, the Holder
thereof or such Holder's attorney duly authorized in writing), and Publishing
shall execute and pursuant to a Publishing Order the Trustee shall authenticate
and deliver to the Holder of such Security, without service charge, one or more
new Securities of any authorized denomination as requested by such Holder in an
aggregate principal amount equal to, and in exchange for, the portion of the
principal amount of the Security so surrendered that is not purchased.

                 (d)  Publishing shall (i) not later than the Change of Control
Purchase Date, accept for payment of 
<PAGE>   121
 
                                                                           113

Securities of such Series or portion thereof tendered pursuant to the
Change of Control Offer, (ii) not later than 11:00 a.m. (New York time) on the
Change of Control Purchase Date, deposit with the Paying Agent an amount of
cash sufficient to pay the aggregate Change of Control Purchase Price of all
the Securities or portions thereof which are to be purchased as of the Change
of Control Purchase Date and (iii) not later than 11:00 a.m. (New York time) on
the Change of Control Purchase Date, deliver to the Paying Agent an Officers'
Certificate stating the Securities of such Series or portions thereof accepted
for payment by Publishing.  The Paying Agent shall promptly mail or deliver to
Holders of Securities of such Series so accepted payment in an amount equal to
the Change of Control Purchase Price of the Securities of such Series purchased
from each such Holder.  Any Securities of such Series not so accepted shall be
promptly mailed or delivered by the Paying Agent at Publishing's expense to the
Holder thereof.  Publishing will publicly announce the results of the Change of
Control Offer on the Change of Control Purchase Date.  For purposes of this
Section 10.14, Publishing shall choose a Paying Agent which shall not be
Publishing.

                 (e)  A tender made in response to a Change of Control Purchase
Notice may be withdrawn before or after delivery by the Holder to the Paying
Agent at the office of the Paying Agent of the Security of such Series to which
such Change of Control Purchase Notice relates, by means of a written notice of
withdrawal delivered by the Holder to the Paying Agent at the office of the
Paying Agent or to the office or agency referred to in Section 10.02 to which
the related Change of Control Purchase Notice was delivered not later than
three Business Days prior to the Change of Control Purchase Date specifying as
applicable:

                 (1) the name of the Holder;

                 (2) the certificate number of the Security in respect of which
         such notice of withdrawal is being submitted;

                 (3) the principal amount of the Security (which shall be
         $1,000 or an integral multiple thereof) delivered for purchase by the
         Holder as to which such notice of withdrawal is being submitted;

                 (4) a statement that such Holder is withdrawing such Holder's
         election to have such principal amount of such Security purchased; and

                 (5) the principal amount, if any, of such Security (which
         shall be $1,000 or an integral multiple thereof) that remains subject
         to the original Change of Control Purchase Notice and that has been or
         will be delivered for purchase by Publishing.
<PAGE>   122

                                                                           114

                 (f)  As provided in the Securities, the Trustee and the Paying
Agent shall return to Publishing any cash that remains unclaimed, together with
interest or dividends, if any, thereon, held by either of them for the payment
of the Change of Control Purchase Price; provided, however, that, (x) to the
extent that the aggregate amount of cash deposited by Publishing pursuant to
clause (ii) of paragraph (d) above exceeds the aggregate Change of Control
Purchase Price of the Securities of any such Series or portions thereof to be
purchased, then the Trustee or the Paying Agent shall hold such excess for
Publishing and (y) unless otherwise directed by Publishing in writing, promptly
after the Business Day following the Change of Control Purchase Date, the
Trustee or the Paying Agent shall return any such excess to Publishing together
with interest, if any, thereon.

                 (g)  Publishing shall comply with the applicable tender offer
rules, including Rule 14e-1 under the Exchange Act, and any other applicable
securities laws or regulations in connection with a Change of Control Offer.

                 (h)  Notwithstanding the occurrence of a Change of Control,
Publishing shall not be obligated to repurchase the Securities of any such
Series pursuant to a Change of Control Offer, or otherwise comply with this
Section 10.14, if Publishing has elected to redeem all of the Securities of
such Series in accordance with Article XI.

                 Publishing shall not, and shall not permit any Subsidiary to,
create or permit to exist or become effective any restriction (other than
restrictions existing under Indebtedness as in effect on the date of this
Indenture as such Indebtedness may be refinanced from time to time, provided
that such restrictions are no less favorable to the Holders than those existing 
on the date of this Indenture) that would expressly impair the ability of
Publishing to make a Change of Control Offer to purchase the Securities or, if
such Change of Control Offer is made, to pay for the Securities tendered for
purchase.

                 SECTION 10.15.  Limitation on Issuance and Sale of Capital
Stock of Restricted Subsidiaries.  (a)  Until such time as both of The
Telegraph and Southam are Restricted Subsidiaries, Publishing will not permit
(i) any Restricted Subsidiary to issue any Capital Stock (other than to a
Publishing or any Wholly Owned Restricted Subsidiary) or (ii) any Person (other
than Publishing or a Wholly Owned Restricted Subsidiary) to acquire any Capital
Stock of any Restricted Subsidiary from Publishing or any Restricted
Subsidiary, except upon the sale of all of the outstanding Capital Stock of
such Restricted Subsidiary owned by Publishing and the designation of such
Subsidiary as an Unrestricted Subsidiary; provided, however, that Publishing or
a Restricted Subsidiary may issue or sell common stock of 
<PAGE>   123

                                                                           115

a Restricted Subsidiary to a Person that is not an Affiliate of Publishing 
so long as, on or prior to the consummation of such issuance or sale, such 
Restricted Subsidiary issues and delivers a supplemental indenture
to this Indenture providing for the guarantee of the Securities, which
guarantee shall be senior to any Subordinated Indebtedness of such Restricted
Subsidiary (and in the case of any Indebtedness of such Restricted Subsidiary
that constitutes a guarantee of Subordinated Indebtedness of Publishing, the
terms of such subordination shall be at least as favorable to the holders of
the Securities as the terms under which the related Subordinated Indebtedness
of Publishing is subordinated to the Securities).

                 (b)  On or after the time that both Southam and The Telegraph
are Restricted Subsidiaries, (i) without limiting the requirements of Section
10.13, in the event that (x) Publishing or a Restricted Subsidiary issues or
sells (other than to a Restricted Subsidiary) Capital Stock of a Restricted
Subsidiary (1) that was a Subsidiary on February 1, 1997 (which, for purposes
of this clause (1), is deemed to include Southam and Hollinger Eastern), (2)
any substantial portion of the operating assets of which were held by a
Subsidiary on February 1, 1997 and were generating material revenue and cash
flows on such date, or (3) any substantial portion of the operating assets of
which consist of assets that are acquired by Publishing or a Restricted
Subsidiary pursuant to the Hollinger Inc. Transaction and (y) such issuance or
sale involves less than 100% of the Capital Stock of such Restricted Subsidiary
held by Publishing and the Restricted Subsidiaries at the time of such 
issuance or sale, then (1) the Net Cash Proceeds of such issuance or sale shall
be applied to permanently repay or otherwise permanently retire any Pari Passu
Indebtedness then outstanding, as permitted or required by the terms thereof and
(2) to the extent not so applied, may be applied to repay or retire other
Indebtedness or otherwise used in the Company's business; provided that the
foregoing clause (i) shall not apply to any new issuance of Capital Stock by
Southam as long as (a) Southam is a Public Entity at the time of such issuance;
(b) neither Publishing nor any other Restricted Subsidiary has at any time after
February 1, 1997 sold any assets and contributed, directly or indirectly, the
proceeds therefrom to Southam; and (c) neither Publishing nor any other
Restricted Subsidiary has at any time after February 1, 1997 contributed,
directly or indirectly, any Newspaper Businesses to Southam other than those
Newspaper Businesses acquired in the Hollinger Inc. Transaction; and (ii) if any
issuance of Capital Stock by a Restricted Subsidiary or sale or disposition of
Capital Stock of a Restricted Subsidiary results in a Restricted Subsidiary
ceasing to qualify as a Subsidiary, such transaction would deemed, for purposes
of Section 10.09, to constitute the designation of such former Restricted
Subsidiary as an Unrestricted Subsidiary.
<PAGE>   124

                                                                           116

                 SECTION 10.16.  Limitation on Dividends and Other Payment
Restrictions Affecting Restricted Subsidiaries.  Publishing will not, and will
not permit any of its Restricted Subsidiaries to, directly or indirectly,
create or otherwise cause or suffer to exist or become effective any
encumbrance or restriction on the ability of any Restricted Subsidiary to (a)
pay dividends or make any other distribution on its Capital Stock to Publishing
or any other Restricted Subsidiary, (b) pay any Indebtedness owed to Publishing
or any other Restricted Subsidiary, (c) make any Investment in Publishing or
(d) transfer any of its properties or assets to Publishing or any Restricted
Subsidiary, except (i) any encumbrance or restriction pursuant to or in
connection with the New Bank Credit Facility or the FDTH Credit Facility, each
as in effect on the date such Subsidiary becomes a Restricted Subsidiary of
this Indenture or any other agreement in effect on the date of this Indenture
(including the AP-91 Senior Notes), (ii) any encumbrance or restriction, with
respect to a Restricted Subsidiary that is not a Restricted Subsidiary of
Publishing on the date of this Indenture, in existence at the time such Person
becomes a Restricted Subsidiary of Publishing and not Incurred in connection
with, or in contemplation of, such Person becoming a Restricted
Subsidiary, (iii) any encumbrance or restriction pursuant to or in connection
with documents existing or securing any Foreign Subsidiary Indebtedness that is
not materially more restrictive than the terms of any such restrictions
existing on the date of the Indenture or the date such Subsidiary becomes a
Restricted Subsidiary, as determined in good faith by an officer of Publishing,
(iv) encumbrances or restrictions entered into by Southam in connection with
Indebtedness of Southam Incurred at a time when Southam is a Public Entity, (v)
encumbrances or restrictions contained in the terms of any Mirror Preferred;
provided that such Mirror Preferred continues to quality as such under the
definition thereof, (vi) customary provisions restricting subletting or
assignment of any lease governing a leasehold interest of Publishing or any
Restricted Subsidiary and (vii) any encumbrance or restriction existing under
any agreement that extends, renews, refinances or replaces the agreements
containing the encumbrances or restrictions in the foregoing clauses (i), (ii)
and (iii) (other than the covenants in the AP-91 Senior Notes); provided that
the terms and conditions of any such encumbrances or restrictions are not
materially less favorable to the Holders than those under or pursuant to the
agreement evidencing the Indebtedness so extended, renewed, refinanced or
replaced.

                 SECTION 10.17.  Provision of Financial Statements.  Whether or
not Hollinger International is subject to Section 13(a) or 15(d) of the
Exchange Act, Hollinger International will, to the extent permitted under the
Exchange Act, file with the Commission the annual reports, quarterly reports
and other documents that it would have 
<PAGE>   125

                                                                           117

been required to file with the Commission pursuant to such Sections 13(a) or 
15(d), including any "summarized information" or other information relating to
Publishing as may be required by Regulation S-X under the Exchange Act or by
the Commission, if it were so subject, such documents to be filed with the
Commission on or prior to the respective dates (the "Required Filing Dates") by
which it would have been required so to file such documents if it were so
subject.  Hollinger International will in any event (x) within 15 days of such
Required Filing Date (i) transmit by mail to all Holders, as their names and
addresses appear in the Security Register, without cost to such Holders and
(ii) file with the Trustee copies of the annual reports, quarterly reports and
other documents which Publishing would have been required to file with the
Commission pursuant to Section 13(a) or 15(d) of the Exchange Act if Hollinger
International were subject to such Sections and (y) if filing such documents by
Hollinger International with the Commission is not permitted under the Exchange
Act, promptly upon written request and payment of the reasonable cost of
duplication and delivery, supply copies of such documents to any prospective
holder of Securities at Publishing's cost.

                 SECTION 10.18.  Statement by Officers as to Default.  (a)
Publishing will deliver to the Trustee, on or before a date not more than 45
days after the end of each fiscal quarter and not more than 90 days after the
end of each fiscal year of Publishing ending after the date hereof, a written
statement signed by two executive officers of Publishing, one of whom shall be
the principal executive officer, principal financial officer or principal
accounting officer of Publishing, stating whether or not, after a review of the
activities of Publishing during such year or such quarter and of Publishing's
performance under this Indenture, to the best knowledge, based on such review,
of the signers thereof, Publishing has fulfilled all its obligations and is in
compliance with all conditions and covenants under this indenture throughout
such year or quarter, as the case may be, and, if there has been a Default,
specifying each Default and the nature and status thereof.

                 (b)  When any Default or Event of Default has occurred and is
continuing, or if the Trustee or any Holder or the trustee for or the holder of
any other evidence of Indebtedness of Publishing or any Restricted Subsidiary
gives any notice or takes any other action with respect to a claimed default,
Publishing shall deliver to the Trustee by registered or certified mail or by
telegram, telex or facsimile transmission followed by hard copy an Officers'
Certificate specifying such Default, Event of Default, notice or other action,
the status thereof and what action Publishing is taking or proposes to take
with respect thereto, within five Business Days of its occurrence.
<PAGE>   126

                                                                             118

                 SECTION 10.19.  Waiver of Certain Covenants.  Publishing may
omit in any particular instance to comply with any covenant or condition set
forth in Sections 10.05 through 10.14 and Sections 10.16 through 10.18 if,
before or after the time for such compliance, the Holders of not less than a
majority in aggregate principal amount of the Securities of any Series at the
time Outstanding waive such compliance in such instance with such covenant or
condition, but no such waiver shall extend to or affect such covenant or
condition except to the extent so expressly waived, and, until such waiver
shall become effective, the obligations of Publishing and the duties of the
Trustee in respect of any such covenant or condition shall remain in full force
and effect.

                 SECTION 10.20.  Limitation on the Designation of Additional
Restricted or Unrestricted Subsidiaries.  (a)  The Board of Directors may
designate any Restricted Subsidiary as an Unrestricted Subsidiary if (i) such
action is in compliance with Section 10.09 of this Indenture and (ii) such
action complies with the definition of "Unrestricted Subsidiaries".

                 (b)  The Board of Directors may designate any Unrestricted
Subsidiary or any Person that is to become a Restricted Subsidiary as a
Restricted Subsidiary if immediately after giving effect to such action (and
treating any Acquired Indebtedness as having been Incurred at the time of such
action), Publishing could have Incurred at least $1.00 of additional
Indebtedness pursuant to Section 10.08 of this Indenture.


                                   ARTICLE XI

                            Redemption of Securities

                 The Securities of any Series will not be subject to redemption
at the option of Publishing at any time prior to maturity.


                                  ARTICLE XII

                           Satisfaction and Discharge

                 SECTION 12.01.  Satisfaction and Discharge of Indenture.  This
Indenture shall cease to be of further effect (except as to surviving rights of
registration of transfer or exchange of the Securities of any Series herein
expressly provided for) and the Trustee, on demand of and at 
<PAGE>   127
 
                                                                             119
the expense of Publishing, shall execute proper instruments acknowledging 
satisfaction and discharge of this Indenture, when

                 (a) either

                 (1) all the Securities of any Series theretofore authenticated
         and delivered (other than (x) lost, stolen or destroyed Securities of
         any Series which have been replaced or paid as provided in Section
         3.06 and (y) Securities of any Series for whose payment United States
         dollars have theretofore been irrevocably  deposited in trust by
         Publishing and thereafter repaid to Publishing or discharged from such
         trust, as provided in Section 10.03) have been delivered to the 
         Trustee for cancellation; or

                 (2) all Securities of any Series not theretofore delivered to 
         the Trustee for cancellation

                          (x) have become due and payable, or

                          (y) will become due and payable at their Stated 
                 Maturity within one year, or

                          (z) are to be called for redemption within one year
                 under arrangements satisfactory to the Trustee for the giving
                 of notice of redemption by the Trustee in the name, and at the
                 expense, of Publishing,

         and Publishing has irrevocably deposited or caused to be deposited
         with the Trustee as trust funds in trust an amount sufficient to pay
         and discharge the entire indebtedness on the Securities of such Series
         not theretofore delivered to the Trustee for cancellation, including
         principal of, premium, if any, and accrued interest on the Securities
         of such Series at such Maturity, Stated Maturity or Redemption Date;

                 (b) Publishing has paid all other sums payable hereunder by 
Publishing; and

                 (c) Publishing has delivered to the Trustee an Officers'
Certificate and an Opinion of Counsel each to the effect that all conditions
precedent herein provided for relating to the satisfaction and discharge of
this Indenture have been complied with and that such satisfaction and discharge
will not result in a breach or violation of, or constitute a default under,
this Indenture.

                 Notwithstanding the satisfaction and discharge of this
Indenture, the obligations of Publishing to the Trustee under Section 6.07 and,
if United States dollars shall have been deposited with the Trustee pursuant to
subclause (2) of 
<PAGE>   128

                                                                             120

Subsection (a) of this Section, the obligations of the Trustee under 
Section 12.02 and the last paragraph of Section 10.03 shall survive.

                 SECTION 12.02.  Application of Trust Money.  Subject to the
provisions of the last paragraph of Section 10.03, all United States dollars 
deposited with the Trustee pursuant to Section 12.01 shall be held in trust
and applied by it, in accordance with the provisions of the Securities and 
this Indenture, to the payment, either directly or through any Paying Agent as 
the Trustee may determine, to the Persons entitled thereto, of the principal
of, premium, if any, and interest on the Securities for whose payment such
United States dollars have been deposited with the Trustee.


                                  ARTICLE XIII

                                   Guarantee

                 SECTION 13.01.  Hollinger International Guarantee.  For value
received, Hollinger International, in accordance with this Article XIII, hereby
absolutely, unconditionally and irrevocably guarantees to the Trustee and the
Holders, as if Hollinger International were the principal debtor, the punctual
payment and performance when due of all Indenture Obligations (which for
purposes of this Guarantee shall also be deemed to include all commissions,
fees, charges, costs and other expenses (including reasonable legal fees and
disbursements of one counsel) arising out of or incurred by the Trustee or the
Holders in connection with the enforcement of this Guarantee).

                 SECTION 13.02.  Continuing Guarantee; No Right of Set-Off;
Independent Obligation.  (a)  This Guarantee shall be a continuing guarantee of
the payment and performance of all Indenture Obligations and shall remain in
full force and effect until the payment in full of all of the Indenture
Obligations and shall apply to and secure any ultimate balance due or remaining
unpaid to the Trustee (including the fees and expenses of its agents and
counsel) or the Holders; and this Guarantee shall not be considered as wholly
or partially satisfied by the payment or liquidation at any time or from time
to time of any sum of money for the time being due or remaining unpaid to the
Trustee or the Holders.  Hollinger International covenants and agrees to comply
with all obligations, covenants, agreements and provisions applicable to it in
this Indenture including those set forth in Article VIII and Section 10.17.
Without limiting the generality of the foregoing, Hollinger International's
liability shall extend to all amounts which constitute part of the Indenture
Obligations and would be owed by Publishing under this Indenture and the
Securities but for the fact that they are unenforceable, reduced, 
<PAGE>   129

                                                                            121

limited, impaired, suspended or not allowable due to the existence of a 
bankruptcy, reorganization or similar proceeding involving Publishing.

                 (b)  Hollinger International hereby guarantees that the
Indenture Obligations will be paid to the Trustee without set-off or
counterclaim or other reduction whatsoever (whether for taxes, withholding 
or otherwise) in lawful currency of the United States of America.

                 (c)  Hollinger International guarantees that the Indenture
Obligations shall be paid strictly in accordance with their terms regardless of
any law, regulation or order now or hereafter in effect in any jurisdiction
affecting any of such terms or the rights of the holders of the Securities.

                 (d)  Hollinger International's liability to pay or perform or
cause the performance of the Indenture Obligations under this Guarantee shall
arise forthwith after demand for payment or performance by the Trustee has been
given to Hollinger International in the manner prescribed in Section 1.06
hereof.

                 (e)  Except as provided herein, the provisions of this Article
XIII cover all agreements between the parties hereto relative to this Guarantee
and none of the parties shall be bound by any representation, warranty or
promise made by any Person relative thereto which is not embodied herein; and
it is specifically acknowledged and agreed that this Guarantee has been
delivered by Hollinger International free of any conditions whatsoever and that
no representations, warranties or promises have been made to Hollinger
International affecting its liabilities hereunder, and that the Trustee shall
not be bound by any representations, warranties or promises now or at any time
hereafter made by Publishing to Hollinger International.

                 SECTION 13.03.  Guarantee Absolute.  The obligations of
Hollinger International hereunder are independent of the obligations of
Publishing under the Securities and this Indenture and a separate action or
actions may be brought and prosecuted against Hollinger International whether
or not an action or proceeding is brought against Publishing and whether or not
Publishing is joined in any such action or proceeding.  The liability of
Hollinger International hereunder is irrevocable, absolute and unconditional
and (to the extent permitted by law) the liability and obligations of Hollinger
International hereunder shall not be released, discharged, mitigated, waived,
impaired or affected in whole or in part by:

                 (a) any defect or lack of validity or enforceability in 
         respect of any Indebtedness or other obligation of Publishing or 
         any other Person 
<PAGE>   130

                                                                             122

         under this Indenture or the Securities, or any agreement or 
         instrument relating to any of the foregoing;

                 (b) any grants of time, renewals, extensions, indulgences,
         releases, discharges or modifications which the Trustee or the Holders
         may extend to, or make with, Publishing, Hollinger International or
         any other Person, or any change in the time, manner or place of
         payment of, or in any other term of, all or any of the Indenture
         Obligations, or any other amendment or waiver of, or any consent to or
         departure from, this Indenture or the Securities, including any
         increase or decrease in the Indenture Obligations;

                 (c) the taking of security from Publishing, Hollinger
         International or any other Person, and the release, discharge or
         alteration of, or other dealing with, such security;

                 (d) the occurrence of any change in the laws, rules,
         regulations or ordinances of any jurisdiction by any present or future
         action of any governmental authority or court amending, varying,
         reducing or otherwise affecting, or purporting to amend, vary, reduce
         or otherwise affect, any of the Indenture Obligations and the
         obligations of Hollinger International hereunder;

                 (e) the abstention from taking security from Publishing,
         Hollinger International or any other Person or from perfecting,
         continuing to keep perfected or taking advantage of any security;

                 (f) any loss, diminution of value or lack of enforceability of
         any security received from Publishing, Hollinger International or any
         other Person, and including any other guarantees received by the
         Trustee;

                 (g) any other dealings with Publishing, Hollinger
         International or any other Person, or with any security;

                 (h) the Trustee's or the Holders' acceptance of or entering
         into any composition with Publishing or Hollinger International;

                 (i) the application by the Holders or the Trustee of all 
         monies at any time and from time to time received from Publishing,
         Hollinger International or any other Person on account of any
         indebtedness and liabilities owing by Publishing or Hollinger
         International to the Trustee or the Holders, in such manner as the
         Trustee or the Holders deems best and the changing of such application
         in whole or in part and at 
<PAGE>   131

                                                                            123

         any time or from time to time, or any manner of application of
         collateral, or proceeds thereof, to all or any of the Indenture
         Obligations, or the manner of sale of any Collateral;

                 (j) the release or discharge of Publishing or Hollinger
         International or of any other Guarantor of the Securities or of any
         Person liable directly as surety or otherwise by operation of law or
         otherwise for the Securities, other than an express release in writing
         given by the Trustee, on behalf of the Holders, of the liability and
         obligations of Hollinger International hereunder;

                 (k) any change in the name, business, capital structure or
         governing instrument of Publishing or Hollinger International or any
         refinancing or restructuring of any of the Indenture Obligations;

                 (l) the sale of Publishing's or Hollinger International's
         business or any part thereof;

                 (m) subject to Section 13.14, any merger or consolidation,
         arrangement or reorganization of Publishing, Hollinger International,
         any Person resulting from the merger or consolidation of Publishing or
         Hollinger International with any other Person or any other successor
         to such Person or merged or consolidated Person or any other change in
         the corporate existence, structure or ownership of Publishing or
         Hollinger International;

                 (n) the insolvency, bankruptcy, liquidation, winding-up,
         dissolution, receivership or distribution of the assets of Publishing
         or its assets or any resulting discharge of any obligations of
         Publishing (whether voluntary or involuntary) or of Hollinger
         International or the loss of corporate existence;

                 (o) subject to Section 13.14, any arrangement or plan of
         reorganization affecting Publishing or Hollinger International;

                 (p) any other circumstance (including any statute of
         limitations) that might otherwise constitute a defense available to, 
         or discharge of, Publishing or Hollinger International; or

                 (q) any modification, compromise, settlement or release by the
         Trustee, or by operation of law or otherwise, of the Indenture
         Obligations or the liability of Publishing or any other obligor under
         the Securities, or of any Collateral, in whole or in part, and any
         refusal of payment by the Trustee, in whole or in part, from any other
         obligor or other guarantor in 
<PAGE>   132

                                                                             124

         connection with any of the Indenture Obligations, whether or not with 
         notice to, or further assent by, or any reservation of rights against, 
         Hollinger International.

                 SECTION 13.04.  Right to Demand Full Performance.  In the
event of any demand for payment or performance by the Trustee from Hollinger
International hereunder, the Trustee or the Holders shall have the right to
demand its full claim and to receive all dividends or other payments in respect
thereof until the Indenture Obligations shall have been paid in full, and
Hollinger International shall continue to be liable hereunder for any balance
which may be owing to the Trustee (including the fees and expenses of its agent
and counsel) or the Holders by Publishing under this Indenture and the
Securities.  The retention by the Trustee or the Holders of any security, prior
to the realization by the Trustee or the Holders of its rights to such security
upon foreclosure thereon, shall not, as between the Trustee and Hollinger
International, be considered as a purchase of such security, or as payment,
satisfaction or reduction of the  Indenture Obligations due to the Trustee or
the Holders by Publishing or any part thereof.

                 SECTION 13.05.  Waivers.  (a)  Hollinger International hereby
expressly waives (to the extent permitted by law) notice of the acceptance of
this Guarantee and notice of the existence, renewal, extension or the
nonperformance, nonpayment, or nonobservance on the part of Publishing of any
of the terms, covenants, conditions and provisions of this Indenture or the
Securities or any other notice whatsoever to or upon Publishing or Hollinger
International with respect to the Indenture Obligations.  Hollinger
International hereby acknowledges communication to it of the terms of this
Indenture and the Securities and all of the provisions therein contained and
consents to and approves the same.  Hollinger International hereby expressly
waives (to the extent permitted by law) diligence, presentment, protest and 
demand for payment.

                 (b)  Without prejudice to any of the rights or recourses which
the Trustee or the Holders may have against Publishing, Hollinger International
hereby expressly waives (to the extent permitted by law) any right to require
the Trustee or the Holders to:

                 (i) initiate or exhaust any rights, remedies or recourse
         against Publishing, Hollinger International or any other Person;

                 (ii) value, realize upon, or dispose of any security of
         Publishing or any other Person held by the Trustee or the Holders; or
<PAGE>   133
                                                                           125


                 (iii) initiate or exhaust any other remedy which the Trustee
         or the Holders may have in law or equity;

before requiring or becoming entitled to demand payment from Hollinger
International under this Guarantee.

                 SECTION 13.06.  Hollinger International Remains Obligated in
Event Publishing Is No Longer Obligated to Discharge Indenture Obligations.  It
is the express intention of the Trustee and Hollinger International that if for
any reason Publishing has no legal existence, is or becomes under no legal
obligation to discharge the Indenture Obligations owing to the Trustee or the
Holders by Publishing or if any of the Indenture Obligations owing by
Publishing to the Trustee or the Holders becomes irrecoverable from Publishing
by operation of law or for any reason whatsoever, this Guarantee and the
covenants, agreements and obligations of Hollinger International contained in
this Article XIII shall nevertheless be binding upon Hollinger International,
as principal debtor, until such time as all such Indenture Obligations have
been paid in full to the Trustee and all Indenture Obligations owing to the
Trustee or the Holders by Publishing have been discharged, or such earlier time
as Section 4.02 shall apply to the Securities and Hollinger International shall
be responsible for the payment thereof to the Trustee or the Holders upon
demand.

                 SECTION 13.07.  Waiver of Rights.  Hollinger International
agrees (to the extent permitted by law) that it hereby waives and will not in
any manner whatsoever claim or take the benefit or advantage of, any rights of
reimbursement, exoneration, contribution, indemnity or subrogation (whether 
contractual, under Section 509 of Title Eleven of the United States Code, 
under common law or otherwise) or any similar rights or "claims" (as such
term is defined under Title Eleven of the United States Code), against
Publishing or any Restricted Subsidiary arising from the existence of, or
performance by, Hollinger International under this Guarantee.

                 SECTION 13.08.  Guarantee Is in Addition to Other Security.
This Guarantee shall be in addition to and not in substitution for any other
guarantees or other security which the Trustee may now or hereafter hold in
respect of the Indenture Obligations owing to the Trustee or the Holders by
Publishing and (except as may be required by law) the Trustee shall be under no
obligation to marshal in favor of Hollinger International any other guarantees
or other security or any moneys or other assets which the Trustee may be
entitled to receive or upon which the Trustee or the Holders may have a claim.

                 SECTION 13.09.  Release of Security Interests.  Without
limiting the generality of the foregoing and except 
<PAGE>   134
                                                                           126


as otherwise provided in this Indenture, Hollinger International hereby
consents and agrees, to the fullest extent permitted by applicable law, that
the rights of the Trustee hereunder, and the liability of Hollinger
International hereunder, shall not be affected by any and all releases for any
purpose of any Collateral, if any, from the Liens and security interests
created by any document relating thereto and that this Guarantee shall continue
to be effective or be reinstated, as the case may be, if at any time any
payment of any of the Indenture Obligations is rescinded or must otherwise be
returned by the Trustee upon the insolvency, bankruptcy or reorganization of
Publishing or otherwise, all as though such payment had not been made.

                 SECTION 13.10.  No Bar to Further Actions.  Except as provided
by law, no action or proceeding brought or instituted under Article XIII and
this Guarantee and no recovery or judgment in pursuance thereof shall be a bar
or defense to any further action or proceeding which may be brought under
Article XIII and this Guarantee by reason of any further default or defaults
under Article XIII and this Guarantee or in the payment of any of the Indenture
Obligations owing by Publishing.

                 SECTION 13.11.  Failure to Exercise Rights Shall Not Operate
as a Waiver; No Suspension of Remedies.  (a)  No failure to exercise and no
delay in exercising, on the part of the Trustee or the Holders, any right,
power, privilege or remedy under this Article XIII and this Guarantee shall 
operate as a waiver thereof, nor shall any single or partial exercise of any 
rights, power, privilege or remedy preclude any other or further exercise 
thereof, or the exercise of any other rights, powers, privileges or remedies.  
The rights and remedies herein provided for are cumulative and not exclusive 
of any rights or remedies provided in law or equity.

                 (b)  Nothing contained in this Article XIII shall limit the
right of the Trustee or the Holders to take any action to accelerate the
maturity of the Securities pursuant to Article V or to pursue any rights or
remedies hereunder or under applicable law.

                 SECTION 13.12.  Trustee's Duties; Notice to Trustee.  (a)  Any
provision in this Article XIII or elsewhere in this Indenture allowing the
Trustee to request any information or to take any action authorized by, or on
behalf of Hollinger International, shall be permissive and shall not be
obligatory on the Trustee except as the Holders may direct in accordance with
the provisions of this Indenture.

                 (b)  The Trustee shall not be required to inquire into the
existence, powers or capacities of Publishing, 
<PAGE>   135
                                                                           127


Hollinger International or the officers, directors or agents acting or 
purporting to act on their respective behalf.

                 (c)  Notwithstanding the provisions of this Article XIII or
any other provision of this Indenture, the Trustee shall not be charged with 
knowledge of the existence of any facts which would prohibit the making of any 
payment to or by the Trustee in respect of the Securities, unless and until
the Trustee shall have received written notice thereof from Hollinger
International; and, prior to the receipt of any such written notice, the
Trustee, subject to the provisions of Section 6.01, shall be entitled in all
respects to assume that no such facts exist; provided, however, that if the
Responsible Officer of the Trustee shall not have received any such notice from
Hollinger International at least three Business Days prior to the date upon
which by the terms hereof any money may become payable for any purpose
(including, without limitation, the payment of the principal of, premium, if
any, or interest on any Security), then, anything herein contained to the
contrary notwithstanding, the Trustee shall have full power and authority to
receive such money and to apply the same to the purpose for which such money
was received and shall not be affected by any notice to the contrary which may
be received by it within three Business Days prior to such date; nor shall the
Trustee be charged with knowledge of the curing of any such default or the
elimination of the act or condition preventing any such payment unless and
until the Responsible Officer of the Trustee shall have received an Officers'
Certificate to such effect.

                 (d)  In the case at any time any Paying Agent other than the
Trustee shall have been appointed by Publishing and be then acting hereunder,
the term "Trustee" as used in this Article XIII shall in such case (unless the
context otherwise requires) be construed as extending to and including such
Paying Agent within its meaning as fully for all intents and purposes as if
such Paying Agent were named in this Article XIII in addition to or in place of
the Trustee; provided, however, that this Section 13.12 shall not apply to
Publishing or any Affiliate of Publishing if Publishing or such Affiliate acts
as Paying Agent.

                 SECTION 13.13.  Successors and Assigns.  All terms, agreements
and conditions of this Article XIII shall extend to and be binding upon
Hollinger International and its successors and permitted assigns and shall
enure to the benefit of and may be enforced by the Trustee and its successors
and assigns; provided, however, that Hollinger International may not assign any
of its rights or obligations hereunder other than in accordance with Article
VIII.

                 SECTION 13.14.  Release of Guarantee.  Concurrently with the
payment in full of all of the 
<PAGE>   136
                                                                           128


Indenture Obligations, Hollinger International shall be released from
and relieved of its obligations under this Article XIII. Upon the delivery by
Publishing to the Trustee of an Officer's Certificate and, if requested by the
Trustee, an Opinion of Counsel to the effect that the transaction giving rise
to the release of this Guarantee was made by Publishing in accordance with the
provisions of this Indenture and the Securities, the Trustee shall execute any
documents reasonably required in order to evidence the release of Hollinger
International from its obligations under this Guarantee.  If any of the
Indenture Obligations are revived and reinstated after the termination of this
Guarantee, then all of the obligations of Hollinger International under this
Guarantee shall be revived and reinstated as if this Guarantee had not been
terminated until such time as the Indenture Obligations are paid in full, and
Hollinger International shall enter into an amendment to this Guarantee,
reasonably satisfactory to the Trustee, evidencing such revival and
reinstatement.

                 This Guarantee shall terminate (a) upon a merger or
consolidation of Hollinger International with Publishing, in accordance with
Article VIII or (b) if after giving effect to a transaction or transactions
permitted to be consummated pursuant to Article VIII, Hollinger International
no longer owns any Capital Stock of Publishing.

                 SECTION 13.15.  Execution of Guarantee.  To evidence the
Guarantee, Hollinger International hereby agrees to execute a guarantee
substantially in the form set forth in Section 2.05, to be endorsed on each
Security authenticated and delivered by the Trustee and that this Indenture
shall be executed on behalf of Hollinger International by its Chairman of the
Board, its President or one of its Vice Presidents, under its corporate seal
reproduced thereon attested by its Secretary or one of its Assistant
Secretaries.  The signature of any of these officers on the Securities may be
manual or facsimile.

                 SECTION 13.16.  Payment Permitted by Hollinger International
if No Default.  Nothing contained in this Article, elsewhere in this Indenture
or in any of the Securities shall prevent Hollinger International from making
payments at any time of principal of, premium, if any, or interest on the
Securities.

                                    * * * *
<PAGE>   137
                                                                            129




                 IN WITNESS WHEREOF, the parties hereto have caused this
Indenture to be duly executed, and their respective corporate seals to be
hereunto affixed and attested, all as of the day and year first above written.


                                       HOLLINGER INTERNATIONAL 
                                       PUBLISHING INC.

                                          by ____________________________
                                             Name: 
                                             Title:


Attest:  ______________________
         Name:
         Title:


                                       HOLLINGER INTERNATIONAL INC., 
                                       solely in its capacity as Guarantor

                                          by ____________________________
                                             Name: 
                                             Title:


Attest:  ______________________
         Name:
         Title:

                                       FLEET NATIONAL BANK

                                          by ____________________________
                                             Name: 
                                             Title:

<PAGE>   1
                                                                   EXHIBIT 4.02

                  UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED
REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION ("DTC"),
NEW YORK, NEW YORK, TO PUBLISHING OR ITS AGENT FOR REGISTRATION OF TRANSFER,
EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF
CEDE & CO. OR SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE
OF DTC (AND ANY PAYMENT IS MADE TO CEDE & CO., OR TO SUCH OTHER ENTITY AS IS
REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE OR
OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL
INASMUCH AS THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.

                  TRANSFERS OF THIS GLOBAL SECURITY SHALL BE LIMITED TO
TRANSFERS IN WHOLE, BUT NOT IN PART, TO A NOMINEE OF DTC, TO DTC, TO A
SUCCESSOR TO DTC SELECTED OR APPROVED BY PUBLISHING, OR TO A NOMINEE OF SUCH
SUCCESSOR, AND TRANSFERS OF PORTIONS OF THIS GLOBAL SECURITY SHALL BE LIMITED
TO TRANSFERS MADE IN ACCORDANCE WITH THE RESTRICTIONS SET FORTH IN THE
INDENTURE REFERRED TO ON THE REVERSE HEREOF.


<PAGE>   2


                    HOLLINGER INTERNATIONAL PUBLISHING INC.

                              --------------------

                          8-5/8% SENIOR NOTES due 2005

No. 001                                                            $260,000,000
                                                           CUSIP No.  435572AC6

                  HOLLINGER INTERNATIONAL PUBLISHING INC., a Delaware
corporation (herein called "Publishing", which term includes any successor
Person under the Indenture hereinafter referred to), for value received, hereby
promises to pay to Cede & Co. or registered assigns, the principal sum of
$260,000,000 on March 15, 2005, at the office or agency of Publishing referred
to below, and to pay interest thereon from March 18, 1997 or from the most
recent Interest Payment Date to which interest has been paid or duly provided
for, semi-annually on March 15 and September 15 commencing September 15, 1997
at the rate of 8-5/8% per annum, in United States dollars, until the principal
hereof is paid or duly provided for.

                  The interest so payable, and punctually paid or duly provided
for, on any Interest Payment Date will, as provided in the Indenture, be paid
to the Person in whose name this Security (or one or more Predecessor
Securities) is registered at the close of business on the Regular Record Date
for such interest, which shall be March 1 or September 1 (whether or not a
Business Day), as the case may be, next preceding such Interest Payment Date.
Any interest not so paid, or duly provided for, and interest on such defaulted
interest at the interest rate borne by the Securities, to the extent lawful,
shall forthwith cease to be payable to the Holder in whose name such Security
is registered as of such Regular Record Date, and may be paid on the Special
Payment Date to the Person in whose name the Security (or one or more
Predecessor Securities) is registered at the close of business on a Special
Record Date to be fixed by the Trustee (and for which notice shall be given to
Holders of Securities not less than 10 days prior to such Special Record Date)
or may be paid at any time in any other lawful manner not inconsistent with the
requirements of any securities exchange on which the Securities may be listed,
and upon such notice as may be required by such exchange, all as more fully
provided in said Indenture.

                  Payment of the principal of, premium, if any, and interest on
this Security will be made at the office or agency of Publishing maintained for
that purpose in the City of New York, or at such other office or agency of
Publishing as may be maintained for such purpose, in such coin or currency of
the United States of America as at the time of payment is legal tender for
payment of public and private debts; provided, however, that payment of
interest may be made at the option of Publishing by check mailed to the address
of the Person entitled thereto as such address shall appear on the Security
Register.  Interest shall be computed on the basis of a 360-day year of twelve
30-day months.


<PAGE>   3

                  Reference is hereby made to the further provisions of this
Security set forth on the reverse hereof, which further provisions shall for
all purposes have the same effect as if set forth at this place.

                  Unless the certificate of authentication hereon has been duly
executed by the Trustee referred to on the reverse hereof or by the
authenticating agent appointed as provided in the Indenture by manual
signature, this Security shall not be entitled to any benefit under the
Indenture, or be valid or obligatory for any purpose.


<PAGE>   4


                  IN WITNESS WHEREOF, Publishing has caused this instrument to
be duly executed by the manual or facsimile signature of its authorized
officers and its corporate seal to be affixed or reproduced hereon.

Dated:                                       HOLLINGER INTERNATIONAL PUBLISHING
                                             INC.

                                                by

                                                   ----------------------------
                                                   Authorized Signatory

[Seal]

Attest:

- ------------------------------
         Secretary

TRUSTEE'S CERTIFICATE OF
       AUTHENTICATION

Fleet National Bank, as Trustee,
certifies that this is one of the
Securities referred to in the                                 [Seal]
within-mentioned Indenture
and Board Resolutions.

FLEET NATIONAL BANK,
as Trustee

         Dated:

         by

             -------------------------
              Authorized Signatory


<PAGE>   5


                             [Reverse of Security]

                    HOLLINGER INTERNATIONAL PUBLISHING INC.

                          8-5/8% SENIOR NOTES due 2005

                  This Security is one of a duly authorized issue of a series
of Securities of Publishing designated as the 8-5/8% Senior Notes due 2005 (the
"Securities"), limited (except as otherwise provided in the Indenture and Board
Resolutions referred to below) in aggregate principal amount to $260,000,000,
which may be issued under and subject to the terms of (a) a senior indenture
(herein called the "Indenture") dated as of March 18, 1997, among Publishing,
Hollinger International Inc. ("Hollinger International") and Fleet National
Bank, as trustee (together with any successor Trustee under the Indenture, the
"Trustee") and (b) resolutions dated as of March 12, 1997 of the Executive
Committee of the Board of Directors of Publishing (herein called the "Board
Resolutions"), to which Indenture, all indentures supplemental thereto and
Resolutions reference is hereby made for a statement of the respective rights,
limitations of rights, obligations, duties and immunities thereunder of the
Trustee and any agent of the Trustee, any Paying Agent, Hollinger
International, Publishing and the Holders of the Securities and the terms upon
which the Securities are, and are to be, authenticated and delivered.

                  The Indenture contains provisions for defeasance at any time
of (a) the entire Indebtedness evidenced by this Security and (b) certain
covenants and related Defaults and Events of Default, in each case upon
compliance with certain conditions set forth therein.

                  The Securities are not subject to redemption at the option of
Publishing prior to maturity.

                  Upon the occurrence of a Change of Control, each Holder shall
have the right to require Publishing to purchase all or a portion of such
Holder's Securities in amounts of $1,000 or integral multiples of $1,000, at a
purchase price in cash equal to 101% of the principal amount thereof, plus
accrued and unpaid interest, if any, to the date of purchase.

                  Under certain circumstances, in the event the Net Cash
Proceeds that are received by Publishing from any Asset Sale, and that are not
applied to repay permanently any Pari Passu Indebtedness then outstanding or
invested in properties or assets used in the businesses of Publishing in
accordance with the terms of the Indenture exceed $20 million, Publishing will
be required to apply such proceeds to the repayment of the Securities and
certain Indebtedness ranking pari passu with the Securities.

                  In the case of any purchase of Securities upon a Change of
Control or Asset Sale, interest installments whose Stated Maturity is on or
prior to the Change of Control Purchase Date or Purchase Date, as the case may
be, will be payable to the Holders of record of such Securities as of the close
of business on the relevant Regular Record Date or Special Record Date referred
to on the face hereof. Securities (or portions thereof) for whose repurchase
provision is made in


<PAGE>   6

accordance with the Indenture shall cease to bear interest from and after the
Change of Control Purchase Date or Purchase Date, as the case may be.

                  In the event of repurchase of this Security in part only, a
new Security or Securities for the portion hereof not repurchased shall be
issued in the name of the Holder hereof upon the cancellation hereof.

                  If an Event of Default shall occur and be continuing, the
principal amount of all the Securities may be declared due and payable in the
manner and with the effect provided in the Indenture.

                  The Indenture permits, with certain exceptions (including
certain amendments permitted without the consent of any Holders) as therein
provided, the amendment thereof and the modification of the rights and
obligations of Publishing and the rights of the Holders under the Indenture and
the Securities at any time with the consent of the Holders of not less than a
majority in aggregate principal amount of the Securities at the time
Outstanding. The Indenture also contains provisions permitting the Holders of
not less than a majority in aggregate principal amount of the Securities at the
time Outstanding, on behalf of the Holders of all the Securities, to waive
compliance by Publishing with certain provisions of the Indenture and the
Securities and certain past Defaults under the Indenture and their
consequences.  Any such consent or waiver by or on behalf of the Holder of this
Security shall be conclusive and binding upon such Holder and upon all future
Holders of this Security and of any Security issued upon the registration of
transfer hereof or in exchange herefor or in lieu hereof whether or not
notation of such consent or waiver is made upon this Security.

                  No reference herein to the Indenture and no provision of this
Security or of the Indenture shall alter or impair the obligation of
Publishing, which is absolute and unconditional, to pay the principal of,
premium, if any, and interest on this Security at the times, place, and rate,
and in the coin or currency, herein prescribed subject to the subordination
provisions of the Indenture.

                  As set forth in, and subject to, the provisions of the
Indenture, no Holder of any Security will have any right to institute any
proceeding with respect to the Indenture or for any remedy thereunder, unless
(a) such Holder shall have previously given to the Trustee written notice of a
continuing Event of Default, (b) the Holders of not less than 25% in principal
amount of the Outstanding Securities shall have made written request, and
offered reasonable indemnity, to the Trustee to institute such proceeding as
trustee, (c) the Trustee shall not have received from the Holders of a majority
in principal amount of the Outstanding Securities a direction inconsistent with
such request and (d) the Trustee shall have failed to institute such proceeding
within 60 days; provided, however, that such limitations do not apply to a suit
instituted by the holder hereof for the enforcement of payment of the principal
of (and premium, if any) or any interest on this Security on or after the
respective due dates expressed herein.

                  As provided in the Indenture and subject to certain
limitations therein set forth, the transfer of this Security is registrable on
the Security Register of Publishing, upon surrender of


<PAGE>   7

this Security for registration of transfer at the office or agency of
Publishing maintained for such purpose in the City of New York or at such other
office or agency of Publishing as may be maintained for such purpose, duly
endorsed by, or accompanied by a written instrument of transfer in form
satisfactory to Publishing and the Security Registrar duly executed by, the
Holder hereof or his attorney duly authorized in writing, and thereupon one or
more new Securities, of authorized denominations and for the same aggregate
principal amount, will be issued to the designated transferee or transferees.

                  The Securities are issuable only in registered form without
coupons in denominations of $1,000 and any integral multiple thereof. As
provided in the Indenture and subject to certain limitations therein set forth,
the Securities are exchangeable for a like aggregate principal amount of
Securities of a different authorized denomination, as requested by the Holder
surrendering the same.

                  No service charge shall be made for any registration of
transfer or exchange or redemption of Securities, but Publishing may require
payment of a sum sufficient to cover any tax or other governmental charge
payable in connection therewith.

                  Prior to due presentment of this Security for registration of
transfer, Publishing, the Trustee and any agent of Publishing or the Trustee
may treat the Person in whose name this Security is registered as the owner
hereof for all purposes, whether or not this Security is overdue, and none of
Publishing, the Trustee nor any agent shall be affected by notice to the
contrary.

                  Upon any consolidation or merger, or any sale, assignment,
conveyance, transfer or disposition (other than pursuant to a lease) of all or
substantially all of the properties and assets of Publishing in accordance with
the Indenture, subject to the terms and conditions of the Indenture, the
successor Person to such transaction shall become the obligor on this Security,
and Publishing shall be discharged from all obligations and covenants under
this Security and the Indenture.

                  All terms used in this Security which are defined in the
Indenture and not otherwise defined herein shall have the meanings assigned to
them in the Indenture.

                   GUARANTEE OF HOLLINGER INTERNATIONAL INC.

                  For value received, HOLLINGER INTERNATIONAL INC., a Delaware
corporation, hereby absolutely, unconditionally and irrevocably guarantees to
the holder of this Security and the Trustee, as if Hollinger International were
the principal debtor, the punctual payment of principal of, premium, if any,
and interest on this Security in the amounts and at the time when due and
interest on the overdue principal and interest, if any, of this Security, if
lawful, and the payment or performance of all other obligations of Publishing
under the Indenture or the Securities, to the holder of this Security and the
Trustee, all in accordance with and subject to the terms and limitations of
this Security and Article Thirteen of the Indenture. This Guarantee will


<PAGE>   8

not become effective until the Trustee duly executes the certificate of
authentication on this Security.

                                                  HOLLINGER INTERNATIONAL INC.

Attest:_________________________                  By___________________________
                                                     Authorized Signatory

<PAGE>   1
                                                                    EXHIBIT 4.03

                    HOLLINGER INTERNATIONAL PUBLISHING INC.

                   9-1/4% Senior Subordinated Notes due 2007

                         Unconditionally Guaranteed by

                          HOLLINGER INTERNATIONAL INC.

                        --------------------------------


                                   INDENTURE

                           Dated as of March 18, 1997

                        -------------------------------


                              FLEET NATIONAL BANK,

                                    Trustee


<PAGE>   2



                               TABLE OF CONTENTS

                                                                            Page

<TABLE>
<S>                                                                         <C>
PARTIES.......................................................................1
RECITALS......................................................................1
</TABLE>

                                   ARTICLE I

            Definitions and Other Provisions of General Application
            -------------------------------------------------------
<TABLE>
<S>                 <C>                                                                                   <C>
SECTION 1.01.       Definitions............................................................................2
SECTION 1.02.       Other Definitions.....................................................................40
SECTION 1.03.       Compliance Certificates and Opinions..................................................40
SECTION 1.04.       Form of Documents Delivered to Trustee................................................41
SECTION 1.05.       Acts of Holders.......................................................................42
SECTION 1.06.       Notices, etc., to Trustee and Publishing..............................................43
SECTION 1.07.       Notice to Holders; Waiver.............................................................43
SECTION 1.08.       Conflict with Trust Indenture Act.....................................................44
SECTION 1.09.       Effect of Headings and Table of Contents..............................................44
SECTION 1.10.       Successors and Assigns................................................................44
SECTION 1.11.       Separability Clause...................................................................44
SECTION 1.12.       Benefits of Indenture.................................................................45
SECTION 1.13.       Governing Law.........................................................................45
SECTION 1.14.       Legal Holidays........................................................................45
SECTION 1.15.       Schedules.............................................................................45
SECTION 1.16.       Counterparts..........................................................................45
</TABLE>


                                   ARTICLE II

                                 Security Forms
                                 -------------- 
<TABLE>
<S>                  <C>                                                                                   <C>
SECTION 2.01.       Forms Generally.......................................................................45
SECTION 2.02.       Forms of Securities...................................................................46
SECTION 2.03.       Form of Trustee's Certificate of Authentication.......................................47
SECTION 2.04.       Form of Guarantee of Hollinger International..........................................47
SECTION 2.05.       Securities Issuable in the Form of a Global Security..................................48
</TABLE>




<PAGE>   3



                                  ARTICLE III

                                 The Securities
                                 --------------
<TABLE>
                                                                                                    PAGE
                                                                                                    ----
<S>                  <C>                                                                             <C>
SECTION 3.01.        General Title; General Limitations; Issuable in Series;
                        Terms of Particular Series...................................................50
SECTION 3.02.        Denominations...................................................................53
SECTION 3.03.        Execution, Authentication, Delivery and Dating..................................53
SECTION 3.04.        Temporary Securities............................................................55
SECTION 3.05.        Registration, Registration of Transfer and Exchange.............................56
SECTION 3.06.        Mutilated, Destroyed, Lost and Stolen Securities................................57
SECTION 3.07.        Payment of Interest; Interest Rights Preserved..................................58
SECTION 3.08         Persons Deemed Owners...........................................................60
SECTION 3.09.        Cancellation....................................................................60
SECTION 3.10.        Computation of Interest.........................................................61
SECTION 3.11.        Delayed Issuance of Securities..................................................61
</TABLE>


                                   ARTICLE IV

                       Defeasance and Covenant Defeasance
                       ----------------------------------
<TABLE>
<S>                  <C>                                                                             <C>
SECTION 4.01.        Publishing's Option to Effect Defeasance or Covenant
                        Defeasance...................................................................62
SECTION 4.02.        Defeasance and Discharge........................................................62
SECTION 4.03.        Covenant Defeasance.............................................................63
SECTION 4.04.        Conditions to Defeasance or Covenant Defeasance.................................63
SECTION 4.05.        Deposited Money and U.S. Government Obligations to be
                        Held in Trust; Other Miscellaneous Provisions................................66
SECTION 4.06.        Reinstatement...................................................................67
</TABLE>


                                   ARTICLE V

                                    Remedies
                                    --------
<TABLE>
<S>                  <C>                                                                             <C>
SECTION 5.01.        Events of Default...............................................................67
</TABLE>

                                       ii


<PAGE>   4




<TABLE>
                                                                                                  PAGE
                                                                                                  ----    
<S>                  <C>                                                                           <C>
SECTION 5.02.        Acceleration of Maturity; Rescission and Annulment..............................70
SECTION 5.03.        Collection of Indebtedness and Suits for Enforcement
                        by Trustee...................................................................71
SECTION 5.04.        Trustee May File Proofs of Claim................................................72
SECTION 5.05.        Trustee May Enforce Claims Without Possession of Securities.....................73
SECTION 5.06.        Application of Money Collected..................................................74
SECTION 5.07.        Limitation on Suits.............................................................74
SECTION 5.08.        Unconditional Right of Holders to Receive Principal,
                        Premium and Interest.........................................................75
SECTION 5.09.        Restoration of Rights and Remedies..............................................75
SECTION 5.10.        Rights and Remedies Cumulative..................................................76
SECTION 5.11.        Delay or Omission Not Waiver....................................................76
SECTION 5.12.        Control by Holders..............................................................76
SECTION 5.13.        Waiver of Past Defaults.........................................................76
SECTION 5.14.        Undertaking for Costs...........................................................77
SECTION 5.15.        Waiver of Stay, Extension or Usury Laws.........................................77
SECTION 5.16.        Remedies Subject to Applicable Law..............................................78
</TABLE>


                                   ARTICLE VI

                                  The Trustee
                                  -----------
<TABLE>
<S>                  <C>                                                                             <C>    
SECTION 6.01.        Duties of Trustee...............................................................78
SECTION 6.02.        Notice of Defaults..............................................................80
SECTION 6.03.        Certain Rights of Trustee.......................................................80
SECTION 6.04.        Trustee Not Responsible for Recitals, Dispositions of Securities
                        or Application of Proceeds Thereof...........................................82
SECTION 6.05.        Trustee and Agents May Hold Securities; Collections; etc........................82
SECTION 6.06.        Money Held in Trust.............................................................82
SECTION 6.07.        Compensation and Indemnification of Trustee and Its Prior
                        Claim........................................................................82
SECTION 6.08.        Conflicting Interests...........................................................83
SECTION 6.09.        Corporate Trustee Required; Eligibility.........................................84
SECTION 6.10.        Resignation and Removal; Appointment of Successor Trustee.......................84
SECTION 6.11.        Acceptance of Appointment by Successor..........................................86
SECTION 6.12.        Merger, Conversion, Consolidation or Succession to Business.....................87
</TABLE>

                                      iii


<PAGE>   5




<TABLE>
                                                                                                   PAGE
                                                                                                   ----
<S>                  <C>                                                                             <C>
SECTION 6.13.        Preferential Collection of Claims Against Publishing............................88
</TABLE>


                                  ARTICLE VII

              Holders' Lists and Reports by Trustee and Publishing
              ----------------------------------------------------
<TABLE>
<S>                  <C>                                                                             <C>
SECTION 7.01.        Publishing to Furnish Trustee Names and Addresses of
                        Holders......................................................................88
SECTION 7.02.        Disclosure of Names and Addresses of Holders....................................89
SECTION 7.03.        Reports by Trustee..............................................................89
SECTION 7.04.        Reports by Publishing...........................................................89
</TABLE>


                                  ARTICLE VIII

                     Consolidation, Merger, Sale of Assets
                     -------------------------------------
<TABLE>
<S>                  <C>                                                                             <C>
SECTION 8.01.        Publishing May Merge, Consolidate, etc., Only on Certain
                        Terms........................................................................90
SECTION 8.02.        Successor Substituted...........................................................93
</TABLE>


                                   ARTICLE IX

                            Supplemental Indentures
                            -----------------------
<TABLE>
<S>                  <C>                                                                             <C>
SECTION 9.01.        Supplemental Indentures and Agreements Without Consent
                        of Holders...................................................................94
SECTION 9.02.        Supplemental Indentures and Agreements with Consent of
                        Holders......................................................................95
SECTION 9.03.        Execution of Supplemental Indentures and Agreements.............................97
SECTION 9.04.        Effect of Supplemental Indentures...............................................98
SECTION 9.05.        Conformity with Trust Indenture Act.............................................98
SECTION 9.06.        Reference in Securities to Supplemental Indentures..............................98
SECTION 9.07.        Record Date.....................................................................98
SECTION 9.08.        Effect on Senior Indebtedness...................................................99
</TABLE>

                                       iv


<PAGE>   6



                                                                      PAGE
                                                                      ----    
                                   ARTICLE X

                                   Covenants
                                   ---------
<TABLE>
<S>                  <C>                                                                            <C>
SECTION 10.01.       Payment of Principal, Premium and Interest......................................99
SECTION 10.02.       Maintenance of Office or Agency.................................................99
SECTION 10.03.       Money for Security Payments to be Held in Trust................................100
SECTION 10.04.       Corporate Existence............................................................101
SECTION 10.05.       Payment of Taxes and Other Claims..............................................102
SECTION 10.06.       Maintenance of Properties......................................................102
SECTION 10.07.       Insurance......................................................................102
SECTION 10.08.       Limitation on Indebtedness.....................................................103
SECTION 10.09.       Limitation on Restricted Payments..............................................104
SECTION 10.10.       Limitation on Transactions with Affiliates.....................................110
SECTION 10.11.       Limitation on Other Subordinated Indebtedness..................................111
SECTION 10.12.       Limitation on Liens............................................................112
SECTION 10.13.       Limitation on Issuances of Guarantees of Indebtedness..........................113
SECTION 10.14.       Limitation on Sale of Assets...................................................114
SECTION 10.15.       Purchase of Securities Upon a Change of Control................................120
SECTION 10.16.       Limitation on Issuance and Sale of Capital Stock of
                        Restricted Subsidiaries.....................................................124
SECTION 10.17.       Limitation on Dividends and Other Payment Restrictions
                        Affecting Restricted Subsidiaries...........................................126
SECTION 10.18.       Provision of Financial Statements..............................................127
SECTION 10.19.       Statement by Officers as to Default............................................127
SECTION 10.20.       Waiver of Certain Covenants....................................................128
SECTION 10.21.       Limitation on the Designation of Additional
                        Restricted or Unrestricted Subsidiaries.....................................128
</TABLE>

                                   ARTICLE XI

                            Redemption of Securities
                            ------------------------
<TABLE>
<S>                  <C>                                                                            <C>
SECTION 11.01.       Right of Redemption............................................................129
SECTION 11.02.       Applicability of Article.......................................................129
</TABLE>

                                       v


<PAGE>   7



                                                                      PAGE
                                                                      ----
<TABLE>
<S>                  <C>                                                                            <C>
SECTION 11.03.       Election to Redeem; Notice to Trustee..........................................129
SECTION 11.04.       Selection by Trustee of Securities to be Redeemed..............................129
SECTION 11.05.       Notice of Redemption...........................................................130
SECTION 11.06.       Deposit of Redemption Price....................................................131
SECTION 11.07.       Securities Payable on Redemption Date..........................................131
SECTION 11.08.       Securities Redeemed or Purchased in Part.......................................132
</TABLE>


                                  ARTICLE XII

                          Subordination of Securities
                          ---------------------------
<TABLE>
<S>                  <C>                                                                            <C> 
SECTION 12.01.       Securities Subordinate to Senior Indebtedness..................................132
SECTION 12.02.       Payment of Proceeds Upon Dissolution, etc......................................133
SECTION 12.03.       Suspension of Payment When Senior Indebtedness in Default......................135
SECTION 12.04.       Payment Permitted if No Default................................................136
SECTION 12.05.       Subrogation to Rights of Holders of Senior Indebtedness........................137
SECTION 12.06.       Provisions Solely to Define Relative Rights....................................137
SECTION 12.07.       Trustee to Effectuate Subordination............................................138
SECTION 12.08.       No Waiver of Subordination Provisions..........................................138
SECTION 12.09.       Notice to Trustee..............................................................139
SECTION 12.10.       Reliance on Judicial Order or Certificate of Liquidating Agent.................140
SECTION 12.11.       Rights of Trustee as a Holder of Senior Indebtedness;
                        Preservation of Trustee's Rights............................................140
SECTION 12.12.       Article Applicable to Paying Agents............................................141
SECTION 12.13.       No Suspension of Remedies......................................................141
SECTION 12.14        Trustee's Relation to Senior Indebtedness......................................141
</TABLE>

                                  ARTICLE XIII

                           Satisfaction and Discharge
                           --------------------------
<TABLE>
<S>                  <C>                                                                            <C>
SECTION 13.01        Satisfaction and Discharge of Indenture........................................142
SECTION 13.02.       Application of Trust Money.....................................................143
</TABLE>


                                       vi


<PAGE>   8



                                                                      PAGE
                                                                      ----
                                  ARTICLE XIV

                                   Guarantee
                                   ---------
<TABLE>
<S>                  <C>                                                                            <C>     
SECTION 14.01.       Hollinger International Guarantee..............................................143
SECTION 14.02.       Continuing Guarantee; No Right of Set-Off; Independent
                        Obligation..................................................................143
SECTION 14.03.       Guarantee Absolute.............................................................145
SECTION 14.04.       Right to Demand Full Performance...............................................147
SECTION 14.05.       Waivers........................................................................148
SECTION 14.06.       Hollinger International Remains Obligated in Event Publishing
                        is No Longer Obligated to Discharge Indenture Obligations...................148
SECTION 14.07.       Waiver of Rights...............................................................149
SECTION 14.08.       Guarantee Is in Addition to Other Security.....................................149
SECTION 14.09.       Release of Security Interests..................................................149
SECTION 14.10.       No Bar to Further Actions......................................................150
SECTION 14.11.       Failure to Exercise Rights Shall Not Operate as a Waiver; No
                        Suspension of Remedies......................................................150
SECTION 14.12.       Trustee's Duties; Notice to Trustee............................................150
SECTION 14.13.       Successors and Assigns.........................................................151
SECTION 14.14.       Release of Guarantee...........................................................151
SECTION 14.15.       Execution of Guarantee.........................................................152
SECTION 14.16.       Guarantee Subordinate to Senior Guarantor Indebtedness.........................152
SECTION 14.17.       Payment Over of Proceeds Upon Dissolution of Hollinger
                        International, etc..........................................................153
SECTION 14.18.       Default on Senior Guarantor Indebtedness.......................................154
SECTION 14.19.       Payment Permitted by Hollinger International if No Default.....................155
SECTION 14.20.       Subrogation to Rights of Holders of Senior Guarantor
                        Indebtedness................................................................155
SECTION 14.21.       Provisions Solely to Define Relative Rights....................................156
SECTION 14.22.       Trustee to Effectuate Subordination............................................156
SECTION 14.23.       No Waiver of Subordination Provisions..........................................157
SECTION 14.24.       Notice to Trustee by Hollinger International...................................158
SECTION 14.25.       Reliance on Judicial Order or Certificate of Liquidating Agent.................159
SECTION 14.26.       Rights of Trustee as a Holder of Senior Guarantor Indebtedness;
                        Preservation of Trustee's Rights............................................159
</TABLE>

                                      vii


<PAGE>   9



                                                                      PAGE
                                                                      ----  
<TABLE>
<S>                  <C>                                                                            <C>
SECTION 14.27.       Article Applicable to Paying Agents............................................159
SECTION 14.28.       No Suspension of Remedies......................................................160
SECTION 14.29.       Trustee's Relation to Senior Guarantor Indebtedness............................160

SIGNATURES AND SEALS................................................................................161

ACKNOWLEDGEMENTS

SCHEDULE I           Permitted Indebtedness
</TABLE>

                                      viii


<PAGE>   10



                             CROSS-REFERENCE TABLE

TIA SECTION                                            INDENTURE SECTION
- -----------                                            -----------------
<TABLE>
<S>   <C>                                                                           <C>
310   (a)(1)................................................................        6.09
      (a)(2)................................................................        6.09
      (a)(5)................................................................        6.11; 6.12
      (b)...................................................................        6.08; 6.10
311   (a)...................................................................        6.13
      (b)...................................................................        6.13
312   (a)...................................................................        7.01
      (c)...................................................................        7.02
313   (a)...................................................................        7.03
      (c)...................................................................        7.03
314   (a)(1)................................................................        7.04(a)
      (a)(2)................................................................        7.04(b)
      (a)(3)................................................................        7.04(c)
      (a)(4)................................................................        10.19
      (c)(1)................................................................        1.03
      (c)(2)................................................................        1.03
      (e)...................................................................        1.03
315   (a)...................................................................        6.01(b)
      (b)...................................................................        6.02
      (c)...................................................................        6.01(a)
      (d)...................................................................        6.01(c)
      (e)...................................................................        5.14
316   (a) (last sentence)...................................................        1.01 ("Outstanding")
      (a)(1)(A).............................................................        5.12
      (a)(1)(B).............................................................        5.13
      (b)...................................................................        5.08
      (c)...................................................................        9.07
317   (a)(1)................................................................        5.03
      (a)(2)................................................................        5.04
      (b)...................................................................        10.03
318   (a)...................................................................        1.08
</TABLE>
- ----------------

Note:    This Cross-Reference Table shall not, for any purpose, be
         deemed to be a part of the Indenture.

                                       ix


<PAGE>   11





                                    SENIOR SUBORDINATED INDENTURE, dated as of
                           March 18, 1997, among HOLLINGER INTERNATIONAL
                           PUBLISHING INC., a Delaware corporation (as more
                           fully defined below, "Publishing"), HOLLINGER
                           INTERNATIONAL INC., a Delaware corporation (as more
                           fully defined below, "Hollinger International") and
                           FLEET NATIONAL BANK, as trustee (the "Trustee").

                             RECITALS OF PUBLISHING

     Publishing has duly authorized the execution and delivery of this
Indenture to provide for the issuance of its senior subordinated debentures,
notes, bonds or other evidences of indebtedness, to be issued in one or more
series pursuant to Article III hereof or a supplemental indenture (each a
"Series" and collectively the "Securities").

     Hollinger International has duly authorized the issuance of a guarantee
(the "Guarantee") of the Securities, of substantially the tenor as hereinafter
set forth, and to provide therefor, Hollinger International has duly authorized
the execution and delivery of this Indenture in its capacity as Guarantor
hereunder.

     This Indenture is subject to, and shall be governed by, the provisions of
the Trust Indenture Act that are required to be part of and to govern
indentures qualified under the Trust Indenture Act; and

     All acts and things necessary have been done to make (i) the Securities,
when executed by Publishing and authenticated and delivered hereunder and duly
issued by Publishing, the valid obligations of Publishing and (ii) this
Indenture a valid agreement of Publishing and Hollinger International in
accordance with the terms of this Indenture.
<PAGE>   12
                                                                           - 2 -

     NOW, THEREFORE, in consideration of the premises and the purchase of the
Securities by the Holders thereof, it is mutually covenanted and agreed, for
the equal and proportionate benefit of all Holders of the Securities, as
follows:

                                   ARTICLE I

            Definitions and Other Provisions of General Application

     SECTION 1.01. Definitions. For all purposes of this Indenture, except as
otherwise expressly provided or unless the context otherwise requires:

     (a) the terms defined in this Article have the meanings assigned to them
   in this Article, and include the plural as well as the singular;

     (b) all other terms used herein which are defined in the Trust Indenture
   Act, either directly or by reference therein, have the meanings assigned to
   them therein;

     (c) all accounting terms not otherwise defined herein have the meanings
   assigned to them in accordance with GAAP;

     (d) the words "herein", "hereof" and "hereunder" and other words of
   similar import refer to this Indenture as a whole and not to any particular
   Article, Section or other subdivision; and

     (e) all references to $, US$, dollars or United States dollars shall refer
   to the lawful currency of the United States of America.

     The following terms shall have the meanings set forth in this Section:

                  "Acceleration Right" means a right, which at the time is
immediately exercisable (without further notice or lapse of time), by the
holders or a trustee to cause the acceleration of the maturity of Indebtedness
of Publishing or a Restricted Subsidiary having an aggregate principal amount
outstanding of at least $5,000,000; provided that this definition shall exclude
the rights of the holders of the existing preference shares of DTH and FDTH to
require that Restricted Subsidiaries or Affiliates purchase those shares
pursuant to the terms of the governing instruments or existing agreements
relating to such preference shares existing on January 1, 1997.

                  "Acquired Indebtedness" means Indebtedness of a Person
(including an Unrestricted Subsidiary) (i) existing at the time

<PAGE>   13
                                                                           - 3 -

such Person becomes a Restricted Subsidiary or (ii) assumed in connection with
the acquisition of assets from such Person, in each case, other than
Indebtedness Incurred in connection with, or in contemplation of, such Person
becoming a Restricted Subsidiary or such acquisition. Acquired Indebtedness
will be deemed to be Incurred on the date of the related acquisition of assets
from any Person or the date the acquired Person becomes a Restricted
Subsidiary.

                  "Affiliate" means, with respect to any specified Person, (i)
any other Person directly or indirectly controlling or controlled by or under
direct or indirect common control with such specified Person or (ii) any other
Person that owns, directly or indirectly, 10% or more of such Person's equity
ownership or Voting Stock or any officer or director of any such Person or
other Person or with respect to any natural Person, any person having a
relationship with such Person by blood, marriage or adoption not more remote
than first cousin. For the purposes of this definition, "control" when used
with respect to any specified Person means the power to direct the management
and policies of such Person directly or indirectly, whether through ownership
of voting securities, by contract or otherwise; and the terms "controlling" and
"controlled" have meanings correlative to the foregoing.

                  "Agent" means the administrative agent under the New Bank
Credit Facility, and its successors and assigns in such capacity.

                  "Amortization Expense" of any Person means, for any period,
amounts recognized during such period as (i) amortization of goodwill or (ii)
amortization of any other intangible assets with an original life of ten years
or more, in each case in accordance with GAAP and to the extent reflected in
the Consolidated Net Income of Publishing and the Restricted Subsidiaries;
provided, however, that in determining the aggregate cumulative Amortization
Expense of Publishing and its Restricted Subsidiaries for purposes of Section
10.09 following the date on which both of The Telegraph and Southam are
Restricted Subsidiaries, the Amortization Expense of Restricted Subsidiaries
that are not Wholly Owned Restricted Subsidiaries shall be determined in
accordance with the actual percentage of Publishing's common equity in such
Restricted Subsidiary on the date of the transaction necessitating the
determination (thus, for example, in the case of a Restricted Subsidiary in
which Publishing owns a 51% common equity interest on the date of the
Restricted Payment, 51% of such Restricted Subsidiary's Amortization Expense
would be included in the calculation of the aggregate cumulative Amortization
Expense of Publishing and the Restricted Subsidiaries).
<PAGE>   14
                                                                           - 4 -

                  "AP-91" means American Publishing (1991) Inc., a wholly
owned, indirect Subsidiary.

                  "AP-91 Senior Notes" means the $150 million in senior secured
notes issued by AP-91 which are held by 19 insurance companies.

                  "Argsub" means a wholly owned subsidiary of Argus.

                  "Argsub Preferred" means Preferred Stock of any Argsub issued
to and held by DTH or FDTH.

                  "Argus" means Argus Corporation Limited, a Canadian
corporation, so long as such corporation is controlled by Hon. Conrad M. Black
or his heirs, executors and legal representatives and his Affiliates.

                  "Asset Sale" means any sale, issuance, conveyance, transfer,
lease or other disposition (including, without limitation, by way of merger,
consolidation or sale and leaseback transaction but not the grant of a pledge
or security interest) (collectively, a "transfer"), directly or indirectly, in
one or a series of related transactions, of (i) any Capital Stock of any
Restricted Subsidiary; (ii) all or substantially all of the properties and
assets of any division or line of business of Publishing or any of its
Restricted Subsidiaries; or (iii) any other properties or assets (other than
cash) of Publishing or any Restricted Subsidiary, other than in the ordinary
course of business. For the purposes of this definition, the term "Asset Sale"
shall not include any transfer of properties and assets (A) that is governed by
the provisions of Article VIII, (B) from any Restricted Subsidiary to
Publishing in accordance with the terms of this Indenture, (C) having a market
value of less than $1,000,000 (it being understood that if the market value of
the properties or assets being transferred exceeds $1,000,000, the entire value
and not just the portion in excess of $1,000,000 shall be deemed to have been
the subject of an Asset Sale), (D) which are obsolete (in the case of
equipment) to Publishing's and its Restricted Subsidiaries' businesses,
(E) to any Wholly Owned Restricted Subsidiary (or, provided that both The
Telegraph and Southam are Restricted Subsidiaries, a Restricted Subsidiary),
(F) from any Wholly Owned Restricted Subsidiary to any other Wholly Owned
Restricted Subsidiary (or, provided that both The Telegraph and Southam are
Restricted Subsidiaries, from a Restricted Subsidiary to a Restricted
Subsidiary), (G) consisting of any transfer of HTH common shares to Hollinger
Inc. pursuant to the provisions of the HTH/FDTH Share Exchange Agreement, (H)
by Southam, provided that (i) Southam is a Restricted Subsidiary; (ii) Southam
is a Public Entity at the time of such sale of assets and (iii) the proceeds of
such sale of assets are not paid as a dividend or distribution of Southam's


<PAGE>   15


                                                                           - 5 -

equity capital; provided, however, that any issuance by Southam of its Capital
Stock shall be subject to the requirements of Section 10.16(b)(i), and (I) any
issuance of Mirror Preferred so long as the conditions set forth in the
definition of Mirror Preferred are satisfied.

                  "Average Life to Stated Maturity" means, as of the date of
determination with respect to any Indebtedness, the quotient obtained by
dividing (i) the sum of the products of (a) the number of years from the date
of determination to the date or dates of each successive scheduled principal
payment of such Indebtedness multiplied by (b) the amount of each such
principal payment by (ii) the sum of all such principal payments.

                  "Bankruptcy Law" means Title 11 of the United States Code, as
amended, or any similar United States federal or state or foreign law relating
to bankruptcy, insolvency, receivership, winding-up, liquidation,
reorganization or relief of debtors or any amendment to, succession to or
change in any such law.

                  "Board of Directors" means the board of directors of
Publishing or any duly authorized committee of such board.

                  "Board Resolution" means a copy of a resolution certified by
the Secretary or an Assistant Secretary of Publishing to have been duly adopted
by such Board of Directors and to be in full force and effect on the date of
such certification, and delivered to the Trustee.

                  "Business Day" means each Monday, Tuesday, Wednesday,
Thursday and Friday which is not a day on which banking institutions in The
City of New York, or the city in which the principal corporate trust office of
the Trustee is located (initially Hartford, Connecticut), are authorized or
obligated by law or executive order to close.

                  "Business Opportunities Agreement" means the Business
Opportunities Agreement dated as of February 7, 1996, between Hollinger Inc.
and Hollinger International and any amendment, modification, or supplement
thereto or restatement thereof and any similar agreements entered into after
the date of the original issuance of the Securities in accordance with the
terms of this Indenture.

                  "Capital Lease Obligation" of any Person means any obligation
of such Person and its subsidiaries on a consolidated basis under any capital
lease of real or personal property which, in accordance with GAAP, has been
recorded as a capitalized lease obligation.

<PAGE>   16
                                                                           - 6 -

                  "Capital Stock" of any Person means any and all shares,
interests, participations or other equivalents (however designated) of such
Person's capital stock.

                  "Cash Equivalents" means (i) any evidence of Indebtedness
with a maturity of 180 days or less issued or directly and fully guaranteed or
insured by the United States of America or any agency or instrumentality
thereof (provided that the full faith and credit of the United States of
America is pledged in support thereof); (ii) certificates of deposit or
acceptances with a maturity of 180 days or less of any financial institution
that is a member of the Federal Reserve System having combined capital and
surplus and undivided profits of not less than $500,000,000; (iii) commercial
paper with a maturity 180 days or less issued by a corporation that is not an
Affiliate of Publishing organized under the laws of any state of the United
States or the District of Columbia and rated A-1 (or higher) according to S&P
or P-1 (or higher) according to Moody's or at least an equivalent rating
category of another nationally recognized securities rating agency; (iv) any
money market deposit accounts issued or offered by a domestic commercial bank
having capital and surplus in excess of $500,000,000; and (v) repurchase
agreements and reverse repurchase agreements relating to marketable direct
obligations issued or unconditionally guaranteed by the government of the
United States of America or issued by any agency thereof and backed by the full
faith and credit of the United States of America, in each case maturing within
180 days from the date of acquisition; provided that the terms of such
agreements comply with the guidelines set forth in the Federal Financial
Agreements of Depository Institutions with Securities Dealers and Others, as
adopted by the Comptroller of the Currency on October 31, 1985.

                  "Change of Control" means the occurrence of any of the
following:

                  (a) there is a report filed on Schedule 13D, 14D-1 or 14D-1F
(or any successor schedule, form or report) pursuant to the Exchange Act,
disclosing that any person (for purposes of this definition, as the term
"person" is used in Section 13(d)(3) or Section 14(d)(2) of the Exchange Act or
any successor provision to either of the foregoing), other than any person
consisting solely of Conrad M. Black (or his heirs, executors or legal
representatives) and his Affiliates, has become the beneficial owner (as the
term "beneficial owner" is defined under Rule 13d-3 or any successor rule or
regulation promulgated under the Exchange Act) of Voting Stock representing 50%
or more of the total voting power attached to all Voting Stock of Hollinger
Inc., Hollinger International or Publishing then outstanding; provided,
however, that a person shall not be deemed to be the beneficial owner of, or to
own beneficially, (i) any securities
<PAGE>   17
                                                                           - 7 -

tendered pursuant to a tender or exchange offer made by or on behalf of such
person or any of such person's Affiliates until such tendered securities are
accepted for purchase or exchange thereunder, or (ii) any securities if such
beneficial ownership (A) arises solely as a result of a revocable proxy
delivered in response to a proxy or consent solicitation made pursuant to
applicable law, and (B) is not also then reportable on Schedule 13D (or any
successor schedule) under the Exchange Act;

                  (b) there is a report filed or required to be filed with any
securities commission or securities regulatory authority in Canada, disclosing
that any offeror (as the term "offeror" is defined in Section 89(1) of
Securities Act (Ontario) for the purpose of Section 101 of such Securities Act
or any successor provision of the foregoing) other than any person consisting
solely of Conrad M. Black (or his heirs, executors or legal representatives)
and his Affiliates, has acquired beneficial ownership (within the meaning of
the Securities Act (Ontario)) of, or the power to exercise control or direction
over, or securities convertible into, any voting or equity shares of Hollinger
Inc. that together with such offeror's securities (as the term "offeror's
securities" is defined in Section 89(1) of the Securities Act (Ontario) or any
successor provision thereto in relation to the voting or equity shares of
Hollinger Inc.), would constitute Voting Stock of Hollinger Inc. representing
50% or more of the total voting power attached to all Voting Stock of Hollinger
Inc. then outstanding;

                  (c) Hollinger International shall cease to own, directly or
indirectly, 100% of the Voting Stock of Publishing;

                  (d) there is consummated a consolidation (involving a
business combination) or merger of Publishing or Hollinger International, as
the case may be, (i) in which Publishing or Hollinger International, as the
case may be, is not the continuing or surviving corporation or (ii) pursuant to
which any Voting Stock of Publishing or Hollinger International, as the case
may be, would be reclassified, changed or converted into or exchanged for cash,
securities or other property, other than (in each case) a consolidation or
merger of Publishing or Hollinger International, as the case may be, in which
the holders of the Voting Stock of Publishing or Hollinger International, as
the case may be, immediately prior to the consolidation or merger have,
directly or indirectly, 50% or more of the Voting Stock of the continuing or
surviving corporation immediately after such transaction; or

                  (e) Conrad M. Black (or his heirs, executors and legal
representatives) and his Affiliates cease to beneficially own and control the
voting of, directly or indirectly, Voting Stock of Publishing or Hollinger
International representing a greater


<PAGE>   18
                                                                           - 8 -

percentage of the total voting power attached to the Voting Stock of Publishing
or Hollinger International than the percentage beneficially owned and
controlled, directly or indirectly, by any other single shareholder of
Publishing or Hollinger International together with its Affiliates (a
"Designated Transaction") and there shall occur a Rating Decline.

                  "Code" means the Internal Revenue Code of 1986, as amended.

                  "Collateral" means any property, assets, proceeds or other
items that may be pledged as security for the Securities, whether pursuant to
Section 10.12 or otherwise.

                  "Commission" means the Securities and Exchange Commission, as
from time to time constituted, created under the Exchange Act, or if at any
time after the execution of this Indenture such Commission is not existing and
performing the duties now assigned to it under the Trust Indenture Act, then
the body performing such duties at such time.

                  "Consolidated Assets" means, with respect to Publishing, the
total assets shown on the balance sheet of Publishing and its Restricted
Subsidiaries, as determined on a consolidated basis in accordance with GAAP, as
of Publishing's latest full fiscal quarter.

                  "Consolidated Cash Flow Ratio" means, as at any date of
determination, the ratio of (i) the aggregate amount of Indebtedness of
Publishing and the Restricted Subsidiaries on a Consolidated basis outstanding
as at such date to (ii) the Operating Cash Flow of Publishing and the
Restricted Subsidiaries (determined on a Consolidated basis) for the most
recently completed period of four consecutive fiscal quarters of Publishing;
provided (a) that once both of The Telegraph and Southam are Restricted
Subsidiaries, for the purpose of determining the Consolidated Cash Flow Ratio,
the Indebtedness and Operating Cash Flow of Restricted Subsidiaries that are
not Wholly Owned Restricted Subsidiaries shall be determined in accordance with
the actual percentage of Publishing's common equity interest in such Restricted
Subsidiary on the date of determination of the Consolidated Cash Flow Ratio
(thus, for example, in the case of a Restricted Subsidiary in which Publishing
owns a 51% common equity interest, 51% each of such Restricted Subsidiary's
Indebtedness and Operating Cash Flow would be included in the calculation of
Publishing's aggregate Indebtedness and Operating Cash Flow, respectively); and
provided further that (i) so long as Southam is a Restricted Subsidiary and
(ii) until such time as Southam is not a Public Entity, the portion of
Operating Cash Flow represented by Southam Operating Cash Flow shall not exceed
thirty-three and one third percent


<PAGE>   19
                                                                           - 9 -

(33 1/3%) and, to the extent Southam Cash Flow represents greater than
thirty-three and one third percent (33 1/3%) of Operating Cash Flow, such excess
shall be deducted from Operating Cash Flow and (b) that, so long as any Southam
shares owned by Publishing or a Restricted Subsidiary are pledged, directly or
indirectly, to secure Indebtedness other than Indebtedness by Publishing or a
Restricted Subsidiary, the equity interest in Southam represented by such
shares shall be excluded for purposes of calculating the percentage of
Southam's Indebtedness and Operating Cash Flow to be included in determining
Publishing's aggregate Indebtedness and Operating Cash Flow on a Consolidated
basis.

                  "Consolidated Net Income (Loss)" of Publishing and the
Restricted Subsidiaries means, for any period, the Consolidated net income (or
loss (and treating a loss as a negative number)) of Publishing and the
Restricted Subsidiaries for such period as determined in accordance with GAAP,
adjusted by (a) excluding, without duplication, to the extent included in
calculating such Consolidated Net Income (or Loss), (i) all extraordinary gains
and losses, (ii) the portion of Consolidated net income (or loss) of Publishing
and its Restricted Subsidiaries allocable to Investments in unconsolidated
Persons (other than Unrestricted Subsidiaries) to the extent that cash
dividends or distributions have not actually been received by such Person or
one of its Restricted Subsidiaries, (iii) the portion of Consolidated net
income (or loss) of Publishing and its Restricted Subsidiaries allocable to
Publishing's Unrestricted Subsidiaries (or to payments received therefrom),
(iv) net income (or loss) of a Person combined with Publishing or any of its
subsidiaries on a "pooling of interests" basis attributable to any period prior
to the date of combination, (v) any gain or loss, net of taxes, realized upon
the termination of any employee pension benefit plan, (vi) aggregate net gains
and losses (less all fees and expenses relating thereto) in respect of
dispositions of assets (including without limitation sales of shares of
Unrestricted Subsidiaries or unconsolidated Persons and noncash writeoffs of
assets (provided that there are no continuing cash expenses related to such
writeoffs)) other than in the ordinary course of business, (vii) any income,
gain or loss resulting from the issuance, sale or redemption of Mirror
Preferred or Argsub Preferred, (viii) the net income of any Restricted
Subsidiary to the extent that the declaration of dividends or similar
distributions by that Restricted Subsidiary of that income is not at the time
permitted, directly or indirectly, by operation of the terms of its charter or
any agreement, instrument, judgment, decree, order, statute, rule or
governmental regulations applicable to that Restricted Subsidiary or its
stockholders; provided, however, that the foregoing shall not apply to the net
income of AP-91 relating to the business of AP-91, as conducted as of the date
of this Indenture on account of restrictions on AP-91 in agreements as in
effect on the date of this Indenture,


<PAGE>   20
                                                                          - 10 -

or restrictions permitted under clauses (iii) and (iv) of Section 10.17 (to the
extent such clauses are applicable at the time of determination), (ix) any
restoration to income of any contingency reserve, except to the extent that
provision for such reserve was made out of income accrued at any time following
the date of this Indenture, (x) any net gain from the collection of proceeds of
life insurance policies, (xi) any gain arising from the acquisition of any
securities, or the extinguishment, under GAAP, of any Indebtedness of
Publishing or one of its Restricted Subsidiaries, (xii) aggregate net gains or
losses relating to foreign currency transactions or translations and (xiii)
redundancy costs relating to the permanent elimination of jobs, provided that
the amount of such expenses are certified by Publishing's independent
accountants, and (b) subtracting, without duplication, the aggregate amount of
dividends on Preferred Stock of Restricted Subsidiaries to the extent that such
Preferred Stock is included as Indebtedness in the calculation of Publishing's
Consolidated Cash Flow Ratio. In calculating the Operating Cash Flow of
Publishing and its Restricted Subsidiaries, the Consolidated Net Income of
Restricted Subsidiaries that are not Wholly Owned Restricted Subsidiaries will
be included only to the extent of Publishing's common equity interest in such
Restricted Subsidiaries.

                  "Consolidated Net Worth" means the common and preferred
stockholders' equity of Publishing and its Restricted Subsidiaries (exclusive
of any redeemable capital stock), as determined on a Consolidated basis and in
accordance with GAAP.

                  "Consolidated Tangible Assets" means the total assets
appearing on a Consolidated balance sheet of Publishing and its Restricted
Subsidiaries less, without duplication, each of the following: (i) all
applicable depreciation, amortization and other valuation reserves, (ii) all
other intangible assets and deferred charges, (iii) deferred income tax assets
(to the extent recorded as an asset) and (iv) all investments in unconsolidated
subsidiaries (including all Unrestricted Subsidiaries).

                  "Consolidation" means, with respect to any Person, the
consolidation of the accounts of such Person and each of its subsidiaries if
and to the extent the accounts of such Person and each of its subsidiaries
would normally be consolidated with those of such Person, all in accordance
with GAAP; provided, however, that the accounts of any Unrestricted Subsidiary
shall not be consolidated with Publishing but instead the interest of
Publishing or any Restricted Subsidiary therein will be accounted for as an
investment. The term "Consolidated" shall have a correlative meaning.

                  "Corporate Trust Office" means the office of the Trustee or
an affiliate or agent thereof at which at any


<PAGE>   21
                                                                          - 11 -

particular time the corporate trust business for the purposes of this Indenture
shall be principally administered, which office at the date of execution of
this Indenture is located at 777 Main Street, Hartford, Connecticut 06115-2001.

                  "CST Real Estate" means the real estate, including land,
building and fixtures, located at 401 North Wabash Avenue, Chicago, Illinois,
where Publishing currently maintains its headquarters, and all improvements
thereon.

                  "CST Real Estate Transaction" means the sale or other
disposition (other than to an Affiliate) of all or any portion of the interest
of Publishing or a Restricted Subsidiary in the CST Real Estate.

                  "Currency Agreements" means one or more of the following
agreements which shall be entered into with one or more financial institutions:
foreign exchange contracts, currency swap agreements or other similar
agreements or arrangements designed to protect against fluctuations in currency
values.

                  "Default" means any event which is, or after notice or
passage of time or both would be, an Event of Default.

                  "Designated Senior Indebtedness" means (i) all Senior
Indebtedness under the New Bank Credit Facility and (ii) any other Senior
Indebtedness which, at the time of determination, has an aggregate principal
amount outstanding of at least $50,000,000 and is specifically designated by
Publishing in the instrument evidencing such Senior Indebtedness or the
agreement under which such Senior Indebtedness arises as "Designated Senior
Indebtedness."

                  "DTH" means DT Holdings Limited, a corporation under the laws
of England and its successors and assigns.

                  "ERISA" means the Employee Retirement Income Security Act of
1974, as amended.

                  "Event of Default" has the meaning specified in Article V.

                  "Exchange Act" means the Securities Exchange Act of 1934, as
amended.

                  "Extraordinary Cash Dividend" means in respect of the Southam
Interests:

                  (i) a cash dividend in respect of a particular calendar year
         representing the excess, if any, of (A) the aggregate of all cash
         dividends declared and paid on such securities


<PAGE>   22
                                                                          - 12 -

         during the calendar year over (B) the greatest of (x) 200% of the
         aggregate of all cash dividends declared and paid on such securities
         during the immediately preceding calendar year; (y) 300% of the average
         of the aggregate of all cash dividends declared and paid on such
         securities during the immediately preceding three calendar years; and
         (z) 100% of the aggregate consolidated net income of the issuer of such
         securities, before extraordinary items, for its immediately preceding
         fiscal year; and

                  (ii) any cash dividend declared by Southam on its common
         shares which the directors of Southam by resolution determine to be
         extraordinary, taking into account the amount of the dividend, the
         effect of the dividend on the market value of such securities after
         payment thereof, the form of payment, the financial position of
         Southam, economic conditions, business practices and such other
         factors as the directors of Southam consider to be relevant.

                  "FDTH" means First DT Holdings Limited, a corporation under
the laws of England and its successors and assigns.

                  "FDTH Credit Facility" means the credit agreement dated as of
May 30, 1996, among FDTH, the financial institutions party thereto and The
Toronto-Dominion Bank, as issuing bank and Agent, as such agreement may be
amended, renewed, extended, substituted, refinanced, restructured, replaced,
supplemented or otherwise modified from time to time (including, without
limitation, any successive renewals, extensions, substitutions, refinancings,
restructurings, replacements, supplementations or other modifications of the
foregoing that increase the aggregate amount of borrowings outstanding or the
aggregate commitments of the lenders thereunder).

                  "Foreign Subsidiary Indebtedness" means Indebtedness Incurred
by a non-U.S. domiciled Subsidiary that has no material U.S. operations.

                  "Generally Accepted Accounting Principles" or "GAAP" means
generally accepted accounting principles in the United States, consistently
applied, which are in effect on the date of this Indenture.

                  "Global Security" means a Security evidencing all or part of
the Securities of any Series and issued to a Depositary in accordance with
Section 3.03 hereof and bearing the legend prescribed in Section 2.05 hereof.

                  "Guarantee" means the guarantee by Hollinger International
and, if the context requires, by any Restricted Subsidiary Guarantor of the
Indenture Obligations.


<PAGE>   23
                                                                          - 13 -

                  "Guaranteed Debt" of any Person means, without duplication,
all Indebtedness of any other Person referred to in the definition of
Indebtedness guaranteed directly or indirectly in any manner by such Person, or
in effect guaranteed directly or indirectly by such Person through an agreement
(i) to pay or purchase such Indebtedness or to advance or supply funds for the
payment or purchase of such Indebtedness (or to indemnify another Person for
the costs thereof), (ii) to purchase, sell or lease (as lessee or lessor)
property, or to purchase or sell services, primarily for the purpose of
enabling the debtor to make payment of such Indebtedness or to assure the
holder of such Indebtedness against loss, (iii) to supply funds to, or in any
other manner invest in, the debtor (including any agreement to pay for property
or services without requiring that such property be received or such services
be rendered), (iv) to maintain working capital or equity capital of the debtor,
or otherwise to maintain the net worth, solvency or other financial condition
of the debtor or (v) otherwise to assure a creditor against loss, provided that
the term "guarantee" shall not include endorsements for collection or deposit,
in either case in the ordinary course of business.

                  "Guarantor" means any guarantor of the Securities in
accordance with the terms of this Indenture, including Hollinger International.

                  "Holder" means a Person in whose name a Security is
registered in the Security Register.

                  "Hollinger Eastern" means Hollinger Eastern Publishing Inc.,
a Canadian corporation, and its successors and assigns.

                  "Hollinger Inc. Transaction" means the transaction, in all
material respects as announced publicly on January 7, 1997, by which Hollinger
Inc. is to transfer, directly or indirectly, to Hollinger Eastern certain of
its owned Canadian publishing interests for an aggregate consideration not to
exceed $382 million, subject to working capital adjustments and currency
exchange adjustments.

                  "Hollinger International" means Hollinger International Inc.,
a corporation incorporated under the laws of Delaware and a Guarantor of the
Indenture Obligations, until a successor Person shall have become such pursuant
to Article VIII of this Indenture and thereafter "Hollinger International"
shall mean such successor Person.

                  "Hollinger International/Hollinger Eastern Interests" means
Preferred Stock of any Person (or other Capital Stock convertible or
exchangeable into Preferred Stock of such Person) which holds the voting
interests of Hollinger Eastern which are


<PAGE>   24
                                                                          - 14 -

owned by Hollinger International and its Subsidiaries as of the date that
Hollinger Eastern is designated as a Restricted Subsidiary.

                  "Hollinger International Guarantee" means the unsecured,
senior subordinated guarantee of the Securities provided by Hollinger
International.

                  "HTH" means Hollinger-Telegraph Holdings Inc., a corporation
continued under the laws of Alberta, and its successors and assigns.

                  "HTH/FDTH Share Exchange Agreement" means the share exchange
agreement dated as of July 19, 1995, between Hollinger Inc. and FDTH, as
amended, supplemented or otherwise modified from to time.

                  "Incur" means create, issue, assume, guarantee or otherwise
in any manner become directly or indirectly liable for or with respect to or
otherwise incur.

                  "Indebtedness" means, with respect to any Person, without
duplication, (i) all indebtedness of such Person for borrowed money or for the
deferred purchase price of property or services (or other obligations to former
owners of acquired businesses), excluding any trade payables and other accrued
current liabilities arising in the ordinary course of business, but including,
without limitation, all obligations, contingent or otherwise, of such Person in
connection with any letters of credit issued under letter of credit facilities,
acceptance facilities or other similar facilities and in connection with any
agreement to purchase, redeem, exchange, convert or otherwise acquire for value
any Capital Stock of such Person, or any warrants, rights or options to acquire
such Capital Stock, now or hereafter outstanding, (ii) all obligations of such
Person evidenced by bonds, notes, debentures or other similar instruments,
(iii) all indebtedness created or arising under any conditional sale or other
title retention agreement with respect to property acquired by such Person
(even if the rights and remedies of the seller or lender under such agreement
in the event of default are limited to repossession or sale of such property),
but excluding trade payables arising in the ordinary course of business, (iv)
all obligations under Interest Rate Agreements and Currency Agreements of such
Person, (v) all Capital Lease Obligations of such Person, (vi) all Indebtedness
referred to in clauses (i) through (v) above of other Persons and all dividends
of other Persons, the payment of which is secured by (or for which the holder
of such Indebtedness has an existing right, contingent or otherwise, to be
secured by) any Lien, upon or with respect to property (including, without
limitation, accounts and contract rights) owned by such Person, even though


<PAGE>   25
                                                                          - 15 -

such Person has not assumed or become liable for the payment of such
Indebtedness, (vii) all Guaranteed Debt of such Person, (viii) all Redeemable
Capital Stock and (without duplication) all Preferred Stock of Restricted
Subsidiaries other then (a) Mirror Preferred, provided that such Mirror
Preferred continues to qualify as such under the definition thereof, (b) the
Hollinger International/Hollinger Eastern Interests, provided that Hollinger
International grants a security interest, in such Hollinger
International/Hollinger Eastern Interests as security for its guarantee of the
Securities, which security interest, in either case, shall be subordinate to
any security interest in the Hollinger International/Hollinger Eastern
Interests that may be granted under the New Bank Credit Facility and (c)
Preferred Stock held by Restricted Subsidiaries or Publishing, in each case
valued at the greater of its voluntary or involuntary maximum fixed repurchase
price plus accrued and unpaid dividends and (ix) any amendment, supplement,
modification, deferral, renewal, extension, refunding or refinancing of any
Indebtedness of the types referred to in clauses (i) through (viii) above;
provided, however, that this definition shall not apply to Indebtedness
represented by Southam-Linked Debentures which are secured, directly or
indirectly, by shares of Southam, which are owned directly or indirectly by
Publishing. For purposes hereof, the "maximum fixed repurchase price" of any
Redeemable Capital Stock or Preferred Stock which does not have a fixed
repurchase price shall be calculated in accordance with the terms of such
Redeemable Capital Stock or Preferred Stock as if such Redeemable Capital Stock
or Preferred Stock were purchased on any date on which Indebtedness shall be
required to be determined pursuant to this Indenture, and if such price is
based upon, or measured by, the fair market value of such Redeemable Capital
Stock or Preferred Stock, such fair market value to be determined in good faith
by the Board of Directors of such Person.

                  "Indenture" means this instrument as originally executed
(including all exhibits and schedules thereto) and as it may from time to time
be supplemented or amended by one or more indentures supplemental hereto
entered into pursuant to the applicable provisions hereof and shall include the
terms of particular Series of Securities established as contemplated by Section
3.01.

                  "Indenture Obligations" means the obligations of Publishing
under this Indenture or under the Securities to pay principal of, premium, if
any, and interest when due and payable, and all other amounts due or to become
due under or in connection with this Indenture and the Securities, and the
performance of all other obligations to the Trustee, the Paying Agent and the
holders under this Indenture and the Securities, according to the terms
thereof.

<PAGE>   26
                                                                          - 16 -

                  "Independent Committee" means a committee of the board of
directors of Publishing whose membership meets the requirements of the New York
Stock Exchange applicable to audit committees as in effect on the date of
original issuance of the Securities or a committee of the board of directors of
Publishing whose membership satisfies any more restrictive requirements of
independence of any securities exchange or market on which Publishing's or
Hollinger International's equity securities are traded or listed.

                  "Independent Director" means a member of the board of
directors of a Person that is not an officer, employee or former officer or
employee of such Person or one of its Affiliates and, with respect to any
transaction or series of related transactions, a member of the board of
directors who does not have any material direct or indirect financial interest
in or with respect to such transaction or series of related transactions
(including for such purpose the interest of any other Person with respect to
whom such director is also a director, officer or employee).

                  "Interest Payment Date" means the Stated Maturity of a
regular installment of interest on the Securities or the Special Payment Date
with respect to Defaulted Interest.

                  "Interest Rate Agreements" means one or more of the following
agreements which shall be entered into from time to time with one or more
financial institutions: interest rate protection agreements (including, without
limitation, interest rate swaps, caps, floors, collars and similar agreements)
and/or other types of interest rate hedging agreements.

                  "Investment" means, with respect to any Person, directly or
indirectly, any advance, loan (including guarantees), or other extension of
credit or capital contribution to (by means of any transfer of cash or other
property to others or any payment for property or services for the account or
use of others), or any purchase, acquisition or ownership by such Person of any
Capital Stock, bonds, notes, debentures or other securities issued or owned by,
any other Person and all other items that are or would be classified as
investments on a balance sheet prepared in accordance with GAAP.

                  "Lien" means any mortgage, charge, pledge, lien (statutory or
otherwise), security interest, hypothecation or other encumbrance upon or with
respect to any property of any kind, real or personal, movable or immovable,
now owned or hereafter acquired.

                  "Marketable Security" means any common stock, debt security
or other security of a Person which is (or will, upon


<PAGE>   27
                                                                          - 17 -

distribution thereof, be) listed on the NYSE, the American Stock Exchange or
any national securities exchange registered under Section 6 of the Securities
Exchange Act of 1934, as amended, or approved for quotation in the Nasdaq
National Market or any similar system of automated dissemination of quotations
of securities prices in the United States or for which there is a recognized
market maker or trading market.

                  "Material Restricted Subsidiary" means each Restricted
Subsidiary of Publishing which (i) for the most recent fiscal year of
Publishing accounted for more than 5% of the Consolidated revenues of
Publishing and its Restricted Subsidiaries or (ii) at the end of such fiscal
year was the owner (beneficial or otherwise) of more than 5% of the
Consolidated Assets of Publishing and its Restricted Subsidiaries, all as shown
on Publishing's Consolidated financial statements for such fiscal year.

                  "Maturity" when used with respect to any Security means the
date on which the principal of such Security becomes due and payable as therein
provided or as provided in this Indenture, whether at Stated Maturity, the
Purchase Date or the Redemption Date and whether by declaration of
acceleration, Offer in respect of Excess Proceeds, Change of Control, call for
redemption or otherwise.

                  "Media Business" means the business of the broadcast of radio
or television broadcasting, cable and satellite programs (including national,
regional or local radio, television, cable and satellite programs).

                  "Mirror Preferred" means Preferred Stock of DTH or FDTH
currently held by or hereafter issued to an Argsub (i) having terms (including,
without limitation, terms with respect to liquidation, redemption and
dividends) identical to those contained in Argsub Preferred issued or
transferred simultaneously with such Argsub's acquisition of such DTH or FDTH
Preferred Stock in equivalent amounts to DTH or FDTH, as the case may be, and
(ii) in respect of which no cash payments are or have been made by the issuer
thereof, except for cash payments in respect of certain Mirror Preferred
directly from FDTH to DTH at the direction of Argsub; provided that, at such
time as (x) the foregoing clauses (i) and (ii) are no longer satisfied, (y) the
issuer of any Argsub Preferred Incurs any Indebtedness or other liability other
than tax liabilities or pursuant to such Argsub Preferred or acquires any other
assets other than the Mirror Preferred, or (z) the holder of any Mirror
Preferred transfers such stock other than to a Wholly Owned Restricted
Subsidiary, then (1) an Event of Default will occur under the Indenture and (2)
such Preferred Stock of FDTH held by Argsub will be deemed to be Redeemable
Capital Stock that is Incurred on such date; and


<PAGE>   28
                                                                          - 18 -

provided further, that in the event that the Mirror Preferred have not been
redeemed, retracted, transferred to DTH or otherwise cancelled without the
payment of cash (except for cash payments in respect of certain Mirror
Preferred directly to DTH) on or before July 1, 1997, then such Preferred Stock
shall be treated as Indebtedness for the purposes of Section 10.08.

                  "Net Cash Proceeds" means (a) with respect to any Asset Sale
by any Person, the proceeds thereof in the form of cash or cash equivalents
including payments of principal and interest in respect of deferred payment
obligations when received in the form of, or stock or other assets when
disposed of for, cash or cash equivalents (except to the extent that such
obligations are financed or sold with recourse to Publishing or any Restricted
Subsidiary) net of (i) brokerage commissions and other reasonable fees and
expenses (including fees and expenses of counsel and investment bankers)
related to such Asset Sale, (ii) provisions for all taxes payable as a result
of such Asset Sale, (iii) payments made to retire indebtedness where payment of
such indebtedness is secured by the assets or properties the subject of such
Asset Sale, (iv) amounts required to be paid to any Person (other than
Publishing or any Restricted Subsidiary) owning a beneficial interest in the
assets subject to the Asset Sale and (v) appropriate amounts to be provided by
Publishing or any Restricted Subsidiary, as the case may be, as a reserve, in
accordance with GAAP, against any liabilities associated with such Asset Sale
and retained by Publishing or any Restricted Subsidiary, as the case may be,
after such Asset Sale, including, without limitation, pension and other
post-employment benefit liabilities, liabilities related to environmental
matters and liabilities under any indemnification obligations associated with
such Asset Sale, all as determined and reflected in an Officers' Certificate
delivered to the Trustee and (b) with respect to any issuance or sale of
Capital Stock or options, warrants or rights to purchase Capital Stock, or debt
securities or Capital Stock that have been converted into or exchanged for
Capital Stock, as referred to in Section 10.09, the proceeds of such issuance
or sale in the form of cash or cash equivalents, including payments in respect
of deferred payment obligations when received in the form of, or stock or other
assets when disposed of for, cash or cash equivalents (except to the extent
that such obligations are financed or sold with recourse to Publishing or any
Restricted Subsidiary), net of attorneys' fees, accountants' fees and
brokerage, consultation, underwriting and other fees and expenses actually
incurred in connection with such issuance or sale and net of taxes paid or
payable as a result thereof.

                  "New Bank Credit Facility" means the credit agreement dated
as of May 30, 1996, among Publishing, the financial institutions party thereto
and The Toronto-Dominion Bank, as issuing bank and the Agent, as such agreement
may be amended,


<PAGE>   29
                                                                          - 19 -

renewed, extended, substituted, refinanced, restructured, replaced,
supplemented or otherwise modified from time to time (including, without
limitation, any successive renewals, extensions, substitutions, refinancings,
restructurings, replacements, supplementations or other modifications of the
foregoing that increase the aggregate amount of borrowings outstanding or the
aggregate commitments of the lenders thereunder).

                  "Newspaper Business" means the business of publishing and
distributing (including distributing by electronic means) newspapers, magazines
and other paid or free publications having national, regional, local or
targeted markets, including publications having limited or no news or editorial
content such as shoppers or other "total market coverage" publications and
similar publications.

                  "Nonpayment Default" means any event (other than a Payment
Default) the occurrence of which entitles one or more Persons to accelerate at
such time the maturity of any Designated Senior Indebtedness.

                  "Officers' Certificate" means a certificate signed by the
Chairman of the Board, Vice Chairman, President or a Vice President (regardless
of Vice Presidential designation), and by the Treasurer, Secretary or an
Assistant Secretary, of Publishing, in form and substance reasonably
satisfactory to, and delivered to, the Trustee.

                  "Operating Cash Flow" means, for any period, an amount equal
to the Consolidated Net Income of Publishing and the Restricted Subsidiaries
for such period, plus, to the extent deducted in calculating such Consolidated
Net Income, (a) interest expense and other financing costs and expenses, (b)
dividends paid on any Preferred Stock of Restricted Subsidiaries to the extent
such Preferred Stock is included as Indebtedness in the calculation of
Publishing's Consolidated Cash Flow Ratio, (c) depreciation and amortization
and (d) all taxes, whether or not deferred, applicable to such period.

                  For purposes of calculating Operating Cash Flow for the four
fiscal quarters most recently completed prior to any date on which an action is
taken that requires a calculation of the Consolidated Cash Flow Ratio, (a) any
Person that is a Restricted Subsidiary on such date (or would become a
Restricted Subsidiary in connection with the transaction that requires the
determination of such ratio) shall be deemed to have been a Restricted
Subsidiary at all times during such period, (b) any Person that is not a
Restricted Subsidiary on such date (or would cease to be a Restricted
Subsidiary in connection with the transaction that requires the determination
of such ratio) shall


<PAGE>   30
                                                                          - 20 -

be deemed not to have been a Restricted Subsidiary at any time during such
period, (c) if Publishing or any Restricted Subsidiary shall have in any manner
acquired or disposed of any operating business (including without limitation
acquisitions accounted for on a "pooling of interests" or "as if pooling of
interests" basis) during or subsequent to such period, such calculation shall
be made on a pro forma basis on the assumption that such acquisition or
disposition has been completed on the first day of such period and (d) in the
case of a Restricted Subsidiary that is not a Wholly Owned Restricted
Subsidiary, the determination of the percentage of the Operating Cash Flow of
such Restricted Subsidiary that is to be included in the calculation of
Publishing's Consolidated Cash Flow Ratio shall be made on a pro forma basis on
the assumption that the percentage of Publishing's common equity interest in
such Restricted Subsidiary on the date of determination (it being understood,
in the case of foregoing clause (c), that if such pro forma calculations shall
have been made in accordance with Regulation S-X under the Exchange Act, such
method of calculation (but not necessarily the adjustments) shall be presumed
to be acceptable) (it being further understood that the foregoing clause (d)
shall not be operative until such time as both of The Telegraph and Southam
shall be Restricted Subsidiaries).

                  "Opinion of Counsel" means a written opinion of counsel, in
form and substance reasonably satisfactory to the Trustee, who may be counsel
for Publishing or the Trustee, and who shall be reasonably acceptable to the
Trustee, including but not limited to an Opinion of Independent Counsel.

                  "Opinion of Independent Counsel" means a written opinion, in
form and substance reasonably satisfactory to the Trustee, by someone who is
not an employee or former employee of Publishing and who shall be reasonably
acceptable to the Trustee.

                  "Original Issue Discount Security" means (i) any Security
which provides for an amount less than the principal amount thereof to be due
and payable upon a declaration of acceleration of the Maturity thereof, and
(ii) any other Security which is issued with "original issue discount" within
the meaning of Section 1273(a) of the Internal Revenue Code of 1986, as
amended, and the regulations thereunder.

                  "Outstanding" when used with respect to Securities means, as
of the date of determination, all Securities theretofore authenticated and
delivered under this Indenture, except:

                  (a) Securities theretofore cancelled by the Trustee or
         delivered to the Trustee for cancellation;

<PAGE>   31
                                                                          - 21 -

                  (b) Securities, or portions thereof, for whose payment or
         redemption money in the necessary amount has been theretofore
         irrevocably deposited with the Trustee or any Paying Agent (other than
         Publishing) in trust or set aside and segregated in trust by
         Publishing (if Publishing shall act as its own Paying Agent) for the
         Holders of such Securities; provided, that if such Securities are to
         be redeemed, notice of such redemption has been duly given pursuant to
         this Indenture or provision therefor reasonably satisfactory to the
         Trustee has been made;

                  (c) Securities, except to the extent provided in Sections
         4.02 and 4.03, with respect to which Publishing has effected
         defeasance or covenant defeasance as provided in Article IV; and

                  (d) Securities in exchange for or in lieu of which other
         Securities have been authenticated and delivered pursuant to this
         Indenture, other than any such Securities in respect of which there
         shall have been presented to the Trustee and Publishing proof
         reasonably satisfactory to each of them that such Securities are held
         by a bona fide purchaser in whose hands the Securities are valid
         obligations of Publishing; provided, however, that in determining
         whether the Holders of the requisite principal amount of Outstanding
         Securities have given any request, demand, authorization, direction,
         notice, consent or waiver hereunder, Securities owned by Publishing or
         any other obligor upon the Securities or any Affiliate of Publishing
         or such other obligor shall be disregarded and deemed not to be
         Outstanding, except that, in determining whether the Trustee shall be
         protected in relying upon any such request, demand, authorization,
         direction, notice, consent or waiver, only Securities which the
         Trustee actually knows to be so owned shall be so disregarded.
         Securities so owned which have been pledged in good faith may be
         regarded as Outstanding if the pledgee establishes to the reasonable
         satisfaction of the Trustee the pledgee's right so to act with respect
         to such Securities and that the pledgee is not Publishing or any other
         obligor upon the Securities or any Affiliate of Publishing or such
         other obligor.

                  "Pari Passu Guarantor Indebtedness" means any Indebtedness of
any Guarantor that is pari passu in right of payment with such Guarantor's
Guarantee.

                  "Pari Passu Indebtedness" means any Indebtedness of
Publishing that is pari passu in right of payment with the Securities.

<PAGE>   32
                                                                          - 22 -

                  "Paying Agent" means any Person authorized by Publishing to
pay the principal, premium, if any, or interest on any Securities on behalf of
Publishing. The Company initially authorizes the Trustee to act as Paying Agent
for the Securities on its behalf. The Company may at any time and from time to
time authorize one or more Persons to act as Paying Agent in addition to or in
place of the Trustee with respect to any Series of Securities issued under this
Indenture.

                  "Payment Default" means any default in the payment of
principal, premium, if any, interest, commitment fees, letter of credit fees,
reimbursement obligations in respect of amounts owing under letters of credit
or payments in respect of interest under Interest Rate Agreements, in each
case, on any Designated Senior Indebtedness.

                  "Permitted Guarantor Junior Securities" means, so long as the
effect of any exclusion employing this definition is not to cause the
Securities to be treated in any case or proceeding or similar event described
in clauses (a), (b) or (c) of the first paragraph of Section 14.17 as part of
the same class of claims as the Senior Guarantor Indebtedness or any class of
claims pari passu with, or senior to, the Senior Guarantor Indebtedness, for
any payment or distribution, debt or equity securities of Hollinger
International or any successor corporation provided for by a plan of
reorganization or readjustment that are subordinated at least to the same
extent that the Guarantee of Hollinger International is subordinated to the
payment of all Senior Guarantor Indebtedness then outstanding; provided that
(1) if a new corporation results from such reorganization or readjustment, such
corporation assumes any Senior Guarantor Indebtedness not paid in full in cash
or Cash Equivalents in connection with such reorganization or readjustment and
(2) the rights of the holders of such Senior Indebtedness are not, without the
consent of such holders, altered by such reorganization or readjustment.

                  "Permitted Indebtedness" means the following:

                  (i) Indebtedness of Publishing or Foreign Subsidiary
         Indebtedness under the New Bank Credit Facility in an aggregate
         principal amount at any one time outstanding not to exceed $150
         million; and once both of The Telegraph and Southam are Restricted
         Subsidiaries, $250 million; and, once the Hollinger Inc. Transaction
         closes, $475 million; provided, however, that Indebtedness under the
         New Bank Credit Facility may not be Incurred under this paragraph for
         purposes of purchasing or otherwise acquiring the Capital Stock or a
         substantial portion of the assets of another Person (including the
         minority interest in Southam but excluding acquisitions of inventory,
         equipment and similar


<PAGE>   33
                                                                          - 23 -

         assets in the ordinary course of business) unless, immediately after
         giving effect to such transaction on a pro forma basis, Publishing
         could Incur $1.00 of additional Indebtedness (other than Permitted
         Indebtedness) under Section 10.08;

                (ii) once Southam is a Restricted Subsidiary and until such
         time as Southam is not a Public Entity, Indebtedness of Southam;
         provided that the Southam Cash Flow Ratio for the four full fiscal
         quarters immediately preceding the Incurrence of such Indebtedness
         taken as one period is not greater than 4.0:1.0 (for purposes of
         determining the Southam Cash Flow Ratio for any period, pro forma
         effect shall be given to (i) the Incurrence of such Indebtedness and
         (if applicable) the application of the net proceeds therefrom,
         including to refinance other Indebtedness, as if such Indebtedness was
         Incurred, and the application of such proceeds occurred, at the
         beginning of such four-quarter period; (ii) the Incurrence, repayment
         or retirement of any other Indebtedness by Southam or any of its
         Restricted Subsidiaries since the first day of such four-quarter
         period as if such Indebtedness was Incurred, repaid or retired at the
         beginning of such four-quarter period; (iii) in the case of Acquired
         Indebtedness, the related acquisition (as if such acquisition had been
         consummated on the first day of such four-quarter period); and (iv)
         any acquisition or disposition by Southam or any of its Restricted
         Subsidiaries of any company or any business or any assets out of the
         ordinary course of business, whether by merger, stock purchase or sale
         or asset purchase or sale or any related repayment of Indebtedness, in
         each case since the first day of such four-quarter period, as if such
         acquisition or disposition had been consummated on the first day of
         such four-quarter period); provided, however, that Southam may not
         Incur Indebtedness under this paragraph for purposes of purchasing or
         otherwise acquiring the Capital Stock or a substantial portion of the
         assets of another Person (including the minority interest in Southam
         but excluding acquisitions of inventory, equipment and similar assets
         in the ordinary course of business) unless, immediately after giving
         effect to such transaction on a pro forma basis, Publishing could
         Incur $1.00 of additional Indebtedness (other than Permitted
         Indebtedness) under Section 10.08;

              (iii) guarantees by, and Liens on the property of, any Restricted
         Subsidiary guaranteeing or securing Indebtedness of Publishing or
         Foreign Subsidiary Indebtedness under the New Bank Credit Facility,
         and provided that both of The Telegraph and Southam are Restricted
         Subsidiaries, guarantees of and Liens securing the FDTH Credit
         Facility, which guarantees or Liens are in existence on the date of


<PAGE>   34
                                                                          - 24 -

         this Indenture or on the date which they become Restricted
         Subsidiaries or guarantees that are otherwise permitted under Section
         10.13;

                (iv) Indebtedness of Publishing pursuant to the Securities
         issued on the date of this Indenture and Indebtedness of any
         Restricted Subsidiary constituting a Guarantee of the Securities;

                 (v) Indebtedness of Publishing or any Restricted Subsidiary
         outstanding on the date of this Indenture and listed on Schedule I
         hereto;

                (vi) Indebtedness (a) of Publishing owing to a Wholly Owned
         Restricted Subsidiary or, provided that both of The Telegraph and
         Southam are Restricted Subsidiaries, a Restricted Subsidiary, or (b)
         of a Wholly Owned Restricted Subsidiary owing to Publishing or another
         Wholly Owned Restricted Subsidiary or, provided that both of The
         Telegraph and Southam are Restricted Subsidiaries, a Restricted
         Subsidiary owing to another Restricted Subsidiary or Publishing;
         provided that any such Indebtedness is made pursuant to an
         intercompany note setting forth the principal amount, interest rate
         and payment dates, the maturity or similar terms, and, in the case of
         Indebtedness of Publishing owing to a Wholly Owned Restricted
         Subsidiary or a Restricted Subsidiary, as the case may be, is
         subordinated in right of payment from and after such time as the
         Securities shall become due and payable (whether at Stated Maturity,
         acceleration or otherwise) to the payment and performance of
         Publishing's obligations under the Securities; provided further, that
         (x) any disposition, pledge or transfer of any such Indebtedness to a
         Person (other than (A) to Publishing or a Wholly Owned Restricted
         Subsidiary or, provided that both of The Telegraph and Southam are
         Restricted Subsidiaries, a Restricted Subsidiary or (B) a pledge of
         such Indebtedness to secure Indebtedness existing at such time under,
         and pursuant to the terms of, the New Bank Credit Facility or the
         AP-91 Senior Notes and provided that both of The Telegraph and Southam
         are Restricted Subsidiaries, the FDTH Credit Facility and the Southam
         credit facilities existing on January 1, 1997, as amended), will be
         deemed to be an Incurrence of such Indebtedness by the obligor not
         permitted by this clause (vi) and (y) any transaction pursuant to
         which any Wholly Owned Restricted Subsidiary (or, provided that both
         of The Telegraph and Southam are Restricted Subsidiaries, a Restricted
         Subsidiary), that has Indebtedness owing to Publishing or any other
         Wholly Owned Restricted Subsidiary (or, provided that both of The
         Telegraph and Southam are Restricted Subsidiaries, any other
         Restricted Subsidiary),


<PAGE>   35
                                                                          - 25 -

         ceases to be a Wholly Owned Restricted Subsidiary or, provided that
         both of The Telegraph and Southam are Restricted Subsidiaries, a
         Restricted Subsidiary, will be deemed to be the Incurrence of
         Indebtedness by Publishing or such other Restricted Subsidiary that is
         not permitted by this clause (vi);

             (vii) obligations of Publishing or any Restricted Subsidiary
         pursuant to Interest Rate Agreements or Currency Agreements designed
         to protect Publishing or any Restricted Subsidiary against
         fluctuations in interest rates or currency exchange rates in respect
         of Indebtedness of Publishing or any of its Restricted Subsidiaries or
         changes in dividend rates in respect of preference shares of DTH, the
         notional amount of which (in the case of Interest Rate Agreements) and
         the notional or exchange amount of which (in the case of Currency
         Agreements) do not exceed the aggregate principal amount of such
         Indebtedness or of such preference shares of DTH, as the case may be;

            (viii) guarantees by Restricted Subsidiaries of Senior Indebtedness
         of Publishing otherwise permitted to be Incurred in accordance with
         the provisions of Section 10.08;

              (ix) Indebtedness of Publishing or a Restricted Subsidiary
         Incurred to finance a new printing plant for the Chicago Sun-Times and
         the liabilities directly associated therewith (collectively, the "CST
         Printing Plant") in an aggregate amount not in excess of the lesser of
         (x) $75,000,000 and (y) the aggregate amount needed to finance the CST
         Printing Plant and associated financing costs;

               (x) letter of credit reimbursement obligations Incurred by
         Publishing or a Restricted Subsidiary in the ordinary course of
         business to support workers' compensation insurance obligations to the
         extent that such obligations are recorded on the balance sheet of the
         issuer;

              (xi) any renewals, extensions, substitutions, refundings,
         refinancings or replacements (collectively, a "refinancing") of any
         Indebtedness Incurred pursuant to the ratio test set forth in
         paragraph (a) of Section 10.08, or described in paragraphs (i), (ii),
         (iii), (iv), (viii), (ix) and (xii) of this definition of "Permitted
         Indebtedness" by Publishing or by the obligor of such Permitted
         Indebtedness, including any successive refinancings, so long as (A)
         such refinancing does not increase the aggregate principal amount of
         Indebtedness represented thereby and, in the case of Pari Passu
         Indebtedness or Subordinated Indebtedness, such


<PAGE>   36
                                                                       - 26 - 

         refinancing does not reduce the Average Life to Stated Maturity
         or the Stated Maturity of such Indebtedness and (B) any such
         refinancing Indebtedness shall not be senior in right of payment to the
         Indebtedness so refinanced;

              (xii) provided that both of The Telegraph and Southam are
         Restricted Subsidiaries, Indebtedness of Publishing or any Restricted
         Subsidiary in an aggregate amount at any time outstanding not to
         exceed $25 million in respect of purchase money obligations, provided
         such Indebtedness (a) is Incurred within 180 days of the purchase of
         the relevant assets, (b) does not exceed the actual purchase price of
         such assets and (c) any related Liens do not extend to any assets
         other than those being purchased; and

             (xiii) provided that both of The Telegraph and Southam are
         Restricted Subsidiaries, Indebtedness of Publishing or any Restricted
         Subsidiary in an aggregate principal amount at any time outstanding
         not to exceed $10 million.

                  "Permitted Investment" means any of the following provided
that, in the case of clauses (vii), (viii), (ix), (x) and (xi), (a) no Default
or Event of Default shall have occurred and be continuing, (b) no holders of
any other Indebtedness of Publishing or any Restricted Subsidiary shall have an
Acceleration Right and (c) immediately before and immediately after giving
effect to such Investment, on a pro forma basis, Publishing could Incur $1.00
of additional Indebtedness (other than Permitted Indebtedness) under the
provisions described in Section 10.08 of this Indenture:

                  (i) Investments in any Wholly Owned Restricted Subsidiary
         (or, provided that both of The Telegraph and Southam are Restricted
         Subsidiaries, a Restricted Subsidiary) or Publishing or Investments in
         a Person, if as a result of such Investment (A) such Person becomes a
         Wholly Owned Restricted Subsidiary (or, provided both of The Telegraph
         and Southam are Restricted Subsidiaries, a Restricted Subsidiary), or
         (B) such Person is merged, consolidated or amalgamated with or into,
         or transfers or conveys substantially all of its assets to, or is
         liquidated into, Publishing or any Wholly Owned Restricted Subsidiary
         (or, provided that both of The Telegraph and Southam are Restricted
         Subsidiaries, a Restricted Subsidiary);

                 (ii) Investments in the Securities;

                (iii) Indebtedness owing to a Wholly Owned Restricted Subsidiary
         or, provided that both of The Telegraph and Southam are Restricted
         Subsidiaries, a Restricted


<PAGE>   37
                                                                          - 27 -

         Subsidiary, in each case as described under clause (vi) of the
         definition of "Permitted Indebtedness";

                 (iv) Temporary Cash Investments;

                  (v) Investments acquired by Publishing or any Subsidiary in
         connection with an Asset Sale permitted under Section 10.14 to the
         extent such Investments are non-cash consideration as permitted under
         such covenant;

                 (vi) Investments in existence on the date of this Indenture;

                (vii) Investments in or in Persons owning Newspaper Business or
         Media Business assets (including Investments in Unrestricted
         Subsidiaries but excluding Investments in Affiliates that control
         Publishing) in an aggregate amount following the date of this
         Indenture not in excess of the greater of (i) $40,000,000 or (ii) 25%
         of the aggregate cumulative cash dividends or distributions received
         by Publishing and its Restricted Subsidiaries from any of Publishing's
         Unrestricted Subsidiaries received during the period (treated as a
         single accounting period) after the date of this Indenture and prior
         to the date of the Permitted Investment; provided, however, that for
         purposes of this clause (vii), cash dividends or distributions shall
         not include the Southam Dividend Amount or any cash dividends or
         distributions received by Publishing or any Wholly Owned Restricted
         Subsidiary in accordance with Section 10.09(b)(vi);

               (viii) provided that The Telegraph is a Restricted Subsidiary,
         Investments in West Ferry Printers and Trafford Park Printers to cover
         The Telegraph's share of operating losses associated with the printing
         of newspapers and to finance capital expenditures related to the
         printing business; provided that at the time of any such Investment,
         neither West Ferry Printers nor Trafford Park Printers shall be
         engaged in any business other than the business of printing
         newspapers, periodicals and similar media;

                 (ix) Investments by Southam in Newspaper Businesses and Media
         Businesses and Media Businesses in Canada; provided that (i) Southam
         is at the time a Restricted Subsidiary, (ii) Southam is at the time a
         Public Entity and (iii) the Investment is not made in an Affiliate of
         Southam (other than a Subsidiary of Southam); and provided further
         that, unless such Investment by Southam otherwise qualifies as a
         Permitted Investment under this definition (other than pursuant to
         this clause (ix)), such Investment will constitute a Restricted
         Payment under Section 10.09;

<PAGE>   38
                                                                          - 28 -

                (x) Investments by DTH or FDTH in Argsub Preferred, provided
         that (x) the issuer of such Argsub Preferred simultaneously makes an
         Investment in Mirror Preferred of DTH or FDTH, as the case may be, in
         an equivalent amount and (y) such Mirror Preferred continues to
         qualify as such under the definition thereof; and

               (xi) in addition to the Investments described in clauses (i)
         through (x) of this definition of "Permitted Investments," Investments
         in any Restricted Subsidiary, Unrestricted Subsidiary or in any joint
         venture or other entity in an amount not to exceed $10,000,000 in the
         aggregate since the date of this Indenture; provided that so long as
         The Telegraph is a Restricted Subsidiary, the loan of $6,000,000 from
         Publishing to FDTH prior to the time The Telegraph became a Restricted
         Subsidiary shall not count against the $10,000,000 amount provided for
         in this clause (xi).

                  "Permitted Junior Securities" means (so long as the effect of
any exclusion employing this definition is not to cause the Securities to be
treated in any case or proceeding or similar event described in clauses (a),
(b) or (c) of the first paragraph of Section 12.02 as part of the same class of
claims as the Senior Indebtedness or any class of claims pari passu with, or
senior to, the Senior Indebtedness, for any payment or distribution) debt or
equity securities of Publishing or any successor corporation provided for by a
plan of reorganization or readjustment that are subordinated at least to the
same extent that the Securities are subordinated to the payment of all Senior
Indebtedness then outstanding; provided that (1) if a new corporation results
from such reorganization or readjustment, such corporation assumes any Senior
Indebtedness not paid in full in cash or Cash Equivalents in connection with
such reorganization or readjustment and (2) the rights of the holders of such
Senior Indebtedness are not, without the consent of such holders, altered by
such reorganization or readjustment.

                  "Permitted Real Estate Sale" means any Asset Sale not
involving an Affiliate of Publishing consisting of the sale of any printing or
distribution facility (including the associated real property and the
improvements and fixtures forming a part thereof) (other than the CST Real
Estate) formerly used by Publishing or a Restricted Subsidiary in the
production of newspapers and related publications (or acquired by one of them
as part of the acquisition of a Newspaper Business whether or not used by
Publishing) and that after such Asset Sale will not be used for the production
of any newspaper or related publication of Publishing or a Restricted
Subsidiary, provided that the aggregate value (as determined by the Board of
Directors of Publishing) of all such Asset Sales completed within any twelve


<PAGE>   39
                                                                          - 29 -

month period shall not exceed $5,000,000 (it being understood that this
definition does not include, among other things, any Asset Sale consisting of
the sale of any printing or distribution facility in connection with the sale
by Publishing or any Restricted Subsidiary of any Newspaper Business).

                  "Permitted Subsidiary Indebtedness" means Indebtedness of the
Restricted Subsidiaries, taken as a whole, with an aggregate principal amount
outstanding (calculated exclusive of the AP-91 Senior Notes) not in excess of
the greater of (x) $40,000,000 and (y) 10% of Consolidated Tangible Assets
measured as of the most recent fiscal quarter.

                  "Person" means any individual, corporation, limited liability
company, limited or general partnership, joint venture, association, joint
stock company, trust, unincorporated organization or government or any agency
or political subdivisions thereof.

                  "Predecessor Security" of any particular Security means every
previous Security evidencing all or a portion of the same debt as that
evidenced by such particular Security; and, for the purposes of this
definition, any Security authenticated and delivered under Section 3.06 in
exchange for a mutilated Security or in lieu of a lost, destroyed or stolen
Security shall be deemed to evidence the same debt as the mutilated, lost,
destroyed or stolen Security.

                  "Preferred Stock" means, with respect to any Person, any
Capital Stock of any class or classes (however designated) which is preferred
as to the payment of dividends or distributions, or as to the distribution of
assets upon any voluntary or involuntary liquidation or dissolution of such
Person, over the Capital Stock of any other class in such Person, provided that
this definition shall not include Mirror Preferred provided that such Mirror
Preferred continues to qualify as such under the definition thereof.

                  "Public Debt" means any notes, bonds or debentures or other
evidence of Indebtedness issued in the public markets or the market for
securities sold pursuant to Rule 144A under the Securities Act of 1933.

                  "Public Entity" means an entity (x) in which the equity
interest of Hollinger International and its Affiliates does not exceed 80%, (y)
in which the market value of the Capital Stock held by nonaffiliates exceeds
$100,000,000 and (z) the Capital Stock of which is traded on a recognized
national securities exchange in the United States or a prescribed securities
exchange in Canada.

<PAGE>   40
                                                                          - 30 -

                  "Publishing" means Hollinger International Publishing Inc., a
corporation incorporated under the laws of Delaware, until a successor Person
shall have become such pursuant to Article VIII of this Indenture and
thereafter "Publishing" shall mean such successor Person. To the extent
necessary to comply with the requirements of the provisions of Trust Indenture
Act Sections 310 through 317 as they are applicable to Publishing, the term
"Publishing" shall include any other obligor with respect to the Securities for
purposes of complying with such provisions, including any Guarantor.

                  "Publishing Request" or "Publishing Order" means a written
request or order signed in the name of Publishing by any one of its Chairman of
the Board, its Vice Chairman, its President or a Vice President (regardless of
Vice Presidential designation), and by any one of its Treasurer, an Assistant
Treasurer, its Secretary or an Assistant Secretary, and in form and substance
reasonably satisfactory to the Trustee and delivered to the Trustee.

                  "Qualified Capital Stock" of any Person means any and all
Capital Stock of such Person other than Redeemable Capital Stock.

                  "Rating Agency" means Standard & Poor's Corporation and its
successors ("S&P"), and Moody's Investors Service, Inc. and its successors
("Moody's"), or if S&P and Moody's or both shall not make a rating of the
Securities publicly available, a nationally recognized United States
statistical rating agency or agencies, substituted for S&P or Moody's or both,
as the case may be.

                  "Rating Category" means each major rating category symbolized
by (a) in the case of S&P, AAA, AA, A, BBB, BB, B, CCC, CC and C and each such
Rating Category shall include pluses or minuses ("gradations") modifying such
capital letters; and (b) in the case of Moody's, Aaa, Aa, A, Baa, Ba, B, Caa,
Ca and C and each such Rating Category shall include added numerals such as 1,
2 or 3 ("gradations") modifying such letters.

                  "Rating Decline" means an event that will be deemed to have
occurred if, on any date within the period (the "Rating Period") beginning on
the date (the "Reference Date") of the earlier to occur of (A) the first public
announcement by Publishing or any other Person of an intention to effect any
Designated Transaction and (B) the occurrence of such Designated Transaction,
and ending on the date 90 days thereafter, either of the following events has
occurred: (1) the Securities of any Series (or any other securities of
Publishing which are rated by a Rating Agency on the date which is 61 days
prior to the Reference Date (the "Rating Date")) shall be rated by any Rating


<PAGE>   41
                                                                          - 31 -

Agency at any time during the Rating Period at a rating which is lower than the
rating of the Securities of such Series (or such other securities of
Publishing, as the case may be) by such Rating Agency on the Rating Date by one
or more gradations (including gradations within Rating Categories as well as
between Rating Categories) or (2) any Rating Agency shall have withdrawn its
rating of the Securities of any Series (or such other securities of Publishing,
as the case may be) during the Rating Period.

                  "Redeemable Capital Stock" means any Capital Stock that,
either by its terms or by the terms of any security into which it is
convertible or exchangeable or otherwise, is, or upon the happening of an event
or passage of time would be, required to be redeemed prior to any Stated
Maturity of the principal of the Securities or is redeemable at the option of
the holder thereof at any time prior to any such Stated Maturity, or is
convertible into or exchangeable for debt securities at any time prior to any
such Stated Maturity at the option of the holder thereof; provided that this
definition shall not include Mirror Preferred provided that such Mirror
Preferred continues to qualify as such under the definition thereof.

                  "Redemption Date" when used with respect to any Security to
be redeemed pursuant to any provision in this Indenture means the date fixed
for such redemption by or pursuant to this Indenture.

                  "Redemption Price" when used with respect to any Security to
be redeemed pursuant to any provision in this Indenture means the price at
which it is to be redeemed pursuant to this Indenture.

                  "Regular Record Date" for the interest payable on any
Interest Payment Date relating to a particular Series means the date specified
in the Board Resolution or supplemental indenture relating to such Series.

                  "Responsible Officer" when used with respect to the Trustee
means any officer assigned to the Corporate Trust Division of the Trustee or
any agent of the Trustee appointed hereunder, including the president, any vice
president, any assistant vice president, the secretary, any assistant
secretary, the treasurer, any assistant treasurer, any trust officer or
assistant trust officer or any other officer of the Trustee customarily
performing functions similar to those performed by any of the above designated
functions similar to those performed by any of the above designated officers or
any other officer appointed hereunder to whom any corporate trust matter is
referred because of his or her knowledge of and familiarity with the particular
subject.


<PAGE>   42
                                                                          - 32 -

                  "Restricted Subsidiary" means, initially, each Subsidiary of
Publishing existing on the date of this Indenture, other than DTH and its
Subsidiaries, and any other Subsidiary designated from time to time by the
Board of Directors of Publishing as a "Restricted Subsidiary" in accordance
with Section 10.21 of this Indenture.

                  "Restricted Subsidiary Guarantor" means each Subsidiary of
Publishing that is required to issue a Guarantee of the Securities under the
terms of this Indenture.

                  "Scheme of Arrangement" means the acquisition by FDTH of the
publicly held shares in The Telegraph not owned by FDTH or any of its
Affiliates effected by way of a "Scheme of Arrangement under Section 425 of the
Companies Act 1985 of England.

                  "Securities" has the meaning specified in the first recital
of this Indenture.

                  "Securities Act" means the Securities Act of 1933, as
amended.

                  "Senior Guarantor Indebtedness" means, with respect to any
Guarantor, such Guarantor's guarantee of Publishing's payment obligations in
respect of the New Bank Credit Facility, the FDTH Credit Agreement and any
other Indebtedness of such Guarantor (other than as otherwise provided in this
definition), whether outstanding on the date of this Indenture or thereafter
created, Incurred or assumed, unless, in the case of any particular
Indebtedness, the instrument creating or evidencing the same or pursuant to
which the same is outstanding expressly provides that such Indebtedness shall
not be senior in right of payment to the Guarantees. Notwithstanding the
foregoing, "Senior Guarantor Indebtedness" shall not include (i) Indebtedness
evidenced by such Guarantor's Guarantee of the Securities; (ii) Indebtedness of
such Guarantor that is subordinate or junior in right of payment to any other
Indebtedness of such Guarantor; (iii) Indebtedness of such Guarantor which,
when Incurred and without respect to any other election under Section 1111(b)
of Title 11, United States Code, is without recourse to such Guarantor; (iv)
Indebtedness which is represented by Redeemable Capital Stock of such
Guarantor; (v) any liability for foreign, federal, state, local or other taxes
owed or owing by such Guarantor; (vi) Indebtedness of such Guarantor to a
Restricted Subsidiary or any other Affiliate of such Guarantor or any of such
Affiliate's subsidiaries; (vii) that portion of any Indebtedness which at the
time of Incurrence is issued in violation of this Indenture; and (viii) trade
payables owed or owing by such Guarantor.


<PAGE>   43
                                                                          - 33 -

                  "Series" means any series of debentures, notes, bonds or
other evidences of indebtedness issued pursuant to Article III hereof or a
supplemental indenture.

                  "Senior Indebtedness" means, with respect to Publishing, the
principal of, premium, if any, and interest in respect of the New Bank Credit
Facility and any other Indebtedness of Publishing (other than as otherwise
provided in this definition), whether outstanding on the date of this Indenture
or thereafter created, Incurred or assumed, unless, in the case of any
particular Indebtedness, the instrument creating or evidencing the same or
pursuant to which the same is outstanding expressly provides that such
Indebtedness shall not be senior in right of payment to the Securities. Without
limiting the generality of the foregoing, "Senior Indebtedness" shall include
the principal of, premium, if any, interest and all other obligations owing to
the lenders under (a) the New Bank Credit Facility and (b) holders under the
Senior Securities. Notwithstanding the foregoing, "Senior Indebtedness" shall
not include (i) Indebtedness evidenced by the Securities; (ii) Indebtedness of
Publishing that is subordinate or junior in right of payment to any other
Indebtedness of Publishing; (iii) Indebtedness of Publishing which, when
Incurred and without respect to any other election under Section 1111(b) of
Title 11, United States Code, is without recourse to Publishing; (iv)
Indebtedness which is represented by Redeemable Capital Stock; (v) any
liability for foreign, federal, state, local or other taxes owed or owing by
Publishing; (vi) Indebtedness of Publishing to a Restricted Subsidiary or any
other Affiliate of Publishing or any of such Affiliate's subsidiaries; (vii)
that portion of any Indebtedness which at the time of Incurrence is issued in
violation of this Indenture; and (viii) trade payables owed or owing by
Publishing.

                 "Series A Preferred Shares" means the Series A Redeemable
Convertible Preferred Stock of Hollinger International, as in effect on the
date of this Indenture.

                  "Services Agreement" means the Services Agreement dated as of
February 7, 1996, as amended in connection with the offering of the Securities,
among Hollinger International, Publishing and Hollinger Inc., and as the same
may be further amended in accordance with the terms of this Indenture.

                  "Southam" means Southam Inc., a corporation continued under
the laws of Canada.

                  "Southam Cash Flow" means, for any period, an amount equal to
the Southam Net Income for such period, plus, to the extent deducted in
calculating such Southam Net Income, (a) interest expense and other financing
costs and expenses, (b)


<PAGE>   44
                                                                          - 34 -

dividends paid on any Preferred Stock of Restricted Subsidiaries of Southam to
the extent such Preferred Stock is included as Indebtedness in the calculation
of the Southam Cash Flow Ratio, (c) depreciation and amortization, and (d) all
taxes, whether or not deferred, applicable to such period.

                  For purposes of calculating Southam Cash Flow for the four
fiscal quarters most recently completed prior to any date on which an action is
taken that requires a calculation of the Southam Cash Flow Ratio, (a) any
Person that is a Restricted Subsidiary of Southam on such date (or would become
a Restricted Subsidiary of Southam in connection with the transaction that
requires the determination of such ratio) shall be deemed to have been a
Restricted Subsidiary of Southam at all times during such period, (b) any
Person that is not a Restricted Subsidiary of Southam on such date (or would
cease to be a Restricted Subsidiary of Southam in connection with the
transaction that requires the determination of such ratio) shall be deemed not
to have been a Restricted Subsidiary of Southam at any time during such period;
(c) if Southam or any of its Restricted Subsidiaries shall have in any manner
acquired or disposed of any operating business during or subsequent to such
period, such calculation shall be made on a pro forma basis on the assumption
that such acquisition or disposition has been completed on the first day of
such period; and (d) in the case of a Restricted Subsidiary that is not a
Wholly Owned Restricted Subsidiary, the determination of the percentage of the
Operating Cash Flow of such Restricted Subsidiary that is to be included in the
calculation of the Consolidated Publishing's Consolidated Cash Flow Ratio shall
be made on a pro forma basis on the assumption that the percentage of
Publishing's common equity interest in such Restricted Subsidiary on the first
day of such period was equivalent to its common equity interest on the date of
the determination (it being understood, in the case of the foregoing clause
(c), that if such pro forma calculations have been made in accordance with
Regulation S-X under the Exchange Act, such method of calculation (but not
necessarily the adjustments) shall be presumed to be acceptable).

                  "Southam Cash Flow Ratio" means, as at any date of
determination, the ratio of (i) the aggregate amount of Indebtedness of Southam
and its Restricted Subsidiaries outstanding as at such date to (ii) the Southam
Cash Flow (determined on a Consolidated basis for Southam and its Restricted
Subsidiaries) for the most recently completed period of four consecutive fiscal
quarters of Southam, provided that once Southam is a Restricted Subsidiary, for
the purpose of determining the Southam Cash Flow Ratio, the Indebtedness and
Southam Cash Flow of Restricted Subsidiaries of Southam that are not Wholly
Owned Restricted Subsidiaries of Southam will be determined in accordance with
the actual percentage of Southam's


<PAGE>   45
                                                                          - 35 -

common equity interest in such Restricted Subsidiary on the date of
determination of the Southam Cash Flow ratio (thus, for example, in the case of
a Restricted Subsidiary of Southam in which Southam owns a 51% common equity
interest, 51% each of such Restricted Subsidiary's indebtedness and Southam
Cash Flow would be included in the calculation of Southam's aggregate
Indebtedness and the aggregate of Southam Cash Flow, respectively).

                  "Southam Dividend Amount" means the lesser of (x) the
aggregate amount paid or payable by the Guarantor since the date of this
Indenture in respect of regularly scheduled periodic dividends on the Series A
Preferred and (y) the aggregate amount of the Southam Interests Dividends
received by Publishing since the date of this Indenture on account of its
ownership interest (whether direct or indirect) in Southam.

                  "Southam Interests" means 7,395,000 Southam common shares
held by Hollinger International or its subsidiaries; provided, however, that if
Southam shall pay a dividend, or make a distribution, on its common shares in
the form of capital stock of the same or another corporation, or subdivide its
outstanding common shares into a greater number of common shares, or combine
its outstanding common shares into a smaller number of common shares, or effect
a reorganization or reclassification of its Capital Stock, or amalgamate, enter
into an arrangement or consolidation or merge with or into another entity
(other than an amalgamation, arrangement, consolidation or merger which does
not result in a reclassification or change of the outstanding common shares of
Southam), the "Southam Interests" shall thereafter include any securities
distributed with respect to any such shares or into which any such shares shall
be converted, changed or reclassified or for which any such shares shall be
exchanged.

                  "Southam Interests Dividend" means a dividend or other
distribution paid on or with respect to the Southam Interests on or prior to
the earlier of (i) the redemption date for the redemption of all the Series A
Preferred Shares outstanding as of such redemption date or (ii) the date of
final distribution to the holders of the Series A Preferred Shares of the full
preferential amount provided under the terms thereof; provided, however, that
the term "Southam Interests Dividend" does not mean or include (x) any part of
any dividend or distribution that is payable otherwise than in cash or that
constitutes an Extraordinary Cash Dividend as applied to the Southam Interests,
or (y) any dividend or distribution on or with respect to the 7,395,000 Southam
common shares held by Publishing or its subsidiaries.


<PAGE>   46
                                                                          - 36 -

                  "Southam-Linked Debentures" means the debentures of Hollinger
Inc. in the original principal amount of Cdn.$125,000,000 due November 1, 1998.

                  "Southam Net Income (Loss)" means, for any period, the
Consolidated net income (or loss) (and treating a loss as a negative number))
of Southam and its Restricted Subsidiaries for such period as determined in
accordance with GAAP, adjusted by (a) excluding, without duplication, to the
extent included in calculating such Consolidated net income (or loss), (i) all
extraordinary gains and losses, (ii) the portion of Consolidated net income (or
loss) of Southam and its Restricted Subsidiaries allocable to Investments in
unconsolidated Persons (other than Unrestricted Subsidiaries) to the extent
that cash dividends or distributions have not actually been received by such
Southam or one of its Restricted Subsidiaries, (iii) the portion of
Consolidated net income (or loss) of Southam and its Restricted Subsidiaries
allocable to Southam's Unrestricted Subsidiaries (or to payments received
therefrom), (iv) net income (or loss) of a Person combined with Southam or any
of its Subsidiaries on a "pooling of interests" basis attributable to any
period prior to the date of combination, (v) any gain or loss, net of taxes,
realized upon the termination of any employee pension benefit plan, (vi)
aggregate net gains and losses (less all fees and expenses relating thereto) in
respect of dispositions of assets (including without limitation sales of shares
of Unrestricted Subsidiaries or unconsolidated Persons and noncash writeoffs of
assets (provided that there are no continuing cash expenses related to such
writeoffs)) other than in the ordinary course of business, (vii) the net income
of any Restricted Subsidiary to the extent that the declaration of dividends or
similar distributions by that Restricted Subsidiary of that income is not at
the time permitted, directly or indirectly, by operation of the terms of its
charter or any agreement, instrument, judgment, decree, order, statute, rule or
governmental regulations applicable to that Restricted Subsidiary or its
stockholders; provided, however, that the foregoing shall not apply to the
restrictions permitted under clause (iv) of Section 10.17 (to the extent such
clause is applicable at the time of determination), (viii) any restoration to
income of any contingency reserve, except to the extent that provision for such
reserve was made out of income accrued at any time following the date of the
Indenture, (ix) any net gain from the collection of proceeds of life insurance
policies, (x) any gain arising from the acquisition of any securities, or the
extinguishment, under GAAP, of any Indebtedness of Southam or one of its
Restricted Subsidiaries, (xi) aggregate net gains or losses relating to foreign
currency transactions or translations, (xii) redundancy costs relating to the
permanent elimination of jobs, provided that the amount of such expenses are
certified by Southam's independent accountants and (b) subtracting, without
duplication,


<PAGE>   47
                                                                          - 37 -

the aggregate amount of dividends on Preferred Stock of Restricted Subsidiaries
of Southam (i) to the extent such Preferred Stock is not equivalent to Common
Stock for purposes of the payment of dividends and (ii) to the extent that such
Preferred Stock is included as Indebtedness in the calculation of the Southam
Cash Flow Ratio.

                  "Special Record Date" for the payment of any Defaulted
Interest means a date fixed by the Trustee pursuant to Section 3.07.

                  "Stated Maturity" when used with respect to any Indebtedness
or any installment of interest thereon, means the dates specified in such
Indebtedness as the fixed date on which the principal of such Indebtedness or
such installment of interest, as the case may be, is due and payable.

                  "Subordinated Guarantor Indebtedness" means Indebtedness of a
Guarantor subordinated in right of payment to such Guarantor's Guarantee.

                  "Subordinated Indebtedness" means(i) in the case of any
person other than Publishing, Indebtedness of such person that is expressly
subordinate in right of payment to any other Indebtedness of such Person
pursuant to a written agreement, and (ii) in the case of Publishing,
Indebtedness of Publishing that is expressly subordinate in right of payment to
the Securities.

                  "Subsidiary" means any Person a majority of the equity
ownership of the Voting Stock of which is at the time owned, directly or
indirectly, by Publishing or by one or more Subsidiaries, or by Publishing and
one or more other Subsidiaries; provided that, notwithstanding the foregoing,
(i) Southam will be a Subsidiary so long as majority of the Voting Stock of
Southam is held by a Person in which, directly or indirectly, (x) 50% of the
Voting Stock is held by Publishing and the remainder is held by Hollinger Inc.
and (y) 100% of the nonvoting Capital Stock is held by Publishing, and (ii)
Hollinger Eastern will be a Subsidiary so long as 50% of its Voting Stock is
held, directly or indirectly, by Publishing and the remainder is held, directly
or indirectly, by Hollinger Inc.

                  "Tax Sharing Agreement" means an agreement providing for the
payment of amounts in lieu of income taxes among Publishing and other companies
with which it forms a single consolidated tax group.

                  "The Telegraph" means Telegraph Group Limited (formerly The
Telegraph plc), a corporation under the laws of England.

<PAGE>   48
                                                                          - 38 -

                  "Temporary Cash Investments" means (i) any evidence of
Indebtedness, maturing not more than one year after the date of acquisition,
issued by the United States of America, or an instrumentality or agency
thereof, and guaranteed fully as to principal, premium, if any, and interest by
the United States of America, (ii) any certificate of deposit, maturing not
more than one year after the date of acquisition, issued by, or time deposit of
the Trustee or a commercial banking institution that is a member of the Federal
Reserve System and that has combined capital and surplus and undivided profits
of not less than $500,000,000, whose debt has a rating, at the time as of which
any investment therein is made, of "P-1" (or higher) according to Moody's or
"A-1" (or higher") according to S&P, (iii) commercial paper, maturing not more
than one year after the date of acquisition, issued by a corporation (other
than an Affiliate or Restricted Subsidiary of Publishing) organized and
existing under the laws of the United States of America with a rating, at the
time as of which any investment therein is made, of "P-1" (or higher according
to Moody's or "A-1" (or higher) according to S&P, (iv) any money market deposit
accounts issued or offered by the Trustee or a domestic commercial bank having
capital and surplus in excess of $500,000,000.

                  "Trustee" means the Person named as the "Trustee" in the
first paragraph of this Indenture, until a successor Trustee shall have become
such pursuant to the applicable provisions of this Indenture, and thereafter
"Trustee" shall mean such successor Trustee. If at any time there is more than
one such Person, "Trustee" as used with respect to the Securities of any Series
shall mean the Trustee with respect to Securities of that Series.

                  "Trust Indenture Act" means the Trust Indenture Act of 1939,
as amended.

                  "Unrestricted Subsidiary" means any Subsidiary that is not a
Restricted Subsidiary, including any Restricted Subsidiary that becomes an
Unrestricted Subsidiary in accordance with Section 10.21 of this Indenture;
provided, however, that a Person may not be designated as an Unrestricted
Subsidiary unless (i) the creditors of such Person have no direct or indirect
recourse (including, but not limited to, recourse with respect to the payment
of principal or interest on Indebtedness of such Subsidiary) to Publishing or a
Restricted Subsidiary and (ii) a default by such Person on any of its
Indebtedness will not result in, or permit any holder of Indebtedness of
Publishing or a Restricted Subsidiary to declare, a default on such
Indebtedness of Publishing or a Restricted Subsidiary or cause the payment
thereof to be accelerated or payable prior to its Stated Maturity. Any
subsidiary of an Unrestricted Subsidiary shall be an Unrestricted Subsidiary
for purposes of this Indenture.

<PAGE>   49
                                                                          - 39 -

                  "Voting Stock" means stock of the class or classes pursuant
to which the holders thereof have the general voting power under ordinary
circumstances to elect at least a majority of the board of directors, managers
or trustees of a corporation (irrespective of whether or not at the time stock
of any other class or classes shall have or might have voting power by reason
of the happening of any contingency).

                  "Wholly Owned Restricted Subsidiary" means a Restricted
Subsidiary all the outstanding Capital Stock (other than directors' qualifying
shares) of which are owned by Publishing or another Wholly Owned Restricted
Subsidiary or, in the case of a Restricted Subsidiary of Southam, all the
outstanding Capital Stock (other than directors' qualifying shares) of which
are owned by Southam or another Wholly Owned Restricted Subsidiary of Southam.


<PAGE>   50


                                                                          - 40 -

                  SECTION 1.02. Other Definitions.

<TABLE>
<CAPTION>
                                                                Defined in
Term                                                              Section
- ----                                                            ----------
<S>                                                                <C>
"Act"                                                               1.05
"Change of Control Offer"                                          10.15
"Change of Control Purchase Date"                                  10.15
"Change of Control Purchase Notice"                                10.15
"Change of Control Purchase Price"                                 10.15
"covenant defeasance"                                               4.03
"Defaulted Interest"                                                3.07
"defeasance"                                                        4.02
"Defeasance Redemption Date"                                        4.04
"Defeased Securities"                                               4.01
"Deficiency"                                                       10.14
"Excess Proceeds"                                                  10.14
"Initial Blockage Period"                                          12.03
"Note Amount"                                                      10.14
"Offer"                                                            10.14
"Offered Price"                                                    10.14
"Pari Passu Debt Amount"                                           10.14
"Pari Passu Offer"                                                 10.14
"Payment Blockage Period"                                          12.03
"Permitted Payment"                                                10.09
"Purchase Date"                                                    10.14
"refinancing"                                                      10.09
"Required Filing Dates"                                            10.18
"Restricted Payments"                                              10.09
"Security Register"                                                 3.05
"Security Registrar"                                                3.05
"Senior Representative"                                            12.03
"Special Payment Date"                                              3.07
"Surviving Entity"                                                  8.01
"U.S. Government Obligations"                                       4.04
</TABLE>

                  SECTION 1.03. Compliance Certificates and Opinions. Upon any
application or request by Publishing to the Trustee to take any action under
any provision of this Indenture, Publishing shall furnish to the Trustee an
Officers' Certificate to the effect that all conditions precedent, if any,
provided for in this Indenture (including any covenant compliance with which
constitutes a condition precedent) relating to the proposed action have been
complied with and an Opinion of Counsel to the effect that in the opinion of
such counsel all such conditions precedent, if any, have been complied with,
except that, in the case of any such application or request as to which the
furnishing of any certificates and/or opinions is specifically required by any
provision of this Indenture


<PAGE>   51
                                                                          - 41 -

relating to such particular application or request, no additional certificate
or opinion need be furnished.

                  Every certificate or Opinion of Counsel with respect to
compliance with a condition or covenant provided for in this Indenture shall
include:

                  (a) a statement to the effect that each individual or firm
         signing such certificate or opinion has read and understands such
         covenant or condition and the definitions herein relating thereto;

                  (b) a brief statement as to the nature and scope of the
         examination or investigation upon which the statements or opinions
         contained in such certificate or opinion are based;

                  (c) a statement to the effect that, in the opinion of each
         such individual or such firm, he has made such examination or
         investigation as is necessary to enable him or them to express an
         informed opinion as to whether or not such covenant or condition has
         been complied with; and

                  (d) a statement as to whether, in the opinion of each such
         individual or such firm, such condition or covenant has been complied
         with.

                  SECTION 1.04. Form of Documents Delivered to Trustee. In any
case where several matters are required to be certified by, or covered by an
opinion of, any specified Person, it is not necessary that all such matters be
certified by, or covered by the opinion of, only one such Person, or that they
be so certified or covered by only one document, but one such Person may
certify or give an opinion with respect to some matters and one or more other
such Persons as to other matters, and any such Person may certify or give an
opinion as to such matters in one or several documents.

                  Any certificate or opinion of an officer of Publishing may be
based, insofar as it relates to legal matters, upon a certificate or opinion
of, or representations by, counsel, unless such officer knows, or in the
exercise of reasonable care should know, that the certificate or opinion or
representations with respect to the matters upon which his certificate or
opinion is based are erroneous. Any certificate or opinion of such an officer
or of counsel may be based, insofar as it relates to factual matters, upon a
certificate or opinion of, or representations by, an officer or officers of
Publishing


<PAGE>   52
                                                                          - 42 -

with respect to such factual matters and which contains a statement to the
effect that the information with respect to such factual matters is in the
possession of Publishing, unless such officer or counsel knows that the
certificate or opinion or representations with respect to such matters are
erroneous. Opinions of Counsel required to be delivered to the Trustee may have
qualifications customary for opinions of the type required and counsel
delivering such Opinions of Counsel may rely on certificates of Publishing or
government or other officials customary for opinions of the type required,
including certificates certifying as to matters of fact, including that various
financial covenants have been complied with.

                  Where any Person is required to make, give or execute two or
more applications, requests, consents, certificates, statements, opinions or
other instruments under this Indenture, they may, but need not, be consolidated
and form one instrument.

                  SECTION 1.05. Acts of Holders. (a) Any request, demand,
authorization, direction, notice, consent, waiver or other action provided by
this Indenture to be given or taken by Holders of any Series may be embodied in
and evidenced by one or more instruments of substantially similar tenor signed
by such Holders in person or by an agent duly appointed in writing; and, except
as herein otherwise expressly provided, such action shall become effective when
such instrument or instruments are delivered to the Trustee and, where it is
hereby expressly required, to Publishing. Such instrument or instruments (and
the action embodied therein and evidenced thereby) are herein sometimes
referred to as the "Act" of the Holders signing such instrument or instruments.
Proof of execution of any such instrument or of a writing appointing any such
agent shall be sufficient for any purpose of this Indenture and conclusive in
favor of the Trustee and Publishing, if made in the manner provided in this
Section.

                  (b)  The ownership of Securities shall be proved by the
Security Register.

                  (c) Any request, demand, authorization, direction, notice,
consent, waiver or other Act by the Holder of any Security shall bind every
future Holder of the same Security or the Holder of every Security issued upon
the transfer thereof or in exchange therefor or in lieu thereof, in respect of
anything done, suffered or omitted to be done by the Trustee, any Paying Agent
or Publishing in reliance thereon, whether or not notation of such action is
made upon such Security.


<PAGE>   53
                                                                          - 43 -

                  (d) The fact and date of the execution by any Person of any
such instrument or writing may be proved by the affidavit of a witness of such
execution or by a certificate of a notary public or other officer authorized by
law to take acknowledgments of deeds, certifying that the individual signing
such instrument or writing acknowledged to him the execution thereof. Where
such execution is by a signer acting in a capacity other than his individual
capacity, such certificate of affidavit shall also constitute sufficient proof
of his authority. The fact and date of the execution of any such instrument or
writing, or the authority of the Person executing the same, may also be proved
in any other manner which the Trustee deems sufficient.

                  SECTION 1.06. Notices, etc., to Trustee and Publishing. Any
request, demand, authorization, direction, notice, consent, waiver or Act of
Holders or other document provided or permitted by this Indenture to be made
upon, given or furnished to, or filed with:

                  (a) the Trustee by any Holder or by Publishing shall be
         sufficient for every purpose hereunder if made, given, furnished or
         filed, in writing, by first-class mail postage prepaid (return receipt
         requested) or delivered in person or by recognized overnight courier
         to or with the Trustee at its Corporate Trust Office, Attention:
         Corporate Trust Division, or at any other address furnished in writing
         prior thereto to the Holders and Publishing by the Trustee; or

                  (b) Publishing or Hollinger International shall be sufficient
         for every purpose (except as provided in Section 5.01(c)) hereunder if
         in writing and mailed, first-class postage prepaid or delivered by
         recognized overnight courier, to Publishing, addressed to it at: 401
         North Wabash Avenue, Chicago, IL 60611 Attn: General Counsel or to
         Hollinger International, addressed to it at: 401 North Wabash Avenue,
         Chicago, IL 60611 Attn: General Counsel, or at any other address
         previously furnished in writing to the Trustee by Publishing or
         Hollinger International, as the case may be.

                  SECTION 1.07. Notice to Holders; Waiver. Where this Indenture
or the Securities of any Series provide for notice to Holders of any event,
such notice shall be sufficiently given (unless otherwise herein expressly
provided) if in writing and mailed, first-class postage prepaid, to each Holder
affected by such event, at such Holder's address as it appears in the Security
Register, not


<PAGE>   54
                                                                          - 44 -

later than the latest date, and not earlier than the earliest date, prescribed
for the giving of such notice. In any case where notice to Holders is given by
mail, neither the failure to mail such notice, nor any defect in any notice so
mailed, to any particular Holder shall affect the sufficiency of such notice
with respect to other Holders. Any notice when mailed to a Holder in the
aforesaid manner shall be conclusively deemed to have been received by such
Holder whether or not actually received by such Holder. Where this Indenture or
the Securities of any Series provide for notice in any manner, such notice may
be waived in writing by the Person entitled to receive such notice, either
before or after the event, and such waiver shall be the equivalent of such
notice. Waivers of notice by Holders shall be filed with the Trustee, but such
filing shall not be a condition precedent to the validity of any action taken
in reliance upon such waiver.

                  In case by reason of the suspension of regular mail service
or by reason of any other cause, it shall be impracticable to mail notice of
any event as required by any provision of this Indenture, then any method of
giving such notice as shall be reasonably satisfactory to the Trustee or
Publishing, as applicable, shall be deemed to be a sufficient giving of such
notice.

                  SECTION 1.08. Conflict with Trust Indenture Act. If any
provision hereof limits, qualifies or conflicts with any provision of the Trust
Indenture Act or another provision which is required or deemed to be included
in this Indenture by any of the provisions of the Trust Indenture Act, the
provision or requirement of the Trust Indenture Act shall control. If any
provision of this Indenture modifies or excludes any provision of the Trust
Indenture Act that may be so modified or excluded, such provision of the Trust
Indenture Act shall be deemed to apply to this Indenture as so modified or to
be excluded, as the case may be.

                  SECTION 1.09. Effect of Headings and Table of Contents. The
Article and Section headings herein and the Table of Contents are for
convenience only and shall not affect the construction hereof.

                  SECTION 1.10.  Successors and Assigns.  All covenants and
agreements in this Indenture by Publishing or any Guarantor shall bind its
successors and assigns, whether so expressed or not.

                  SECTION 1.11. Separability Clause. In case any provision in
this Indenture or in the Securities of any Series shall be invalid, illegal or
unenforceable, the

<PAGE>   55
                                                                          - 45 -

validity, legality and enforceability of the remaining provisions shall not in
any way be affected or impaired thereby.

                  SECTION 1.12. Benefits of Indenture. Nothing in this
Indenture or in the Securities, express or implied, shall give to any Person
(other than the parties hereto and their successors hereunder, any Paying Agent
and the Holders) any benefit or any legal or equitable right, remedy or claim
under this Indenture.

                  SECTION 1.13. GOVERNING LAW. THIS INDENTURE AND THE
SECURITIES SHALL BE GOVERNED BY, AND CONSTRUED IN ACCORDANCE WITH, THE LAWS OF
THE STATE OF NEW YORK (WITHOUT GIVING EFFECT TO THE CONFLICT OF LAWS PRINCIPLES
THEREOF).

                  SECTION 1.14. Legal Holidays. In any case where any Interest
Payment Date, Redemption Date or Stated Maturity of any Security shall not be a
Business Day, then (notwithstanding any other provision of this Indenture or of
the Securities) payment of interest or principal or premium, if any, need not
be made on such date, but may be made on the next succeeding Business Day with
the same force and effect as if made on the Interest Payment Date or Redemption
Date, or at Maturity or the Stated Maturity, and no interest shall accrue with
respect to such payment for the period from and after such Interest Payment
Date, Redemption Date, Maturity or Stated Maturity, as the case may be, to the
next succeeding Business Day.

                  SECTION 1.15.  Schedules.  All schedules attached hereto are
by this reference made a part with the same effect as if herein set forth in
full.

                  SECTION 1.16.  Counterparts.  This Indenture may be executed
in any number of counterparts, each of which shall be an original; but such
counterparts shall together constitute but one and the same instrument.

                                   ARTICLE II

                                 Security Forms

                  SECTION 2.01. Forms Generally. The Securities and the
Trustee's certificate of authentication thereof shall be in substantially the
forms set forth in this Article II, with such appropriate insertions,
omissions, substitutions and other variations as are required or permitted by
this Indenture and may have such letters, numbers or other marks of
identification and such legends or


<PAGE>   56
                                                                          - 46 -

endorsements placed thereon as may be required to comply with the rules of any
securities exchange, any organizational document or governing instrument or
applicable law or as may, consistently herewith, be determined by the officers
executing such Securities, as evidenced by their execution of the Securities.
Any portion of the text of any Security may be set forth on the reverse
thereof, with an appropriate reference thereto on the face of the Security.

                  The definitive Securities shall be printed, lithographed or
engraved or produced by any combination of these methods or may be produced in
any other manner permitted by the rules of any securities exchange on which the
Securities may be listed, all as determined by the officers executing such
Securities, as evidenced by their execution of such Securities.

                  SECTION 2.02. Forms of Securities. Each Security shall be in
one of the forms approved from time to time by or pursuant to a Board
Resolution, or established in one or more indentures supplemental hereto. Prior
to the delivery of a Security to the Trustee for authentication in any form
approved by or pursuant to a Board Resolution, Publishing shall deliver to the
Trustee the Board Resolution by or pursuant to which such form of Security has
been approved, which Board Resolution shall have attached thereto a true and
correct copy of the form of Security which has been approved thereby or, if a
Board Resolution authorizes a specific officer or officers to approve of form
of Security, a certificate of such officer or officers approving the form of
Security attached thereto. Any form of Security approved by or pursuant to a
Board Resolution must be acceptable as to form to the Trustee, such acceptance
to be evidenced by the Trustee's authentication of Securities in that form or a
certificate signed by a Responsible Officer of the Trustee and delivered to
Publishing.


<PAGE>   57


                                                                          - 47 -

                  SECTION 2.03.  Form of Trustee's Certificate of
Authentication.  The Trustee's certificate of authentication shall be included
on the form of the face of the Securities substantially in the following form:

                  TRUSTEE'S CERTIFICATE OF AUTHENTICATION.

                  This is one of the Securities referred to in the
within-mentioned Indenture.

                                                FLEET NATIONAL BANK, as
                                                Trustee

                                                by  _________________________
                                                    Authorized Signatory

                  SECTION 2.04.  Form of Guarantee of Hollinger International.

                  The form of Guarantee of Hollinger International shall be set
forth on the Securities substantially as follows:

                   GUARANTEE OF HOLLINGER INTERNATIONAL INC.

                  For value received, HOLLINGER INTERNATIONAL INC., a Delaware
corporation, hereby absolutely, unconditionally and irrevocably guarantees to
the holder of this Security and the Trustee, as if Hollinger International were
the principal debtor, the punctual payment of principal of, premium, if any,
and interest on this Security in the amounts and at the time when due and
interest on the overdue principal and interest, if any, of this Security, if
lawful, and the payment or performance of all other obligations of Publishing
under the Indenture or the Securities, to the holder of this Security and the
Trustee, all in accordance with and subject to the terms and limitations of
this Security and Article Fourteen of the Indenture. This Guarantee will not
become effective until the Trustee duly executes the certificate of
authentication on this Security.

                                                 HOLLINGER INTERNATIONAL INC.

Attest:_____________________                     By_______________________
                                                   Authorized Signatory


<PAGE>   58


                                                                          - 48 -

                  SECTION 2.05. Securities Issuable in the Form of a Global
Security. (a) If Publishing shall establish pursuant to Sections 2.02 and 3.01
that the Securities of a particular Series are to be issued in whole or in part
in the form of one or more Global Securities, then Publishing shall execute and
the Trustee or its agent shall, in accordance with Section 3.03 and any order
by Publishing delivered to the Trustee or its agent thereunder, authenticate
and deliver, such Global Security or Securities, which (i) shall represent, and
shall be denominated in an amount equal to the aggregate principal amount of,
the Outstanding Securities of such Series to be represented by such Global
Security or Securities, or such portion thereof as Publishing shall specify in
such order, (ii) shall be registered in the name of the Depository for such
Global Security or Securities or its nominee, (iii) shall be delivered by the
Trustee or its agent to the Depository or pursuant to the Depository's
instruction and (iv) shall bear a legend substantially to the following effect:
"Unless this certificate is presented by an authorized representative of the
Depository to Issuer or its agent for registration of transfer, exchange, or
payment, and any certificate issued is registered in the name of the nominee of
the Depository or in such other name as is requested by an authorized
representative of the Depository (and any payment is made to the nominee of the
Depository or to such other entity as is requested by an authorized
representative of the Depository), ANY TRANSFER, PLEDGE, OR OTHER USE HEREOF
FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL inasmuch as the
registered owner hereof, the nominee of the Depository, has an interest
herein."

                  (b) Notwithstanding any other provision of this Section 2.05
or of Section 3.05, and subject to the provisions of paragraph (c) below,
unless the terms of a Global Security expressly permit such Global Security to
be exchanged in whole or in part for individual Securities, a Global Security
may be transferred, in whole but not in part and in the manner provided in
Section 3.05, only to a nominee of the Depository for such Global Security, or
to the Depository, or a successor Depository for such Global Security selected
or approved by the Company, or to a nominee of such successor Depository.

                  (c) (i) If at any time the Depository for a Global Security
notifies Publishing that it is unwilling or unable to continue as Depository
for such Global Security or if at any time the Depository for the Securities
for such Series shall no longer be eligible or in good standing under the
Securities Exchange Act of 1934, as amended, or other applicable statute or
regulation, Publishing shall appoint a


<PAGE>   59
                                                                          - 49 -

successor Depository with respect to such Global Security. If a successor
Depository for such Global Security is not appointed by Publishing within 90
days after Publishing receives such notice or becomes aware of such
ineligibility, Publishing will execute, and the Trustee or its agent, upon
receipt of a request by Publishing for the authentication and delivery of
individual Securities of such Series in exchange for such Global Security, will
authenticate and deliver, individual Securities of such Series of like tenor
and terms in an aggregate principal amount equal to the principal amount of the
Global Security in exchange for such Global Security.

                (ii) Publishing may at any time and in its sole discretion
determine that the Securities of any Series or portion thereof issued or
issuable in the form of one or more Global Securities shall no longer be
represented by such Global Security or Securities. In such event Publishing
will execute, and the Trustee, upon receipt of a Company Request for the
authentication and delivery of individual Securities of such Series in exchange
in whole or in part for such Global Security, will authenticate and deliver
individual Securities of such Series of like tenor and terms in definitive form
in an aggregate principal amount equal to the principal amount of such Global
Security or Securities representing such Series or portion thereof in exchange
for such Global Security or Securities.

              (iii) If specified by Publishing pursuant to Sections 2.02 and
3.01 with respect to Securities issued or issuable in the form of a Global
Security, the Depository for such Global Security may surrender such Global
Security in exchange in whole or in part for individual Securities of such
Series of like tenor and terms in definitive form on such terms as are
acceptable to Publishing and such Depository. Thereupon Publishing shall
execute, and the Trustee or its agent shall authenticate and deliver, without
service charge, (1) to each Person specified by such Depository a new Security
or Securities of the same Series of like tenor and terms and of any authorized
denomination as requested by such Person in aggregate principal amount equal to
and in exchange for such Person's beneficial interest as specified by such
Depository in the Global Security; and (2) to such Depository a new Global
Security of like tenor and terms and in an authorized denomination equal to the
difference, if any, between the principal amount of the surrendered Global
Security and the aggregate principal amount of Securities delivered to Holders
thereof.

                (iv) In any exchange provided for in any of the preceding three
paragraphs, Publishing will execute and the


<PAGE>   60
                                                                          - 50 -

Trustee or its agent will authenticate and deliver individual Securities in
definitive registered form in authorized denominations. Upon the exchange of
the entire principal amount of a Global Security for individual Securities,
such Global Security shall be cancelled by the Trustee or its agent. Except as
provided in the preceding paragraph, Securities issued in exchange for a Global
Security pursuant to this Section shall be registered in such names and in such
authorized denominations as the Depository for such Global Security, pursuant
to instructions from its direct or indirect participants or otherwise, shall
instruct the Trustee or the Security Registrar. The Trustee or the Security
Registrar shall deliver at its Corporate Trust Office such Securities to the
Persons in whose names such Securities are so registered.

                                  ARTICLE III

                                 The Securities

                  SECTION 3.01.  General Title; General Limitations; Issuable
in Series; Terms of Particular Series.  The aggregate principal amount of
Securities which may be authenticated and delivered under this Indenture is not
limited.

                  The Securities may be issued in one or more Series as from
time to time may be authorized by the Board of Directors. There shall be
established in or pursuant to a Board Resolution or in a supplemental
indenture, subject to Section 3.11, prior to the issuance of Securities of any
such Series:

                  (1) the title of the Securities of such Series (which shall
         distinguish the Securities of such Series from Securities of any other
         Series);

                  (2) any limit upon the aggregate principal amount of the
         Securities of such Series which may be authenticated and delivered
         under this Indenture (except for Securities authenticated and
         delivered upon registration of transfer of, or in exchange for, or in
         lieu of, other Securities of such Series pursuant to Section 3.04,
         3.05, 3.06, 9.06, and 11.08 and except for any Securities which,
         pursuant to Section 3.03, are deemed never to have been authenticated
         and delivered hereunder);

                  (3) the Person to whom any interest on a Security of such
         Series shall be payable, if other than the


<PAGE>   61
                                                                          - 51 -

         Person in whose name that Security (or one or more Predecessor
         Securities) is registered at the close of business on the Regular
         Record Date for such interest;

                  (4) the date or dates on which the principal of the
         Securities of such Series is payable;

                  (5) the rate or rates at which the Securities of such Series
         shall bear interest, if any, the date or dates from which such
         interest shall accrue, the Interest Payment Dates on which any such
         interest shall be payable and the Regular Record Date for any interest
         payable on any Interest Payment Date;

                  (6) the place or places where the principal of and any
         premium and interest on Securities of such Series shall be payable;

                  (7) the price or prices at which the Securities of such
         Series shall be issued;

                  (8) the period or periods within which the Redemption Price
         or Prices at which and the terms and conditions upon which Securities
         of such Series may be redeemed or repaid, as the case may be, in whole
         or in part, at the option of Publishing or the Holder;

                  (9) the obligation, if any, of Publishing to purchase
         Securities of such Series pursuant to any sinking fund or analogous
         provisions or at the option of a Holder thereof and the period or
         periods within which, the price or prices at which and the terms and
         conditions upon which Securities of such Series shall be purchased, in
         whole or in part, pursuant to such obligation;

                (10) provisions, if any, with regard to the conversion or
         exchange of the Securities of such Series, at the option of the
         Holders thereof or the Company, as the case may be, for or into new
         Securities of a different Series, Common Stock or other securities
         and, if the Securities of such Series are convertible into Common
         Stock or other Marketable Securities, the Conversion Price therefor;

                (11) any terms applicable to Securities of such Series issued
         at an issue price below their stated principal amount, including the
         issue price thereof and the rate or rates at which such original issue
         discount will occur;

<PAGE>   62
                                                                          - 52 -

                (12) if other than denominations of $1,000 and any integral
         multiple thereof, the denominations in which Securities of such Series
         shall be issuable;

                (13) if other than U.S. dollars, the currency or currencies or
         units based on or related to currencies in which the Securities of
         such Series shall be denominated and in which payments of principal
         of, and any premium and interest on, such Securities shall or may be
         payable;

                (14) if the amount of payments of principal of (and premium, if
         any) or interest, if any, on the Securities of such Series may be
         determined with reference to an index based on a coin or currency
         (including a composite currency) other than that in which the
         Securities are stated to be payable, the manner in which such amounts
         shall be determined;

                (15) if the principal of (and premium, if any) or interest, if
         any, on the Securities of such Series are to be payable, at the
         election of Publishing or a Holder thereof, in a coin or currency
         (including a composite currency) other than that in which the
         Securities are stated to be payable, the period or periods within
         which, and the terms and conditions upon which, such election may be
         made;

                (16) the portion of the principal amount of Securities of the
         Series, if other than the principal amount thereof, which shall be
         payable upon declaration of acceleration of the Maturity thereof
         pursuant to Section 5.02 or provable in bankruptcy pursuant to Section
         5.04;

                (17) any Event of Default with respect to the Securities of
         such Series, if not set forth herein, and any additions, deletions or
         other changes to the Events of Default set forth herein that shall be
         applicable to the Securities of such Series;

                (18) any special United States Federal income tax
         considerations applicable to the Securities of such Series;

                (19) if the Securities of such Series shall be issued in whole
         or in part in the form of a Global Security or Securities, the terms
         and conditions, if any, upon which such Global Security or Securities
         may be exchanged in whole or in part for other individual


<PAGE>   63
                                                                          - 53 -

         Securities; and the Depository for such Global Security or Securities;
and

                (20) any other terms of such Series,

all upon such terms as may be determined in or pursuant to such Board
Resolution or supplemental indenture with respect to such Series.

                  The form of the Securities of each Series shall be
established pursuant to the provisions of this Indenture in or pursuant to the
Board Resolution or in the supplemental indenture creating such Series. The
Securities of each Series shall be distinguished from the Securities of each
other Series in such manner, reasonably satisfactory to the Trustee, as the
Board of Directors may determine.

                  Unless otherwise provided with respect to Securities of a
particular Series, the Securities of any Series may only be issuable in
registered form, without coupons.

                  Any terms or provisions in respect of the Securities of any
Series issued under this Indenture may be determined pursuant to this Section
by providing for the method by which such terms or provisions shall be
determined.

                  SECTION 3.02. Denominations. The Securities of each Series
shall be issuable in such denominations and currency as shall be provided in
the provisions of this Indenture or in or pursuant to the Board Resolution or
the supplemental indenture creating such Series. In the absence of any such
provisions with respect to the Securities of any Series, the Securities of that
Series shall be issuable only in fully registered form in denominations of
$1,000 and any integral multiple thereof.

                  The Securities shall be redeemable as provided in Article XI.

                  At the election of Publishing, the entire indebtedness on the
Securities or certain of Publishing's obligations and covenants and certain
Events of Default thereunder may be defeased as provided in Article IV.

                  The Securities shall be subordinated in right of payment to
Senior Indebtedness as provided in Article XII.

                  SECTION 3.03. Execution, Authentication, Delivery and Dating.
The Securities shall be executed on behalf of


<PAGE>   64
                                                                          - 54 -

Publishing by one of its Chairman of the Board, Vice-Chairman, President or one
of its Vice Presidents under its corporate seal reproduced thereon attested by
its Secretary or one of its Assistant Secretaries. The signature of any of
these officers on the Securities may be manual or facsimile.

                  Securities bearing the manual or facsimile signatures of
individuals who were at any time the proper officers of Publishing shall bind
Publishing, notwithstanding that such individuals or any of them have ceased to
hold such offices prior to the authentication and delivery of such Securities
or did not hold such offices on the date of such Securities.

                  At any time and from time to time after the execution and
delivery of this Indenture, Publishing may deliver Securities executed by
Publishing to the Trustee for authentication, together with a Publishing Order
for the authentication and delivery of such Securities; and the Trustee in
accordance with such Company Order shall authenticate and deliver such
Securities as provided in this Indenture and not otherwise.

                  Each Security shall be dated the date of its authentication.

                  No Security shall be entitled to any benefit under this
Indenture or be valid or obligatory for any purpose unless there appears on
such Security a certificate of authentication substantially in the form
provided for herein duly executed by the Trustee by manual signature of an
authorized signatory, and such certificate upon any Security shall be
conclusive evidence, and the only evidence, that such Security has been duly
authenticated and delivered hereunder and is entitled to the benefits of this
Indenture.

                  In case Publishing, pursuant to Article VIII, shall be
consolidated or merged with or into any other Person or shall sell, convey,
assign, transfer, lease or otherwise dispose of substantially all of its
properties and assets to any Person, and the successor Person resulting from
such consolidation, or surviving such merger, or into which Publishing shall
have been merged or consolidated, or the successor Person which shall have
received a conveyance, transfer, lease or other disposition as aforesaid, shall
have executed an indenture supplemental hereto with the Trustee pursuant to
Article VIII, any of the Securities authenticated or delivered prior to such
consolidation, merger, conveyance, transfer, lease or other disposition may,
from time to time, at the request of the successor


<PAGE>   65
                                                                          - 55 -

Person, be exchanged for other Securities executed in the name of the successor
Person with such changes in phraseology and form as may be appropriate, but
otherwise in substance of like tenor as the Securities surrendered for such
exchange and of like principal amount; and the Trustee, upon a Publishing
Request of the successor Person, shall authenticate and deliver Securities as
specified in such request for the purpose of such exchange. If Securities shall
at any time be authenticated and delivered in any new name of a successor
Person pursuant to this Section in exchange or substitution for or upon
registration of transfer of any Securities, such successor Person, at the
option of a Holder but without expense to such Holder, shall provide for the
exchange of all Securities at the time Outstanding held by such Holder for
Securities authenticated and delivered in such new name.

                  The Trustee may appoint an authenticating agent reasonably
acceptable to Publishing to authenticate Securities on behalf of the Trustee.
Unless limited by the terms of such appointment, an authenticating agent may
authenticate Securities whenever the Trustee may do so. Each reference in this
Indenture to authentication by the Trustee includes authentication by such
agent. An authenticating agent has the same rights as any Security Registrar or
Paying Agent to deal with Publishing and its Affiliates.

                  SECTION 3.04. Temporary Securities. Pending the preparation
of definitive Securities of any Series, Publishing may execute, and upon a
Publishing Order the Trustee shall authenticate and deliver, temporary
Securities which are printed, lithographed, typewritten or otherwise produced,
in any authorized denomination, substantially of the tenor of the definitive
Securities in lieu of which they are issued and with such appropriate
insertions, omissions, substitutions and other variations as the officers
executing such Securities may determine, as conclusively evidenced by their
execution of such Securities.

                  If temporary Securities of any Series are issued, Publishing
will cause definitive Securities to be prepared without unreasonable delay.
After the preparation of definitive Securities, the temporary Securities shall
be exchangeable for definitive Securities upon surrender of the temporary
Securities at the office or agency of Publishing designated for such purpose
pursuant to Section 10.02 (or in accordance with Section 3.03, in the case of
the initial Securities), without charge to the Holders thereof. Upon surrender
for cancellation of any one or more temporary Securities, Publishing shall
execute and upon a Publishing


<PAGE>   66
                                                                          - 56 -

Order the Trustee shall authenticate and deliver in exchange therefor a like
principal amount of definitive Securities of such Series of authorized
denominations. Until so exchanged the temporary Securities of such Series shall
in all respects be entitled to the same benefits under this Indenture as
definitive Securities.

                  SECTION 3.05. Registration, Registration of Transfer and
Exchange. Publishing shall cause to be kept at the Corporate Trust Office of
the Trustee, or such other office as the Trustee may designate, a register (the
register maintained in such office and in any other office or agency designated
pursuant to Section 10.02 being herein sometimes referred to as the "Security
Register") in which, subject to such reasonable regulations as the Security
Registrar may prescribe, Publishing shall provide for the registration of
Securities, or of Securities of a particular Series, and of transfers of
Securities or of Securities of such Series. The Trustee or an agent thereof or
of Publishing shall initially be the "Security Registrar" for the purpose of
registering Securities and transfers of Securities as herein provided.
Publishing may appoint one or more co-registrars, but there shall be only one
Security Register per Series of Securities.

                  Upon surrender for registration of transfer of any Security
at the office or agency of Publishing designated pursuant to Section 10.02,
Publishing shall execute, and the Trustee shall authenticate and deliver, in
the name of the designated transferee or transferees, one or more new
Securities of such Series of any authorized denomination or denominations, of a
like aggregate principal amount.

                  At the option of the Holder, Securities may be exchanged for
other Securities of any authorized denomination or denominations, of a like
aggregate principal amount, upon surrender of the Securities to be exchanged at
such office or agency. Whenever any Securities are so surrendered for exchange,
Publishing shall execute, and the Trustee shall authenticate and deliver, the
Securities which the Holder making the exchange is entitled to receive.

                  All Securities issued upon any registration of transfer or
exchange of Securities shall be the valid obligations of Publishing, evidencing
the same Indebtedness, and entitled to the same benefits under this Indenture,
as the Securities surrendered upon such registration of transfer or exchange.

                  Every Security presented or surrendered for registration of
transfer, or for exchange or redemption,


<PAGE>   67
                                                                          - 57 -
shall (if so required by Publishing or the Trustee) be duly endorsed, or be
accompanied by a written instrument of transfer in form satisfactory to
Publishing, the Trustee and the Security Registrar, duly executed by the Holder
thereof or such Holder's attorney duly authorized in writing.

                  No service charge shall be made to a Holder for any
registration of, transfer, exchange or redemption of Securities, but Publishing
or the Trustee may require payment of a sum sufficient to pay all or other
governmental charges that may be imposed in connection with any registration
of, transfer, exchange or redemption of Securities, other than exchanges
pursuant to Section 3.03 3.04, 3.06, 9.06, 10.14, 10.16 or 11.08 not involving
any transfer.

                  Publishing shall not be required (a) to issue, register the
transfer of or exchange any Security of any Series during a period beginning at
the opening of business (i) 15 days before the mailing of a notice of
redemption of the Securities selected for redemption under Section 11.04 and
ending at the close of business on the day of such mailing or (ii) 15 days
before an Interest Payment Date and ending on the close of business on the
Interest Payment Date, or (b) to register the transfer of or exchange any
Security so selected for redemption in whole or in part, except the unredeemed
portion of Securities being redeemed in part.

                  None of Publishing, the Trustee, any agent of the Trustee,
any Paying Agent or the Security Registrar will have any responsibility or
liability for any aspect of the records relating to or payments made on account
of beneficial ownership interests of a Global Security or for maintaining,
supervising or reviewing any records relating to such beneficial ownership
interests.

                  SECTION 3.06. Mutilated, Destroyed, Lost and Stolen
Securities. If (a) any mutilated Security is surrendered to the Trustee, or (b)
Publishing and the Trustee receive evidence to their satisfaction of the
destruction, loss or theft of any Security, and there is delivered to
Publishing or the Trustee, such security and/or indemnity, in each case as may
be required by them to save each of them harmless, then, in the absence of
notice to Publishing or the Trustee that such Security has been acquired by a
bona fide purchaser, Publishing shall execute and upon receipt of a Publishing
Request the Trustee shall authenticate and deliver, in exchange for any such
mutilated Security or in lieu of any such destroyed, lost or stolen


<PAGE>   68
                                                                          - 58 -

Security, a replacement Security of like tenor and principal amount, bearing a
number not contemporaneously outstanding.

                  In case any such mutilated, destroyed, lost or stolen
Security has become or is about to become due and payable, Publishing in its
discretion may, instead of issuing a replacement Security, pay such Security.

                  Upon the issuance of any replacement Securities under this
Section, Publishing may require the payment of a sum sufficient to pay all
documentary, stamp or similar issue or transfer taxes or other governmental
charge that may be imposed in relation thereto and any other expenses
(including the fees and expenses of the Trustee and its agents and counsel)
connected therewith.

                  Every replacement Security issued pursuant to this Section in
lieu of any destroyed, lost or stolen Security shall constitute an original
additional contractual obligation of Publishing, whether or not the destroyed,
lost or stolen Security shall be at any time enforceable by anyone, and shall
be entitled to all benefits of this Indenture equally and proportionately with
any and all other Securities of the same Series duly issued hereunder.

                  The provisions of this Section are exclusive and shall
preclude (to the extent lawful) all other rights and remedies with respect to
the replacement or payment of mutilated, destroyed, lost or stolen Securities.

                  SECTION 3.07.  Payment of Interest; Interest Rights
Preserved.  Interest on any Security which is payable, and is punctually paid
or duly provided for, on the Stated Maturity of such interest shall be paid to
the Person in whose name that Security is registered at the close of business
on the Regular Record Date for such interest payment.

                  Any interest on any Security which is payable, but is not
paid or duly provided for on the Stated Maturity of such interest (or within 15
days after the Stated Maturity of such interest) and interest on such defaulted
interest at the then applicable interest rate borne by the Securities, to the
extent lawful (such defaulted interest and interest thereon herein collectively
called "Defaulted Interest") shall forthwith cease to be payable to the Holder
in whose name such Security is registered as of the Regular Record


<PAGE>   69
                                                                          - 59 -

Date; and such Defaulted Interest may be paid by Publishing, at its election in
each case, as provided in Subsection (a) or (b) below:

                  (a) Publishing may elect to make payment of any Defaulted
         Interest to the Persons in whose names the Securities are registered
         at the close of business on a Special Record Date for the payment of
         such Defaulted Interest, which shall be fixed in the following manner.

                  Publishing shall notify the Trustee in writing of the amount
         of Defaulted Interest proposed to be paid on each Security and the
         date of the proposed payment (the "Special Payment Date"), and at the
         same time Publishing shall irrevocably deposit with the Trustee an
         amount of money equal to the aggregate amount proposed to be paid in
         respect of such Defaulted Interest or shall make arrangements
         satisfactory to the Trustee for such deposit prior to the Special
         Payment Date, such money when deposited to be held in trust for the
         benefit of the Persons entitled to such Defaulted Interest as in this
         Subsection provided.  Such notice shall be received by the Trustee no
         less than 30 days prior to the Special Payment Date. Thereupon the
         Trustee shall fix a Special Record Date for the payment of such
         Defaulted Interest which Special Record Date shall be not more than 15
         days and not less than 10 days prior to the Special Payment Date and
         not less than 10 days after the receipt by the Trustee of the notice
         of the proposed payment. The Trustee shall promptly notify Publishing
         in writing of such Special Record Date. In the name and at the expense
         of Publishing, the Trustee shall cause notice of the proposed payment
         of such Defaulted Interest and the Special Record Date and Special
         Payment Date therefor to be mailed, certified or registered (return
         receipt requested) first-class postage prepaid, to each Holder at his
         address as it appears in the Security Register, not less than 10 days
         prior to such Special Record Date.  Notice of the Proposed payment of
         such Defaulted Interest and the Special Record Date therefor having
         been so mailed, such Defaulted Interest shall be paid to the Persons
         in whose names the Securities are registered on such Special Record
         Date and shall no longer be payable pursuant to the following
         Subsection (b).

                  (b) Publishing may make payment to the Persons in whose name
         the Securities are registered at the close of business on the Special
         Record Date of any Defaulted Interest in any other lawful manner not
         inconsistent


<PAGE>   70
                                                                          - 60 -

         with the requirements of any securities exchange on which the
         Securities may be listed, and upon such notice as may be required by
         such exchange, unless, after written notice given by Publishing to the
         Trustee of the proposed payment pursuant to this Subsection, such
         manner of payment shall not be deemed practicable by the Trustee
         (acting reasonably). The Trustee shall give prompt written notice to
         Publishing of any such determination.

                  Subject to the foregoing provisions of this Section 3.07,
each Security delivered under this Indenture upon registration of transfer of
or in exchange for or in lieu of any other Security shall carry the rights to
interest accrued and unpaid, and to accrue, which were carried by such other
Security.

                  SECTION 3.08. Persons Deemed Owners. Prior to due presentment
of a Security for registration of transfer, Publishing, the Trustee and any
agent of Publishing or the Trustee may treat the Person in whose name any
Security is registered on the Security Register as the owner of such Security
for the purpose of receiving payment of principal of, premium, if any, and
(subject to Section 3.07) interest on such Security and for all other purposes
whatsoever, whether or not such Security is overdue, and none of Publishing,
the Trustee or any agent of Publishing or the Trustee shall be affected by
notice to the contrary.

                  None of the Company, the Trustee, any Paying Agent or the
Security Registrar will have any responsibility or liability for any aspect of
the records relating to or payments made on account of beneficial ownership
interests in a Global Security or for maintaining, supervising or reviewing any
records relating to such beneficial ownership interests.

                  SECTION 3.09. Cancellation. All Securities surrendered for
payment, purchase, redemption, registration of transfer or exchange shall be
delivered to the Trustee and, if not already canceled, shall be promptly
canceled by it. Publishing or any Restricted Subsidiary may at any time deliver
to the Trustee for cancellation any Securities previously authenticated and
delivered hereunder which Publishing or any such Restricted Subsidiary may have
acquired in any manner whatsoever, and all Securities so delivered shall upon
receipt of a Publishing Order be promptly canceled by the Trustee. No
Securities shall be authenticated in lieu of or in exchange for any Securities
canceled as provided in this Section, except as expressly permitted by this
Indenture. All canceled securities held


<PAGE>   71
                                                                          - 61 -

by the Trustee shall, unless by a Publishing Order received by the Trustee
prior to such destruction Publishing shall direct that the canceled Securities
be returned to it, be destroyed in accordance with its customary procedures and
certification of their destruction delivered to Publishing. The Trustee shall
provide Publishing a list of all Securities that have been canceled from time
to time as requested by Publishing.

                  SECTION 3.10.  Computation of Interest.  Unless otherwise
provided as contemplated in Section 3.01, interest on the Securities shall be
computed on the basis of a 360-day year of twelve 30-day months.

                  SECTION 3.11. Delayed Issuance of Securities. Notwithstanding
any contrary provision herein, if all Securities of a Series are not to be
originally issued at one time, it shall not be necessary for Publishing to
deliver to the Trustee an Officers' Certificate, Board Resolution, supplemental
indenture or Opinion of Counsel otherwise required pursuant to Sections 1.03,
2.02, 3.01 and 3.03 at or prior to the time of authentication of each Security
of such Series if such documents are delivered to the Trustee or its agent at
or prior to the authentication upon original issuance of the first Security of
such Series to be issued; provided that any subsequent request by Publishing to
the Trustee to authenticate Securities of such Series upon original issuance
shall constitute a representation and warranty by Publishing that as of the
date of such request, the statements made in the Officers' Certificate or other
certificates delivered pursuant to Sections 1.02 and 2.02 shall be true and
correct as if made on such date.

                  An Officers' Certificate or Board Resolution or supplemental
indenture delivered by Publishing to the Trustee in the circumstances set forth
in the preceding paragraph may provide that Securities which are the subject
thereof will be authenticated and delivered by the Trustee or its agent on
original issue from time to time in the aggregate principal amount, if any,
established for such Series pursuant to such procedures acceptable to the
Trustee as may be specified from time to time upon the telephonic, electronic
or written order of Persons designated in such Officers' Certificate,
supplemental indenture or Board Resolution (any such telephonic or electronic
instructions to be promptly confirmed in writing by such Persons) and that such
Persons are authorized to determine, consistent with such Officers'
Certificate, supplemental indenture or Board Resolution, such terms and
conditions of said


<PAGE>   72
                                                                          - 62 -

Securities as are specified in such Officers' Certificate, supplemental
indenture or Board Resolution.

                                   ARTICLE IV

                       Defeasance and Covenant Defeasance

                  SECTION 4.01. Publishing's Option To Effect Defeasance or
Covenant Defeasance. Publishing may, at its option by Board Resolution, at any
time, with respect to any Series of Securities, elect to have either Section
4.02 or Section 4.03 be applied to all of the Outstanding Securities of such
Series (the "Defeased Securities"), upon compliance with the conditions set
forth below in this Article IV.

                  SECTION 4.02. Defeasance and Discharge. Upon Publishing's
exercise under Section 4.01 of the option applicable to this Section 4.02,
Publishing shall be deemed to have been discharged from its obligations with
respect to the Defeased Securities on the date the conditions set forth below
are satisfied (hereinafter, "defeasance") and each Guarantor shall be deemed to
be discharged from its obligations with respect to its Guarantee relating to
the Defeased Securities. For this purpose, such defeasance means that
Publishing shall be deemed to have paid and discharged the entire indebtedness
represented by the Defeased Securities, which shall thereafter be deemed to be
"Outstanding" only for the purposes of Section 4.05 and the other Sections of
this Indenture referred to in (a) and (b) below, and to have satisfied all its
other obligations under such Securities and this Indenture insofar as such
Securities are concerned (and the Trustee, at the expense of Publishing and
upon written request, shall execute proper instruments acknowledging the same),
except for the following which shall survive until otherwise terminated or
discharged hereunder: (a) the rights of Holders of Defeased Securities to
receive, solely from the trust fund described in Section 4.04 and as more fully
set forth in such Section, payments in respect of the principal of, premium, if
any, and interest on such Securities when such payments are due, (b)
Publishing's obligations with respect to such Defeased Securities under
Sections 3.04, 3.05, 3.06, 10.02 and 10.03, (c) the rights, powers, trusts,
duties, indemnities and immunities of the Trustee hereunder, and (d) this
Article IV. Subject to compliance with this Article IV, Publishing may exercise
its option under this Section 4.02 notwithstanding the prior exercise of its
option under Section 4.03 with respect to the Securities.

<PAGE>   73
                                                                          - 63 -

                  SECTION 4.03. Covenant Defeasance. Upon Publishing's exercise
under Section 4.01 of the option applicable to this Section 4.03, Publishing
shall be released from its obligations under any covenant or provision
contained in Sections 10.05 through 10.19, inclusive, and the provisions of
Article XII and Sections 14.16 through 14.29 shall not apply, with respect to
the Defeased Securities on and after the date the conditions set forth below
are satisfied (hereinafter, "covenant defeasance"), and the Defeased Securities
shall thereafter be deemed to be not "Outstanding" for the purposes of any
direction, waiver, consent or declaration or Act of Holders (and the
consequences of any thereof) in connection with such covenants and provisions,
but shall continue to be deemed "Outstanding" for all other purposes hereunder.
For this purpose, such covenant defeasance means that, with respect to the
Defeased Securities, Publishing may omit to comply with and shall have no
liability in respect of any term, condition or limitation set forth in any such
Section or Article, whether directly or indirectly, by reason of any reference
elsewhere herein or in such Defeased Securities to any such Section or Article
or by reason of any reference in any such Section or Article to any other
provision herein or in any other document and such omission to comply shall not
constitute a Default or an Event of Default under Section 5.01(c), (d) or (f)
but, except as specified above, the remainder of this Indenture and such
Defeased Securities shall be unaffected thereby.

                  SECTION 4.04.  Conditions to Defeasance or Covenant
Defeasance.  The following shall be the conditions to application of either
Section 4.02 or Section 4.03 to the Defeased Securities:

                  (1) Publishing shall irrevocably have deposited or caused to
be deposited with the Trustee as trust funds in trust for the purpose of making
the following payments, specifically pledged as security for, and dedicated
solely to, the benefit of the Holders of such Series of Securities, (a) United
States dollars in an amount, (b) U.S. Government Obligations which through the
scheduled payment of principal and interest in respect thereof in accordance
with their terms will provide, not later than one day before the due date of
any payment, money in an amount, or (c) a combination thereof, in such amounts
as will be sufficient, as reflected in the written report of a nationally
recognized firm of independent public accountants or a nationally recognized
investment banking firm delivered to the Trustee, to pay and discharge (and
which shall be applied by the Trustee to pay and discharge) the principal of,
premium, if any, and interest on, the Defeased


<PAGE>   74
                                                                          - 64 -

Securities on (x) the Stated Maturity thereof or (y) any date selected by
Publishing on which the Defeased Securities may be redeemed in whole at the
option of Publishing (such date being referred to as the "Defeasance Redemption
Date"), if (in the case of clause (y)) when electing either defeasance or
covenant defeasance, Publishing has delivered to the Trustee an irrevocable
notice to redeem all of the outstanding Securities of such Series on the
Defeasance Redemption Date) of such principal or installment of interest;
provided that the Trustee (or such qualifying trustee) shall have been
irrevocably instructed to apply such United States dollars or the proceeds of
such U.S. Government Obligations to said payments with respect to the
Securities of such Series. For this purpose, "U.S. Government Obligations"
means securities that are (i) direct obligations of the United States of
America for the timely payment of which its full faith and credit is pledged or
(ii) obligations of a Person controlled or supervised by and acting as an
agency or instrumentality of the United States of America the timely payment of
which is unconditionally guaranteed as a full faith and credit obligation by
the United States of America, which, in either case, are not callable or
redeemable at the option of the issuer thereof, and shall also include a
depository receipt issued by a bank (as defined in Section 3(a)(2) of the
Securities Act), as custodian with respect to any such U.S. Government
Obligation or a specific payment of principal of or interest on any such U.S.
Government Obligation held by such custodian for the account of the holder of
such depository receipt; provided that (except as required by law) such
custodian is not authorized to make any deduction from the amount payable to
the holder of such depository receipt from any amount received by the custodian
in respect of the U.S. Government Obligation or the specific payment of
principal of or interest on the U.S. Government Obligation evidenced by such
depository receipt.

                  (2) In the case of an election under Section 4.02, Publishing
shall have delivered to the Trustee an Opinion of Independent Counsel in the
United States to the effect that (A) Publishing has received from, or there has
been published by, the Internal Revenue Service a ruling or (B) since the date
of this Indenture, there has been a change in the applicable Federal income tax
law, in either case to the effect that the Holders of the Outstanding
Securities of such Series will not recognize income, gain or loss for Federal
income tax purposes as a result of such defeasance and will be subject to
Federal income tax on the same amounts, in the same manner and at the same
times as would have been the case if such defeasance had not occurred.

<PAGE>   75
                                                                          - 65 -

                  (3) In the case of an election under Section 4.03, Publishing
shall have delivered to the Trustee an Opinion of Independent Counsel in the
United States to the effect that the Holders of the Outstanding Securities of
such Series will not recognize income, gain or loss for Federal income tax
purposes as a result of such covenant defeasance and will be subject to federal
income tax on the same amounts, in the same manner and at the same times as
would have been the case if such covenant defeasance had not occurred.

                  (4) No Default or Event of Default shall have occurred and be
continuing on the date of such deposit or insofar as subsections 5.01(g) and
(h) are concerned, at any time during the period ending on the 121st day after
the date of deposit.

                  (5) Such defeasance or covenant defeasance shall not cause
the Trustee to have a conflicting interest with respect to any securities of
Publishing.

                  (6) Such defeasance or covenant defeasance shall not result
in a breach or violation of, or constitute a Default under, this Indenture or a
breach or violation of any provision of any agreement relating to any Senior
Indebtedness.

                  (7) Publishing shall have delivered to the Trustee an Opinion
of Independent Counsel in the United States to the effect that (A) the trust
funds will not be subject to any rights of holders of Senior Indebtedness,
including without limitation, those arising under this Indenture and (B) after
the 121st day following the deposit, the trust funds will not be subject to the
effect of any applicable bankruptcy, insolvency, reorganization or similar laws
affecting creditors' rights generally.

                  (8) Publishing shall have delivered to the Trustee an
Officers' Certificate stating that the deposit was not made by Publishing with
the intent of preferring the holders of the Securities of such Series over the
other creditors of Publishing or with the intent of defeating, hindering,
delaying or defrauding creditors of Publishing.

                  (9) No event or condition shall exist that would prevent
Publishing from making payments of the principal of, premium, if any, and
interest on the Securities of such Series on the date of such deposit or at any
time ending on the 121st day after the date of such deposit.

<PAGE>   76
                                                                          - 66 -

                (10) Publishing shall have delivered to the Trustee an
Officers' Certificate and an Opinion of Independent Counsel, each to the effect
that all conditions precedent provided for relating to either the defeasance
under Section 4.02 or the covenant defeasance under Section 4.03 (as the case
may be) have been complied with as contemplated by this Section 4.04.

                  Opinions of Counsel required to be delivered under this
Section may have qualifications customary for opinions of the type required and
counsel delivering such Opinions of Counsel may rely on certificates of
Publishing or government or other officials customary for opinions of the type
required, which certificates shall be limited to matters of fact, including
that various financial covenants have been complied with.

                  SECTION 4.05.  Deposited Money and U.S. Government
Obligations To Be Held in Trust; Other Miscellaneous Provisions.  Subject to
the provisions of the last paragraph of Section 10.03, all United States
dollars and U.S. Government Obligations (including the proceeds thereof)
deposited with the Trustee pursuant to Section 4.04 in respect of the Defeased
Securities shall be held in trust and applied by the Trustee, in accordance
with the provisions of such Series of Securities and this Indenture, to the
payment, either directly or through any Paying Agent as the Trustee may
determine, to the Holders of such Series of Securities of all sums due and to
become due thereon in respect of principal, premium, if any, and interest, but
such money need not be segregated from other funds except to the extent
required by law.

                  Publishing shall fully pay and indemnify the Trustee against
any tax, fee or other charge imposed on or assessed against the U.S. Government
Obligations deposited pursuant to Section 4.04 or the principal and interest
received in respect thereof, other than any such tax, fee or other charge which
by law is for the account of the Holders of the Defeased Securities.

                  Anything in this Article IV to the contrary notwithstanding,
the Trustee shall deliver or pay to Publishing from time to time upon a
Publishing Request any United States dollars or U.S. Government Obligations
held by it as provided in Section 4.04 which, in the opinion of a nationally
recognized firm of independent public accountants or nationally recognized
investment banking firm expressed in a written report delivered to the Trustee,
are in excess of the amount thereof which would then be required to be
deposited to effect defeasance or covenant defeasance. In


<PAGE>   77
                                                                          - 67 -

the event of an error in any calculation resulting in a withdrawal hereunder,
Publishing shall deposit an amount equal to the amount erroneously withdrawn as
promptly as practicable after becoming aware of such error.

                  SECTION 4.06. Reinstatement. If the Trustee or Paying Agent
is unable to apply any United States dollars or U.S. Government Obligations in
accordance with Section 4.02 or 4.03, as the case may be, by reason of any
order or judgment of any court or governmental authority enjoining, restraining
or otherwise prohibiting such application, then Publishing's obligations under
this Indenture and the Securities shall be revived and reinstated as though no
deposit had occurred pursuant to Section 4.02 or 4.03, as the case may be,
until such time as the Trustee or Paying Agent is permitted to apply all such
United States dollars or U.S. Government Obligations in accordance with Section
4.02 or 4.03, as the case may be; provided, however, that (a) if Publishing
makes any payment to the Trustee or Paying Agent of principal, premium, if any,
or interest on any Security following the reinstatement of its obligations, the
Trustee or Paying Agent shall promptly pay any such amount to the Holders of
the Securities and Publishing shall be subrogated to the rights of the Holders
of such Securities to receive such payment from the United States dollars and
U.S. Government Obligations held by the Trustee or Paying Agent and (b) the
Trustee or Paying Agent shall return all such United States dollars and U.S.
Government Obligations to Publishing promptly after receiving a Publishing
Request therefor at any time, if the Trustee or Paying Agent receives written
notice from Publishing that such reinstatement of Publishing's obligations has
occurred and continues to be in effect at such time.

                                   ARTICLE V

                                    Remedies

                  SECTION 5.01. Events of Default. "Event of Default", wherever
used herein, means with respect to any Series of Securities any one of the
following events (whatever the reason for such Event of Default and whether it
shall be occasioned by the provisions of Article XII or be voluntary or
involuntary or be effected by operation of law or pursuant to any judgment,
decree or order of any court or any order, rule or regulation of any
administrative or governmental body), unless such event is either inapplicable
to a particular Series or it is specifically


<PAGE>   78
                                                                          - 68 -

modified in or pursuant to the supplemental indenture or Board Resolution
creating such Series of Security or in the form of Security for such Series:

                  (a) there shall be a default in the payment of any interest
         on any Security of that Series when it becomes due and payable, and
         such default shall continue for a period of 30 days;

                  (b) there shall be a default in the payment of the principal
         of (or premium, if any, on) any Security of that Series when and as
         the same shall become due and payable at its Maturity (upon
         acceleration, optional or mandatory redemption, required repurchase or
         otherwise);

                  (c) (i) there shall be a default in the performance, or
         breach, of any covenant or agreement of Publishing under this
         Indenture (other than a default in the performance, or breach, of a
         covenant or agreement which is specifically dealt with in Section
         5.01(a) or (b) or in clauses (ii) or (iii) of this Section 5.01(c)),
         and such default or breach shall continue for a period of 30 days
         after written notice has been given, by certified mail, (x) to
         Publishing by the Trustee or (y) to Publishing and the Trustee by the
         Holders of at least 25% in aggregate principal amount of the
         Outstanding Securities; (ii) there shall be a default in the
         performance or breach of the provisions of Article VIII; or (iii)
         Publishing shall have failed to make or consummate a Change of Control
         Offer in accordance with the provisions of Section 10.15;

                  (d) one or more defaults shall have occurred under any
         agreements, indentures or instruments under which Publishing, any
         Guarantor or any Restricted Subsidiary then has outstanding
         Indebtedness in excess of $5,000,000 in the aggregate and, if not
         already matured at its final maturity in accordance with its terms,
         such Indebtedness shall have been accelerated;

                  (e) any Guarantee relating to such Series shall for any
         reason cease to be, or be asserted in writing by any Guarantor or
         Publishing not to be, in full force and effect, enforceable in
         accordance with its terms, except to the extent contemplated by the
         Indenture and any such Guarantee;

                  (f) one or more final judgments, orders or decrees for the
         payment of money in excess of $5,000,000, either individually or in
         the aggregate, shall be


<PAGE>   79
                                                                          - 69 -

         entered against Publishing, any Guarantor or any Restricted Subsidiary
         or any of their respective properties and shall not be discharged and
         either (i) enforcement proceedings shall have been commenced upon such
         judgment, order or decree or (ii) there shall have been a period of 60
         consecutive days during which a stay of enforcement of such judgment or
         order, by reason of an appeal or otherwise, shall not be in effect;

                  (g) there shall have been the entry by a court of competent
         jurisdiction of (i) a decree or order for relief in respect of
         Publishing, any Guarantor or any Material Restricted Subsidiary in an
         involuntary case or proceeding under any applicable Bankruptcy Law or
         (ii) a decree or order adjudging Publishing, any Guarantor or any
         Material Restricted Subsidiary bankrupt or insolvent, or seeking
         reorganization, arrangement, adjustment or composition of or in
         respect of Publishing, any Guarantor or any Material Restricted
         Subsidiary under any applicable Federal or state law, or appointing a
         custodian, receiver, liquidator, assignee, trustee, sequestrator or
         similar official of Publishing, any Guarantor or any Material
         Restricted Subsidiary or of any substantial part of its property, or
         ordering the winding up or liquidation of its affairs, and any such
         decree or order for relief shall continue to be in effect, or any such
         other decree or order shall be unstayed and in effect, for a period of
         60 consecutive days;

                  (h) (i) Publishing, any Guarantor or any Material Restricted
         Subsidiary commences a voluntary case or proceeding under any
         applicable Bankruptcy Law or any other case or proceeding to be
         adjudicated bankrupt or insolvent, (ii) Publishing, any Guarantor or
         any Material Restricted Subsidiary consents to the entry of a decree
         or order for relief in respect of Publishing, any Guarantor or such
         Material Restricted Subsidiary in an involuntary case or proceeding
         under any applicable Bankruptcy Law or to the commencement of any
         bankruptcy or insolvency case or proceeding against it, (iii)
         Publishing, any Guarantor or any Material Restricted Subsidiary files
         a petition or answer or consent seeking reorganization or relief under
         any applicable Federal or state law, (iv) Publishing, any Guarantor or
         any Material Restricted Subsidiary (x) consents to the filing of such
         petition or the appointment of, or taking possession by, a custodian,
         receiver, liquidator, assignee, trustee, sequestrator or similar
         official of Publishing, any Guarantor or


<PAGE>   80
                                                                          - 70 -

         such Material Restricted Subsidiary or of any substantial part of its
         property, (y) makes an assignment for the benefit of creditors or (z)
         admits in writing its inability to pay its debts generally as they
         become due or (v) Publishing, any Guarantor or any Material Restricted
         Subsidiary takes any corporate action in furtherance of any such
         actions in this paragraph (h); or

                  (i) any outstanding Mirror Preferred shall cease to qualify
         as Mirror Preferred under the definition thereof.

                  SECTION 5.02.  Acceleration of Maturity; Rescission and
Annulment.  If an Event of Default (other than an Event of Default specified in
Sections 5.01(g) and (h) with respect to Publishing) occurs and is continuing
with respect to any Series, the Trustee or the Holders of not less than 25% in
aggregate principal amount of the Outstanding Securities hereunder (each such
Series acting as a separate class) may, and the Trustee upon the request of the
Holders of not less than 25% in aggregate principal amount of the Outstanding
Securities of such Series shall, declare the principal amount (or, if the
Securities of such Series are Original Issue Discount Securities, such portion
of the principal amount as may be specified in the terms of that Series) of all
the Securities of such Series to be due and payable immediately in an amount
equal to the principal amount of the Securities of such Series, together with
accrued and unpaid interest, if any, to the date the Securities of such Series
shall have become due and payable, by a notice in writing to Publishing (and to
the Trustee, if given by Holders) and, if the New Bank Credit Facility is in
effect, to the Agent, and upon any such declaration such amount shall become
immediately due and payable. If an Event of Default specified in Sections
5.01(g) or (h) (if the Event of Default under these paragraphs is with respect
to all Series of Securities then Outstanding) occurs with respect to Publishing
and is continuing, then all the Securities shall ipso facto become and be
immediately due and payable, in an amount equal to the principal amount of the
Securities of any Series (or, if any Securities are Original Issue Discount
Securities, such portion of the principal amount as may be specified in the
terms thereof), together with accrued and unpaid interest, if any, to the date
the Securities become due and payable, without any declaration or other act on
the part of the Trustee or any Holder.

                  At any time after such declaration or acceleration has been
made with respect to the Securities of any or all


<PAGE>   81
                                                                          - 71 -

Series, as the case may be, and before a judgment or decree for payment of the
money due has been obtained by the Trustee as provided hereinafter in this
Article, the Holders of at least a majority in aggregate principal amount of
the Outstanding Securities of such Series, by written notice to Publishing and
the Trustee, may rescind and annul such declaration and its consequences if:

                  (a) Publishing has paid or irrevocably deposited with the
Trustee a sum sufficient to pay

                  (i) all sums paid or advanced by the Trustee under Section
         6.07 and the reasonable compensation, expenses, disbursements and
         advances of the Trustee, its agents and counsel;
 
                 (ii) all overdue interest on all Securities of such Series;

                (iii) the principal and the premium, if any, on any Securities
         of such Series which have become due otherwise than by such declaration
         of acceleration and interest thereon at the rate or rates presented
         therefor by the terms of the Securities of such Series, to the extent
         that payment of such interest is lawful;

                 (iv) interest upon overdue interest at the rate or rates
         presented therefor by the terms of the Securities of such Series, to
         the extent that payment of such interest is lawful; and

                  (b) all Events of Default with respect to such Series of
Securities, other than the nonpayment of principal of the Securities of such
Series which have become due solely by such declaration of acceleration, have
been cured or waived as provided in Section 5.13.

No such rescission shall affect any subsequent Default or impair any right
consequent thereon.

                SECTION 5.03.  Collection of Indebtedness and Suits for
Enforcement by Trustee.  Publishing covenants that if

                  (a) default is made in the payment of any interest on any
         Security of any Series when such interest becomes due and payable and
         such default continues for a period of 30 days, or

                  (b) default is made in the payment of the principal of (or
         premium, if any, on) any Security at


<PAGE>   82
                                                                          - 72 -

         the Stated Maturity (upon acceleration, optional or mandatory
         redemption, required repurchase or otherwise) thereof,

Publishing will, upon demand of the Trustee, pay to it, for the benefit of the
Holders of such Securities the whole amount then due and payable on such
Securities for principal and premium, if any, and interest, with interest upon
the overdue principal and premium, if any, and, to the extent that payment of
such interest shall be legally enforceable, upon overdue installments of
interest, at the rate or rates as may be presented therefor by the terms of any
such Security.

                  If Publishing fails to pay such amounts forthwith upon such
demand, the Trustee, in its own name and as trustee of an express trust, may
institute a judicial proceeding for the collection of the sums so due and
unpaid and may prosecute such proceeding to judgment or final decree, and may
enforce the same against Publishing or any other obligor upon the Securities of
such Series and collect the moneys adjudged or decreed to be payable in the
manner provided by law out of the property of Publishing or any other obligor
upon such Securities, wherever situated.

                  If an Event of Default with respect to any Series of
Securities occurs and is continuing, the Trustee may in its discretion proceed
to protect and enforce its rights and the rights of the Holders of Securities
of such Series under this Indenture by such appropriate private or judicial
proceedings as the Trustee shall deem most effectual to protect and enforce
such rights, whether for the specific enforcement of any covenant or agreement
in this Indenture or in aid of the exercise of any power granted herein or
therein, or to enforce any other proper remedy.

                  The rights and remedies under this Section 5.03 are in
addition to the other rights and remedies under this Article V or Article XIV.

                  SECTION 5.04. Trustee May File Proofs of Claim. In case of
the pendency of any receivership, insolvency, liquidation, bankruptcy,
reorganization, arrangement, adjustment, composition or other similar judicial
proceeding relative to Publishing or the property of Publishing, the Trustee
(irrespective of whether the principal of the Securities shall then be due and
payable as therein expressed or by declaration or otherwise and irrespective of
whether the Trustee shall have made any demand on Publishing


<PAGE>   83
                                                                          - 73 -

for the payment of overdue principal or interest) shall be entitled and
empowered, by intervention in such proceeding or otherwise:

                  (a) to file and prove a claim for the whole amount of
         principal, and premium, if any, and interest owing and unpaid in
         respect of the Securities and to file such other papers or documents
         as may be necessary or advisable in order to have the claims of the
         Trustee (including any claim for the reasonable compensation,
         expenses, disbursements and advances of the Trustee, its agents and
         counsel) and of the Holders allowed in such judicial proceeding; and

                  (b) subject to Article XII, to collect and receive any moneys
         or other property payable or deliverable on any such claims and to
         distribute the same;

and any custodian, receiver, assignee, trustee, liquidator, sequestrator or
similar official in any such judicial proceeding is hereby authorized by each
Holder to make such payments to the Trustee and, in the event that the Trustee
shall consent to the making of such payments directly to the Holders, to pay
the Trustee any amount due it for the reasonable compensation, expenses,
disbursements and advances of the Trustee, its agents and counsel, and any
other amounts due the Trustee under Section 6.07.

                  Nothing herein contained shall be deemed to authorize the
Trustee to authorize or consent to or accept or adopt on behalf of any Holder
any plan of reorganization, arrangement, adjustment, composition or other
similar arrangement affecting the Securities or the rights of any Holder
thereof, or to authorize the Trustee to vote in respect of the claim of any
Holder in any such proceeding.

                  SECTION 5.05. Trustee May Enforce Claims Without Possession
of Securities. All rights of action and claims under this Indenture or the
Securities of any Series may be prosecuted and enforced by the Trustee without
the possession of any of the Securities of such Series or the production
thereof in any proceeding relating thereto, and any such proceeding instituted
by the Trustee shall be brought in its own name and as trustee of an express
trust, and any recovery of judgment shall, after provision for the payment of
the reasonable compensation, expenses, disbursements and advances of the
Trustee, its agents and counsel, be for the ratable benefit of the Holders of
the Securities of the Series in respect of which such judgment has been
recovered.

<PAGE>   84
                                                                          - 74 -

                  SECTION 5.06. Application of Money Collected. Any money
collected by the Trustee with respect to a Series of Securities pursuant to
this Article or otherwise on behalf of the Holders or the Trustee pursuant to
this Article or through any proceeding or any arrangement or restructuring in
anticipation or in lieu of any proceeding contemplated by this Article shall be
applied, subject to applicable law, in the following order, at the date or
dates fixed by the Trustee and, in case of the distribution of such money on
account of principal, premium, if any, or interest, upon presentation of the
Securities of such Series and the notation thereon of the payment if only
partially paid and upon surrender thereof if fully paid:

                  FIRST:  To the payment of all amounts due the Trustee under
Section 6.07;

                  SECOND: Subject to Article XII, to the payment in full of the
amounts then due and unpaid upon the Securities of that Series for principal,
premium, if any, and interest, in respect of which or for the benefit of which
such money has been collected, ratably, without preference or priority of any
kind, according to the amounts due and payable on such Securities for
principal, premium, if any, and interest; and

                  THIRD: Subject to Article XII, the balance, if any, to the
Person or Persons entitled thereto as a court of competent jurisdiction shall
direct, or to Publishing; provided that all sums due and owing to the Holders
and the Trustee have been paid in full as required by this Indenture.

                  SECTION 5.07. Limitation on Suits. No Holder of any
Securities of any Series shall have any right to institute any proceeding,
judicial or otherwise, with respect to this Indenture or the Securities, or for
the appointment of a receiver or trustee, or for any other remedy hereunder,
unless

                  (a) such Holder has previously given written notice to the
         Trustee of a continuing Event of Default with respect to Securities of
         such Series;

                  (b) the Holders of not less than 25% in principal amount of
         the Outstanding Securities of such Series shall have made written
         request to the Trustee to institute proceedings in respect of such
         Event of Default in its own name as Trustee hereunder;


<PAGE>   85
                                                                          - 75 -

                  (c) such Holder or Holders have offered, and if requested
         have provided, to the Trustee an indemnity satisfactory to the Trustee
         in its sole discretion against the costs, expenses and liabilities
         that may be incurred in compliance with such request;

                  (d) the Trustee for 60 days after its receipt of such notice,
         request and offer (and if requested, provision) of indemnity has
         failed to institute any such proceeding; and

                  (e) no direction inconsistent with such written request has
         been given to the Trustee during such 60-day period by the Holders of
         a majority in principal amount of the Outstanding Securities of such
         Series;

it being understood and intended that no one or more Holders of Securities of
such Series shall have any right in any manner whatever by virtue of, or by
availing of, any provision of this Indenture to affect, disturb or prejudice
the rights of any other Holders of such Series, or to obtain or to seek to
obtain priority or preference over any other Holders or to enforce any right
under this Indenture, except in the manner provided in this Indenture and for
the equal and ratable benefit of all the Holders of all Securities of such
Series.

                  SECTION 5.08. Unconditional Right of Holders To Receive
Principal, Premium and Interest. Notwithstanding any other provision in this
Indenture, the Holder of any Security shall have the right on the terms stated
herein, which is absolute and unconditional, to receive payment of the
principal of, premium, if any, and (subject to Section 3.07) interest on such
Security on the respective Stated Maturities expressed in such Security (or, in
the case of redemption, on the Redemption Date) and to institute suit for the
enforcement of any such payment, and such rights shall not be impaired without
the consent of such Holder, subject to Article XII.

                  SECTION 5.09. Restoration of Rights and Remedies. If the
Trustee or any Holder has instituted any proceeding to enforce any right or
remedy under this Indenture and such proceeding has been discontinued or
abandoned for any reason, or has been determined adversely to the Trustee or to
such Holder, then and in every such case, subject to any determination in such
proceeding, (a) Publishing, the Trustee and the Holders shall be restored
severally and respectively to their former positions hereunder, and (b)
thereafter all rights and remedies of the Trustee and the


<PAGE>   86
                                                                          - 76 -

Holders shall continue as though no such proceeding had been instituted.

                  SECTION 5.10.  Rights and Remedies Cumulative.  Except as
provided in Section 3.06, no right or remedy herein conferred upon or reserved
to the Trustee or to the Holders is intended to be exclusive of any other right
or remedy, and every right and remedy shall, to the extent permitted by law, be
cumulative and in addition to every other right and remedy given hereunder or
now or hereafter existing at law or in equity or otherwise. The assertion or
employment of any right or remedy hereunder, or otherwise, shall not prevent
the concurrent assertion or employment of any other appropriate right or
remedy.

                  SECTION 5.11.  Delay or Omission Not Waiver.  No delay or
omission of the Trustee or of any Holder of any Security to exercise any right
or remedy accruing upon any Event of Default shall impair any such right or
remedy or constitute a waiver of any such Event of Default or an acquiescence
therein.  Every right and remedy given by this Article or by law to the Trustee
or to the Holders may be exercised from time to time, and as often as may be
deemed expedient, by the Trustee or by the Holders, as the case may be.

                  SECTION 5.12. Control by Holders. The Holders of not less
than a majority in aggregate principal amount of the Outstanding Securities of
any Series shall have the right to direct the time, method and place of
conducting any proceeding for any remedy available to the Trustee, or
exercising any trust or power conferred on the Trustee; provided that:

                  (a) such direction shall not be in conflict with any rule of
         law or with this Indenture (including, without limitation, Section
         5.07) or expose the Trustee to personal liability; and

                  (b) subject to the provisions of Section 315 of the Trust
         Indenture Act, the Trustee may take any other action deemed proper by
         the Trustee which is not inconsistent with such direction.

                  SECTION 5.13. Waiver of Past Defaults. The Holders of not
less than a majority in aggregate principal amount of the Outstanding
Securities of any Series may on


<PAGE>   87
                                                                          - 77 -

behalf of the Holders of all the Securities of such Series waive any past
Default hereunder and its consequences, except a Default

                  (a) in the payment of the principal of, premium, if any, or
         interest on any Security of such Series, or

                  (b) in respect of a covenant or provision hereof which under
         Article IX cannot be modified or amended without the consent of the
         Holder of each Outstanding Security of such Series affected by such
         modification or amendment.

                  Upon any such waiver, such Default shall cease to exist, and
any Event of Default arising therefrom shall be deemed to have been cured, for
every purpose of this Indenture; but no such waiver shall extend to any
subsequent or other Default or impair any right consequent thereon.

                  SECTION 5.14. Undertaking for Costs. All parties to this
Indenture agree, and each Holder of any Security by his acceptance thereof
shall be deemed to have agreed, that any court may in its discretion require,
in any suit for the enforcement of any right or remedy under this Indenture, or
in any suit against the Trustee for any action taken, suffered or omitted by it
as Trustee, the filing by any party litigant in such suit of an undertaking to
pay the costs of such suit, and that such court may in its discretion assess
reasonable costs, including reasonable attorneys' fees, against any party
litigant in such suit, having due regard to the merits and good faith of the
claims or defenses made by such party litigant; but the provisions of this
Section shall not apply to any suit instituted by the Trustee, to any suit
instituted by any Holder, or group of Holders, holding in the aggregate more
than 10% in principal amount of the Outstanding Securities of any Series to
which the suit relates, or to any suit instituted by any Holder for the
enforcement of the payment of the principal of, premium, if any, or interest on
any Security on or after the respective Stated Maturities expressed in such
Security (or, in the case of redemption, on or after the Redemption Date).

                  SECTION 5.15. Waiver of Stay, Extension or Usury Laws.
Publishing (to the extent that it may lawfully do so) covenants that it will
not at any time insist upon, or plead, or in any manner whatsoever claim or
take the benefit or advantage of, any stay or extension law or any usury or
other similar law wherever enacted, now or at any time hereafter in force,
which would prohibit or forgive Publishing from paying all or any portion of
the principal

<PAGE>   88
                                                                          - 78 -

of, premium, if any, or interest on the Securities contemplated herein or in
the Securities or which may affect the covenants or the performance of this
Indenture; and Publishing (to the extent that it may lawfully do so) hereby
expressly waives all benefit or advantage of any such law, and covenants that
it will not hinder, delay or impede the execution of any power herein granted
to the Trustee, but will suffer and permit the execution of every such power as
though no such law had been enacted.

                  SECTION 5.16. Remedies Subject to Applicable Law. All rights,
remedies and powers provided by this Article may be exercised only to the
extent that the exercise thereof does not violate any applicable provision of
law in the premises, and all the provisions of this Indenture are intended to
be subject to all applicable mandatory provisions of law which may be
controlling in the premises and to be limited to the extent necessary so that
they will not render this Indenture invalid, unenforceable or not entitled to
be recorded, registered or filed under the provisions of any applicable law.

                                   ARTICLE VI

                                  The Trustee

                  SECTION 6.01. Duties of Trustee. (a) If a Default or an Event
of Default with respect to any Series of Securities actually known to the
Trustee has occurred and is continuing, the Trustee shall exercise such of the
rights and powers vested in it by this Indenture and use the same degree of
care and skill in its exercise thereof as a prudent person would exercise or
use under the circumstances in the conduct of his own affairs. The Trustee
shall not be charged with knowledge of any Default or Event of Default with
respect to any Series of Securities, Asset Sale or Change of Control unless
written notice thereof shall have been delivered to a Responsible Officer by
Publishing or any other Person.

                  (b) Except during the continuance of a Default or an Event of
Default with respect to any Series of Securities actually known to the Trustee:

                  (1) the Trustee need perform only those duties as are
         specifically set forth in this Indenture and no covenants or
         obligations shall be implied in this Indenture that are adverse to the
         Trustee; and


<PAGE>   89
                                                                          - 79 -

                  (2) in the absence of bad faith or wilful misconduct on its
         part, the Trustee may with respect to any Series of Securities,
         conclusively rely, as to the truth of the statements and the
         correctness of the opinions expressed therein, upon certificates or
         opinions furnished to the Trustee and conforming to the requirements
         of this Indenture. However, the Trustee shall examine the certificates
         and opinions to determine whether or not they conform to the
         requirements of this Indenture.

                  (c) The Trustee may not be relieved from liability for its
own negligent action, its own negligent failure to act, or its own wilful
misconduct, except that:

                  (1) this paragraph does not limit the effect of paragraph (b)
         of this Section 6.01;

                  (2) the Trustee shall not be liable for any error of judgment
         made in good faith by a Responsible Officer, unless it is proved that
         the Trustee was negligent in ascertaining the pertinent facts; and

                  (3) the Trustee shall not be liable with respect to any
         action it takes or omits to take in good faith in accordance with a
         direction of the Holders of a majority in principal amount of
         Outstanding Securities of any Series relating to the time, method and
         place of conducting any proceeding for any remedy available to the
         Trustee, or exercising any trust or power confirmed upon the Trustee
         under this Indenture.

                  (d) No provision of this Indenture shall require the Trustee
to expend or risk its own funds or otherwise incur any loss, expense, fees or
financial liability in the performance of any of its duties hereunder or in the
exercise of any of its rights or powers if it shall have reasonable grounds for
believing that repayment of such funds or adequate indemnity against such risk
or loss, expense, fees or financial liability is not reasonably assured to it.

                  (e) Whether or not therein expressly so provided, every
provision of this Indenture that in any way relates to the Trustee is subject
to paragraphs (a), (b), (c) and (d) of this Section 6.01.

                  (f) The Trustee shall not be liable for interest on any money
or assets received by it except as the Trustee may agree with Publishing.
Assets held in trust by the


<PAGE>   90
                                                                          - 80 -

Trustee need not be segregated from other assets except to the extent required
by law.

                  SECTION 6.02.  Notice of Defaults.  Within 30 days after a
Responsible Officer of the Trustee receives notice of the occurrence of any
Default with respect to Securities of any Series, the Trustee shall, at
Publishing's expense, transmit by mail to all Holders of such Series or any
other persons entitled to receive reports pursuant to Trust Indenture Act
Section 313(c), as their names and addresses appear in the Security Register,
notice of such Default, unless such Default shall have been cured or waived;
provided, however, that, except in the case of a Default in the payment of the
principal of, premium, if any, or interest on any Security, the Trustee shall
be protected in withholding such notice if and so long as a trust committee of
Responsible Officers of the Trustee in good faith determines that the
withholding of such notice is in the interest of the Holders of such Series.

                  SECTION 6.03.  Certain Rights of Trustee.  Subject to the
provisions of Trust Indenture Act Sections 315(a) through 315(d):

                  (a) the Trustee may rely conclusively and shall be protected
         in acting or refraining from acting upon any resolution, certificate,
         statement, instrument, opinion, report, notice, request, direction,
         consent, order, bond, debenture, note, other evidence of indebtedness
         or other paper or document believed by it to be genuine and to have
         been signed or presented by the proper party or parties;

                  (b) any request or direction of Publishing mentioned herein
         shall be sufficiently evidenced by a Publishing Request or Publishing
         Order and any resolution of the Board of Directors may be sufficiently
         evidenced by a Board Resolution;

                  (c) wherever in the administration of this Indenture the
         Trustee shall deem it desirable that a matter be proved or established
         prior to the taking, suffering or omitting any action hereunder, the
         Trustee (unless other evidence be herein specifically prescribed) in
         the absence of bad faith on its part, may rely conclusively, upon an
         Officers' Certificate and/or an Opinion of Counsel;

                  (d) the Trustee may consult with counsel and any written
         advice of such counsel or any Opinion of Counsel shall be full and
         complete authorization and


<PAGE>   91
                                                                          - 81 -

         protection in respect of any action taken, suffered or omitted by it
         hereunder in good faith and in reliance thereon in accordance with such
         advice or Opinion of Counsel;

                  (e) notwithstanding any other provisions contained in this
         Indenture, the Trustee shall be under no obligation to exercise any of
         the rights or powers vested in it by this Indenture at the request or
         direction of any of the Holders pursuant to this Indenture, unless
         such Holders shall have offered to the Trustee security or indemnity
         satisfactory to the Trustee in its sole discretion against the costs,
         expenses and liabilities which might be incurred therein or thereby in
         compliance with such request or direction;

                  (f) the Trustee shall not be liable for any action taken or
         omitted by it in good faith and believed by it to be authorized or
         within the discretion, rights or powers conferred upon it by this
         Indenture other than any liabilities arising out of the negligence or
         wilful misconduct of the Trustee;

                  (g) the Trustee shall not be bound to make any investigation
         into the facts or matters stated in any resolution, certificate,
         statement, instrument, opinion, report, notice, request, direction,
         consent, order, approval, appraisal, bond, debenture, note, coupon,
         security or other paper or document; but the Trustee in its discretion
         may make such further inquiry or investigation in accordance with any
         of the provisions of this Indenture into such facts or matters as it
         may see fit, and, if the Trustee shall determine to make such further
         inquiry or investigation, it shall be entitled to examine such
         relevant books, records and premises of Publishing as may be
         reasonable, personally or by agent or attorney;

                  (h) the Trustee may execute any of the trusts or powers
         hereunder or perform any duties hereunder either directly or by or
         through agents or attorneys and the Trustee shall not be responsible
         for any misconduct or negligence on the part of any agent or attorney
         appointed with due care by it hereunder; and

                  (i) no provision of this Indenture shall require the Trustee
         to expend or risk its own funds or otherwise incur any financial
         liability in the performance of any of its duties hereunder, or in the
         exercise of any of its rights and powers.


<PAGE>   92
                                                                          - 82 -

                  SECTION 6.04. Trustee Not Responsible for Recitals,
Dispositions of Securities or Application of Proceeds Thereof. The recitals
contained herein and in the Securities, except the Trustee's certificates of
authentication, shall be taken as the statements of Publishing, and the Trustee
assumes no responsibility for their correctness. The Trustee makes no
representations as to the validity or sufficiency of this Indenture or the
Securities, except that the Trustee represents that it is duly authorized to
execute and deliver this Indenture, authenticate the Securities and perform its
obligations hereunder and that the statements made by it in a Statement of
Eligibility and Qualification on Form T-1 supplied to Publishing are true and
accurate subject to the qualifications set forth therein. The Trustee shall not
be accountable for the use or application by Publishing of Securities or the
proceeds thereof.

                  SECTION 6.05. Trustee and Agents May Hold Securities;
Collections; etc. The Trustee, any Paying Agent, Security Registrar or any
other agent of Publishing, in its individual or any other capacity, may become
the owner or pledgee of Securities, with the same rights it would have if it
were not the Trustee, Paying Agent, Security Registrar or such other agent and,
subject to Trust Indenture Act Sections 310 and 311, may otherwise deal with
Publishing and receive, collect, hold and retain collections from Publishing
with the same rights it would have if it were not the Trustee, Paying Agent,
Security Registrar or such other agent.

                  SECTION 6.06. Money Held in Trust. All moneys received by the
Trustee shall, until used or applied as herein provided, be held in trust for
the purposes for which they were received, but need not be segregated from
other funds except to the extent required by mandatory provisions of law.
Except for funds or securities deposited with the Trustee pursuant to Article
IV, the Trustee shall only be required to invest moneys received by the
Trustee, until used or applied as herein provided, in Temporary Cash
Investments in accordance with the directions of Publishing.

                  SECTION 6.07. Compensation and Indemnification of Trustee and
Its Prior Claim. Publishing covenants and agrees to pay to the Trustee from
time to time, and the Trustee shall be entitled to, reasonable compensation for
all services rendered by it hereunder (which, to the extent lawful, shall not
be limited by any provision of law in regard to the compensation of a trustee
of an express trust) and Publishing covenants and agrees to pay or reimburse
the Trustee and each predecessor Trustee upon its request for


<PAGE>   93
                                                                          - 83 -

all reasonable expenses, disbursements and advances incurred or made by or on
behalf of it in accordance with any of the provisions of this Indenture
(including the reasonable compensation and the expenses and disbursements of
its counsel and of all agents and other persons not regularly in its employ)
except any such expense, disbursement or advance as may arise from its
negligence, bad faith or wilful misconduct. When the Trustee incurs expenses or
renders services in connection with an Event of Default specified in Section
5.01(g) or Section 5.01(h), the expenses (including the reasonable compensation
and the expenses and disbursements of its counsel) and the compensation for the
services are intended to constitute expenses of administration under any
applicable Federal or state bankruptcy, insolvency or other similar law.
Publishing also covenants to indemnify the Trustee and each predecessor
Trustee, and their respective officers, agents and employees for, and to hold
them harmless against, any claim, loss, liability, tax, assessment or other
governmental charge (other than taxes applicable to the Trustee's compensation
hereunder) or expense incurred without negligence, bad faith or wilful
misconduct on its part, arising out of or in connection with the acceptance or
administration of this Indenture or the trusts hereunder and its duties
hereunder, including enforcement of this Section 6.07 and also including any
liability which the Trustee may incur as a result of failure to withhold, pay
or report any tax, assessment or other governmental charge, and the costs and
expenses of defending itself against or investigating any claim of liability in
the premises. The obligations of Publishing under this Section to compensate
and indemnify the Trustee and each predecessor Trustee and to pay or reimburse
the Trustee and each predecessor Trustee for expenses, disbursements and
advances shall constitute an additional obligation hereunder and shall survive
the satisfaction and discharge of this Indenture and the resignation or removal
of the Trustee and each predecessor Trustee. As security for the performance of
the obligations of Publishing under this Section, the Trustee shall have a lien
prior to the Securities upon all property and funds held or collected by the
Trustee as such, except funds held in trust for the benefit of Holders of
particular Securities.

                  SECTION 6.08.  Conflicting Interests.  The Trustee shall
comply with the provisions of Section 310(b) of the Trust Indenture Act.  In
determining whether the Trustee has a conflicting interest as defined in
Section 310(b) of the Trust Indenture Act with respect to the Securities of any
Series, there shall be excluded this Indenture with respect to Securities of
any particular Series of Securities other


<PAGE>   94
                                                                          - 84 -

than that Series. Nothing herein shall prevent the Trustee from filing with the
Commission the application referred to in the second to last paragraph of
Section 310(b) of the Trust Indenture Act.

                  SECTION 6.09. Corporate Trustee Required; Eligibility. There
shall at all times be a Trustee hereunder which shall be eligible to act as
Trustee under the Trust Indenture Act Section 310(a)(1) and which shall have a
combined capital and surplus of at least $100,000,000, and have a Corporate
Trust Office in The City of New York to the extent there is such an institution
eligible and willing to serve. If the Trustee does not have an office in the
City of New York, the Trustee shall appoint an agent in the City of New York
reasonably acceptable to Publishing to conduct any activities which the Trustee
is required under this Indenture to conduct in the City of New York. The
Trustee may not rescind any such agency without the consent of Publishing,
which consent may not be unreasonably withheld, unless the Trustee appoints a
satisfactory replacement or has a Corporate Trust Office in the City of New
York. If such corporation publishes reports of conditions at least annually,
pursuant to law or to the requirements of Federal, state, territorial or
District of Columbia supervising or examining authority, then for the purposes
of this Section, the combined capital and surplus of such corporation shall be
deemed to be its combined capital and surplus as set forth in its most recent
report of conditions so published. If at any time the Trustee shall cease to be
eligible in accordance with the provisions of this Section, the Trustee shall
resign immediately in the manner and with the effect hereinafter specified in
this Article.

                  SECTION 6.10. Resignation and Removal; Appointment of
Successor Trustee. (a) No resignation or removal of the Trustee and no
appointment of a successor Trustee pursuant to this Article shall become
effective until the acceptance of appointment by the successor Trustee under
Section 6.11.

                  (b) The Trustee, or any trustee or trustees hereafter
appointed, may at any time resign with respect to any Series of Securities by
giving written notice thereof to Publishing. Upon receiving such notice of
resignation, Publishing shall use its best efforts to promptly appoint a
successor Trustee by Board Resolution or written instrument executed by
authority of the Board of Directors of Publishing, a copy of which shall be
delivered to the resigning Trustee and a copy to the successor Trustee. If an
instrument of acceptance by a successor Trustee shall not


<PAGE>   95
                                                                          - 85 -

have been delivered to the Trustee within 30 days after the giving of such
notice of resignation, the resigning Trustee may, or any Holder who has been a
bona fide Holder of a Security for at least six months may, on behalf of
himself and all others similarly situated, petition any court of competent
jurisdiction for the appointment of a successor Trustee. Such court may
thereupon, after such notice, if any, as it may deem proper, appoint a
successor Trustee.

                  (c) The Trustee may be removed with respect to any Series of
Securities at any time by an Act of the Holders of not less than a majority in
aggregate principal amount of the Outstanding Securities of that Series,
delivered to the Trustee and to Publishing.

                  (d)  If at any time:

                  (1) the Trustee shall fail to comply with the provisions of
         Trust Indenture Act Section 310(b) with respect to any Series of
         Securities after written request therefor by Publishing or by any
         Holder who has been a bona fide Holder of a Security for at least six
         months, or

                  (2) the Trustee shall cease to be eligible under Section 6.09
         with respect to any Series of Securities and shall fail to resign
         after written request therefor by Publishing or by any such Holder, or

                  (3) the Trustee shall become incapable of acting with respect
         to any Series of Securities or shall be adjudged a bankrupt or
         insolvent, or a receiver of the Trustee or of its property shall be
         appointed or any public officer shall take charge or control of the
         Trustee or of its property or affairs for the purpose of
         rehabilitation, conservation or liquidation,

then, in any case, (i) Publishing by a Board Resolution may remove the Trustee,
with respect to any Series of Securities or in the case of bankruptcy or
insolvency or receivership pursuant to clause (3) above, with respect to all
Series, or (ii) subject to Section 5.14, any Holder of any Security who has
been a bona fide Holder of a Security of such Series for at least six months
may, on behalf of himself and all others similarly situated, petition any court
of competent jurisdiction for the removal of the Trustee and the appointment of
a successor Trustee with respect to the Series, or in the case of bankruptcy or
insolvency or receivership pursuant to clause (3) above, with respect to all
Series. Such court may thereupon, after such notice, if


<PAGE>   96
                                                                          - 86 -

any, as it may deem proper and prescribe, remove the Trustee and appoint a
successor Trustee.

                  (e) If the Trustee shall resign, be removed or become
incapable of acting with respect to any Series of Securities, or if a vacancy
shall occur in the office of Trustee with respect to any Series for any cause,
Publishing, by a Board Resolution or written instrument executed by authority
of the Board of Directors of Publishing, shall use its best efforts to promptly
appoint a successor Trustee for that Series of Securities and shall comply with
the applicable requirements of Section 6.11. If, within one year after such
resignation, removal or incapability, or the occurrence of such vacancy,
Publishing or a court of competent jurisdiction has not appointed a successor
Trustee, a successor Trustee with respect to such Series of Securities shall be
appointed by Act of the Holders of a majority in principal amount of the
Outstanding Securities of such Series delivered to Publishing and the retiring
Trustee, and the successor Trustee so appointed shall, forthwith upon its
acceptance of such appointment, become the successor Trustee with respect to
such Series of Securities and supersede the successor Trustee appointed by
Publishing with respect to such Series of Securities. If no successor Trustee
shall have been so appointed by Publishing or the Holders of such Series of
Securities and accepted appointment in the manner hereinafter provided, any
Holder of a Security who has been a bona fide Holder of a Security of that
Series for at least six months may, subject to Section 5.14, on behalf of
himself and all other similarly situated, petition any court of competent
jurisdiction for the appointment of a successor Trustee with respect to such
Series.

                  (f) Publishing shall give notice of each resignation and each
removal of the Trustee with respect to any Series and each appointment of a
successor Trustee with respect to any Series by mailing written notice of such
event by first-class mail, postage prepaid, to the Holders of Securities of
that Series as their names and addresses appear in the Security Register. Each
notice shall include the name of the successor Trustee and the address of its
Corporate Trust Office or agent hereunder.

                  SECTION 6.11. Acceptance of Appointment by Successor. In case
of the appointment hereunder of a successor Trustee with respect to the
Securities, every such successor Trustee so appointed shall execute,
acknowledge and deliver to Publishing and to the retiring Trustee an instrument
accepting such appointment, and thereupon the resignation or removal of the
retiring Trustee shall become


<PAGE>   97
                                                                          - 87 -

effective and such successor Trustee, without any further act, deed or
conveyance, shall become vested with all the rights, powers, trusts and duties
of the retiring Trustee under this Indenture with respect to any such Series;
but, nevertheless, on the written request of Publishing or the successor
Trustee, upon payment of its charges then unpaid, such retiring Trustee shall
pay over to the successor Trustee all moneys at the time held by it hereunder
with respect to any such Series and shall execute and deliver an instrument
transferring to such successor Trustee all such rights, powers, duties and
obligations.

                  Upon request of any such successor Trustee, Publishing shall
execute any and all instruments for more fully and certainly vesting in and
confirming to such successor Trustee all such rights and powers. Any Trustee
ceasing to act shall, nevertheless, retain a prior claim upon all property or
funds held or collected by such Trustee or such successor Trustee to secure any
amounts then due such Trustee pursuant to the provisions of Section 6.07.

                  No successor Trustee with respect to the Securities shall
accept appointment as provided in this Section 6.11 unless at the time of such
acceptance such successor Trustee shall be eligible to act as Trustee under the
provisions of Trust Indenture Act Section 310(a) and this Article VI and shall
have a combined capital and surplus of at least $100,000,000 and have a
Corporate Trust Office or an agent selected in accordance with Section 6.09 in
the City of New York.

                  Upon acceptance of appointment by any successor Trustee as
provided in this Section 6.11, Publishing shall give notice thereof to the
Holders of the Securities of such Series, by mailing such notice to such
Holders at their addresses as they shall appear on the Security Register. If
the acceptance of appointment is substantially contemporaneous with the
resignation, then the notice called for by the preceding sentence may be
combined with the notice called for by Section 6.10. If Publishing fails to
give such notice within 10 days after acceptance of appointment by the
successor Trustee, the successor Trustee shall cause such notice to be given at
the expense of Publishing.

                  SECTION 6.12. Merger, Conversion, Consolidation or Succession
to Business. Any corporation into which the Trustee may be merged or converted
or with which it may be consolidated, or any corporation resulting from any
merger, conversion or consolidation to which the Trustee shall be a party, or
any corporation succeeding to all or substantially


<PAGE>   98
                                                                          - 88 -

all of the corporate trust business of the Trustee, shall be the successor of
the Trustee hereunder, without the execution or filing of any paper or any
further act on the part of any of the parties hereto; provided such corporation
shall be eligible under Trust Indenture Act Section 310(a) and this Article VI
and shall have a combined capital and surplus of at least $100,000,000.

                  In case at the time such successor to the Trustee shall
succeed to the trusts created by this Indenture any of the Securities shall
have been authenticated but not delivered, any such successor to the Trustee
may adopt the certificate of authentication of any predecessor Trustee and
deliver such Securities so authenticated; and, in case at that time any of the
Securities shall not have been authenticated, any successor to the Trustee may
authenticate such Securities either in the name of any predecessor hereunder or
in the name of the successor Trustee. In all such cases such certificates shall
have the full force and effect which this Indenture provides for the
certificate of authentication of the Trustee; provided that the right to adopt
the certificate of authentication of any predecessor Trustee or to authenticate
Securities in the name of any predecessor Trustee shall apply only to its
successor or successors by merger, amalgamation, conversion or consolidation.

                  SECTION 6.13. Preferential Collection of Claims Against
Publishing. If and when the Trustee shall be or become a creditor of
Publishing, the Trustee shall be subject to the provisions of the Trust
Indenture Act regarding the collection of claims against Publishing.

                                  ARTICLE VII

              Holders' Lists and Reports by Trustee and Publishing

                  SECTION 7.01. Publishing To Furnish Trustee Names and
Addresses of Holders. Publishing will furnish or cause to be furnished to the
Trustee:

                  (a) semiannually, not more than 10 days after each Regular
         Record Date, a list, in such form as the Trustee may reasonably
         require, of the names and addresses of the Holders of Securities of
         each Series as of such Regular Record Date; and

                  (b) at such other times as the Trustee may reasonably request
         in writing, within 30 days after receipt by Publishing of any such
         request, a list of


<PAGE>   99
                                                                          - 89 -

         similar form and content to that in subsection (a) hereof as of a date
         not more than 15 days prior to the time such list is furnished;

provided, however, that if and so long as the Trustee shall be the Security
Registrar for Securities of a Series, no such list need be furnished with
respect to such Series of Securities.

                  SECTION 7.02. Disclosure of Names and Addresses of Holders.
Every Holder of Securities of any Series, by receiving and holding the same,
agrees with Publishing and the Trustee that neither Publishing nor the Trustee
or any agent of either of them shall be held accountable by reason of the
disclosure of any information as to the names and addresses of the Holders in
accordance with Trust Indenture Act Section 312, regardless of the source from
which such information was derived, and that the Trustee shall not be held
accountable or liable by reason of mailing any material pursuant to a request
made under Trust Indenture Act Section 312.

                  SECTION 7.03. Reports by Trustee. (a) Within 60 days after
May 15 of each year commencing with the first May 15 after the issuance of
Securities of any Series, the Trustee shall transmit by mail, at Publishing's
expense, to all Holders, as their names and addresses appear in the Security
Register, as provided in Trust Indenture Act Section 313(c), a brief report
dated as of such May 15 in accordance with and with respect to the matters
required by Trust Indenture Act Section 313(a).

                  (b) The Trustee shall promptly transmit to Publishing a copy
of any report it transmits to Holders of such Series pursuant to this Section
7.03.

                  SECTION 7.04.  Reports by Publishing.  Publishing shall do
the following:

                  (a) file with the Trustee, in accordance with Section 10.18
hereof, and in any event within 30 days after Publishing is required to file
the same with the Commission, copies of the annual reports and of the
information, documents and other reports (or copies of such portions of any of
the foregoing as the Commission may from time to time by rules and regulations
prescribe) which Publishing is required to file with the Commission separately
or together with Hollinger International pursuant to Section 13 or Section
15(d) of the Exchange Act; or, if Publishing is not required to file
information, documents or reports pursuant to either of said Sections, then it
shall (i) deliver to the


<PAGE>   100
                                                                          - 90 -

Trustee annual audited financial statements of Publishing and its Restricted
Subsidiaries, prepared on a Consolidated basis in conformity with GAAP, within
120 days after the end of each fiscal year of Publishing, and (ii) file with
the Trustee and the Commission, in accordance with, and so long as not
prohibited by, the rules and regulations prescribed from time to time by the
Commission, such of the supplementary and periodic information, documents and
reports which may be required pursuant to Section 13 of the Exchange Act in
respect of a security listed and registered on a national securities exchange
as may be prescribed from time to time in such rules and regulations;

                  (b) file with the Trustee and the Commission, in accordance
with the rules and regulations prescribed from time to time by the Commission,
such additional information, documents and reports with respect to compliance
by Publishing with the conditions and covenants of this Indenture as is
required from time to time by such rules and regulations (including such rules
and regulations, if any, referred to in Trust Indenture Act Section 314(a));
and

                  (c) transmit by mail to all Holders or any other persons
entitled to receive a report pursuant to Trust Indenture Act Section 313(c),
within 30 days after the filing thereof with the Trustee, in the manner and to
the extent provided in Trust Indenture Act Section 313(c), such summaries of
any information, documents and reports required to be filed by Publishing
pursuant to Section 10.18 hereunder and subsections (a) and (b) of this Section
as is required and not prohibited by rules and regulations prescribed from time
to time by the Commission.

                                  ARTICLE VIII

                     Consolidation, Merger, Sale of Assets

                  SECTION 8.01. Publishing May Merge, Consolidate, etc., Only
on Certain Terms. (a) Publishing shall not, in a single transaction or a series
of related transactions, consolidate with or merge with or into any other
Person or sell, assign, convey, transfer, lease or otherwise dispose of all or
substantially all of its properties and assets to any Person or group of
affiliated Persons, or permit any of its Restricted Subsidiaries to enter into
any such transaction or transactions (other than, in the case of a Restricted
Subsidiary, such a consolidation, merger or transfer with or to one or more
Wholly Owned Restricted Subsidiaries) if such transaction or transactions, in
the aggregate, would result in a sale, assignment, conveyance,


<PAGE>   101
                                                                          - 91 -

transfer, lease or disposition of all or substantially all of the properties
and assets of Publishing and its Restricted Subsidiaries on a Consolidated
basis to any other Person or group of affiliated Persons, unless at the time
and after giving effect thereto:

                  (i) either (a) Publishing shall be the continuing
         corporation, or (b) the Person (if other than Publishing) formed by
         such consolidation or into which Publishing is merged or the Person
         which acquires by sale, assignment, conveyance, transfer, lease or
         disposition all or substantially all of the properties and assets of
         Publishing and its Restricted Subsidiaries on a Consolidated basis
         (the "Surviving Entity") shall be a corporation duly organized and
         validly existing under the laws of the United States of America, any
         state thereof or the District of Columbia and shall expressly assume,
         by a supplemental indenture hereto, executed and delivered to the
         Trustee, in form and substance reasonably satisfactory to the Trustee,
         all the obligations of Publishing under the Securities and this
         Indenture, and this Indenture shall remain in full force and effect;

                (ii) immediately before and immediately after giving effect to
         such transaction on a pro forma basis, no Default or Event of Default
         shall have occurred and be continuing;

              (iii) immediately after giving effect to the transaction on a pro
         forma basis, the Consolidated Net Worth of the Surviving Entity is not
         less than the Consolidated Net Worth of Publishing and the Restricted
         Subsidiaries immediately prior to the transaction;

                (iv) immediately before and immediately after giving effect to
         such transaction on a pro forma basis (on the assumption that the
         transaction occurred on the first day of the four-quarter period
         immediately prior to the consummation of such transaction with the
         appropriate adjustments with respect to the transaction being included
         in such pro forma calculation), Publishing (or the Surviving Entity if
         Publishing is not the continuing obligor under this Indenture) could
         Incur $1.00 of additional Indebtedness under the provisions of Section
         10.08 (other than Permitted Indebtedness);

                  (v) if any of the property or assets of Publishing or any of
         its Restricted Subsidiaries would thereupon


<PAGE>   102
                                                                          - 92 -

         become subject to any Lien, the provisions of Section 10.12 are
         complied with; and

                (vi) Publishing or the Surviving Entity shall have delivered,
         or caused to be delivered, to the Trustee, in form and substance
         reasonably satisfactory to the Trustee, an Officers' Certificate and
         an Opinion of Counsel, each to the effect that such consolidation,
         merger, transfer, sale, assignment, lease or other transaction and the
         supplemental indenture in respect thereof comply with the provisions
         described in this Section 8.01(a) and that all conditions precedent
         herein provided for in this Section 8.01(a) relating to such
         transaction have been complied with.

                  (b) Neither Hollinger International nor any Restricted
Subsidiary Guarantor shall, and Publishing shall not permit a Restricted
Subsidiary Guarantor to, in a single transaction or series of related
transactions, consolidate with or merge with or into any other Person (other
than Publishing, Hollinger International or any other Restricted Subsidiary
Guarantor), or sell, assign, convey, transfer, lease or otherwise dispose of
all or substantially all of its properties and assets on a Consolidated basis
to any Person (other than Publishing, Hollinger International or any other
Restricted Subsidiary Guarantor) if such transaction or transactions, in the
aggregate, would result in a sale, assignment, conveyance, transfer, lease or
disposition of all or substantially all of the properties and assets of such
Guarantor to any other Person or group of affiliated Persons, unless at the
time and after giving effect thereto:

                  (i) either (a) Hollinger International or such Restricted
Subsidiary Guarantor shall be the continuing corporation or (b) the Person (if
other than Hollinger International or such Restricted Subsidiary Guarantor)
formed by such consolidation or into which Hollinger International or such
Restricted Subsidiary Guarantor, as the case may be, is merged or the Person
which acquires by sale, assignment, conveyance, transfer, lease or disposition
all or substantially all of the properties and assets of Hollinger
International or such Restricted Subsidiary Guarantor shall be a corporation
duly organized and validly existing under the laws of the United States of
America, any state thereof or the District of Columbia and shall (except where
Hollinger International or such Restricted Subsidiary Guarantor is the
continuing corporation) expressly assume, by a supplemental indenture hereto,
executed and delivered to the Trustee, in form and substance reasonably
satisfactory to the Trustee, all the obligations of


<PAGE>   103
                                                                          - 93 -

Hollinger International or such Restricted Subsidiary Guarantor, as the case
may be, under the Securities and this Indenture, and this Indenture shall
remain in full force and effect;

                  (ii) immediately before and immediately after giving effect
to such transaction on a pro forma basis, no Default or Event of Default shall
have occurred and be continuing; and

                  (iii) Hollinger International or such Restricted Subsidiary
Guarantor, as the case may be, shall have delivered, or caused to be delivered,
to the Trustee, in form and substance reasonably satisfactory to the Trustee,
an Officers' Certificate and an Opinion of Counsel, each stating that such
consolidation, merger, sale, assignment, conveyance, transfer, lease or other
transaction and the supplemental indenture in respect thereof comply with the
provisions described in this Section 8.01(b), and that all conditions precedent
herein provided for in this Section 8.01(a) relating to such transactions have
been complied with.

                  (c)  Notwithstanding anything in this Article Eight to the
contrary, any Guarantee by a Restricted Subsidiary of the Securities may be
released in accordance with the provisions of Section 10.14(c).

                  SECTION 8.02. Successor Substituted. Upon any consolidation
or merger, or any sale, assignment, conveyance, transfer, lease or disposition
of all or substantially all of the properties and assets on a Consolidated
basis of Publishing, Hollinger International or any Restricted Subsidiary
Guarantor in accordance with Section 8.01 with respect to which Publishing,
Hollinger International or such Restricted Subsidiary Guarantor is not the
continuing corporation, the successor Person formed by such consolidation or
into which Publishing, Hollinger International or such Restricted Subsidiary
Guarantor is merged or the successor Person to which such sale, assignment,
conveyance, transfer, lease or disposition is made shall succeed to, and be
substituted for, and may exercise every right and power of, Publishing,
Hollinger International or such Restricted Subsidiary Guarantor, as the case
may be, under this Indenture, with the same effect as if such successor had
been named as Publishing, Hollinger International or such Restricted Subsidiary
Guarantor, as the case may be, herein. When a successor assumes all the
obligations and covenants of its predecessor under this Indenture or the
Securities, the predecessor shall be released from those obligations and
covenants; provided



<PAGE>   104
                                                                          - 94 -

that, in the case of a transfer by lease, the predecessor shall not be released
from the payment of principal and interest on the Securities or, in the case of
Hollinger International or a Restricted Subsidiary Guarantor, such Guarantee,
as the case may be.

                  Any successor to Publishing described in the foregoing
paragraph may cause to be signed, and may issue either in its own name or in
the name of Publishing, any or all of the Securities issuable hereunder which
theretofore shall not have been signed by Publishing and delivered to the
Trustee; and, upon the order of such successor, instead of Publishing, and
subject to all the terms, conditions and limitations in this Indenture
prescribed, the Trustee shall authenticate and shall deliver any Securities
which previously shall have been signed and delivered by the officers of
Publishing to the Trustee for authentication, and any Securities which such
successor thereafter shall cause to be signed and delivered to the Trustee for
that purpose. All the Securities so issued shall in all respects have the same
legal rank and benefit under this Indenture as the Securities theretofore or
thereafter issued in accordance with the terms of this Indenture as though all
of such Securities had been issued at the date of the execution of this
Indenture.

                                   ARTICLE IX

                            Supplemental Indentures

                  SECTION 9.01. Supplemental Indentures and Agreements Without
Consent of Holders. Without the consent of any Holders of the Securities of any
Series, Publishing, each Guarantor and the Trustee, at any time and from time
to time, may enter into one or more indentures supplemental hereto, in form and
substance reasonably satisfactory to the Trustee, for any of the following
purposes:

                  (a) to evidence the succession of another Person to
         Publishing or any Guarantor, and the assumption by any such successor
         of the covenants of Publishing or such Guarantor, as the case may be,
         herein and in the Securities of any Series;

                  (b) to add to the covenants of Publishing or the Guarantors
         for the benefit of the Holders of the Securities of any or all Series
         (and if such covenants or the surrender of such right or power are to
         be for the benefit of less than all Series of Securities, stating that
         such covenants are expressly being


<PAGE>   105
                                                                          - 95 -

         included or such surrenders are expressly being made solely for the
         benefit of one or more specified Series), or to surrender any right or
         power conferred upon Publishing or the Guarantors in this Indenture or
         the Securities of any Series;

                  (c) to cure any ambiguity or to correct or supplement any
         provision in this Indenture or the Securities of any Series which may
         be defective or inconsistent with any other provision in this
         Indenture or the Securities;

                  (d) to comply with the requirements of the Commission in
         order to effect or maintain the qualification of this Indenture under
         the Trust Indenture Act, as contemplated by Section 9.05 or otherwise;

                  (e) to add a Guarantee of the Indenture Obligations;

                  (f) to evidence and provide the acceptance of the appointment
         of a successor Trustee hereunder;

                  (g) to mortgage, pledge, hypothecate or grant a security
         interest in favor of the Trustee for the benefit of the Holders as
         additional security, pursuant to the requirements of Section 10.13 or
         otherwise, for the payment and performance of the Indenture
         Obligations, in any property or assets, including any which are
         required to be mortgaged, pledged or hypothecated, or in which a
         security interest is required to be granted, to the Trustee pursuant
         to this Indenture or otherwise;

                  (h) to clarify or make any other provisions with respect to
         matters or questions arising under this Indenture or the Securities;
         provided that, in each case, such clarification or provision thus made
         shall not adversely affect the interests of the Holders; and

                  (i) to establish any form of Security, as provided in Article
         Two, and to provide for the issuance of any Series of Securities as
         provided in Article Three and to set forth the terms thereof, and/or
         to add to the rights of the Holders of the Securities of any Series.

                  SECTION 9.02. Supplemental Indentures and Agreements with
Consent of Holders. Except as permitted by Section 9.01, with the consent of
the Holders of not less than a majority in aggregate principal amount of the


<PAGE>   106
                                                                          - 96 -

Outstanding Securities of each Series affected by such supplemental indenture
or indentures, by Act of said Holders delivered to Publishing and the Trustee,
Publishing and each Guarantor (if a party thereto) and the Trustee may (i)
enter into an indenture or indentures supplemental hereto, in form and
substance reasonably satisfactory to the Trustee, for the purpose of adding any
provisions to or amending, modifying or changing in any manner or eliminating
any of the provisions of this Indenture or the Securities of each such Series
(including, but not limited to, for the purpose of modifying in any manner the
rights of the Holders of the Securities of each such Series under this
Indenture) or (ii) waive compliance with any provision in this Indenture or the
Securities of each such Series (other than waivers of past Defaults covered by
Section 5.13 and waivers of covenants which are covered by Section 10.20);
provided, however, that no such supplemental indenture, agreement or instrument
shall, without the consent of the Holder of each Outstanding Securities of any
Series affected thereby:

                  (a) change the Stated Maturity of the principal of, or any
         installment of interest on, any Security of any Series or waive a
         default in the payment of the principal or interest on any Security of
         any Series or reduce the principal amount thereof or the rate of
         interest thereon or any premium payable upon the redemption thereof,
         or change the coin or currency in which the principal of any Security
         of any Series or any premium or the interest thereon is payable, or
         impair the right to institute suit for the enforcement of any such
         payment after the Stated Maturity thereof;

                  (b) amend, change or modify the obligation of Publishing to
         make and consummate a Change of Control Offer in the event of a Change
         of Control in accordance with Section 10.15, including amending,
         changing or modifying any of the provisions or definitions with
         respect thereto;

                  (c) reduce the percentage in principal amount of the
         Outstanding Securities of any Series, the consent of whose Holders is
         required for any such supplemental indenture or the consent of whose
         Holders is required for any waiver of compliance with certain
         provisions of this Indenture or certain Defaults hereunder and their
         consequences provided for in this Indenture;

                  (d) modify any of the provisions of this Section or Sections
         5.13 or 10.20, except to increase the percentage of Outstanding
         Securities of any Series required for such actions or to provide that
         certain


<PAGE>   107
                                                                          - 97 -

         other provisions of this Indenture cannot be modified or waived without
         the consent of the Holder of each Security affected thereby;

                  (e) except as otherwise permitted under Article VIII, consent
         to the assignment or transfer by Publishing or any Guarantor of any of
         its rights and obligations under this Indenture; or

                  (f) amend or modify any of the provisions of this Indenture
         relating to the subordination of the Securities of any Series or any
         Guarantee in any manner adverse to the holders of the Securities of
         such Series.

                  A supplemental indenture which changes or eliminates any
covenant or other provision of this Indenture which has expressly been included
solely for the benefit of one or more particular Series of Securities, or which
modifies the rights of the Holders of Securities of such Series with respect to
such covenant or other provision, shall be deemed not to affect the rights
under this Indenture of the Holders of Securities of any other Series.

                  Upon the written request of Publishing, accompanied by a copy
of a Board Resolution authorizing the execution of any such supplemental
indenture, and upon the filing with the Trustee of evidence of the consent of
Holders as aforesaid, the Trustee shall join with Publishing in the execution
of such supplemental indenture.

                  It shall not be necessary for any Act of Holders under this
Section to approve the particular form of any proposed supplemental indenture
or agreement, but it shall be sufficient if such Act shall approve the
substance thereof.

                  SECTION 9.03. Execution of Supplemental Indentures and
Agreements. In executing, or accepting the additional trusts created by, any
supplemental indenture, agreement or instrument permitted by this Article or
the modifications thereby of the trusts created by this Indenture, the Trustee
shall be entitled to receive, and (subject to Trust Indenture Act Section
315(a) through 315(d) and Section 6.03 hereof) shall be fully protected in
relying upon, an Opinion of Counsel and an Officers' Certificate to the effect
that the execution of such supplemental indenture, agreement or instrument is
authorized or permitted by this Indenture. The Trustee may, but shall not be
obligated to, enter into any such supplemental indenture, agreement or
instrument which


<PAGE>   108
                                                                          - 98 -

affects the Trustee's own rights, duties or immunities under this Indenture or
otherwise.

                  SECTION 9.04. Effect of Supplemental Indentures. Upon the
execution of any supplemental indenture under this Article, this Indenture
shall be modified in accordance therewith, and such supplemental indenture
shall form a part of this Indenture for all purposes; and every Holder of
Securities theretofore or thereafter authenticated and delivered hereunder
shall be bound thereby.

                  SECTION 9.05. Conformity with Trust Indenture Act. Every
supplemental indenture executed pursuant to this Article shall conform to the
requirements of the Trust Indenture Act as then in effect.

                  SECTION 9.06. Reference in Securities to Supplemental
Indentures. Securities authenticated and delivered after the execution of any
supplemental indenture pursuant to this Article IX may, and shall if required
by the Trustee, bear a notation in form approved by the Trustee as to any
matter provided for in such supplemental indenture. If Publishing shall so
determine, new Securities modified so as to conform to any such supplemental
indenture, in the opinion of the Trustee and the Board of Directors, may be
prepared and executed by Publishing and authenticated and delivered by the
Trustee in exchange for Outstanding Securities.

                  SECTION 9.07. Record Date. If Publishing shall solicit from
the Holders of any Series of Securities any request, demand, authorization,
direction, notice, consent, waiver or other Act, Publishing may, but shall not
be obligated to, fix a record date for the purpose of determining the Holders
of such Series entitled to consent to any supplemental indenture, agreement or
instrument or any waiver, and shall promptly notify the Trustee of any such
record date. If a record date is fixed, those Persons who were Holders of such
Series at such record date (or their duly designated proxies), and only those
Persons, shall be entitled to consent to such supplemental indenture, agreement
or instrument or waiver or to revoke any consent previously given, whether or
not such Persons continue to be Holders after such record date. The record date
shall be a date no more than 30 days prior to the first solicitation of Holders
generally in connection therewith and no later than the date such solicitation
is completed. No such consent shall be valid or effective for more than six
months after such record date. Subject to applicable law, until any
supplemental indenture, agreement, instrument or waiver


<PAGE>   109
                                                                          - 99 -

becomes effective, or a consent to it by a Holder of a Security of such Series
shall cease to be valid and effective as set forth in the preceding sentence,
such consent is a continuing consent by the Holder and every subsequent Holder
of a Security of such Series or portion of a Security of such Series that
evidences the same debt as the consenting Holder's Security.

                  SECTION 9.08.  Effect on Senior Indebtedness.  No
supplemental indenture shall adversely affect the rights under Article XII, or
any definitions or provisions related thereto, or the guarantees of any holder
of Senior Indebtedness unless the requisite holders of each issue of Senior
Indebtedness affected thereby shall have consented to such supplemental
indenture.

                                   ARTICLE X

                                   Covenants

                  SECTION 10.01. Payment of Principal, Premium and Interest.
With respect to each Series of Securities, Publishing will duly and punctually
pay the principal of, premium, if any, and interest on such Securities in
accordance with the terms of such Securities and this Indenture.

                  SECTION 10.02. Maintenance of Office or Agency. Publishing
will maintain in The City of New York an office or agency where Securities may
be presented or surrendered for payment, where Securities may be surrendered
for registration of transfer or exchange and where notices and demands to or
upon Publishing in respect of the Securities and this Indenture may be served.
The office of the Trustee at 14 Wall Street, Window #2, New York, New York
10005, shall be such office or agency of Publishing, unless Publishing shall
designate and maintain some other office or agency for one or more of such
purposes.  Publishing will give prompt written notice to the Trustee of any
change in the location of any such office or agency. If at any time Publishing
shall fail to maintain any such required office or agency or shall fail to
furnish the Trustee with the address thereof, such presentations, surrenders,
notices and demands may be made or served at the Corporate Trust Office, and
Publishing hereby appoints the Trustee as its agent to receive all such
presentations, surrenders, notices and demands.

                  Publishing may from time to time designate one or more other
offices or agencies (in or outside of The City of


<PAGE>   110
                                                                         - 100 -

New York) where the Securities may be presented or surrendered for any or all
such purposes, and may from time to time rescind such designation; provided,
however, that no such designation or rescission shall in any manner relieve
Publishing of its obligation to maintain an office or agency in The City of New
York for such purposes. Publishing will give prompt written notice to the
Trustee of any such designation or rescission and any change in the location of
any such office or agency.

                  SECTION 10.03. Money for Security Payments To Be Held in
Trust. Publishing will, on or before Noon, New York time, on each due date of
the principal of, premium, if any, or interest on, Securities with respect to
each Series of Securities, deposit with a Paying Agent (which shall not be
Publishing) a sum in same-day funds sufficient to pay the principal, premium,
if any, or interest so becoming due, such sum to be held in trust for the
benefit of the Persons entitled to such principal, premium or interest, and
(unless such Paying Agent is the Trustee) Publishing will promptly notify the
Trustee of such action or any failure so to act.

                  Publishing will cause each Paying Agent other than the
Trustee for any Series of Securities to execute and deliver to the Trustee an
instrument in which such Paying Agent shall agree with the Trustee, subject to
the provisions of this Section, that such Paying Agent will:

                  (a) hold all sums held by it for the payment of the principal
         of, premium, if any, or interest on Securities of such Series in trust
         for the benefit of the Persons entitled thereto until such sums shall
         be paid to such Persons or otherwise disposed of as herein provided;

                  (b) give the Trustee notice of any Default by Publishing (or
         any other obligor upon the Securities of such Series) in the making of
         any payment of principal, premium, if any, or interest on the
         Securities of such Series;

                  (c) at any time during the continuance of any such Default,
         upon the written request of the Trustee, forthwith pay to the Trustee
         all sums so held in trust by such Paying Agent; and

                  (d) acknowledge, accept and agree to comply in all aspects
         with the provisions of this Indenture relating to the duties, rights
         and liabilities of such Paying Agent.

<PAGE>   111
                                                                         - 101 -

                  Publishing may at any time, for the purpose of obtaining the
satisfaction and discharge of this Indenture with respect to any Series of
Securities or for any other purpose, by Publishing Order direct any Paying
Agent to pay to the Trustee all sums held in trust by such Paying Agent in
respect of each and every Series of Securities as to which it seeks to
discharge this Indenture or, if for any other purpose, all sums so held in
trust by Publishing in respect of all Securities, such sums to be held by the
Trustee upon the same trusts as those upon which such sums were held by such
Paying Agent; and, upon such payment by any Paying Agent to the Trustee, such
Paying Agent shall be released from all further liability with respect to such
money.

                  Any money deposited with the Trustee or any Paying Agent in
trust for the payment of the principal of, premium, if any, or interest on any
Security of any Series and remaining unclaimed for two years after such
principal and premium, if any, or interest has become due and payable shall
promptly be paid to Publishing upon Publishing Request; and the Holder of such
Security shall thereafter, as an unsecured general creditor, look only to
Publishing for payment thereof, and all liability of the Trustee or such Paying
Agent with respect to such trust money, and all liability of Publishing as
trustee thereof, shall thereupon cease; provided, however, that the Trustee or
such Paying Agent, before being required to make any such payment to
Publishing, may at the expense of Publishing cause to be published once, in The
New York Times and The Wall Street Journal (national edition), notice that such
money remains unclaimed and that, after a date specified therein, which shall
not be less than 30 days from the date of such notification or publication, any
unclaimed balance of such money then remaining will promptly be repaid to
Publishing.

                  SECTION 10.04. Corporate Existence. Subject to Article VIII,
Publishing will do or cause to be done all things necessary to preserve and
keep in full force and effect its corporate existence and related rights and
franchises (charter and statutory) of Publishing and each Restricted
Subsidiary; provided, however, that Publishing shall not be required to
preserve any such right or franchise or the corporate existence of any such
Restricted Subsidiary if the Board of Directors of Publishing shall determine
that the preservation thereof is no longer desirable in the conduct of the
business of Publishing and its Restricted Subsidiaries as a whole and that the
loss thereof would not reasonably be expected to have a material adverse effect
on the ability of Publishing to perform its obligations hereunder; and provided
further, however, that


<PAGE>   112
                                                                         - 102 -

the foregoing shall not prohibit a sale, transfer or conveyance of a Restricted
Subsidiary or any of its assets in compliance with the terms of this Indenture.

                  SECTION 10.05. Payment of Taxes and Other Claims. Publishing
will pay or discharge or cause to be paid or discharged, on or before the date
the same shall become due and payable, (a) all material taxes, assessments and
governmental charges levied or imposed upon Publishing or any Restricted
Subsidiary shown to be due on any tax return of Publishing or any Restricted
Subsidiary or otherwise assessed or upon the income, profits or property of
Publishing or any Restricted Subsidiary and (b) all material lawful claims for
labor, materials and supplies, which, if unpaid, would by law become a Lien
upon the property of Publishing or any Restricted Subsidiary, except for any
Lien permitted to be Incurred under Section 10.12; provided, however, that
Publishing shall not be required to pay or discharge or cause to be paid or
discharged any such tax, assessment, charge or claim whose amount,
applicability or validity is being contested in good faith by appropriate
proceedings properly instituted and diligently conducted and in respect of
which appropriate reserves (in the good-faith judgment of management of
Publishing) are being maintained in accordance with GAAP consistently applied.

                  SECTION 10.06. Maintenance of Properties. Publishing will
cause all material properties owned by Publishing or any Restricted Subsidiary
or used or held for use in the conduct of its business or the business of any
Restricted Subsidiary to be maintained and kept in good condition, repair and
working order (ordinary wear and tear excepted) and supplied with all necessary
equipment and will cause to be made all necessary repairs, renewals,
replacements, betterments and improvements thereof, all as in the judgment of
Publishing may be consistent with sound business practice and reasonably
necessary so that the business carried on in connection therewith may be
properly and advantageously conducted at all times; provided, however, that
nothing in this Section 10.06 shall prevent Publishing from discontinuing the
maintenance of any of such properties if such discontinuance is, in the
judgment of Publishing, desirable in the conduct of the business of Publishing
and its Restricted Subsidiaries and not reasonably expected to have a material
adverse effect on the ability of Publishing to perform its obligations
hereunder.

                  SECTION 10.07. Insurance. Publishing will at all times keep
all of its and its Restricted Subsidiaries' properties which are of an
insurable nature reasonably self-insured or insured with insurers, believed by
Publishing to


<PAGE>   113
                                                                         - 103 -

be responsible, against loss or damage to the extent that property of similar
character is usually so insured by corporations similarly situated and owning
like properties in the same general geographic areas in which Publishing and
its Restricted Subsidiaries operate, except where the failure to do so would
not reasonably be expected to have a material adverse effect on the condition
(financial or otherwise), earnings, business affairs or prospects of Publishing
and its Restricted Subsidiaries, taken as a whole.

                  SECTION 10.08. Limitation on Indebtedness. (a) Publishing
will not, and will not permit any of its Restricted Subsidiaries to, Incur any
Indebtedness (including any Acquired Indebtedness but excluding any Permitted
Indebtedness) except for (x) Indebtedness of Publishing or (y) Indebtedness of
a Restricted Subsidiary constituting Acquired Indebtedness, Permitted
Subsidiary Indebtedness or Foreign Subsidiary Indebtedness, provided that, in
the case of the foregoing clauses (x) and (y), the Consolidated Cash Flow Ratio
for Publishing and the Restricted Subsidiaries for the four full fiscal
quarters immediately preceding the Incurrence of such Indebtedness taken as one
period is greater than 6.0:1.0. In addition (and without limiting the foregoing
requirement), unless both of The Telegraph and Southam are Restricted
Subsidiaries, Publishing shall not permit any Restricted Subsidiary to Incur
any Indebtedness other than Acquired Indebtedness or Permitted Subsidiary
Indebtedness. For purposes of determining the Consolidated Cash Flow Ratio for
any period, pro forma effect shall be given to (i) the Incurrence of such
Indebtedness and (if applicable) the application of the net proceeds therefrom,
including to refinance other Indebtedness, as if such Indebtedness was
Incurred, and the application of such proceeds occurred, at the beginning of
such four-quarter period; (ii) the Incurrence, repayment or retirement of any
other Indebtedness by Publishing and its Restricted Subsidiaries since the
first day of such four-quarter period as if such Indebtedness was Incurred,
repaid or retired at the beginning of such four-quarter period; (iii) in the
case of Acquired Indebtedness, the related acquisition (as if such acquisition
had been consummated on the first day of such four-quarter period); and (iv)
any acquisition or disposition by Publishing and its Restricted Subsidiaries of
any company or any business or any assets out of the ordinary course of
business, whether by merger, stock purchase or sale or asset purchase or sale
or any related repayment of Indebtedness, in each case since the first day of
such four-quarter period (as if such acquisition or


<PAGE>   114
                                                                         - 104 -

disposition had been consummated on the first day of such four-quarter period).

                  (b) Prior to September 1, 1997, neither Publishing nor any
Restricted Subsidiary will issue any Public Debt unless the aggregate principal
amount (or initial proceeds in the case of Public Debt sold with "original
issue discount" (within the meaning of Section 1273(a) of the Internal Revenue
Code of 1986, as amended)) of Public Debt so issued since the date of this
Indenture that is Senior Indebtedness does not exceed the aggregate principal
amount (or initial proceeds in the case of Public Debt sold with "original
issue discount") of Public Debt so issued since the date of this Indenture that
is pari passu with or subordinated to the Securities.

                  SECTION 10.09. Limitation on Restricted Payments. (a)
Publishing will not, and will not permit any Restricted Subsidiary to, directly
or indirectly:

                  (i) declare or pay any dividend or make any other
         distribution or payment on or in respect of Publishing's Capital Stock
         (including dividends or distributions of the Capital Stock of any
         Subsidiary), or make any other payment to the direct or indirect
         holders (in their capacities as such) of Publishing's Capital Stock
         (other than (x) dividends or distributions payable in shares of
         Publishing's Qualified Capital Stock or in options, warrants or other
         rights to acquire such Qualified Capital Stock and (y) a dividend or
         distribution of up to $175 million payable to Hollinger International;
         provided that, simultaneously or in connection with such dividend or
         distribution, Hollinger International contributes or transfers,
         directly or indirectly, to Publishing all of the Capital Stock of
         Hollinger Eastern then held by Hollinger International; and provided
         further, that Hollinger Eastern then holds not less than 42% of the
         voting interest of Southam);

                (ii) purchase, redeem or otherwise acquire or retire for value,
         directly or indirectly, any Capital Stock of Publishing or any Capital
         Stock of any Affiliate of Publishing (other than Capital Stock of any
         Wholly Owned Restricted Subsidiary (or, provided that both of The
         Telegraph and Southam are Restricted Subsidiaries, Capital Stock of a
         Restricted Subsidiary) or Capital Stock of a Person that is, or
         immediately following such repurchase will become, a Wholly Owned
         Restricted Subsidiary (or, provided that both of The Telegraph and
         Southam are Restricted Subsidiaries, a


<PAGE>   115
                                                                         - 105 -

         Restricted Subsidiary)) or options, warrants or other rights to acquire
         such Capital Stock;

              (iii) make any principal payment on, or repurchase, redeem,
         defease, retire or otherwise acquire for value, prior to any scheduled
         principal payment, sinking fund payment or maturity, any Subordinated
         Indebtedness;

               (iv) declare or pay any dividend or distribution on any Capital
         Stock of any Restricted Subsidiary to any Person (other than (x)
         dividends and distributions on Preferred Stock of Restricted
         Subsidiaries or Mirror Preferred or (y) dividends and distributions
         made to any Person (other than a controlling Affiliate of Publishing
         or an Affiliate of such Affiliate (other than Publishing and any
         Restricted Subsidiary)) on a pro rata basis consistent with the
         ownership interests in such Capital Stock to the owners of such
         Capital Stock, except that, in the case of the Capital Stock of a
         Restricted Subsidiary that is a Guarantor, (i) no Default or Event of
         Default shall have occurred and be continuing; and (ii) no holders of
         any other Indebtedness of Publishing or any Restricted Subsidiary
         shall have an Acceleration Right);

                (v) Incur, create or assume any guarantee of Indebtedness of
         any Affiliate of Publishing (other than a Wholly Owned Restricted
         Subsidiary of Publishing (or, provided that both of The Telegraph and
         Southam are Restricted Subsidiaries, a Restricted Subsidiary of
         Publishing)) except as permitted by Section 10.13;

               (vi) make any Investment in any Person (other than any
         Permitted Investments); or

              (vii) designate any Restricted Subsidiary as an Unrestricted
         Subsidiary;

(any of the payments described in paragraphs (i) through (vii) above, other
than any such action that is a Permitted Payment (as defined below),
collectively, "Restricted Payments") unless at the time of and after giving
effect to the proposed Restricted Payment (the amount of any such Restricted
Payment, if other than cash, as determined by the Board of Directors, whose
determination shall be conclusive and evidenced by a Board Resolution), (1) no
Default or Event of Default shall have occurred and be continuing; (2) no
holders of any other Indebtedness of Publishing or any Restricted Subsidiary
shall have an Acceleration Right; (3) immediately before and immediately after
giving effect to such transaction on a pro forma basis, Publishing could


<PAGE>   116
                                                                         - 106 -

Incur $1.00 of additional Indebtedness (other than Permitted Indebtedness)
under the provisions of Section 10.08; and (4) the aggregate amount of all such
Restricted Payments declared or made after the date of this Indenture (provided
that, in the case of a Restricted Payment by a Restricted Subsidiary, such
Restricted Payment is calculated for the purposes of this paragraph (4) by
multiplying the amount of the Restricted Payment by the percentage of
Publishing's common equity interest in such Restricted Subsidiary at the time
of such Restricted Payment but disregarding, in the case of Southam, common
equity interests which are pledged to secure the Southam-Linked Debentures)
does not exceed the sum of:

                  (A) 50% of the sum of (i) the aggregate cumulative
         Consolidated Net Income of Publishing and its Restricted Subsidiaries
         accrued during the period (treated as a single accounting period)
         beginning on the first day of Publishing's fiscal quarter commencing
         prior to the date of this Indenture and ending on the last day of
         Publishing's last fiscal quarter ending prior to the date of the
         Restricted Payment (or, if such aggregate cumulative Consolidated Net
         Income shall be a loss, 100% of such loss (treating a loss as a
         negative number)) and (ii) the aggregate cumulative Amortization
         Expense of Publishing and its Restricted Subsidiaries accrued during
         the period (treated as a single accounting period) beginning on the
         first day of Publishing's fiscal quarter commencing prior to the date
         of this Indenture and ending on the last day of Publishing's last
         fiscal quarter ending prior to the date of the Restricted Payment;

                  (B) 50% of the aggregate cumulative cash dividends or
         distributions received by Publishing and its Consolidated Restricted
         Subsidiaries from any of Publishing's Unrestricted Subsidiaries during
         the period (treated as a single accounting period) beginning on the
         first day of Publishing's fiscal quarter commencing prior to the date
         of this Indenture and ending on the last day of Publishing's last
         fiscal quarter ending prior to the date of the Restricted Payment;
         provided, however, that for purposes of this clause (B), cash
         dividends and distributions shall not include, without duplication,
         (x), prior to the time that Southam shall be a Restricted Subsidiary,
         cash dividends received by Publishing from Publishing's Unrestricted
         Subsidiaries not in excess of the Southam Dividend Amount, (y) cash
         dividends or distributions received by Publishing or any Wholly Owned
         Restricted Subsidiary in accordance with Section (b)(vii) or


<PAGE>   117
                                                                         - 107 -

         (z) dividends or distributions on any Argsub Preferred received by FDTH
         or DTH;

                  (C) the aggregate Net Cash Proceeds received after the date
         of this Indenture by Publishing from the issuance or sale (other than
         to any of its Restricted Subsidiaries) of its Qualified Capital Stock
         or any options, warrants or rights to purchase such Qualified Capital
         Stock (except, in each case, to the extent such proceeds are used to
         purchase, redeem or otherwise retire Capital Stock, Subordinated
         Indebtedness or Pari Passu Indebtedness as set forth below);

                  (D) the aggregate Net Cash Proceeds received after the date
         of this Indenture by Publishing (other than from any of its Restricted
         Subsidiaries) upon the exercise of any options or warrants to purchase
         Qualified Capital Stock of Publishing;

                  (E) the aggregate Net Cash Proceeds received after the date
         of this Indenture by Publishing (other than from any of its
         Subsidiaries) from cash capital contributions made to Publishing;

                  (F) the aggregate amount by which any Indebtedness (other
         than Permitted Indebtedness) of Publishing or any Restricted
         Subsidiary is reduced after the date of this Indenture as a result of
         the conversion or exchange of debt securities or Redeemable Capital
         Stock of Publishing that has been converted into or exchanged for
         Qualified Capital Stock of Publishing to the extent such debt
         securities or Redeemable Capital Stock were originally sold for cash
         plus the aggregate Net Cash Proceeds received by Publishing at the
         time of any such conversion or exchange; and

                  (G) $25,000,000.

                  (b) Notwithstanding the foregoing, and, in the case of
clauses (ii) through (x) below, so long as (1) there is no Default or Event of
Default continuing and (2) no holders of any other Indebtedness of Publishing
or any Restricted Subsidiary have an Acceleration Right, the foregoing
provisions will not prohibit the following actions (clauses (i) through (x)
being referred to as "Permitted Payments"):

                  (i) the payment of any dividend or distribution within 60
         days after the date of declaration thereof, if at such date of
         declaration such payment would be permitted by the provisions of
         paragraph (a) of this


<PAGE>   118
                                                                         - 108 -

         section and such payment will be deemed to have been paid on such date
         of declaration for purposes of the calculation required by paragraph
         (a) of this section;

                (ii) the repurchase, redemption or other acquisition or
         retirement of any shares of Capital Stock of Publishing in exchange
         for (including any such exchange pursuant to the exercise of a
         conversion right or privilege in connection with which cash is paid in
         lieu of the issuance of fractional shares or scrip), or out of the Net
         Cash Proceeds of a substantially concurrent issue and sale for cash
         (other than to a Restricted Subsidiary) of other Qualified Capital
         Stock of Publishing; provided that the Net Cash Proceeds from the
         issuance of such shares of Qualified Capital Stock are excluded from
         clauses (4)(D) and (4)(E) of paragraph (a) of this section;

              (iii) any repurchase, redemption, defeasance, retirement or
         acquisition for value or payment of principal of any Subordinated
         Indebtedness in exchange for, or out of the net proceeds of, a
         substantially concurrent issuance and sale for cash (other than to any
         Restricted Subsidiary of Publishing) of any Qualified Capital Stock of
         Publishing; provided that the Net Cash Proceeds from the issuance of
         such Qualified Capital Stock are excluded from clauses (4)(D) and
         (4)(E) of paragraph (a) of this section;

                (iv) the repurchase, redemption, defeasance, retirement,
         refinancing, acquisition for value or payment of principal of any
         Subordinated Indebtedness (other than Redeemable Capital Stock) or
         Pari Passu Indebtedness (a "refinancing") through the issuance of new
         Subordinated Indebtedness of Publishing; provided that any such new
         Subordinated Indebtedness (1) shall be in a principal amount that does
         not exceed the principal amount so refinanced (or, if the Subordinated
         Indebtedness so refinanced provides for an amount less than the
         principal amount thereof to be due and payable upon a declaration or
         acceleration thereof, then such lesser amount as of the date of
         determination), plus the amount of any premium required to be paid in
         connection with such refinancing pursuant to the terms of such
         refinanced Indebtedness and any reasonable out-of-pocket expenses of
         Publishing incurred in connection with such refinancing; (2) has an
         Average Life to Stated Maturity greater than the remaining Average
         Life to Stated Maturity of the Securities; (3) has a Stated Maturity
         for its final scheduled


<PAGE>   119
                                                                         - 109 -

         principal payment later than the Stated Maturity for the final
         scheduled principal payment of the Securities; and (4) is expressly
         subordinated in right of payment to the Securities at least to the same
         extent as the Indebtedness to be refinanced;

                 (v) dividends paid to Hollinger International after the date
         of this Indenture to the extent not in excess of the Southam Dividend
         Amount;

                (vi) loans, advances, dividends or distributions by any
         Restricted Subsidiary to Publishing or any Wholly Owned Restricted
         Subsidiary and by FDTH or, to the extent it has received such funds
         directly or indirectly from FDTH, DTH or Publishing to Hollinger
         International for the purpose of redeeming shares of Series A
         Preferred Stock not exceeding in the aggregate any payments made by
         Hollinger Inc. to FDTH pursuant to the provisions of the HTH/FDTH
         Share Exchange Agreement;

               (vii) loans, advances, dividends or distributions to Hollinger
         International in amounts not to exceed $1 million per year to permit
         Hollinger International to repurchase, redeem or otherwise acquire or
         retire any shares of its Capital Stock from employees, former
         employees or their estates upon disability, death, retirement or
         termination of employment;

              (viii) tax payments pursuant to a Tax Sharing Agreement to the
         extent that the aggregate amount of such payments do not exceed the
         aggregate amount of the tax payments that Publishing and the
         Restricted Subsidiaries would have been required to make if they alone
         constituted a single consolidated tax group;

                (ix) payments by Publishing or a Restricted Subsidiary in
         connection with the Scheme of Arrangement; and

                 (x) the issuance or redemption of or payment of distributions
         on Mirror Preferred, but only to the extent Argsub Preferred is
         simultaneously issued, redeemed or pays (or is deemed to pay)
         dividends, respectively, and only so long as no cash is transferred in
         any such transaction, except for cash payments in respect of certain
         Mirror Preferred made directly from FDTH to DTH at the direction of
         Argsub.

                  For purposes of this Section, if the Board of Directors
designates a Restricted Subsidiary as an


<PAGE>   120
                                                                         - 110 -

Unrestricted Subsidiary, or a Restricted Subsidiary is deemed to be so
designated, a "Restricted Payment" shall be deemed to have been made in an
amount equal to the fair value of the Investment of Publishing and its other
Restricted Subsidiaries in such Restricted Subsidiary as determined by the
Board of Directors with the concurrence of a majority of the Independent
Directors (there being at least one Independent Director), whose good faith
determination shall be conclusive. If a particular Restricted Payment involves
a non-cash payment, including a distribution of assets, then such Restricted
Payment shall be deemed to be in an amount equal to the fair market value of
the non-cash portion of such Restricted Payment as determined by the Board of
Directors, whose good faith determination shall be conclusive.

                  SECTION 10.10. Limitation on Transactions with Affiliates.
(a) Publishing will not, and will not permit any of its Restricted Subsidiaries
to, directly or indirectly, enter into or suffer to exist any transaction or
series of related transactions (including, without limitation, the sale,
purchase, exchange or lease of assets, property or services) with any Affiliate
of Publishing (other than Publishing or a Wholly Owned Restricted Subsidiary,
or, if both of The Telegraph and Southam are Restricted Subsidiaries, a
Restricted Subsidiary) unless (a) such transaction or series of related
transactions is on terms that are no less favorable to Publishing or such
Restricted Subsidiary, as the case may be, than would be available in a
comparable transaction in arm's-length dealings with an unrelated third party
and (b) with respect to any transaction or series of related transactions
involving aggregate payments in excess of $5,000,000, Publishing delivers an
Officers' Certificate to the Trustee certifying that such transaction or series
of related transactions complies with clause (a) above and such transaction or
series of related transactions has been approved by a majority of the
Independent Directors of the Board of Directors; provided that any transaction
or series of related transactions otherwise permitted under this paragraph
(other than any transaction or series of related transactions with respect to
the making of any Permitted Investment pursuant to clause (ix) of the
definition of "Permitted Investment" or any Restricted Payment permitted
pursuant to Section 10.09 pursuant to which Publishing or any Restricted
Subsidiary shall receive or render value exceeding $15,000,000 shall not be
permitted unless, prior to the consummation of any such transaction or series
of related transactions, Publishing shall have received an opinion, from an
independent nationally recognized investment banking firm or firm experienced
in the appraisal


<PAGE>   121
                                                                         - 111 -

or similar review of similar types of transactions, that such transaction is
fair to Publishing from a financial point of view; provided further, that this
covenant shall not apply to (i) transactions or agreements as in effect or
securities outstanding on the date of the Indenture (provided that any
amendment to any existing agreement (including the Services Agreement and the
Business Opportunities Agreement), and any transaction pursuant to the Business
Opportunities Agreement, shall require approval pursuant to this covenant;
notwithstanding the foregoing, any amendment to the Services Agreement or the
Business Opportunities Agreement shall require the approval of a majority of
the Independent Directors); (ii) directors' fees approved by the Board of
Directors; (iii) any employee benefit plan or arrangement entered into or made
available to officers or other employees of Publishing or the Restricted
Subsidiaries in the ordinary course of business; (iv) sales by Publishing and
its Restricted Subsidiaries of their products in the ordinary course of
business on arm's-length terms; (v) tax payments pursuant to a Tax Sharing
Agreement to the extent that the aggregate amount of such payments do not
exceed the aggregate amount of the tax payments that Publishing and the
Restricted Subsidiaries would have been required to make if they alone
constituted a single consolidated tax group; (vi) loans, advances, dividends or
distributions by FDTH, DTH or Publishing to Hollinger International in amounts
and for the purpose permitted by Section (b)(v) and (vii); (vii) payments made
to Hollinger Inc. pursuant to the Services Agreement that constitute the
reimbursement for the fair value (as determined by a majority of the
Independent Directors serving on an Independent Committee) of services received
by Publishing or a Restricted Subsidiary consistent with past practices; and
(viii) the issuance or redemption, retraction or transfer of or payment of
dividends, distributions or other amounts on Mirror Preferred by DTH or FDTH to
an Argsub, but only to the extent that such Argsub simultaneously, as the case
may be, issues or redeems or pays dividends, distributions or other amounts (or
is deemed to have taken any such action) to DTH or FDTH, in each case in
equivalent amounts.

                  SECTION 10.11. Limitation on Other Subordinated Indebtedness.
Neither Publishing nor any Restricted Subsidiary Guarantor will Incur or permit
to exist any Indebtedness (other than the Securities or a Guarantee thereof
pursuant to this Indenture, as applicable) that is subordinate in right of
payment to any Senior Indebtedness of Publishing (or such Guarantor) unless
such Indebtedness is also pari passu with, or subordinate in right of payment
to, the Securities or the Guarantee of such Guarantor, as


<PAGE>   122
                                                                         - 112 -

the case may be. For purposes of this covenant, Indebtedness will be deemed to
be pari passu with the Securities or such Guarantee if it is subordinate to
Senior Indebtedness of Publishing or the relevant Guarantee pursuant to
subordination provisions substantially similar to those described in Section
12.01.

                  SECTION 10.12. Limitation on Liens. (a) Publishing will not,
and will not permit any Restricted Subsidiary to Incur, affirm or suffer to
exist any Lien of any kind securing any Pari Passu Indebtedness or Subordinated
Indebtedness of Publishing (including any assumption, guarantee or other
liability with respect thereto by any Restricted Subsidiary) upon any property
or assets (including any intercompany notes) of Publishing or any Restricted
Subsidiary owned on the date of this Indenture or acquired after the date of
this Indenture, or any income or profits therefrom, unless (i) in the case of
any Lien securing Pari Passu Indebtedness, the Securities are secured by a Lien
on such property, assets or proceeds that is senior in priority to or pari
passu with such Lien and (ii) in the case of any Lien securing Subordinated
Indebtedness of Publishing, the Securities are secured by a Lien on such
property, assets or proceeds that is senior in priority to such Lien, except
for (x) any Lien securing Acquired Indebtedness created prior to (and not
created in connection with, or in contemplation of) the Incurrence of such Pari
Passu Indebtedness or Subordinated Indebtedness by Publishing or any Restricted
Subsidiary, in each case which Indebtedness is permitted under the provisions
of Section 10.08 (provided that any such Lien only extends to the assets that
were subject to such Lien securing such Acquired Indebtedness prior to the
related acquisition by Publishing or its Restricted Subsidiaries) and (y) any
Lien securing Indebtedness owing to Publishing or a Wholly Owned Restricted
Subsidiary by a Restricted Subsidiary.

                  (b) Notwithstanding the foregoing, any security interest
granted by Publishing or any Restricted Subsidiary to secure the Securities
created pursuant to paragraph (a) above shall provide by its terms that such
security interest shall be automatically and unconditionally released and
discharged upon the release by the holders of the Indebtedness of Publishing or
any Restricted Subsidiary described in paragraph (a) above of their security
interest (including any deemed release upon payment in full of all obligations
under such Indebtedness), at a time when (A) no other Pari Passu Indebtedness
and Subordinated Indebtedness of Publishing or any Restricted Subsidiary has
been secured by such property or assets of Publishing or any such Restricted
Subsidiary or (B) the holders of all such other


<PAGE>   123
                                                                         - 113 -

Pari Passu Indebtedness and Subordinated Indebtedness which is secured by such
property or assets of Publishing or any such Restricted Subsidiary also release
their security interest in such property or assets (including any deemed
release upon payment in full of all obligations under such Indebtedness).

                  SECTION 10.13. Limitation on Issuances of Guarantees of
Indebtedness. (a) Publishing will not permit any Restricted Subsidiary,
directly or indirectly, to guarantee, assume or in any other manner become
liable with respect to any Pari Passu Indebtedness or Subordinated Indebtedness
unless such Restricted Subsidiary simultaneously executes and delivers a
supplemental indenture to this Indenture providing for a guarantee of the
Securities and (A) if the Securities are subordinated in right of payment to
such Indebtedness, the guarantee under the supplemental indenture shall be
subordinated to the same extent as the Securities are subordinated to such
Indebtedness under this Indenture and (B) if such Indebtedness of Publishing is
by its terms expressly subordinated to the Securities, any such assumption,
guarantee or other liability of such Restricted Subsidiary with respect to such
Indebtedness shall be subordinated to such Restricted Subsidiary's guarantee to
the same extent as such Indebtedness is subordinated to the Securities.

                  (b) Notwithstanding the foregoing, any guarantee by a
Restricted Subsidiary of the Securities that is provided pursuant to the
foregoing paragraph or under the provisions of Section 10.16 may provide by its
terms that it shall be automatically and unconditionally released and
discharged (i) upon any sale, exchange or transfer, to any Person not an
Affiliate of Publishing, of all of Publishing's Capital Stock in, or all or
substantially all the assets of, such Restricted Subsidiary, which sale,
exchange or transfer is in compliance with this Indenture, (ii) if the
Restricted Subsidiary issuing such guarantee ceases to be a Restricted
Subsidiary or (iii) upon the release by the holders of the Indebtedness of
Publishing described in paragraph (a) above of their Guarantee by such
Restricted Subsidiary (including any deemed release upon payment in full of all
obligations under such Indebtedness), at a time when (A) no Indebtedness of
Publishing or any Restricted Subsidiary has been guaranteed by such Restricted
Subsidiary or (B) the holders of all such other Indebtedness which is
guaranteed by such Restricted Subsidiary also release their Guarantee by such
Restricted Subsidiary (including any deemed release upon payment in full of all
obligations under such Indebtedness).

<PAGE>   124
                                                                         - 114 -

                  SECTION 10.14. Limitation on Sale of Assets. (a) Publishing
will not, and will not permit any of its Restricted Subsidiaries to, directly
or indirectly, consummate an Asset Sale unless (i) at least 80% of the proceeds
from such Asset Sale are received in cash (provided that the amount of (A) any
Senior Indebtedness (as shown on Publishing's or such Restricted Subsidiaries'
most recent balance sheet or in the notes thereto) of Publishing or any such
Restricted Subsidiary that is assumed by the transferee of any asset in
connection with any Asset Sale and (B) any deferred payment obligations
received by Publishing or any such Restricted Subsidiary as proceeds of an
Asset Sale that are concurrently with the Asset Sale converted into cash
without recourse to Publishing or any of its Restricted Subsidiaries shall be
deemed to be cash for purposes of this provision; provided further that, for
purposes of this clause (i), "cash" shall include any cash proceeds received
from the sale of securities received in an Asset Sale as long as at the time of
such Asset Sale, Publishing or its Restricted Subsidiary, as applicable, has
entered into a legally binding agreement for the sale of such securities and
such securities are sold within 90 days of such Asset Sale; and provided
further that this clause (i) shall not apply to (x) Newspaper Businesses
received by Publishing or a Restricted Subsidiary from the transferee as
consideration for an Asset Sale (an "Asset Swap") so long as, immediately
before and immediately after giving effect to such transaction on a pro forma
basis, Publishing could Incur $1.00 of additional Indebtedness (other than
Permitted Indebtedness) under the provisions of Section 10.08, (y) a CST Real
Estate Transaction or (z) a Permitted Real Estate Sale)) and (ii) Publishing or
such Restricted Subsidiary receives consideration at the time of such Asset
Sale at least equal to the fair market value of the shares or assets sold (as
determined by the Board of Directors of Publishing and evidenced by a board
resolution). The value of any properties or assets (other than cash) received
pursuant to an Asset Sale shall be determined by the Board of Directors of
Publishing and evidenced by a Board Resolution; provided that if the value of
the asset which is the subject of the Asset Sale is in excess of $25,000,000,
the value of the properties or assets received shall be determined by an
independent nationally recognized investment banking firm or firm experienced
in the appraisal or similar review of similar types of assets (provided that
for purposes of this sentence, any CST Real Estate Transaction shall be deemed
to involve an asset whose value exceeds $25,000,000).

                  (b) If all or a portion of the Net Cash Proceeds of any Asset
Sale is not applied to permanently repay or otherwise permanently retire any
Senior Indebtedness then


<PAGE>   125
                                                                         - 115 -

outstanding as permitted or required by the terms thereof, or if no such Senior
Indebtedness is then outstanding, Publishing or a Restricted Subsidiary, as the
case may be, may, within 12 months of the Asset Sale, invest the Net Cash
Proceeds in properties and assets that (as determined by the Board of
Directors) replace the properties and assets that were the subject of the Asset
Sale or in properties and assets that will be used in the businesses of
Publishing or its Restricted Subsidiaries existing on the date of this
Indenture or in businesses reasonably related thereto. The amount of such Net
Cash Proceeds neither used to permanently repay or prepay Senior Indebtedness
nor used or invested as set forth in this paragraph constitutes "Excess
Proceeds."

                  (c) When the aggregate amount of Excess Proceeds equals or
exceeds $20,000,000, Publishing shall apply the Excess Proceeds to the
repayment of the Securities and any Pari Passu Indebtedness required to be
repurchased under the instrument governing such Pari Passu Indebtedness as
follows: (i) Publishing shall make an offer to purchase (an "Offer") from all
Holders in accordance with the procedures set forth in this Indenture in the
maximum principal amount (expressed as a multiple of $1,000) of Securities that
may be purchased out of an amount (the "Note Amount") equal to the product of
such Excess Proceeds multiplied by a fraction, the numerator of which is the
outstanding principal amount of the Securities, and the denominator of which is
the sum of the outstanding principal amount of the Securities and such Pari
Passu Indebtedness (subject to proration in the event such amount is less than
the aggregate Offered Price (as defined herein) of all Securities tendered) and
(ii) to the extent required by such Pari Passu Indebtedness to permanently
reduce the principal amount of such Pari Passu Indebtedness, Publishing shall
make an offer to purchase or otherwise repurchase or redeem Pari Passu
Indebtedness (a "Pari Passu Offer") in an amount (the "Pari Passu Debt Amount")
equal to the excess of the Excess Proceeds over the Note Amount; provided that
in no event shall the Pari Passu Debt Amount exceed the principal amount of
such Pari Passu Indebtedness plus the amount of any premium required to be paid
to repurchase such Pari Passu Indebtedness. The offer price shall be payable in
cash in an amount equal to 100% of the principal amount of the Securities plus
accrued and unpaid interest, if any, to the date (the "Purchase Date") such
Offer is consummated (the "Offered Price"), in accordance with the procedures
set forth in this Indenture. To the extent that the aggregate Offered Price of
the Securities tendered pursuant to the Offer is less than the Note Amount
relating thereto or the aggregate amount of Pari Passu Indebtedness that is
purchased is less than the Pari Passu Debt Amount (the



<PAGE>   126
                                                                         - 116 -

amount of such shortfall, if any, constituting a "Deficiency"), Publishing
shall use such Deficiency in the business of Publishing and its Restricted
Subsidiaries. Upon completion of the purchase of all Securities tendered
pursuant to an Offer and repurchase of the Pari Passu Indebtedness pursuant to
a Pari Passu Offer, the amount of Excess Proceeds, if any, shall be reset at
zero.

                  (d) Whenever the aggregate amount of Excess Proceeds received
by Publishing exceeds $20,000,000, such Excess Proceeds shall, prior to the
purchase of Securities or any Pari Passu Indebtedness described in paragraph
(c) above, be set aside by Publishing in a separate account pending (i) deposit
with the depository or a Paying Agent of the amount required to purchase the
Securities or Pari Passu Indebtedness tendered in an Offer or a Pari Passu
Offer, (ii) delivery by Publishing of the Offered Price to the holders of the
Securities or Pari Passu Indebtedness tendered in an Offer or a Pari Passu
Offer and (iii) application, as set forth above, of Excess Proceeds in the
business of Publishing and its Restricted Subsidiaries. Such Excess Proceeds
may be invested in Temporary Cash Investments; provided that the maturity date
of any such investment made after the amount of Excess Proceeds equals or
exceeds $20,000,000 shall not be later than the Purchase Date. Publishing shall
be entitled to any interest or dividends accrued, earned or paid on such
Temporary Cash Investments; provided that Publishing shall not be entitled to
such interest and shall not withdraw such interest from the separate account,
if an Event of Default has occurred and is continuing.

                  (e) If Publishing becomes obligated to make an Offer pursuant
to paragraph (c) above, the Securities shall be purchased by Publishing, at the
option of the Holder thereof, in whole or in part in integral multiples of
$1,000, on a date that is not earlier than 30 days and not later than 60 days
from the date the notice is given to Holders, or such later date as may be
necessary for Publishing to comply with the requirements under the Exchange
Act, subject to proration in the event the Note Amount is less than the
aggregate Offered Price of all Securities tendered.

                  (f) Publishing shall comply with the applicable tender offer
rules, including Rule 14e-1 under the Exchange Act, and any other applicable
securities laws or regulations in connection with an Offer.

                  (g) Publishing shall not, and shall not permit any Subsidiary
to, create or permit to exist or become


<PAGE>   127
                                                                         - 117 -

effective any restriction (other than restrictions existing under (i)
Indebtedness as in effect on the date of this Indenture as such Indebtedness
may be refinanced from time to time or (ii) any Senior Indebtedness existing on
the date of this Indenture or thereafter; provided, in each case, that such
restrictions are no less favorable to the Holders than those existing on the
date of this Indenture) that would expressly impair the ability of Publishing
to make an Offer to purchase the Securities or, if such Offer is made, to pay
for the Securities tendered for purchase.

                  (h) Within 30 days after the date on which the amount of
Excess Proceeds equals or exceeds $20,000,000, Publishing shall send by
first-class mail, postage prepaid, to the Trustee and to each Holder of the
Securities of that Series, at such Holder's address appearing in the Security
Register, a notice stating or including:

                           A. that the Holder of such Series has the right to
                  require Publishing to repurchase, subject to proration, part
                  or all of such Holder's Securities at the Offered Price;

                           B. the Purchase Date;

                           C. the instructions a Holder of such Series must
                  follow in order to have its Securities purchased in
                  accordance with paragraph (c) of this Section; and

                           D. (i) the most recently filed Annual Report on Form
                  10-K (including audited consolidated financial statements) of
                  Publishing, the most recent subsequently filed Quarterly
                  Report on Form 10-Q, as applicable, and any Current Report on
                  Form 8-K of Publishing filed subsequent to such Quarterly
                  Report, other than Current Reports describing Asset Sales
                  otherwise described in the offering materials (or
                  corresponding successor reports) (or in the event Publishing
                  is not required to prepare any of the foregoing Forms, the
                  comparable information required pursuant to Section 10.18),
                  (ii) a description of material developments in Publishing's
                  business subsequent to the date of the latest of such
                  Reports, (iii) if material, appropriate pro forma financial
                  information, and (iv) such other information, if any,
                  concerning the business of Publishing and its Restricted
                  Subsidiaries which Publishing in good faith believes will
                  enable such Holders to make an informed investment decision
                  regarding the Offer;

<PAGE>   128
                                                                         - 118 -

                           E. the Offered Price;

                           F. the names and addresses of the Paying Agent and
                  the offices or agencies referred to in Section 10.02;

                           G. that Securities of such Series must be
                  surrendered at least three Business Days prior to the
                  Purchase Date to the Paying Agent or to an office or agency
                  referred to in Section 10.02 to collect payment;

                           H. that any Securities of such Series not tendered
                  will continue to accrue interest and that unless Publishing
                  defaults in the payment of the purchase price, any Security
                  accepted for payment pursuant to the Offer shall cease to
                  accrue interest on and after the Purchase Date; and

                           I. the procedures for withdrawing a tender.

                  (i) Holders electing to have Securities of such Series
purchased hereunder will be required to surrender such Securities at the
address specified in the notice at least three Business Days prior to the
Purchase Date.  Holders will be entitled to withdraw their election to have
their Securities purchased pursuant to this Section 10.14 if Publishing
receives, not later than three Business Days prior to the Purchase Date, a
telegram, telex, facsimile transmission or letter setting forth (1) the name of
the Holder, (2) the certificate number of the Security in respect of which such
notice of withdrawal is being submitted, (3) the principal amount of the
Security (which shall be $1,000 or an integral multiple thereof) delivered for
purchase by the Holder as to which his election is to be withdrawn, (4) a
statement that such Holder is withdrawing such Holder's election to have such
principal amount of such Security purchased, and (5) the principal amount, if
any, of such Security (which shall be $1,000 or an integral multiple thereof)
that remains subject to the original notice of the Offer and that has been or
will be delivered for purchase by Publishing.

                  (j) Publishing shall (i) not later than the Purchase Date,
accept for payment Securities of such Series or portions thereof tendered
pursuant to the Offer, (ii) not later than 11:00 a.m. (New York time) on the
Purchase Date, deposit with the Trustee or with a Paying Agent an amount of
money in same day funds (or New York Clearing House funds if such deposit is
made prior to the Purchase Date) sufficient to pay the aggregate Offered Price
of all the Securities or


<PAGE>   129
                                                                         - 119 -

portions thereof which are to be purchased on that date and (iii) not later
than 11:00 a.m. (New York time) on the Purchase Date, deliver to the Paying
Agent an Officers' Certificate stating the Securities or portions thereof have
been accepted for payment by Publishing.

                  The Trustee and the Paying Agent shall return to Publishing
any cash that remains unclaimed, together with interest, if any, thereon, held
by them for the payment of the Offered Price; provided, however, that, (x) to
the extent that the aggregate amount of cash deposited by Publishing with the
Trustee or a Paying Agent in respect of an Offer exceeds the aggregate Offered
Price of the Securities or portions thereof to be purchased, then the Trustee
or a Paying Agent shall hold such excess for Publishing and (y) unless
otherwise directed by Publishing in writing, promptly after the Business Day
following the Purchase Date the Trustee or a Paying Agent shall return any such
excess to Publishing together with interest or dividends, if any, thereon.

                  (k) Securities of that Series to be purchased shall, on the
Purchase Date, become due and payable at the Offered Price and from and after
such date (unless Publishing shall default in the payment of the Offered Price)
such Securities shall cease to bear interest. The Offered Price shall be paid
to such Holder promptly following the later of the Purchase Date and the time
of delivery of such Security to the relevant Paying Agent at the office of such
Paying Agent by the Holder thereof in the manner required. Upon surrender of
any such Security for purchase in accordance with the foregoing provisions,
such Security shall be paid by Publishing at the Offered Price; provided,
however, that installments of interest whose Stated Maturity is on or prior to
the Purchase Date shall be payable to the Holders of such Securities, or one or
more Predecessor Securities, registered as such on the relevant Regular Record
Dates according to the terms and the provisions of Section 3.07; provided
further that Securities of that Series to be purchased are subject to proration
in the event the Excess Proceeds are less than the aggregate Offered Price of
all Securities of such Series tendered for purchase, with such adjustments as
may be deemed appropriate by the Trustee so that only Securities of such Series
in denominations of $1,000 or integral multiples thereof shall be purchased. If
any Security of such Series tendered for purchase in accordance with the terms
of this Section shall not be so paid upon surrender thereof by deposit of funds
with the Trustee or a Paying Agent in accordance with paragraph (j) above, the
principal thereof (and premium, if any, thereon) shall, until paid, bear
interest from the


<PAGE>   130
                                                                         - 120 -

Purchase Date at the rate borne by such Security. Any Security of such Series
that is to be purchased only in part shall be surrendered to a Paying Agent in
accordance with the terms of this Section at the office of such Paying Agent
(with, if Publishing or the Trustee so requires, due endorsement by, or a
written instrument of transfer in form satisfactory to Publishing and the
Trustee duly executed by, the Holder thereof or such Holder's attorney duly
authorized in writing), and Publishing shall execute and pursuant to a
Publishing Order the Trustee shall authenticate and deliver to the Holder of
such Security, without service charge, one or more new Securities of any
authorized denomination as requested by such Holder in an aggregate principal
amount equal to, and in exchange for, the portion of the principal amount of
the Security so surrendered that is not purchased.

                  SECTION 10.15. Purchase of Securities upon a Change of
Control. (a) If a Change of Control shall occur at any time, then each Holder
with respect to Securities of any Series shall have the right to require that
Publishing purchase such Holder's Securities, pursuant to an offer described in
subsection (b) of this Section (a "Change of Control Offer"), in whole or in
part in integral multiples of $1,000, at a purchase price (the "Change of
Control Purchase Price") in cash in an amount equal to 101% of the principal
amount of such Securities, plus accrued and unpaid interest, if any, to the
date of purchase (the "Change of Control Purchase Date"), in accordance with
the procedures set forth in paragraphs (b), (c), (d) and (e) of this Section.

                  (b) Within 30 days following any Change of Control,
Publishing shall notify the Trustee thereof and give written notice (a "Change
of Control Purchase Notice") of such Change of Control to each Holder by
first-class mail, postage prepaid, to the Trustee and to each Holder at his
address appearing in the Security Register, stating or including:

                  A. that a Change of Control has occurred, the date of such
         event, and that such Holder has the right to require Publishing to
         repurchase such Holder's Securities at the Change of Control Purchase
         Price;

                  B. the circumstances and relevant facts regarding such Change
         of Control (including but not limited to information with respect to
         pro forma historical income, cash flow and capitalization after giving
         effect to such Change of Control, if any);

<PAGE>   131
                                                                         - 121 -

                  C. that the Change of Control Offer is being made pursuant to
         Section 10.15(a) and that all Securities properly tendered pursuant to
         the Change of Control Offer will be accepted for payment at the Change
         of Control Offer Purchase Price;

                  D. the Change of Control Purchase Date, which shall be a
         Business Day no earlier than 30 days nor later than 60 days from the
         date such notice is mailed or such later date as may be necessary for
         Publishing to comply with the requirements under the Exchange Act;

                  E. (i) the most recently filed Annual Report on Form 10-K
         (including audited consolidated financial statements) of Publishing,
         the most recent subsequently filed Quarterly Report on Form 10-Q, as
         applicable, and any Current Report on Form 8-K of Publishing filed
         subsequent to such Quarterly Report (or in the event Publishing is not
         required to prepare any of the foregoing Forms, the comparable
         information required to be prepared by Publishing pursuant to Section
         10.18), (ii) a description of material developments in Publishing's
         business subsequent to the date of the latest of such reports and
         (iii) such other information, if any, concerning the business of
         Publishing and its Restricted Subsidiaries which Publishing in good
         faith believes will enable such Holders to make an informed investment
         decision regarding the Change of Control Offer;

                  F. the Change of Control Purchase Price;

                  G. the names and addresses of the Paying Agent and the
         offices or agencies referred to in Section 10.02;

                  H. that Securities of that Series must be surrendered at
         least three Business Days prior to the Change of Control Purchase Date
         to the Paying Agent at the Office of the Paying Agent or to an office
         or agency referred to in Section 10.02 to collect payment;

                  I. that the Change of Control Purchase Price for any Security
         which has been properly tendered and not withdrawn will be paid
         promptly following the Change of Control Purchase Date;

                  J. the procedures for withdrawing a tender of Securities and
         Change of Control Purchase Notice;

                  K. that any Security of such Series not tendered will
         continue to accrue interest; and

<PAGE>   132
                                                                         - 122 -

                  L. that, unless Publishing defaults in the payment of the
         Change of Control Purchase Price, any Security of such Series accepted
         for payment pursuant to the Change of Control Offer shall cease to
         accrue interest after the Change of Control Purchase Date.

                  (c) Upon receipt by Publishing of the proper tender of
Securities of such Series, each Holder of a Security in respect of which such
proper tender was made shall (unless the tender of such Security is properly
withdrawn) thereafter be entitled to receive solely the Change of Control
Purchase Price with respect to such Security. Upon surrender of any such
Security for purchase in accordance with the foregoing provisions, such
Security shall be paid by Publishing at the Change of Control Purchase Price;
provided, however, that installments of interest whose Stated Maturity is on or
prior to the Change of Control Purchase Date shall be payable to the Holders of
such Securities, or one or more Predecessor Securities, registered as such on
the relevant Regular Record Dates according to the terms and the provisions of
Section 3.07. If any Security tendered for purchase in accordance with the
provisions of this Section shall not be so paid upon surrender thereof by
deposit of funds with the Paying Agent in accordance with paragraph (d) below,
the principal thereof (and premium, if any, thereon) shall, until paid, bear
interest from the Change of Control Purchase Date at the rate borne by such
Security. Holders electing to have Securities of such Series purchased will be
required to surrender such Securities to the Paying Agent at the address
specified in the notice at least three Business Days prior to the Change of
Control Purchase Date. Any Security of such Series that is to be purchased only
in part shall be surrendered to a Paying Agent in accordance with the
provisions of this Section at the office of such Paying Agent (with, if
Publishing or the Trustee so requires, due endorsement by, or a written
instrument of transfer in form satisfactory to Publishing and the Trustee duly
executed by, the Holder thereof or such Holder's attorney duly authorized in
writing), and Publishing shall execute and pursuant to a Publishing Order the
Trustee shall authenticate and deliver to the Holder of such Security, without
service charge, one or more new Securities of any authorized denomination as
requested by such Holder in an aggregate principal amount equal to, and in
exchange for, the portion of the principal amount of the Security so
surrendered that is not purchased.

                  (d) Publishing shall (i) not later than the Change of Control
Purchase Date, accept for payment of Securities of such Series or portion
thereof tendered pursuant to the Change of Control Offer, (ii) not later than


<PAGE>   133
                                                                         - 123 -

11:00 a.m. (New York time) on the Change of Control Purchase Date, deposit with
the Paying Agent an amount of cash sufficient to pay the aggregate Change of
Control Purchase Price of all the Securities or portions thereof which are to
be purchased as of the Change of Control Purchase Date and (iii) not later than
11:00 a.m. (New York time) on the Change of Control Purchase Date, deliver to
the Paying Agent an Officers' Certificate stating the Securities of such Series
or portions thereof accepted for payment by Publishing. The Paying Agent shall
promptly mail or deliver to Holders of Securities of such Series so accepted
payment in an amount equal to the Change of Control Purchase Price of the
Securities of such Series purchased from each such Holder. Any Securities of
such Series not so accepted shall be promptly mailed or delivered by the Paying
Agent at Publishing's expense to the Holder thereof. Publishing will publicly
announce the results of the Change of Control Offer on the Change of Control
Purchase Date. For purposes of this Section 10.15, Publishing shall choose a
Paying Agent which shall not be Publishing.

                  (e) A tender made in response to a Change of Control Purchase
Notice may be withdrawn before or after delivery by the Holder to the Paying
Agent at the office of the Paying Agent of the Security of such Series to which
such Change of Control Purchase Notice relates, by means of a written notice of
withdrawal delivered by the Holder to the Paying Agent at the office of the
Paying Agent or to the office or agency referred to in Section 10.02 to which
the related Change of Control Purchase Notice was delivered not later than
three Business Days prior to the Change of Control Purchase Date specifying as
applicable:

                  (1) the name of the Holder;

                  (2) the certificate number of the Security in respect of
         which such notice of withdrawal is being submitted;

                  (3) the principal amount of the Security (which shall be
         $1,000 or an integral multiple thereof) delivered for purchase by the
         Holder as to which such notice of withdrawal is being submitted;

                  (4) a statement that such Holder is withdrawing such Holder's
         election to have such principal amount of such Security purchased; and

                  (5) the principal amount, if any, of such Security (which
         shall be $1,000 or an integral multiple thereof) that remains subject
         to the original Change of Control


<PAGE>   134
                                                                         - 124 -

         Purchase Notice and that has been or will be delivered for purchase 
         by Publishing.

                  (f) As provided in the Securities, the Trustee and the Paying
Agent shall return to Publishing any cash that remains unclaimed, together with
interest or dividends, if any, thereon, held by either of them for the payment
of the Change of Control Purchase Price; provided, however, that, (x) to the
extent that the aggregate amount of cash deposited by Publishing pursuant to
clause (ii) of paragraph (d) above exceeds the aggregate Change of Control
Purchase Price of the Securities of any such Series or portions thereof to be
purchased, then the Trustee or the Paying Agent shall hold such excess for
Publishing and (y) unless otherwise directed by Publishing in writing, promptly
after the Business Day following the Change of Control Purchase Date, the
Trustee or the Paying Agent shall return any such excess to Publishing together
with interest, if any, thereon.

                  (g) Publishing shall comply with the applicable tender offer
rules, including Rule 14e-1 under the Exchange Act, and any other applicable
securities laws or regulations in connection with a Change of Control Offer.

                  (h) Notwithstanding the occurrence of a Change of Control,
Publishing shall not be obligated to repurchase the Securities of any such
Series pursuant to a Change of Control Offer, or otherwise comply with this
Section 10.15, if Publishing has elected to redeem all of the Securities of
such Series in accordance with Article XI.

                  Publishing shall not, and shall not permit any Subsidiary to,
create or permit to exist or become effective any restriction (other than
restrictions existing under (i) Indebtedness as in effect on the date of this
Indenture as such Indebtedness may be refinanced from time to time or (ii) any
Senior Indebtedness existing on the date of this Indenture or thereafter;
provided, in each case, that such restrictions are no less favorable to the
Holders than those existing on the date of this Indenture) that would expressly
impair the ability of Publishing to make a Change of Control Offer to purchase
the Securities or, if such Change of Control Offer is made, to pay for the
Securities tendered for purchase.

                  SECTION 10.16. Limitation on Issuance and Sale of Capital
Stock of Restricted Subsidiaries. (a) Until such time as both of The Telegraph
and Southam are Restricted Subsidiaries, Publishing will not permit (i) any
Restricted Subsidiary to issue any Capital Stock (other than to a


<PAGE>   135
                                                                         - 125 -

Publishing or any Wholly Owned Restricted Subsidiary) or (ii) any Person (other
than Publishing or a Wholly Owned Restricted Subsidiary) to acquire any Capital
Stock of any Restricted Subsidiary from Publishing or any Restricted
Subsidiary, except upon the sale of all of the outstanding Capital Stock of
such Restricted Subsidiary owned by Publishing and the designation of such
Subsidiary as an Unrestricted Subsidiary; provided, however, that Publishing or
a Restricted Subsidiary may issue or sell common stock of a Restricted
Subsidiary to a Person that is not an Affiliate of Publishing so long as, on or
prior to the consummation of such issuance or sale, such Restricted Subsidiary
issues and delivers a supplemental indenture to this Indenture providing for
the guarantee of the Securities, which guarantee shall be subordinated in right
of payment to any Senior Indebtedness of such Restricted Subsidiary, on
substantially the same terms as the Securities are subordinated to all Senior
Indebtedness of Publishing.

                  (b) On or after the time that both Southam and The Telegraph
are Restricted Subsidiaries, (i) without limiting the requirements of Section
10.14, in the event that (x) Publishing or a Restricted Subsidiary issues or
sells (other than to a Restricted Subsidiary) Capital Stock of a Restricted
Subsidiary (1) that was a Subsidiary on February 1, 1997 (which, for purposes
of this clause (1), is deemed to include Southam and Hollinger Eastern), (2)
any substantial portion of the operating assets of which were held by a
Subsidiary on February 1, 1997 and were generating material revenue and cash
flows on such date, or (3) any substantial portion of the operating assets of
which consist of assets that are acquired by Publishing or a Restricted
Subsidiary pursuant to the Hollinger Inc. Transaction and (y) such issuance or
sale involves less than 100% of the Capital Stock of such Restricted Subsidiary
held by Publishing and the Restricted Subsidiaries at the time of such issuance
or sale, then the Net Cash Proceeds of such issuance or sale (1) shall be
applied to permanently repay or otherwise permanently retire any Senior
Indebtedness then outstanding, as permitted or required by the terms thereof,
or (2) if there is no Senior Indebtedness then outstanding, then the balance of
such Net Cash Proceeds shall be deemed to constitute Excess Proceeds for
purposes of Section 10.14(c); provided that the foregoing clause (i) shall not
apply to any new issuance of Capital Stock by Southam as long as (a) Southam is
a Public Entity at the time of such issuance; (b) neither Publishing nor any
other Restricted Subsidiary has at any time after February


<PAGE>   136
                                                                         - 126 -

1, 1997 sold any assets and contributed, directly or indirectly, the proceeds
therefrom to Southam; and (c) neither Publishing nor any other Restricted
Subsidiary has at any time after February 1, 1997 contributed, directly or
indirectly, any Newspaper Businesses to Southam other than those Newspaper
Businesses acquired in the Hollinger Inc. Transaction; and (ii) if any issuance
of Capital Stock by a Restricted Subsidiary or sale or disposition of Capital
Stock of a Restricted Subsidiary results in a Restricted Subsidiary ceasing to
qualify as a Subsidiary, such transaction would deemed, for purposes of Section
, to constitute the designation of such former Restricted Subsidiary as an
Unrestricted Subsidiary.

                  SECTION 10.17. Limitation on Dividends and Other Payment
Restrictions Affecting Restricted Subsidiaries. Publishing will not, and will
not permit any of its Restricted Subsidiaries to, directly or indirectly,
create or otherwise cause or suffer to exist or become effective any
encumbrance or restriction on the ability of any Restricted Subsidiary to (a)
pay dividends or make any other distribution on its Capital Stock to Publishing
or any other Restricted Subsidiary, (b) pay any Indebtedness owed to Publishing
or any other Restricted Subsidiary, (c) make any Investment in Publishing or
(d) transfer any of its properties or assets to Publishing or any Restricted
Subsidiary, except (i) any encumbrance or restriction pursuant to or in
connection with the New Bank Credit Facility or the FDTH Credit Facility, each
as in effect on the date such Subsidiary becomes a Restricted Subsidiary or any
other agreement in effect on the date of this Indenture (including the AP-91
Senior Notes), (ii) any encumbrance or restriction, with respect to a
Restricted Subsidiary that is not a Restricted Subsidiary of Publishing on the
date of this Indenture, in existence at the time such Person becomes a
Restricted Subsidiary of Publishing and not Incurred in connection with, or in
contemplation of, such Person becoming a Restricted Subsidiary, (iii) any
encumbrance or restriction pursuant to or in connection with documents existing
or securing any Foreign Subsidiary Indebtedness that is not materially more
restrictive than the terms of any such restrictions existing on the date of the
Indenture or the date such Subsidiary becomes a Restricted Subsidiary, as
determined in good faith by an officer of Publishing, (iv) encumbrances or
restrictions entered into by Southam in connection with Indebtedness of Southam
Incurred at a time when Southam is a Public Entity, (v) encumbrances or
restrictions contained in the terms of any Mirror Preferred, provided that such
Mirror Preferred continues to quality as such under the definition thereof,
(vi) customary provisions restricting subletting or assignment of any lease
governing a leasehold interest of Publishing or any Restricted Subsidiary and
(vii) any encumbrance or restriction existing under any agreement that extends,
renews, refinances or replaces the agreements containing the encumbrances or


<PAGE>   137
                                                                         - 127 -

restrictions in the foregoing clauses (i), (ii) and (iii) (other than the
covenants in the AP-91 Senior Notes); provided that the terms and conditions of
any such encumbrances or restrictions are not materially less favorable to the
Holders than those under or pursuant to the agreement evidencing the
Indebtedness so extended, renewed, refinanced or replaced.

                  SECTION 10.18. Provision of Financial Statements. Whether or
not Hollinger International is subject to Section 13(a) or 15(d) of the
Exchange Act, Hollinger International will, to the extent permitted under the
Exchange Act, file with the Commission the annual reports, quarterly reports
and other documents that it would have been required to file with the
Commission pursuant to such Sections 13(a) or 15(d), including any "summarized
information" or other information relating to Publishing as may be required by
Regulation S-X under the Exchange Act or by the Commission, if it were so
subject, such documents to be filed with the Commission on or prior to the
respective dates (the "Required Filing Dates") by which it would have been
required so to file such documents if it were so subject. Hollinger
International will in any event (x) within 15 days of such Required Filing Date
(i) transmit by mail to all Holders, as their names and addresses appear in the
Security Register, without cost to such Holders and (ii) file with the Trustee
copies of the annual reports, quarterly reports and other documents which
Publishing would have been required to file with the Commission pursuant to
Section 13(a) or 15(d) of the Exchange Act if Hollinger International were
subject to such Sections and (y) if filing such documents by Hollinger
International with the Commission is not permitted under the Exchange Act,
promptly upon written request and payment of the reasonable cost of duplication
and delivery, supply copies of such documents to any prospective holder of
Securities at Publishing's cost.

                  SECTION 10.19. Statement by Officers as to Default. (a)
Publishing will deliver to the Trustee, on or before a date not more than 45
days after the end of each fiscal quarter and not more than 90 days after the
end of each fiscal year of Publishing ending after the date hereof, a written
statement signed by two executive officers of Publishing, one of whom shall be
the principal executive officer, principal financial officer or principal
accounting officer of Publishing, stating whether or not, after a review of the
activities of Publishing during such year or such quarter and of Publishing's
performance under this Indenture, to the best knowledge, based on such review,
of the signers thereof, Publishing has fulfilled all its obligations and is in
compliance with all conditions and


<PAGE>   138

                                                                         - 128 -

covenants under this indenture throughout such year or quarter, as the case may
be, and, if there has been a Default, specifying each Default and the nature
and status thereof.

                  (b) When any Default or Event of Default has occurred and is
continuing, or if the Trustee or any Holder or the trustee for or the holder of
any other evidence of Indebtedness of Publishing or any Restricted Subsidiary
gives any notice or takes any other action with respect to a claimed default,
Publishing shall deliver to the Trustee by registered or certified mail or by
telegram, telex or facsimile transmission followed by hard copy an Officers'
Certificate specifying such Default, Event of Default, notice or other action,
the status thereof and what action Publishing is taking or proposes to take
with respect thereto, within five Business Days of its occurrence.

                  SECTION 10.20. Waiver of Certain Covenants. Publishing may
omit in any particular instance to comply with any covenant or condition set
forth in Sections 10.05 through 10.15 and Sections 10.17 through 10.19 if,
before or after the time for such compliance, the Holders of not less than a
majority in aggregate principal amount of the Securities of any Series at the
time Outstanding waive such compliance in such instance with such covenant or
condition, but no such waiver shall extend to or affect such covenant or
condition except to the extent so expressly waived, and, until such waiver
shall become effective, the obligations of Publishing and the duties of the
Trustee in respect of any such covenant or condition shall remain in full force
and effect.

                  SECTION 10.21. Limitation on the Designation of Additional
Restricted or Unrestricted Subsidiaries. (a) The Board of Directors may
designate any Restricted Subsidiary as an Unrestricted Subsidiary if (i) such
action is in compliance with Section 10.09 of this Indenture and (ii) such
action complies with the definition of "Unrestricted Subsidiaries".

                  (b) The Board of Directors may designate any Unrestricted
Subsidiary or any Person that is to become a Restricted Subsidiary as a
Restricted Subsidiary if immediately after giving effect to such action (and
treating any Acquired Indebtedness as having been Incurred at the time of such
action), Publishing could have Incurred at least $1.00 of additional
Indebtedness pursuant to Section 10.08 of this Indenture.


<PAGE>   139

                                                                         - 129 -

                                   ARTICLE XI

                            Redemption of Securities

                  SECTION 11.01. Right of Redemption. The Securities of any
Series may be redeemed, at the election of Publishing, as a whole or in part,
at any time on or after March 15, 2002, subject to the conditions and at the
Redemption Prices specified in the form of Security of such Series or in the
indenture supplemental hereto with respect to Securities of such Series as
provided in Section 3.01, together with accrued and unpaid interest, if any, to
the Redemption Date (subject to the right of Holders of record of Securities of
such Series on relevant Regular Record Dates and Special Record Dates to
receive interest due on relevant Interest Payment Dates) to the extent that
this Article does not conflict with the terms of the form of Security of such
Series.

                  SECTION 11.02. Applicability of Article. Redemption of
Securities at the election of Publishing or otherwise, as permitted or required
by any provision of this Indenture, shall be made in accordance with such
provision and this Article.

                  SECTION 11.03. Election To Redeem; Notice to Trustee. The
election of Publishing to redeem any Securities pursuant to Section 11.01 shall
be evidenced by a Publishing Order and an Officers' Certificate. In case of any
redemption at the election of Publishing, Publishing shall, not less than 30
nor more than 60 days prior to the Redemption Date fixed by Publishing (unless
a shorter notice period shall be satisfactory to the Trustee), notify the
Trustee in writing of such Redemption Date and of the principal amount of
Securities of such Series and the Tranche (as defined in Section 11.04) to be
redeemed.

                  SECTION 11.04. Selection by Trustee of Securities To Be
Redeemed. If less than all the Securities of like tenor and terms of any Series
(a "Tranche") are to be redeemed, the particular Securities or portions thereof
to be redeemed shall be selected not more than 60 days prior to the Redemption
Date by the Trustee (or such shorter period as the Trustee may agree upon),
from the Outstanding Securities of such Tranche not previously called for
redemption, by lot or such other method as the Trustee shall deem fair and
reasonable, and the amounts to be redeemed may be equal to $1,000 or any
integral multiple thereof, unless otherwise provided in the terms of a
particular Series of Securities.

<PAGE>   140
                                                                         - 130 -

                  The Trustee shall promptly notify Publishing and each
Security Registrar in writing of the Securities selected for redemption and, in
the case of the Securities selected for partial redemption, the principal
amount thereof to be redeemed.

                  For all purposes of this Indenture, unless the context
otherwise requires, all provisions relating to redemption of Securities shall
relate, in the case of any Security redeemed or to be redeemed only in part, to
the portion of the principal amount of such Security which has been or is to be
redeemed.

                  SECTION 11.05. Notice of Redemption. Notice of redemption
shall be given by first-class mail, postage prepaid, mailed not less than 30
nor more than 60 days prior to the Redemption Date, to each Holder of
Securities to be redeemed, at his address appearing in the Security Register.

                  All notices of redemption shall state:

                  (a) the Redemption Date;

                  (b) the Redemption Price;

                  (c) if less than all the Outstanding Securities of any Series
         are to be redeemed, the identification of the particular Securities to
         be redeemed;

                  (d) in the case of a Security to be redeemed in part, the
         principal amount of such Security to be redeemed and that after the
         Redemption Date upon surrender of such Security, a new Security or
         Securities in the aggregate principal amount equal to the unredeemed
         portion thereof will be issued;

                  (e) that Securities called for redemption must be surrendered
         to the Paying Agent to collect the Redemption Price;

                  (f) that on the Redemption Date the Redemption Price will
         become due and payable upon each such Security or portion thereof to
         be redeemed, and that (unless Publishing shall default in payment of
         the Redemption Price) interest thereon shall cease to accrue on and
         after said date;

                  (g) the place or places where such Securities are to be
         surrendered for payment of the Redemption Price; and

<PAGE>   141
                                                                         - 131 -

                  (h) the CUSIP number, if any, relating to such Securities.

                  Notice of redemption of Securities to be redeemed at the
election of Publishing shall be given by Publishing or at Publishing's written
request, by the Trustee in the name and at the expense of Publishing. If
Publishing elects to give notice of redemption, it shall provide the Trustee
with a certificate stating that such notice has been given in compliance with
the requirements of this Section 11.05.

                  Such notice if mailed in the manner herein provided shall be
conclusively presumed to have been given, whether or not the Holder receives
such notice. In any case, failure to give such notice by mail or any defect in
the notice to the Holder of any Security designated for redemption as a whole
or in part shall not effect the validity of the proceedings for the redemption
of any other Security.

                  SECTION 11.06. Deposit of Redemption Price. Prior to 11:00
a.m., New York City time, on any Redemption Date, Publishing shall irrevocably
deposit with the Trustee or with a Paying Agent an amount of money in same day
funds sufficient to pay the Redemption Price of, and, except if the Redemption
Date shall be an Interest Payment Date, accrued interest on, all the Securities
or portions thereof which are to be redeemed on that date. The Trustee or the
Paying Agent shall hold in trust for, and return to, Publishing promptly after
the Business Day following the Redemption Date any interest or dividends, if
any, earned on amounts deposited with the Trustee or the Paying Agent remaining
after the payment of the aggregate Redemption Price for all securities to be
redeemed; provided that neither the Trustee nor the Paying Agent shall be under
any obligation to place or invest such funds in an interest bearing account.

                  SECTION 11.07. Securities Payable on Redemption Date. Notice
of redemption having been given as aforesaid, the Securities so to be redeemed
shall, on the Redemption Date, become due and payable at the Redemption Price
therein specified and from and after such date (unless Publishing shall not
have deposited funds in accordance with Section 11.06 in respect of the payment
of the Redemption Price and accrued interest) such Securities shall cease to
bear interest. Upon surrender of any such Security for redemption in accordance
with said notice, such Security shall be paid by Publishing at the Redemption
Price together with accrued interest to the Redemption Date; provided, however,
that installments of interest whose Stated Maturity


<PAGE>   142
                                                                         - 132 -

is on or prior to the Redemption Date shall be payable to the Holders of such
Securities, or one or more Predecessor Securities, registered as such on the
relevant Regular Record Dates according to the terms and the provisions of
Section 3.07.

                  If any Security called for redemption shall not be so paid
upon surrender thereof for redemption, by deposit or segregation of funds in
accordance with Section 11.06, the principal and premium, if any, shall, until
paid, bear interest from the Redemption Date at the rate then borne by such
Security.

                  SECTION 11.08. Securities Redeemed or Purchased in Part. Any
Security which is to be redeemed or purchased only in part shall be surrendered
to the Paying Agent at the office or agency maintained for such purpose
pursuant to Section 10.02 (with, if Publishing, the Security Registrar or the
Trustee so requires, due endorsement by, or a written instrument of transfer in
form satisfactory to Publishing, the Security Registrar or the Trustee as the
case may be, duly executed by the Holder thereof or such Holder's attorney duly
authorized in writing), and Publishing shall execute, and pursuant to a
Publishing Order the Trustee shall authenticate and deliver to the Holder of
such Security without service charge, a new Security or Securities, of any
authorized denomination as requested by such Holder in aggregate principal
amount equal to, and in exchange for, the unredeemed portion of the principal
of the Security so surrendered that is not redeemed or purchased.

                                  ARTICLE XII

                          Subordination of Securities

                  SECTION 12.01.  Securities Subordinate to Senior
Indebtedness.  Publishing covenants and agrees, and each Holder, by such
Holder's acceptance of the Securities, likewise covenants and agrees, that, to
the extent and in the manner hereinafter set forth in this Article, the
Indebtedness represented by the Securities and the payment of the principal of,
premium, if any, and interest on each and all of the Securities are hereby
expressly made subordinate and subject in right of payment as provided in this
Article to the prior payment in full, in cash or Cash Equivalents or in any
manner acceptable to the requisite holders of Designated Senior Indebtedness,
of all Senior Indebtedness.  For purposes of this Indenture, the requisite
holders of Designated Senior Indebtedness shall be


<PAGE>   143
                                                                         - 133 -

determined by the instruments governing Designated Senior Indebtedness.

                  This Article XII shall constitute a continuing offer to all
Persons who, in reliance upon such provisions, become holders of, or continue
to hold Senior Indebtedness; and such provisions are made for the benefit of
the holders of Senior Indebtedness; and such holders are made obligees
hereunder and they or each of them may enforce such provisions.

                  SECTION 12.02. Payment of Proceeds Upon Dissolution, etc. In
the event of (a) any insolvency or bankruptcy case or proceeding, or any
receivership, liquidation, reorganization or other similar case or proceeding
in connection therewith, relative to Publishing or to its assets, or (b) any
liquidation, dissolution or other winding up of Publishing, whether voluntary
or involuntary and whether or not involving insolvency or bankruptcy, or (c)
any assignment for the benefit of creditors or any other marshaling of assets
or liabilities of Publishing (except a distribution in connection with a
consolidation of Publishing with, or the merger of Publishing into, another
corporation or the liquidation or dissolution of Publishing following
conveyance, transfer or lease of its properties and assets substantially as an
entirety to another corporation upon the terms and subject to the conditions of
Article VIII, then and in any such event:

                  (1) the holders of Senior Indebtedness shall be entitled to
receive payment in full in cash or Cash Equivalents or in any other manner
acceptable to the requisite holders of Designated Senior Indebtedness, of all
amounts due on or in respect of all Senior Indebtedness, before the Holders of
the Securities are entitled to receive any payment or distribution of any kind
or character (excluding Permitted Junior Securities) on account of the
principal of, premium, if any, or interest on the Securities or on account of
the purchase, redemption, defeasance or other acquisition of or in respect of
the Securities (including any payment or other distribution which may be
received from the holders of Subordinated Indebtedness as a result of any
payment on such Subordinated Indebtedness); and

                  (2) any payment or distribution of assets of Publishing of
any kind or character, whether in cash, property or securities (excluding
Permitted Junior Securities), by set-off or otherwise, to which the Holders or
the Trustee would be entitled but for the provisions of


<PAGE>   144
                                                                         - 134 -

this Article shall be paid by the liquidating trustee or agent or other Person
making such payment or distribution, whether a trustee in bankruptcy, a
receiver or liquidating trustee or otherwise, directly to the holders of Senior
Indebtedness or their representative or representatives or to the trustee or
trustees under any indenture under which any instruments evidencing any of such
Senior Indebtedness may have been issued, ratably according to the aggregate
amounts remaining unpaid on account of the Senior Indebtedness held or
represented by each, to the extent necessary to make payment in full in cash or
Cash Equivalents or in any other manner acceptable to the requisite holders of
Designated Senior Indebtedness, of all Senior Indebtedness remaining unpaid,
after giving effect to any concurrent payment or distribution to the holders of
such Senior Indebtedness; and

                  (3) in the event that, notwithstanding the foregoing
provisions of this Section, the Trustee or the Holder of any Security shall
have received any payment or distribution of assets of Publishing of any kind
or character, whether in cash, property or securities, in respect of principal,
premium, if any, and interest on the Securities or on account of the purchase,
redemption, defeasance or other acquisition of or in respect of the Securities
before all Senior Indebtedness is paid in full; then and in such event such
payment or distribution (excluding Permitted Junior Securities) (including any
payment or other distribution which may be received from the holders of
Subordinated Indebtedness as a result of any payment on such Subordinated
Indebtedness) shall be paid over or delivered forthwith to the trustee in
bankruptcy, receiver, liquidating trustee, custodian, assignee, agent or other
person making payment or distribution of assets of Publishing for application
to the payment of all Senior Indebtedness remaining unpaid, to the extent
necessary to pay all Senior Indebtedness in full in cash or Cash Equivalents or
in any other manner acceptable to the requisite holders of Designated Senior
Indebtedness, after giving effect to any concurrent payment or distribution to
or for the holders of Senior Indebtedness and until so paid shall be held in
trust for the benefit of the holders of Senior Indebtedness.

                  The consolidation of Publishing with, or the merger of
Publishing with or into, another Person or the liquidation or dissolution of
Publishing following the sale, assignment, conveyance, transfer, lease or other
disposal of all or substantially all of Publishing's properties or assets to
another Person upon the terms and conditions set forth in Article VIII shall
not be deemed a dissolution,


<PAGE>   145
                                                                         - 135 -

winding up, liquidation, reorganization, assignment for the benefit of
creditors or marshaling of assets and liabilities of Publishing for the
purposes of this Section if the Person formed by such consolidation or the
surviving entity of such merger or the Person which acquires by sale,
assignment, conveyance, transfer, lease or other disposal of all or
substantially all of Publishing's properties or assets, as the case may be,
shall, as a part of such consolidation, merger, sale, assignment, conveyance,
transfer, lease or other disposal, comply with the conditions set forth in
Article VIII.

                  SECTION 12.03. Suspension of Payment When Senior Indebtedness
in Default. (a) Unless Section 12.02 shall be applicable, upon the occurrence
and continuation of a Payment Default beyond the applicable grace period, no
payment (other than any payments previously made pursuant to the provisions
described in Article IV) or distribution of any assets of Publishing of any
kind or character (excluding Permitted Junior Securities) shall be made by
Publishing on account of principal of, premium, if any, or interest on, the
Securities or on account of the purchase, redemption, defeasance or other
acquisition of or in respect of the Securities unless and until such Payment
Default shall have been cured or waived or shall have ceased to exist or the
Designated Senior Indebtedness shall have been discharged or paid in full in
cash or Cash Equivalents, or in any other manner acceptable to the requisite
holders of such Designated Senior Indebtedness, after which Publishing shall
resume making any and all required payments in respect of the Securities,
including any missed payments.

                  (b) Unless Section 12.02 shall be applicable, upon (1) the
occurrence and continuation of a Non-payment Default and (2) receipt by the
Trustee (with a copy to Publishing) from a Senior Representative (as defined
below) of written notice of such occurrence, no payment (other than any
payments previously made pursuant to the provision described in Article IV) or
distribution of any assets of Publishing of any kind or character (excluding
Permitted Junior Securities) shall be made by Publishing on account of any
principal of, premium, if any, or interest on, the Securities or on account of
the purchase, redemption, defeasance or other acquisition of or in respect of
Securities for a period ("Payment Blockage Period") commencing on the date of
receipt by the Trustee of such notice unless and until the earliest of (subject
to any blockage of payments that may then or thereafter be in effect under
subsection (a) of this Section 12.03) (x) 179 days having elapsed since receipt
of such written notice by the Trustee (provided any Designated Senior


<PAGE>   146
                                                                         - 136 -

Indebtedness as to which notice was given shall not theretofore have been
accelerated), (y) the date such Nonpayment Default and all other Non-payment
Defaults as to which notice is also given after such Payment Blockage Period is
initiated shall have been cured or waived or shall have ceased to exist or the
Designated Senior Indebtedness related thereto shall have been discharged or
paid in full in cash or Cash Equivalents or in any other manner acceptable to
the requisite holders of such Designated Senior Indebtedness or (z) the date on
which such Payment Blockage Period (and all Non-Payment Defaults as to which
notice is given after such Payment Blockage Period is initiated) shall have
been terminated by written notice to Publishing or the Trustee from the Agent
or such other representative of holders of Designated Senior Indebtedness (a
"Senior Representative"), after which, in each such case, Publishing shall
resume making any and all required payments in respect of the Securities,
including any missed payments and accrued interest thereon. Notwithstanding any
other provision of this paragraph (b), in no event shall a Payment Blockage
Period extend beyond 179 days from the date of the receipt by the Trustee of
the notice referred to in clause (2) of this paragraph (b) (such 179-day period
referred to as the "Initial Blockage Period"). Any number of notices of
Non-Payment Defaults may be given during the Initial Blockage Period; provided
that during any 365-day consecutive period only one Payment Blockage Period
during which payment of principal of, premium, if any, or interest on, the
Securities may not be made may commence and the duration of such Payment
Blockage Period may not exceed 179 days. No Non-payment Default with respect to
Designated Senior Indebtedness which existed or was continuing on the date of
the commencement of any Payment Blockage Period will be, or can be, made the
basis for the commencement of a second Payment Blockage Period, whether or not
within a period of 365 consecutive days, unless such Non-payment Default shall
have been cured or waived for a period of not less than 90 consecutive days.

                  (c) In the event that, notwithstanding the foregoing,
Publishing shall make any payment to the Trustee or the Holder of any Security
prohibited by the foregoing provisions of this Section, then and in such event
such payment shall be paid over and delivered forthwith to a Senior
Representative of the holders of the Designated Senior Indebtedness or as a
court of competent jurisdiction shall direct and until so paid shall be held in
trust for the benefit of the holders of Senior Indebtedness.

                  SECTION 12.04. Payment Permitted if No Default. Nothing
contained in this Article, elsewhere in


<PAGE>   147
                                                                         - 137 -

this Indenture or in any of the Securities shall prevent Publishing, at any
time except during the pendency of any case, proceeding, dissolution,
liquidation or other winding up, assignment for the benefit of creditors or
other marshaling of assets and liabilities of Publishing referred to in Section
12.02 or under the conditions described in Section 12.03, from making payments
at any time of principal of, premium, if any, or interest on the Securities in
accordance with the terms of this Indenture.

                  SECTION 12.05. Subrogation to Rights of Holders of Senior
Indebtedness. Subject to the payment in full of all Senior Indebtedness in cash
or Cash Equivalents or in any other manner acceptable to the requisite holders
of Designated Senior Indebtedness, the Holders of the Securities shall be
subrogated to the rights of the holders of all Senior Indebtedness to receive
payments and distributions of cash, property and securities applicable to the
Senior Indebtedness until the principal of, premium, if any, and interest on
the Securities shall be paid in full. For purposes of such subrogation, no
payments or distributions to the holders of Senior Indebtedness of any cash,
property or securities to which the Holders of the Securities or the Trustee
would be entitled except for the provisions of this Article, and no payments
over pursuant to the provisions of this Article to the holders of Senior
Indebtedness by Holders of the Securities or the Trustee, shall, as among
Publishing, its creditors other than holders of Senior Indebtedness, and the
Holders of the Securities, be deemed to be a payment or distribution by
Publishing to or on account of the Senior Indebtedness.

                  SECTION 12.06. Provisions Solely To Define Relative Rights.
The provisions of this Article are intended solely for the purpose of defining
the relative rights of the Holders of the Securities on the one hand and the
holders of Senior Indebtedness on the other hand. Nothing contained in this
Article or elsewhere in this Indenture or in the Securities is intended to or
shall (a) impair, as among Publishing, its creditors other than holders of
Senior Indebtedness and the Holders of the Securities, the obligation of
Publishing, which is absolute and unconditional, to pay to the Holders of the
Securities the principal of, premium, if any, and interest on the Securities as
and when the same shall become due and payable in accordance with their terms;
or (b) affect the relative rights against Publishing of the Holders of the
Securities and creditors of Publishing other than the holders of Senior
Indebtedness; or (c) prevent the Trustee or the Holder of any Security from
exercising all remedies otherwise permitted by applicable law upon default
under this


<PAGE>   148
                                                                         - 138 -

Indenture, subject to the rights, if any, under this Article of the holders of
Senior Indebtedness (1) in any case, proceeding, dissolution, liquidation or
other winding up, assignment for the benefit of creditors or other marshaling
of assets and liabilities of Publishing referred to in Section 12.02, to
receive, pursuant to and in accordance with such Section, cash, property and
securities otherwise payable or deliverable to the Trustee or such Holder, or
(2) under the conditions specified in Section 12.03, to prevent any payment
prohibited by such Section or enforce their rights pursuant to Section
12.03(c).

                  SECTION 12.07. Trustee To Effectuate Subordination. Each
Holder of a Security by his acceptance thereof authorizes and directs the
Trustee on his behalf to take such action as may be necessary or appropriate to
effectuate the subordination provided in this Article and appoints the Trustee
his attorney-in-fact for any and all such purposes, including, in the event of
any dissolution, winding-up, liquidation or reorganization of Publishing
whether in bankruptcy, insolvency, receivership proceedings, or otherwise, the
timely filing of a claim for the unpaid balance of the Indebtedness of
Publishing owing to such Holder in the form required in such proceedings and
the causing of such claim to be approved. If the Trustee does not file a proper
claim at least 30 days before the expiration of the time to file such claim,
then the holders of Senior Indebtedness, and their agents, trustees or other
representatives are authorized to do so for and on behalf of the Holders. The
Trustee shall not be liable to any Holder for failure to file such claim unless
such failure is due to its negligence or wilful misconduct.

                  SECTION 12.08. No Waiver of Subordination Provisions. (a) No
right of any present or future holder of any Senior Indebtedness to enforce
subordination as herein provided shall at any time in any way be prejudiced or
impaired by any act or failure to act on the part of Publishing or by any act
or failure to act by any such holder, or by any non-compliance by Publishing
with the terms, provisions and covenants of this Indenture, regardless of any
knowledge thereof any such holder may have or be otherwise charged with.

                  (b) Without limiting the generality of Subsection (a) of this
Section, the holders of Senior Indebtedness may, at any time and from time to
time, without the consent of or notice to the Trustee or the Holders of the
Securities, without incurring responsibility to the Holders of the Securities
and without impairing or releasing the subordination provided in this Article
or the


<PAGE>   149
                                                                         - 139 -

obligations hereunder of the Holders of the Securities to the holders of Senior
Indebtedness, do any one or more of the following: (1) change the manner, place
or terms of payment or extend the time of payment of, or renew or alter, Senior
Indebtedness or any instrument evidencing the same or any agreement under which
Senior Indebtedness is outstanding; (2) sell, exchange, release or otherwise
deal with any property pledged, mortgaged or otherwise securing Senior
Indebtedness; (3) release any Person liable in any manner for the collection or
payment of Senior Indebtedness; and (4) exercise or refrain from exercising any
rights against Publishing and any other Person; provided, however, that in no
event shall any such actions limit the right of the Holders of the Securities
to take any action to accelerate the maturity of the Securities in accordance
with the provisions set forth in Article V in this Indenture or to pursue any
rights or remedies hereunder or under applicable laws if the taking of such
action does not otherwise violate the terms of this Article.

                  SECTION 12.09. Notice to Trustee. (a) Publishing shall give
prompt written notice to the Trustee of any fact known to Publishing which
would prohibit the making of any payment to or by the Trustee in respect of the
Securities. Notwithstanding the provisions of this Article or any provision of
this Indenture, the Trustee shall not be charged with knowledge of the
existence of any facts which would prohibit the making of any payment to or by
the Trustee in respect of the Securities, unless and until the Trustee shall
have received written notice thereof from Publishing or a holder of Senior
Indebtedness or from a Senior Representative or any trustee, fiduciary or agent
therefore; and, prior to the receipt of any such written notice, the Trustee
shall be entitled in all respects to assume that no such facts exist; provided,
however, that if the Trustee shall not have received the notice provided for in
this Section at least two Business Days prior to the date upon which by the
terms hereof any money may become payable for any purpose (including, without
limitation, the payment of the principal of, premium, if any, or interest on
any Security), then, anything herein contained to the contrary notwithstanding
but without limiting the rights and remedies of the holders of Senior
Indebtedness or any trustee, fiduciary or agent thereof, the Trustee shall have
full power and authority to receive such money and to apply the same to the
purpose for which such money was received and shall not be affected by any
notice to the contrary which may be received by it within two Business Days
prior to such date; nor shall the Trustee be charged with knowledge of the
curing of any such default or the elimination of the act or condition
preventing any such payment unless and until the


<PAGE>   150
                                                                         - 140 -

Trustee shall have received an Officers' Certificate to such effect.

                  (b) The Trustee shall be entitled to rely on the delivery to
it of a written notice to the Trustee by a Person representing himself to be a
Senior Representative or a holder of Senior Indebtedness (or a trustee,
fiduciary or agent therefore) to establish that such notice has been given by a
Senior Representative or a holder of Senior Indebtedness (or a trustee,
fiduciary or agent therefor); provided, however, that failure to give such
notice to Publishing shall not affect in any way the ability of the Trustee to
rely on such notice. In the event that the Trustee determines in good faith
that further evidence is required with respect to the right of any Person as a
holder of Senior Indebtedness to participate in any payment or distribution
pursuant to this Article, the Trustee may request such Person to furnish
evidence to the reasonable satisfaction of the Trustee as to the amount of
Senior Indebtedness held by such Person, the extent to which such Person is
entitled to participate in such payment or distribution and any other facts
pertinent to the rights of such Person under this Article, and if such evidence
is not furnished, the Trustee may defer any payment to such Person pending
judicial determination as to the right of such Person to receive such Payment.

                  SECTION 12.10. Reliance on Judicial Order or Certificate of
Liquidating Agent. Upon any payment or distribution of assets of Publishing
referred to in this Article, the Trustee and the Holders of the Securities
shall be entitled to rely upon any order or decree entered by any court of
competent jurisdiction in which such insolvency, bankruptcy, receivership,
liquidation, reorganization, dissolution, winding up or similar case or
proceeding is pending, or a certificate of the trustee in bankruptcy, receiver,
liquidating trustee, custodian, assignee for the benefit of creditors, agent or
other person making such payment or distribution, delivered to the Trustee or
to the Holders of Securities, for the purpose of ascertaining the Persons
entitled to participate in such payment or distribution, the holders of Senior
Indebtedness and other Indebtedness of Publishing, the amount thereof or
payable thereon, the amount or amounts paid or distributed thereon and all
other facts pertinent thereto or to this Article; provided that the foregoing
shall apply only if such court has been fully apprised of the provisions of
this Article.

                  SECTION 12.11. Rights of Trustee as a Holder of Senior
Indebtedness; Preservation of Trustee's Rights. The Trustee in its individual
capacity shall be entitled to all


<PAGE>   151
                                                                         - 141 -

the rights set forth in this Article with respect to any Senior Indebtedness
which may at any time be held by it, to the same extent as any other holder of
Senior Indebtedness, and nothing in this Indenture shall deprive the Trustee of
any of its rights as such holder. Nothing in this Article shall apply to claims
of, or payments to, the Trustee under or pursuant to the provisions in this
Indenture regarding compensation and indemnification of the Trustee.

                  SECTION 12.12. Article Applicable to Paying Agents. In case
at any time any Paying Agent other than the Trustee shall have been appointed
by Publishing and be then acting under this Indenture, the term "Trustee" as
used in this Article shall in such case (unless the context otherwise requires)
be construed as extending to and including such Paying Agent within its meaning
as fully for all intents and purposes as if such Paying Agent were named in
this Article in addition to or in place of the Trustee; provided, however, that
Section 12.11 shall not apply to Publishing or any Affiliate of Publishing if
it or such Affiliate acts as Paying Agent.

                  SECTION 12.13.  No Suspension of Remedies.  Nothing contained
in this Article shall limit the right of the Trustee or the Holders of
Securities to take any action to accelerate the maturity of the Securities
pursuant to the provisions described under "Events of Default" and as set forth
in this Indenture or to pursue any rights or remedies hereunder or under
applicable law, subject to the rights, if any, under this Article of the
holders, from time to time, of Senior Indebtedness to receive the cash,
property or securities receivable upon the exercise of such rights or remedies.

                  SECTION 12.14. Trustee's Relation to Senior Indebtedness.
With respect to the holders of Senior Indebtedness, the Trustee undertakes to
perform or to observe only such of its covenants and obligations as are
specifically set forth in this Article, and no implied covenants or obligations
with respect to the holders of Senior Indebtedness shall be read into this
Article against the Trustee. The Trustee shall not be deemed to owe any
fiduciary duty to the holders of Senior Indebtedness and the Trustee shall not
be liable to any holder of Senior Indebtedness if it shall, in the absence of
gross negligence or wilful misconduct, pay over or deliver to Holders,
Publishing or any other Person moneys or assets to which any holder of Senior
Indebtedness shall be entitled by virtue of this Article or otherwise.



<PAGE>   152
                                                                         - 142 -

                                  ARTICLE XIII

                           Satisfaction and Discharge

                  SECTION 13.01. Satisfaction and Discharge of Indenture. This
Indenture shall cease to be of further effect (except as to surviving rights of
registration of transfer or exchange of the Securities of any Series herein
expressly provided for) and the Trustee, on demand of and at the expense of
Publishing, shall execute proper instruments acknowledging satisfaction and
discharge of this Indenture, when

                  (a) either

                  (1) all the Securities of any Series theretofore
         authenticated and delivered (other than (x) lost, stolen or destroyed
         Securities of any Series which have been replaced or paid as provided
         in Section 3.06 and (y) Securities of any Series for whose payment
         United States dollars have theretofore been irrevocably deposited in
         trust by Publishing and thereafter repaid to Publishing or discharged
         from such trust, as provided in Section 10.03) have been delivered to
         the Trustee for cancellation; or

                  (2) all Securities of any Series not theretofore delivered to
         the Trustee for cancellation

                           (x) have become due and payable, or

                           (y) will become due and payable at their Stated
                  Maturity within one year, or

                           (z) are to be called for redemption within one year
                  under arrangements satisfactory to the Trustee for the giving
                  of notice of redemption by the Trustee in the name, and at
                  the expense, of Publishing,

         and Publishing has irrevocably deposited or caused to be deposited
         with the Trustee as trust funds in trust an amount sufficient to pay
         and discharge the entire indebtedness on the Securities of such Series
         not theretofore delivered to the Trustee for cancellation, including
         principal of, premium, if any, and accrued interest on the Securities
         of such Series at such Maturity, Stated Maturity or Redemption Date;

                  (b) Publishing has paid all other sums payable hereunder by
Publishing; and



<PAGE>   153
                                                                         - 143 -

                  (c) Publishing has delivered to the Trustee an Officers'
Certificate and an Opinion of Counsel each to the effect that all conditions
precedent herein provided for relating to the satisfaction and discharge of
this Indenture have been complied with and that such satisfaction and discharge
will not result in a breach or violation of, or constitute a default under,
this Indenture or a breach or violation of any agreement relating to any Senior
Indebtedness.

                  Notwithstanding the satisfaction and discharge of this
Indenture, the obligations of Publishing to the Trustee under Section 6.07 and,
if United States dollars shall have been deposited with the Trustee pursuant to
subclause (2) of Subsection (a) of this Section, the obligations of the Trustee
under Section 13.02 and the last paragraph of Section 10.03 shall survive.

                  SECTION 13.02.  Application of Trust Money.  Subject to the
provisions of the last paragraph of Section 10.03, all United States dollars
deposited with the Trustee pursuant to Section 13.01 shall be held in trust and
applied by it, in accordance with the provisions of the Securities and this
Indenture, to the payment, either directly or through any Paying Agent as the
Trustee may determine, to the Persons entitled thereto, of the principal of,
premium, if any, and interest on the Securities for whose payment such United
States dollars have been deposited with the Trustee.

                                  ARTICLE XIV

                                   Guarantee

                  SECTION 14.01. Hollinger International Guarantee. For value
received, Hollinger International, in accordance with this Article XIV, hereby
absolutely, unconditionally and irrevocably guarantees to the Trustee and the
Holders, as if Hollinger International were the principal debtor, the punctual
payment and performance when due of all Indenture Obligations (which for
purposes of this Guarantee shall also be deemed to include all commissions,
fees, charges, costs and other expenses (including reasonable legal fees and
disbursements of one counsel) arising out of or incurred by the Trustee or the
Holders in connection with the enforcement of this Guarantee).

                  SECTION 14.02. Continuing Guarantee; No Right of Set-Off;
Independent Obligation. (a) This Guarantee shall be a continuing guarantee of
the payment and performance of


<PAGE>   154
                                                                         - 144 -

all Indenture Obligations and shall remain in full force and effect until the
payment in full of all of the Indenture Obligations and shall apply to and
secure any ultimate balance due or remaining unpaid to the Trustee (including
the fees and expenses of its agents and counsel) or the Holders; and this
Guarantee shall not be considered as wholly or partially satisfied by the
payment or liquidation at any time or from time to time of any sum of money for
the time being due or remaining unpaid to the Trustee or the Holders. Hollinger
International covenants and agrees to comply with all obligations, covenants,
agreements and provisions applicable to it in this Indenture including those
set forth in Article VIII and Section 10.18.  Without limiting the generality
of the foregoing, Hollinger International's liability shall extend to all
amounts which constitute part of the Indenture Obligations and would be owed by
Publishing under this Indenture and the Securities but for the fact that they
are unenforceable, reduced, limited, impaired, suspended or not allowable due
to the existence of a bankruptcy, reorganization or similar proceeding
involving Publishing.

                  (b) Hollinger International hereby guarantees that the
Indenture Obligations will be paid to the Trustee without set-off or
counterclaim or other reduction whatsoever (whether for taxes, withholding or
otherwise) in lawful currency of the United States of America.

                  (c) Hollinger International guarantees that the Indenture
Obligations shall be paid strictly in accordance with their terms regardless of
any law, regulation or order now or hereafter in effect in any jurisdiction
affecting any of such terms or the rights of the holders of the Securities.

                  (d) Hollinger International's liability to pay or perform or
cause the performance of the Indenture Obligations under this Guarantee shall
arise forthwith after demand for payment or performance by the Trustee has been
given to Hollinger International in the manner prescribed in Section 1.06
hereof.

                  (e) Except as provided herein, the provisions of this Article
XIV cover all agreements between the parties hereto relative to this Guarantee
and none of the parties shall be bound by any representation, warranty or
promise made by any Person relative thereto which is not embodied herein; and
it is specifically acknowledged and agreed that this Guarantee has been
delivered by Hollinger International free of any conditions whatsoever and that
no representations, warranties or promises have been made to



<PAGE>   155
                                                                         - 145 -

Hollinger International affecting its liabilities hereunder, and that the
Trustee shall not be bound by any representations, warranties or promises now
or at any time hereafter made by Publishing to Hollinger International.

                  SECTION 14.03. Guarantee Absolute. The obligations of
Hollinger International hereunder are independent of the obligations of
Publishing under the Securities and this Indenture and a separate action or
actions may be brought and prosecuted against Hollinger International whether
or not an action or proceeding is brought against Publishing and whether or not
Publishing is joined in any such action or proceeding. The liability of
Hollinger International hereunder is irrevocable, absolute and unconditional
and (to the extent permitted by law) the liability and obligations of Hollinger
International hereunder shall not be released, discharged, mitigated, waived,
impaired or affected in whole or in part by:

                  (a) any defect or lack of validity or enforceability in
         respect of any Indebtedness or other obligation of Publishing or any
         other Person under this Indenture or the Securities, or any agreement
         or instrument relating to any of the foregoing;

                  (b) any grants of time, renewals, extensions, indulgences,
         releases, discharges or modifications which the Trustee or the Holders
         may extend to, or make with, Publishing, Hollinger International or
         any other Person, or any change in the time, manner or place of
         payment of, or in any other term of, all or any of the Indenture
         Obligations, or any other amendment or waiver of, or any consent to or
         departure from, this Indenture or the Securities, including any
         increase or decrease in the Indenture Obligations;

                  (c) the taking of security from Publishing, Hollinger
         International or any other Person, and the release, discharge or
         alteration of, or other dealing with, such security;

                  (d) the occurrence of any change in the laws, rules,
         regulations or ordinances of any jurisdiction by any present or future
         action of any governmental authority or court amending, varying,
         reducing or otherwise affecting, or purporting to amend, vary, reduce
         or otherwise affect, any of the Indenture Obligations and the
         obligations of Hollinger International hereunder;

<PAGE>   156
                                                                         - 146 -

                  (e) the abstention from taking security from Publishing,
         Hollinger International or any other Person or from perfecting,
         continuing to keep perfected or taking advantage of any security;

                  (f) any loss, diminution of value or lack of enforceability
         of any security received from Publishing, Hollinger International or
         any other Person, and including any other guarantees received by the
         Trustee;

                  (g) any other dealings with Publishing, Hollinger
         International or any other Person, or with any security;

                  (h) the Trustee's or the Holders' acceptance of or entering
         into any composition with Publishing or Hollinger International;

                  (i) the application by the Holders or the Trustee of all
         monies at any time and from time to time received from Publishing,
         Hollinger International or any other Person on account of any
         indebtedness and liabilities owing by Publishing or Hollinger
         International to the Trustee or the Holders, in such manner as the
         Trustee or the Holders deems best and the changing of such application
         in whole or in part and at any time or from time to time, or any
         manner of application of collateral, or proceeds thereof, to all or
         any of the Indenture Obligations, or the manner of sale of any
         Collateral;

                  (j) the release or discharge of Publishing or Hollinger
         International or of any other Guarantor of the Securities or of any
         Person liable directly as surety or otherwise by operation of law or
         otherwise for the Securities, other than an express release in writing
         given by the Trustee, on behalf of the Holders, of the liability and
         obligations of Hollinger International hereunder;

                  (k) any change in the name, business, capital structure or
         governing instrument of Publishing or Hollinger International or any
         refinancing or restructuring of any of the Indenture Obligations;

                  (l) the sale of Publishing's or Hollinger International's
         business or any part thereof;

                  (m) subject to Section 14.14, any merger or consolidation,
         arrangement or reorganization of


<PAGE>   157
                                                                         - 147 -

         Publishing, Hollinger International, any Person resulting from the 
         merger or consolidation of Publishing or Hollinger International with 
         any other Person or any other successor to such Person or merged or 
         consolidated Person or any other change in the corporate existence, 
         structure or ownership of Publishing or Hollinger International;

                  (n) the insolvency, bankruptcy, liquidation, winding-up,
         dissolution, receivership or distribution of the assets of Publishing
         or its assets or any resulting discharge of any obligations of
         Publishing (whether voluntary or involuntary) or of Hollinger
         International or the loss of corporate existence;

                  (o) subject to Section 14.14, any arrangement or plan of
         reorganization affecting Publishing or Hollinger International;

                  (p) any other circumstance (including any statute of
         limitations) that might otherwise constitute a defense available to,
         or discharge of, Publishing or Hollinger International; or

                  (q) any modification, compromise, settlement or release by
         the Trustee, or by operation of law or otherwise, of the Indenture
         Obligations or the liability of Publishing or any other obligor under
         the Securities, or of any Collateral, in whole or in part, and any
         refusal of payment by the Trustee, in whole or in part, from any other
         obligor or other guarantor in connection with any of the Indenture
         Obligations, whether or not with notice to, or further assent by, or
         any reservation of rights against, Hollinger International.

                  SECTION 14.04. Right to Demand Full Performance. In the event
of any demand for payment or performance by the Trustee from Hollinger
International hereunder, the Trustee or the Holders shall have the right to
demand its full claim and to receive all dividends or other payments in respect
thereof until the Indenture Obligations shall have been paid in full, and
Hollinger International shall continue to be liable hereunder for any balance
which may be owing to the Trustee (including the fees and expenses of its agent
and counsel) or the Holders by Publishing under this Indenture and the
Securities. The retention by the Trustee or the Holders of any security, prior
to the realization by the Trustee or the Holders of its rights to such security
upon foreclosure thereon, shall not, as between the Trustee and Hollinger
International, be considered as a purchase of such


<PAGE>   158
                                                                         - 148 -

security, or as payment, satisfaction or reduction of the Indenture Obligations
due to the Trustee or the Holders by Publishing or any part thereof.

                  SECTION 14.05.  Waivers.  (a)  Hollinger International hereby
expressly waives (to the extent permitted by law) notice of the acceptance of
this Guarantee and notice of the existence, renewal, extension or the
nonperformance, nonpayment, or nonobservance on the part of Publishing of any
of the terms, covenants, conditions and provisions of this Indenture or the
Securities or any other notice whatsoever to or upon Publishing or Hollinger
International with respect to the Indenture Obligations. Hollinger
International hereby acknowledges communication to it of the terms of this
Indenture and the Securities and all of the provisions therein contained and
consents to and approves the same. Hollinger International hereby expressly
waives (to the extent permitted by law) diligence, presentment, protest and
demand for payment.

                  (b) Without prejudice to any of the rights or recourses which
the Trustee or the Holders may have against Publishing, Hollinger International
hereby expressly waives (to the extent permitted by law) any right to require
the Trustee or the Holders to:

                 (i)  initiate or exhaust any rights, remedies or recourse
                      against Publishing, Hollinger International or any other 
                      Person;

                (ii)  value, realize upon, or dispose of any security of
                      Publishing or any other Person held by the Trustee or 
                      the Holders; or

               (iii)  initiate or exhaust any other remedy which the Trustee 
                      or the Holders may have in law or equity;

before requiring or becoming entitled to demand payment from Hollinger
International under this Guarantee.

                  SECTION 14.06. Hollinger International Remains Obligated in
Event Publishing Is No Longer Obligated to Discharge Indenture Obligations. It
is the express intention of the Trustee and Hollinger International that if for
any reason Publishing has no legal existence, is or becomes under no legal
obligation to discharge the Indenture Obligations owing to the Trustee or the
Holders by Publishing or if any of the Indenture Obligations owing by
Publishing to the Trustee or the Holders becomes irrecoverable from Publishing
by operation of law or for any reason whatsoever, this Guarantee and the
covenants,


<PAGE>   159
                                                                         - 149 -

agreements and obligations of Hollinger International contained in this Article
XIV shall nevertheless be binding upon Hollinger International, as principal
debtor, until such time as all such Indenture Obligations have been paid in
full to the Trustee and all Indenture Obligations owing to the Trustee or the
Holders by Publishing have been discharged, or such earlier time as Section
4.02 shall apply to the Securities and Hollinger International shall be
responsible for the payment thereof to the Trustee or the Holders upon demand.

                  SECTION 14.07. Waiver of Rights. Hollinger International
agrees (to the extent permitted by law) that it hereby waives and will not in
any manner whatsoever claim or take the benefit or advantage of, any rights of
reimbursement, exoneration, contribution, indemnity or subrogation (whether
contractual, under Section 509 of Title Eleven of the United States Code, under
common law or otherwise) or any similar rights or "claims" (as such term is
defined under Title Eleven of the United States Code), against Publishing or
any Restricted Subsidiary arising from the existence of, or performance by,
Hollinger International under this Guarantee.

                  SECTION 14.08. Guarantee Is in Addition to Other Security.
This Guarantee shall be in addition to and not in substitution for any other
guarantees or other security which the Trustee may now or hereafter hold in
respect of the Indenture Obligations owing to the Trustee or the Holders by
Publishing and (except as may be required by law) the Trustee shall be under no
obligation to marshal in favor of Hollinger International any other guarantees
or other security or any moneys or other assets which the Trustee may be
entitled to receive or upon which the Trustee or the Holders may have a claim.

                  SECTION 14.09. Release of Security Interests. Without
limiting the generality of the foregoing and except as otherwise provided in
this Indenture, Hollinger International hereby consents and agrees, to the
fullest extent permitted by applicable law, that the rights of the Trustee
hereunder, and the liability of Hollinger International hereunder, shall not be
affected by any and all releases for any purpose of any Collateral, if any,
from the Liens and security interests created by any document relating thereto
and that this Guarantee shall continue to be effective or be reinstated, as the
case may be, if at any time any payment of any of the Indenture Obligations is
rescinded or must otherwise be returned by the Trustee upon the insolvency,
bankruptcy or reorganization of Publishing or otherwise, all as though such
payment had not been made.

<PAGE>   160
                                                                         - 150 -

                  SECTION 14.10.  No Bar to Further Actions.  Except as
provided by law, no action or proceeding brought or instituted under Article
XIV and this Guarantee and no recovery or judgment in pursuance thereof shall
be a bar or defense to any further action or proceeding which may be brought
under Article XIV and this Guarantee by reason of any further default or
defaults under Article XIV and this Guarantee or in the payment of any of the
Indenture Obligations owing by Publishing.

                  SECTION 14.11. Failure to Exercise Rights Shall Not Operate
as a Waiver; No Suspension of Remedies. (a) No failure to exercise and no delay
in exercising, on the part of the Trustee or the Holders, any right, power,
privilege or remedy under this Article XIV and this Guarantee shall operate as
a waiver thereof, nor shall any single or partial exercise of any rights,
power, privilege or remedy preclude any other or further exercise thereof, or
the exercise of any other rights, powers, privileges or remedies. The rights
and remedies herein provided for are cumulative and not exclusive of any rights
or remedies provided in law or equity.

                  (b) Nothing contained in this Article XIV shall limit the
right of the Trustee or the Holders to take any action to accelerate the
maturity of the Securities pursuant to Article V or to pursue any rights or
remedies hereunder or under applicable law.

                  SECTION 14.12. Trustee's Duties; Notice to Trustee. (a) Any
provision in this Article XIV or elsewhere in this Indenture allowing the
Trustee to request any information or to take any action authorized by, or on
behalf of Hollinger International, shall be permissive and shall not be
obligatory on the Trustee except as the Holders may direct in accordance with
the provisions of this Indenture.

                  (b) The Trustee shall not be required to inquire into the
existence, powers or capacities of Publishing, Hollinger International or the
officers, directors or agents acting or purporting to act on their respective
behalf.

                  (c) Notwithstanding the provisions of this Article XIV or any
other provision of this Indenture, the Trustee shall not be charged with
knowledge of the existence of any facts which would prohibit the making of any
payment to or by the Trustee in respect of the Securities, unless and until the
Trustee shall have received written notice thereof from Hollinger
International; and, prior to the receipt of any such written notice, the
Trustee, subject to



<PAGE>   161
                                                                         - 151 -

the provisions of Section 6.01, shall be entitled in all respects to assume
that no such facts exist; provided, however, that if the Responsible Officer of
the Trustee shall not have received any such notice from Hollinger
International at least three Business Days prior to the date upon which by the
terms hereof any money may become payable for any purpose (including, without
limitation, the payment of the principal of, premium, if any, or interest on
any Security), then, anything herein contained to the contrary notwithstanding,
the Trustee shall have full power and authority to receive such money and to
apply the same to the purpose for which such money was received and shall not
be affected by any notice to the contrary which may be received by it within
three Business Days prior to such date; nor shall the Trustee be charged with
knowledge of the curing of any such default or the elimination of the act or
condition preventing any such payment unless and until the Responsible Officer
of the Trustee shall have received an Officers' Certificate to such effect.

                  (d) In the case at any time any Paying Agent other than the
Trustee shall have been appointed by Publishing and be then acting hereunder,
the term "Trustee" as used in this Article XIV shall in such case (unless the
context otherwise requires) be construed as extending to and including such
Paying Agent within its meaning as fully for all intents and purposes as if
such Paying Agent were named in this Article XIV in addition to or in place of
the Trustee; provided, however, that this Section 14.12 shall not apply to
Publishing or any Affiliate of Publishing if Publishing or such Affiliate acts
as Paying Agent.

                  SECTION 14.13. Successors and Assigns. All terms, agreements
and conditions of this Article XIV shall extend to and be binding upon
Hollinger International and its successors and permitted assigns and shall
enure to the benefit of and may be enforced by the Trustee and its successors
and assigns; provided, however, that Hollinger International may not assign any
of its rights or obligations hereunder other than in accordance with Article
VIII.

                  SECTION 14.14. Release of Guarantee. Concurrently with the
payment in full of all of the Indenture Obligations, Hollinger International
shall be released from and relieved of its obligations under this Article XIV.
Upon the delivery by Publishing to the Trustee of an Officer's Certificate and,
if requested by the Trustee, an Opinion of Counsel to the effect that the
transaction giving rise to the release of this Guarantee was made by Publishing
in accordance with the provisions of this


<PAGE>   162
                                                                         - 152 -

Indenture and the Securities, the Trustee shall execute any documents
reasonably required in order to evidence the release of Hollinger International
from its obligations under this Guarantee. If any of the Indenture Obligations
are revived and reinstated after the termination of this Guarantee, then all of
the obligations of Hollinger International under this Guarantee shall be
revived and reinstated as if this Guarantee had not been terminated until such
time as the Indenture Obligations are paid in full, and Hollinger International
shall enter into an amendment to this Guarantee, reasonably satisfactory to the
Trustee, evidencing such revival and reinstatement.

                  This Guarantee shall terminate (a) upon a merger or
consolidation of Hollinger International with Publishing, in accordance with
Article VIII or (b) if after giving effect to a transaction or transactions
permitted to be consummated pursuant to Article VIII, Hollinger International
no longer owns any Capital Stock of Publishing.

                  SECTION 14.15. Execution of Guarantee. To evidence the
Guarantee, Hollinger International hereby agrees to execute a guarantee
substantially in the form set forth in Section 2.05, to be endorsed on each
Security authenticated and delivered by the Trustee and that this Indenture
shall be executed on behalf of Hollinger International by its Chairman of the
Board, its President or one of its Vice Presidents, under its corporate seal
reproduced thereon attested by its Secretary or one of its Assistant
Secretaries. The signature of any of these officers on the Securities may be
manual or facsimile.

                  SECTION 14.16. Guarantee Subordinate to Senior Guarantor
Indebtedness. Hollinger International covenants and agrees, and each Holder of
a security, by his acceptance thereof, likewise covenants and agrees, that, to
the extent and in the manner hereinafter set forth in this Article, this
Guarantee is hereby made subordinate and subject in right of payment as
provided in this Article to the prior payment in full, in cash or Cash
Equivalents of all Senior Guarantor Indebtedness; provided, however, that the
Indebtedness represented by this Guarantee in all respects shall rank equally
with, or prior to, all existing and future unsecured Indebtedness of Hollinger
International that is subordinated to Senior Guarantor Indebtedness.

                  This Article XIV shall constitute a continuing offer to all
Persons who, in reliance upon such provisions, become holders of, or continue
to hold Senior Guarantor Indebtedness; and such provisions are made for the
benefit


<PAGE>   163
                                                                         - 153 -

of the holders of Senior Guarantor Indebtedness; and such holders are made
obligees hereunder and they or each of them may enforce such provisions.

                  SECTION 14.17. Payment Over of Proceeds Upon Dissolution of
Hollinger International, etc. In the event of (a) any insolvency or bankruptcy
case or proceeding, or any receivership, liquidation, reorganization or other
similar case or proceeding in connection therewith, relative to Hollinger
International or to its creditors, as such, or to its assets, or (b) any
liquidation, dissolution or other winding up of Hollinger International,
whether voluntary or involuntary and whether or not involving insolvency or
bankruptcy, or (c) any assignment for the benefit of creditors or any other
marshaling of assets or liabilities of Hollinger International, then and in any
such event:

                  (1) the holders of Senior Guarantor Indebtedness shall be
         entitled to receive payment in full in cash or Cash Equivalents of all
         amounts due on or in respect of all Senior Guarantor Indebtedness,
         before the Holders of the Securities are entitled to receive any
         payment or distribution of any kind or character (excluding Permitted
         Guarantor Junior Securities) on account of principal of, premium, if
         any, or interest on the Securities (including any payment or other
         distribution which may be received from the holders of Subordinated
         Guarantor Indebtedness as a result of any payment on such Subordinated
         Guarantor Indebtedness); and

                  (2) any payment or distribution of assets of Publishing of
         any kind or character, whether in cash, property or securities
         (excluding Permitted Junior Guarantor Securities), by set-off or
         otherwise, to which the Holders or the Trustee would be entitled but
         for the provisions of this Article shall be paid by the liquidating
         trustee or agent or other Person making such payment or distribution,
         whether a trustee in bankruptcy, a receiver or liquidating trustee or
         otherwise, directly to the holders of Senior Guarantor Indebtedness or
         their representative or representatives or to the trustee or trustees
         under any indenture under which any instruments evidencing any of such
         Senior Guarantor Indebtedness may have been issued, ratably according
         to the aggregate amounts remaining unpaid on account of the Senior
         Guarantor Indebtedness held or represented by each, to the extent
         necessary to make payment in full in cash or Cash Equivalents or in
         any other form acceptable to the requisite holders of Designated
         Senior Guarantor Indebtedness, of all Senior Guarantor Indebtedness
         remaining unpaid, after giving


<PAGE>   164
                                                                         - 154 -

         effect to any concurrent payment or distribution to the holders of 
         such Senior Guarantor Indebtedness; and

                  (3) in the event that, notwithstanding the foregoing
         provisions of this Section, the Trustee or the Holder of any Security
         shall have received any payment or distribution of assets of
         Publishing of any kind or character, whether in cash, property or
         securities, in respect of principal, premium, if any, and interest on
         the Securities before all Senior Guarantor Indebtedness is paid in
         full, then and in such event such payment or distribution (excluding
         Permitted Guarantor Junior Securities) (including any payment or other
         distribution which may be received from the holders of Subordinated
         Indebtedness as a result of any payment on such Subordinated
         Indebtedness) shall be paid over or delivered forthwith to the trustee
         in bankruptcy, receiver, liquidating trustee, custodian, assignee,
         agent or other person making payment or distribution of assets of
         Publishing for application to the payment of all Senior Guarantor
         Indebtedness remaining unpaid, to the extent necessary to pay all
         Senior Guarantor Indebtedness in full in cash or Cash Equivalents
         after giving effect to any concurrent payment or distribution to or
         for the holders of Senior Guarantor Indebtedness and until so paid
         shall be held in trust for the benefit of the holders of Senior
         Guarantor Indebtedness.

                  The consolidation of Hollinger International with, or the
merger of Hollinger International with or into, another Person or the
liquidation or dissolution of Hollinger International following the conveyance,
transfer or lease of its properties and assets substantially as an entirety to
another Person upon the terms and conditions set forth in Article VIII shall
not be deemed a dissolution, winding up, liquidation, reorganization,
assignment for the benefit of creditors or marshaling of assets and liabilities
of Hollinger International for the purposes of this Section if the Person
formed by such consolidation or the surviving entity of such merger or the
Person which acquires by conveyance, transfer or lease such properties and
assets substantially as an entirety, as the case may be, shall, as a part of
such consolidation, merger, conveyance, transfer or lease, comply with the
conditions set forth in Article VIII.

                  SECTION 14.18. Default on Senior Guarantor Indebtedness. (a)
Upon the maturity of any Senior Guarantor Indebtedness by lapse of time,
acceleration or otherwise, all principal thereof and interest thereon and


<PAGE>   165
                                                                         - 155 -

other amounts due in connection therewith shall first be paid in full in cash
or Cash Equivalents or such payment duly provided for before any payment is
made by Hollinger International or any Person acting on behalf of Hollinger
International in respect of the Securities.

                  (b) No payment (excluding payments in the form of Permitted
Guarantor Junior Securities) shall be made by Hollinger International in
respect of the Securities by Hollinger International during the period in which
Section 14.17 shall be applicable, during any suspension of payments in effect
under Section 12.03(a) of this Indenture or during any Payment Blockage Period
in effect under Section 12.03(b) of this Indenture.

                  (c) In the event that, notwithstanding the foregoing,
Hollinger International shall make any payment to the Trustee or the Holder of
any Security prohibited by the foregoing provisions of this Section, then and
in such event such payment shall be paid over and delivered forthwith to the
representatives of Senior Guarantor Indebtedness or as a court of competent
jurisdiction shall direct and until so paid shall be held in trust for the
benefit of the holders of Senior Indebtedness.

                  SECTION 14.19. Payment Permitted by Hollinger International
if No Default. Nothing contained in this Article, elsewhere in this Indenture
or in any of the Securities shall prevent Hollinger International, at any time
except during the pendency of any case, proceeding, dissolution, liquidation or
other winding up, assignment for the benefit of creditors or other marshaling
of assets and liabilities of Publishing referred to in Section 14.17 or under
the conditions described in Section 14.18, from making payments at any time of
principal of, premium, if any, or interest on the Securities.

                  SECTION 14.20. Subrogation to Rights of Holders of Senior
Guarantor Indebtedness. Subject to the payment in full of all Senior Guarantor
Indebtedness, the Holders of the Securities shall be subrogated to the rights
of the holders of such Senior Guarantor Indebtedness to receive payments and
distributions of cash, property and securities applicable to the Senior
Guarantor Indebtedness until the principal of, premium, if any, and interest on
the Securities shall be paid in full. For purposes of such subrogation, no
payments or distributions to the holders of Senior Guarantor Indebtedness of
any cash, property or securities to which the Holders of the Securities or the
Trustee would be entitled except for the provisions of this Article, and no
payments over pursuant to the provisions of


<PAGE>   166
                                                                         - 156 -

this Article to the holders of Senior Guarantor Indebtedness by Holders of the
Securities or the Trustee, shall, as among Hollinger International, its
creditors other than holders of Senior Guarantor Indebtedness, and the Holders
of the Securities, be deemed to be a payment or distribution by Hollinger
International to or on account of the Senior Guarantor Indebtedness.

                  SECTION 14.21. Provisions Solely to Define Relative Rights.
The provisions of Sections 14.16 through 14.29 of this Indenture are intended
solely for the purpose of defining the relative rights of the Holders of the
Securities on the one hand and the holders of Senior Guarantor Indebtedness on
the other hand. Nothing contained in this Article or elsewhere in this
Indenture or in the Securities is intended to or shall (a) impair, as among
Hollinger International, its creditors other than holders of Senior Guarantor
Indebtedness and the Holders of the Securities, the obligation of Hollinger
International, which is absolute and unconditional, to pay to the Holders of
the Securities the principal of, premium, if any, and interest on the
Securities as and when the same shall become due and payable in accordance with
their terms; or (b) affect the relative rights against Hollinger International
of the Holders of the Securities and creditors of Hollinger International other
than the holders of Senior Guarantor Indebtedness; or (c) prevent the Trustee
or the Holder of any Security from exercising all remedies otherwise permitted
by applicable law upon default under this Indenture, subject to the rights, if
any, under this Article of the holders of Senior Guarantor Indebtedness (1) in
any case, proceeding, dissolution, liquidation or other winding up, assignment
for the benefit of creditors or other marshaling of assets and liabilities of
Hollinger International referred to in Section 14.17, to receive, pursuant to
and in accordance with such Section, cash, property and securities otherwise
payable or deliverable to the Trustee or such Holder, or (2) under the
conditions specified in Section 14.18, to prevent any payment prohibited by
such Section or enforce their rights pursuant to Section 14.18(c).

                  SECTION 14.22. Trustee to Effectuate Subordination. Each
Holder of a Security by his acceptance thereof authorizes and directs the
Trustee on his behalf to take such action as may be necessary or appropriate to
effectuate the subordination provided in this Article and appoints the Trustee
his attorney-in-fact for any and all such purposes, including, in the event of
any dissolution, winding-up, liquidation or reorganization of Hollinger
International whether in bankruptcy, insolvency,


<PAGE>   167
                                                                         - 157 -

receivership proceedings, or otherwise, the timely filing of a claim for the
unpaid balance of the indebtedness of Hollinger International owing to such
Holder in the form required in such proceedings and the causing of such claim
to be approved. If the Trustee does not file a proper claim at least 30 days
before the expiration of the time to file such claim, then the holders of
Senior Guarantor Indebtedness, and their agents, trustees or other
representative are authorized to do so on behalf of the Holders.

                  SECTION 14.23. No Waiver of Subordination Provisions. (a) No
right of any present or future holder of any Senior Guarantor Indebtedness to
enforce subordination as herein provided shall at any time in any way be
prejudiced or impaired by any act or failure to act on the part of Publishing
or by any act or failure to act by any such holder, or by any noncompliance by
Hollinger International with the terms, provisions and covenants of this
Indenture, regardless of any knowledge thereof any such holder may have or be
otherwise charged with.

                  (b) Without limiting the generality of Subsection (a) of this
Section, the holders of Senior Guarantor Indebtedness may, at any time and from
time to time, without the consent of or notice to the Trustee or the Holders of
the Securities, without incurring responsibility to the Holders of the
Securities and without impairing or releasing the subordination provided in
this Article or the obligations hereunder of the Holders of the Securities to
the holders of Senior Guarantor Indebtedness, do any one or more of the
following: (1) change the manner, place or terms of payment or extend the time
of payment of, or renew or alter, Senior Guarantor Indebtedness or any
instrument evidencing the same or any agreement under which Senior Guarantor
Indebtedness is outstanding; (2) sell, exchange, release or otherwise deal with
any property pledged, mortgaged or otherwise securing Senior Guarantor
Indebtedness; (3) release any Person liable in any manner for the collection or
payment of Senior Guarantor Indebtedness; and (4) exercise or refrain from
exercising any rights against Hollinger International and any other Person;
provided, however, that in no event shall any such actions limit the right of
the Holders of the Securities to take any action to accelerate the maturity of
the Securities in accordance with provisions described under "Events of
Default" and as set forth pursuant to Article V in this Indenture or to pursue
any rights or remedies hereunder or under applicable laws if the taking of such
action does not otherwise violate the terms of this Article.

<PAGE>   168
                                                                         - 158 -

                  SECTION 14.24. Notice to Trustee by Hollinger International.
(a) Hollinger International shall give prompt written notice to the Trustee of
any fact known to Hollinger International which would prohibit the making of
any payment to or by the Trustee in respect of the Guarantee. Notwithstanding
the provisions of this Article or any provision of this Indenture, the Trustee
shall not be charged with knowledge of the existence of any facts which would
prohibit the making of any payment to or by the Trustee in respect of the
Securities, unless and until the Trustee shall have received written notice
thereof from Hollinger International or a holder of Senior Guarantor
Indebtedness or from a Senior Guarantor Representative or any trustee,
fiduciary or agent therefor; and, prior to the receipt of any such written
notice, the Trustee shall be entitled in all respects to assume that no such
facts exist; provided, however, that if the Trustee shall not have received the
notice provided for in this Section at least two Business Days prior to the
date upon which by the terms hereof any money may become payable for any
purpose (including, without limitation, the payment of the principal of,
premium, if any, or interest on any Security), then, anything herein contained
to the contrary notwithstanding but without limiting the rights and remedies of
the holders of Senior Guarantor Indebtedness or any trustee, fiduciary or agent
thereof, the Trustee shall have full power and authority to receive such money
and to apply the same to the purpose for which such money was received and
shall not be affected by any notice to the contrary which may be received by it
two Business Days prior to such date; nor shall the Trustee be charged with
knowledge of the curing of any such default or the elimination of the act or
condition preventing any such payment unless and until the Trustee shall have
received an officers' certificate to such effect.

                  (b) The Trustee shall be entitled to rely on the delivery to
it of a written notice to the Trustee and Hollinger International by a Person
representing himself to be a Senior Guarantor Representative or a holder of
Senior Guarantor Indebtedness (or a trustee, fiduciary or agent therefor) to
establish that such notice has been given by a Senior Guarantor Representative
or a holder of Senior Guarantor Indebtedness (or a trustee, fiduciary or agent
therefor); provided, however, that failure to give such notice to Publishing
shall not affect in any way the ability of the Trustee to rely on such notice.
In the event that the Trustee determines in good faith that further evidence is
required with respect to the right of any Person as a holder of Senior
Guarantor Indebtedness to participate in any payment or distribution pursuant
to this Article, the Trustee may request such Person to furnish evidence to the


<PAGE>   169
                                                                         - 159 -

reasonable satisfaction of the Trustee as to the amount of Senior Guarantor
Indebtedness held by such Person, the extent to which such Person is entitled
to participate in such payment or distribution and any other facts pertinent to
the rights of such Person under this Article, and if such evidence is not
furnished, the Trustee may defer any payment to such Person pending judicial
determination as to the right of such Person to receive such payment.

                  SECTION 14.25. Reliance on Judicial Order or Certificate of
Liquidating Agent. Upon any payment or distribution of assets of Hollinger
International referred to in this Article, the Trustee and the Holders of the
Securities shall be entitled to rely upon any order or decree entered by any
court of competent jurisdiction in which such insolvency, bankruptcy,
receivership, liquidation, reorganization, dissolution, winding up or similar
case or proceeding is pending, or a certificate of the trustee in bankruptcy,
receiver, liquidating trustee, custodian, assignee for the benefit of
creditors, agent or other person making such payment or distribution, delivered
to the Trustee or to the Holders of Securities, for the purpose of ascertaining
the Persons entitled to participate in such payment or distribution, the
holders of Senior Guarantor Indebtedness and other indebtedness of Hollinger
International, the amount thereof or payable thereon, the amount or amounts
paid or distributed thereon and all other facts pertinent thereto or to this
Article; provided that the foregoing shall apply only if such court has been
fully apprised of the provisions of this Article.

                  SECTION 14.26. Rights of Trustee as a Holder of Senior
Guarantor Indebtedness; Preservation of Trustee's Rights. The Trustee in its
individual capacity shall be entitled to all the rights set forth in this
Article with respect to any Senior Guarantor Indebtedness which may at any time
be held by it, to the same extent as any other holder of Senior Guarantor
Indebtedness, and nothing in this Indenture shall deprive the Trustee of any of
its rights as such holder. Nothing in this Article shall apply to claims of, or
payments to, the Trustee under or pursuant to the provisions in this Indenture
regarding compensation and indemnification of the Trustee.

                  SECTION 14.27. Article Applicable to Paying Agents. In case
at any time any Paying Agent other than the Trustee shall have been appointed
by Publishing and be then acting under this Indenture, the term "Trustee" as
used in this Article shall in such case (unless the context otherwise requires)
be construed as extending to and including such Paying Agent within its meaning
as fully for


<PAGE>   170
                                                                         - 160 -

all intents and purposes as if such Paying Agent were named in this Article in
addition to or in place of the Trustee; provided, however, that Section 14.26
shall not apply to Publishing or any Affiliate of Publishing if it or such
Affiliate acts as Paying Agent.

                  SECTION 14.28. No Suspension of Remedies. Nothing contained
in this Article shall limit the right of the Trustee or the Holders of
Securities to take any action to accelerate the maturity of the Securities
pursuant to Article V of this Indenture or to pursue any rights or remedies
hereunder or under applicable law, subject to the rights, if any, under this
Article of the holders, from time to time, of Senior Guarantor Indebtedness to
receive the cash, property or securities receivable upon the exercise of such
rights or remedies.

                  SECTION 14.29. Trustee's Relation to Senior Guarantor
Indebtedness. With respect to the holders of Senior Guarantor Indebtedness, the
Trustee undertakes to perform or to observe only such of its covenants and
obligations as are specifically set forth in this Article, and no implied
covenants or obligations with respect to the holders of Senior Guarantor
Indebtedness shall be read into this Article against the Trustee. The Trustee
shall not be deemed to owe any fiduciary duty to the holders of Senior
Guarantor Indebtedness and the Trustee shall not be liable to any holder of
Senior Guarantor Indebtedness if it shall mistakenly in the absence of gross
negligence or wilful misconduct pay over or deliver to Holders, Publishing or
any other Person moneys or assets to which any holder of Senior Guarantor
Indebtedness shall be entitled by virtue of this Article or otherwise.

                                    * * * *
<PAGE>   171


                  IN WITNESS WHEREOF, the parties hereto have caused this
Indenture to be duly executed, and their respective corporate seals to be
hereunto affixed and attested, all as of the day and year first above written.

                                     HOLLINGER INTERNATIONAL
                                     PUBLISHING INC.

                                     by  ________________________________
                                         Name:
                                         Title:

Attest:  _________________________
         Name:
         Title:

                                     HOLLINGER INTERNATIONAL INC.,
                                     solely in its capacity as
                                     Guarantor

                                     by  __________________________________
                                         Name:
                                         Title:

Attest:  _________________________
         Name:
         Title:

                                     FLEET NATIONAL BANK

                                     by  ___________________________________
                                         Name:
                                         Title:



<PAGE>   1
                                                                   EXHIBIT 4.04

                  UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED
REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION ("DTC"),
NEW YORK, NEW YORK, TO PUBLISHING OR ITS AGENT FOR REGISTRATION OF TRANSFER,
EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF
CEDE & CO. OR SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE
OF DTC (AND ANY PAYMENT IS MADE TO CEDE & CO., OR TO SUCH OTHER ENTITY AS IS
REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE OR
OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL
INASMUCH AS THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.

                  TRANSFERS OF THIS GLOBAL SECURITY SHALL BE LIMITED TO
TRANSFERS IN WHOLE, BUT NOT IN PART, TO A NOMINEE OF DTC, TO DTC, TO A
SUCCESSOR OF DTC SELECTED OR APPROVED BY PUBLISHING, OR TO A NOMINEE OF SUCH
SUCCESSOR, AND TRANSFERS OF PORTIONS OF THIS GLOBAL SECURITY SHALL BE LIMITED
TO TRANSFERS MADE IN ACCORDANCE WITH THE RESTRICTIONS SET FORTH IN THE
INDENTURE REFERRED TO ON THE REVERSE HEREOF.


<PAGE>   2


                    HOLLINGER INTERNATIONAL PUBLISHING INC.

                             ----------------------

                   9-1/4% SENIOR SUBORDINATED NOTES DUE 2007

No. 001                                                            $290,000,000
                                                            CUSIP No. 435572AB8

                  HOLLINGER INTERNATIONAL PUBLISHING INC., a Delaware
corporation (herein called "Publishing", which term includes any successor
Person under the Indenture hereinafter referred to), for value received, hereby
promises to pay to Cede & Co. or registered assigns, the principal sum of
$290,000,000 on March 15, 2007, at the office or agency of Publishing referred
to below, and to pay interest thereon from March 18, 1997 or from the most
recent Interest Payment Date to which interest has been paid or duly provided
for, semi-annually on March 15 and September 15 commencing September 15, 1997
at the rate of 9-1/4% per annum, in United States dollars, until the principal
hereof is paid or duly provided for.

                  The interest so payable, and punctually paid or duly provided
for, on any Interest Payment Date will, as provided in the Indenture, be paid
to the Person in whose name this Security (or one or more Predecessor
Securities) is registered at the close of business on the Regular Record Date
for such interest, which shall be March 1 or September 1 (whether or not a
Business Day), as the case may be, next preceding such Interest Payment Date.
Any interest not so paid, or duly provided for, and interest on such defaulted
interest at the interest rate borne by the Securities, to the extent lawful,
shall forthwith cease to be payable to the Holder in whose name such Security
is registered as of such Regular Record Date, and may be paid on the Special
Payment Date to the Person in whose name the Security (or one or more
Predecessor Securities) is registered at the close of business on a Special
Record Date to be fixed by the Trustee (and for which notice shall be given to
Holders of Securities not less than 10 days prior to such Special Record Date)
or may be paid at any time in any other lawful manner not inconsistent with the
requirements of any securities exchange on which the Securities may be listed,
and upon such notice as may be required by such exchange, all as more fully
provided in said Indenture.

                  Payment of the principal of, premium, if any, and interest on
this Security will be made at the office or agency of Publishing maintained for
that purpose in the City of New York, or at such other office or agency of
Publishing as may be maintained for such purpose, in such coin or currency of
the United States of America as at the time of payment is legal tender for
payment of public and private debts; provided, however, that payment of
interest may be made at the option of Publishing by check mailed to the address
of the Person entitled thereto as such address shall appear on the Security
Register.  Interest shall be computed on the basis of a 360-day year of twelve
30-day months.

                  Reference is hereby made to the further provisions of this
Security set forth on the reverse hereof, which further provisions shall for
all purposes have the same effect as if set forth at this place.


<PAGE>   3

                  Unless the certificate of authentication hereon has been duly
executed by the Trustee referred to on the reverse hereof or by the
authenticating agent appointed as provided in the Indenture by manual
signature, this Security shall not be entitled to any benefit under the
Indenture, or be valid or obligatory for any purpose.

                  IN WITNESS WHEREOF, Publishing has caused this instrument to
be duly executed by the manual or facsimile signature of its authorized
officers and its corporate seal to be affixed or reproduced hereon.

Dated:                                       HOLLINGER INTERNATIONAL PUBLISHING
                                             INC.

                                                by
                                                  ----------------------------
                                                      Authorized Signatory

[Seal]

Attest:

- --------------------------------
         Secretary


TRUSTEE'S CERTIFICATE OF
  AUTHENTICATION

Fleet National Bank, as Trustee, certifies
that this is one of the Securities referred                [Seal]
to in the within-mentioned Indenture and
Board Resolutions.

FLEET NATIONAL BANK,
as Trustee

Dated:

by
  ------------------------------
        Authorized Signatory


<PAGE>   4


                             [REVERSE OF SECURITY]

                    HOLLINGER INTERNATIONAL PUBLISHING INC.

                   9-1/4% SENIOR SUBORDINATED NOTES DUE 2007

                  This Security is one of a duly authorized issue of a series
of Securities of Publishing designated as the 9-1/4% Senior Subordinated Notes
due 2007 (the "Securities"), limited (except as otherwise provided in the
Indenture and Board Resolutions referred to below) in aggregate principal
amount to $290,000,000, which may be issued under and subject to the terms of
(a) a senior subordinated indenture (herein called the "Indenture") dated as of
March 18, 1997, among Publishing, Hollinger International Inc. ("Hollinger
International") and Fleet National Bank, as trustee (together with any
successor Trustee under the Indenture, the "Trustee") and (b) resolutions dated
as of March 12, 1997 of the Executive Committee of the Board of Directors of
Publishing (herein called the "Board Resolutions"), to which Indenture, all
indentures supplemental thereto and Resolutions reference is hereby made for a
statement of the respective rights, limitations of rights, obligations, duties
and immunities thereunder of the Trustee and any agent of the Trustee, any
Paying Agent, Hollinger International, Publishing and the Holders of the
Securities and the terms upon which the Securities are, and are to be,
authenticated and delivered.

                  The Indenture contains provisions for defeasance at any time
of (a) the entire Indebtedness evidenced by this Security and (b) certain
covenants and related Defaults and Events of Default, in each case upon
compliance with certain conditions set forth therein.

                  The Indebtedness evidenced by the Securities is, to the
extent and in the manner provided in the Indenture, subordinated and subject in
right of payment to the prior payment in full of all Senior Indebtedness,
whether Outstanding on the date of the Indenture or thereafter, and this
Security is issued subject to such provisions. Each Holder of this Security, by
accepting the same, (a) agrees to and shall be bound by such provisions, (b)
authorizes and directs the Trustee on such Holder's behalf to take such action
as may be necessary or appropriate to effectuate the subordination as provided
in the Indenture and (c) appoints the Trustee as such Holder's attorney-in-fact
for such purpose; provided, however, that the Indebtedness evidenced by this
Security shall cease to be so subordinated and subject to right of payment upon
any defeasance of this Security referred to in clause (a) or (b) of the
preceding paragraph.

                  The Securities are subject to redemption, in whole or in
part, at any time on or after March 15, 2002, at the option of Publishing upon
not less than 30 nor more than 60 days' prior notice to the Holders by
first-class mail, in amounts of $1,000 or integral multiples of $1,000 at the
following redemption prices (expressed as a percentage of the principal amount)
if redeemed during the 12-month period beginning March 15 of the years
indicated below:


<PAGE>   5

<TABLE>
<CAPTION>
                                                           REDEMPTION
                YEAR                                          PRICE
                ----                                       ----------
                <S>                                         <C>
                2002  . . . . . . . . . . . . . . . . . . . 104.625%

                2003  . . . . . . . . . . . . . . . . . . . 103.083%

                2004  . . . . . . . . . . . . . . . . . . . 101.541%
</TABLE>


and thereafter at 100% of the principal amount, in each case together with
accrued and unpaid interest, if any, to the Redemption Date (subject to the
right of Holders of record on relevant Regular Record Dates or Special Record
Dates to receive interest due on an Interest Payment Date).

                  If less than all of the Securities are to be redeemed, the
Trustee shall select the Securities or the portion thereof to be redeemed pro
rata or by any other method the Trustee shall deem fair and reasonable.

                  Upon the occurrence of a Change of Control, each Holder shall
have the right to require Publishing to purchase all or a portion of such
Holder's Securities in amounts of $1,000 or integral multiples of $1,000, at a
purchase price in cash equal to 101% of the principal amount thereof, plus
accrued and unpaid interest, if any, to the date of purchase.

                  Under certain circumstances, in the event the Net Cash
Proceeds that are received by Publishing from any Asset Sale, and that are not
applied to repay permanently any Senior Indebtedness then outstanding or
invested in properties or assets used in the businesses of Publishing in
accordance with the terms of the Indenture exceed $20 million, Publishing will
be required to apply such proceeds to the repayment of the Securities and
certain Indebtedness ranking pari passu with the Securities.

                  In the case of any redemption of Securities or purchase of
Securities upon a Change of Control or Asset Sale, interest installments whose
Stated Maturity is on or prior to the Redemption Date, Change of Control
Purchase Date or Purchase Date, as the case may be, will be payable to the
Holders of record of such Securities as of the close of business on the
relevant Regular Record Date or Special Record Date referred to on the face
hereof.  Securities (or portions thereof) for whose redemption and payment or
repurchase provision is made in accordance with the Indenture shall cease to
bear interest from and after the Redemption Date, Change of Control Purchase
Date or Purchase Date, as the case may be.

                  In the event of redemption or repurchase of this Security in
part only, a new Security or Securities for the portion hereof not redeemed or
repurchased shall be issued in the name of the Holder hereof upon the
cancellation hereof.


<PAGE>   6

                  If an Event of Default shall occur and be continuing, the
principal amount of all the Securities may be declared due and payable in the
manner and with the effect provided in the Indenture.

                  The Indenture permits, with certain exceptions (including
certain amendments permitted without the consent of any Holders) as therein
provided, the amendment thereof and the modification of the rights and
obligations of Publishing and the rights of the Holders under the Indenture and
the Securities at any time with the consent of the Holders of not less than a
majority in aggregate principal amount of the Securities at the time
Outstanding. The Indenture also contains provisions permitting the Holders of
not less than a majority in aggregate principal amount of the Securities at the
time Outstanding, on behalf of the Holders of all the Securities, to waive
compliance by Publishing with certain provisions of the Indenture and the
Securities and certain past Defaults under the Indenture and their
consequences.  Any such consent or waiver by or on behalf of the Holder of this
Security shall be conclusive and binding upon such Holder and upon all future
Holders of this Security and of any Security issued upon the registration of
transfer hereof or in exchange herefor or in lieu hereof whether or not
notation of such consent or waiver is made upon this Security.

                  No reference herein to the Indenture and no provision of this
Security or of the Indenture shall alter or impair the obligation of
Publishing, which is absolute, and unconditional, to pay the principal of,
premium, if any, and interest on this Security at the times, place, and rate,
and in the coin or currency, herein prescribed subject to the subordination
provisions of the Indenture.

                  As set forth in, and subject to, the provisions of the
Indenture, no Holder of any Security will have any right to institute any
proceeding with respect to the Indenture or for any remedy thereunder, unless
(a) such Holder shall have previously given to the Trustee written notice of a
continuing Event of Default, (b) the Holders of not less than 25% in principal
amount of the Outstanding Securities shall have made written request, and
offered reasonable indemnity, to the Trustee to institute such proceeding as
trustee, (c) the Trustee shall not have received from the Holders of a majority
in principal amount of the Outstanding Securities a direction inconsistent with
such request and (d) the Trustee shall have failed to institute such proceeding
within 60 days; provided, however, that such limitations do not apply to a suit
instituted by the holder hereof for the enforcement of payment of the principal
of (and premium, if any) or any interest on this Security on or after the
respective due dates expressed herein.

                  As provided in the Indenture and subject to certain
limitations therein set forth, the transfer of this Security is registrable on
the Security Register of Publishing, upon surrender of this Security for
registration of transfer at the office or agency of Publishing maintained for
such purpose in the City of New York or at such other office or agency of
Publishing as may be maintained for such purpose, duly endorsed by, or
accompanied by a written instrument of transfer in form satisfactory to
Publishing and the Security Registrar duly executed by, the Holder hereof or
his attorney duly authorized in writing, and thereupon one or more new
Securities, of authorized denominations and for the same aggregate principal
amount, will be issued to the designated transferee or transferees.


<PAGE>   7

                  The Securities are issuable only in registered form without
coupons in denominations of $1,000 and any integral multiple thereof. As
provided in the Indenture and subject to certain limitations therein set forth,
the Securities are exchangeable for a like aggregate principal amount of
Securities of a different authorized denomination, as requested by the Holder
surrendering the same.

                  No service charge shall be made for any registration of
transfer or exchange or redemption of Securities, but Publishing may require
payment of a sum sufficient to cover any tax or other governmental charge
payable in connection therewith.

                  Prior to due presentment of this Security for registration of
transfer, Publishing, the Trustee and any agent of Publishing or the Trustee
may treat the Person in whose name this Security is registered as the owner
hereof for all purposes, whether or not this Security is overdue, and none of
Publishing, the Trustee nor any agent shall be affected by notice to the
contrary.

                  Upon any consolidation or merger, or any sale, assignment,
conveyance, transfer or disposition (other than pursuant to a lease) of all or
substantially all of the properties and assets of Publishing in accordance with
the Indenture, subject to the terms and conditions of the Indenture, the
successor Person to such transaction shall become the obligor on this Security,
and Publishing shall be discharged from all obligations and covenants under
this Security and the Indenture.

                  All terms used in this Security which are defined in the
Indenture and not otherwise defined herein shall have the meanings assigned to
them in the Indenture.


<PAGE>   8

                   GUARANTEE OF HOLLINGER INTERNATIONAL INC.

                  For value received, HOLLINGER INTERNATIONAL INC., a Delaware
corporation, hereby absolutely, unconditionally and irrevocably guarantees to
the holder of this Security and the Trustee, as if Hollinger International were
the principal debtor, the punctual payment of principal of, premium, if any,
and interest on this Security in the amounts and at the time when due and
interest on the overdue principal and interest, if any, of this Security, if
lawful, and the payment or performance of all other obligations of Publishing
under the Indenture or the Securities, to the holder of this Security and the
Trustee, all in accordance with and subject to the terms and limitations of
this Security and Article Fourteen of the Indenture. This Guarantee will not
become effective until the Trustee duly executes the certificate of
authentication on this Security.

                                                   HOLLINGER INTERNATIONAL INC.

Attest:                                               By
        ---------------------------                     -----------------------
                                                         Authorized Signatory

<PAGE>   1
                                                                  EXHIBIT 10.01

               HOLLINGER/APC SHARE EXCHANGE AGREEMENT - AMENDMENT

THIS AGREEMENT, made this 18th day of March, 1997,

BETWEEN:             HOLLINGER INC., a corporation continued under the laws of
                     Canada ("HOLLINGER"),

AND:                 HOLLINGER INTERNATIONAL INC., a corporation incorporated
                     under the laws of Delaware ("INTERNATIONAL").

WHEREAS, Hollinger is contemplating a reorganisation of certain shareholdings
and debt obligations of certain of Hollinger's subsidiaries (the "Southam
Consolidation");

WHEREAS, Hollinger and International (formerly "American Publishing Company")
concluded an agreement dated as of July 19, 1995 (the "Hollinger/APC Share
Exchange Agreement") providing for the acquisition by International from
Hollinger of all of Hollinger's indirect interest in Telegraph Group Limited
(formerly The Telegraph plc) in exchange for, among other things, 739,500
Series A Redeemable Convertable Preferred Shares of International
("International Series A Preferred Stock");

WHEREAS, Hollinger and First DT Holdings Inc. ("FDTH") concluded an agreement
dated as of July 19, 1995 (the "HTH/FDTH Share Exchange Agreement") providing
for the acquisition by FDTH from Hollinger of all of Hollinger's right, title
and interest in and to 129,324,500 common shares in the capital of
Hollinger-Telegraph Holdings Inc. beneficially owned by Hollinger (the "HTH
Shares");

WHEREAS, pursuant to various corporate reorganisations, all of FDTH's rights
and obligations under the HTH/FDTH Share Ehchange Agreement have been
transferred to and assumed by Hollinger Canadian Publishing Holdings Inc.
("HCPH");

WHEREAS, Hollinger and International have ongoing rights and obligations under,
and there are provisions relating to the redemption of International Series A
Preferred Stock set forth in, Sections 5(iii) through (vi) of the Hollinger/APC
Share Exchange Agreement which relate, in part, to the delivery to HCPH of
stock certificates representing some or all of the HTH Shares;

WHEREAS, pursuant to the terms of the proposed Southam Consolidation, among
other things, HTH Shares pledged to and registered in the name of the Montreal
Trust Company of Canada (the "Trustee") in its capacity as trustee under the
Trust Indenture dated December 1, 1993 relating to the 7% Southam-Linked
Debentures (the "Debentures") of Hollinger due November 1, 1998 (the "Pledge")
will be released, 5,874,282 common shares in the capital of Southam Inc.
("Southam") will be pledged to the Trustee pursuant to the Pledge (the "Southam
Shares") and HTH will be dissolved;

AND WHEREAS, the parties hereto have determined that it is in their best
interests to amend the HTH/FDTH Share Exchange Agreement as provided for herein
to account for the dissolution of HTH and the Southam Consolidation;

NOW, THEREFORE, in consideration of the premises, the agreements and the
covenants contained herein and other good and valuable consideration, the
receipt and adequacy of which are hereby acknowledged, the parties hereby agree
as follows:


<PAGE>   2

1.       Capitalized terms used herein which are not otherwise defined in this
         Amendment have the same meanings as are ascribed to them in the
         Hollinger/APC Share Exchange Agreement.

2.       The parties' respective rights and obligations under, and the
         provision relating to the redemption of International Series A
         Preferred Stock pursuant to, Sections 5(h)(iii) through (vi) of the
         Hollinger/APC Share Exchange Agreement are amended as provided for
         herein.

3.       Hollinger agrees that, so long as any of the Southam Shares are
         subject to the Pledge, Hollinger shall not:

         (a)      undertake, approve, consent or take any action in furtherance
                  of any plan, scheme, transaction or series of transactions
                  which would result in any breach or violation of, or default
                  under, the Pledge; or

         (b)      redeem, or attempt to cause the redemption of, any
                  International Series A Preferred Stock except in accordance
                  with the terms set forth in Exhibit A attached to the
                  Hollinger/APC Share Exchange Agreement and the provisions of
                  Section 7, below.

4.       So long as any of the Southam Shares are subject to the Pledge,
         International shall use its reasonable commercial efforts not to take
         any action, without the consent of Hollinger, which itself would
         constitute an event of default by Hollinger under the Pledge resulting
         in an acceleration of the maturity of the debentures issued pursuant
         to the Pledge.

5.       Hollinger agrees that:

         (a)      prior to April 1, 1999, Hollinger upon five days' notice to
                  HCPH (with a copy to International) may from time to time
                  deliver to HCPH stock certificates representing some or all
                  of the Southam Shares, and on or before April 1, 1999,
                  Hollinger shall deliver to HCPH stock certificates
                  representing all of the Southam Shares not previously
                  delivered to HCPH; and

         (b)      notwithstanding paragraph 5(a) hereof, HCPH may at any time,
                  on not less than 30 days' written demand, require Hollinger
                  to deliver to HCPH stock certificates representing some or
                  all of the Southam Shares;

         in each case free and clear of the Pledge and all Encumbrances
         whatsoever, together with:

         (c)      a certificate signed on behalf of Hollinger by the
                  Vice-President, Finance and Treasury of Hollinger
                  substantially in the form attached as Exhibit D to the
                  Hollinger/APC Share Exchange Agreements;

         (d)      the legal opinion of counsel to Hollinger substantially in
                  the form attached as Exhibit E to the Hollinger/APC Share
                  Exchange Agreement.

6.       The parties agree that HCPH shall not be required to accept delivery
         of any Southam Shares if HCPH, International or any subsidiary of
         International has notice of any adverse claim or interest with respect
         to the ownership thereof or of any Encumbrance with respect thereto or
         if Hollinger has not otherwise complied with its obligations under
         Section 5 hereof.

         International acknowledges the delivery of: (i) 250,000 common shares
         in the capital of Southam to FDTH on the closing date under the
         HTH/FDTH Share Exchange Agreement, and (ii) an additional 1,270,718
         common shares in the capital of Southam to HCPH in connection with the
         retirement by Hollinger of C$22,238,452.00 principal amount of
         Debentures in December, 1996 and the resulting release by the Trustee
         of 23,000,000 HTH Shares.

7.       If the International Series A Preferred Stock is redeemed in whole or
         in part at the option of Hollinger, the maximum number of shares of
         International Series A Preferred Stock that may be so redeemed shall
         be determined by the formula:

                                       2
<PAGE>   3

                      S
         X = ---------------------  - P
               Applicable Factor

         where:

         X = the maximum number of shares that may be redeemed at such time
             pursuant to this Amendment;

         S = the number of Southam common shares delivered or deemed to have
             been delivered to HCPH on or prior to such redemption date in
             accordance with this Amendment; and

         P = the number of shares of International Series A Preferred Stock
             redeemed prior to such redemption date pursuant to this Amendment.

         For purposes of this Section 7, the "APPLICABLE FACTOR" shall
         initially have a value of 10, which shall be adjusted from time to
         time as follows. If Southam shall pay a dividend, or make a
         distribution, on its common shares in the form of capital stock of the
         same or another corporation (other than a stock dividend payable by
         Southam in lieu of an ordinary course cash dividend), or subdivide its
         outstanding common shares into a greater number of common shares, or
         combine its outstanding common shares into a smaller number of common
         shares, or effect a reorganization or reclassification of its capital
         stock, or amalgamate, enter into an arrangement or consolidation or
         merge with or into another entity (other than an amalgamation,
         arrangement, consolidation or merger which does not result in a
         reclassification or change of the outstanding Southam common shares),
         the value of the Applicable Factor relating to Southam common shares
         deemed to be delivered to HCPH after such action shall be adjusted (to
         the nearest 1/100 of a whole number) so that the maximum number of
         shares of International Series A Preferred Stock that Hollinger or a
         permitted transferee shall be entitlted to redeem pursuant to this
         Section 7 after such action shall be the same as such number of shares
         prior to such action.

         The previous paragraph of this Section 7 shall be applied without
         duplication.

8.       Hollinger agrees to cause any transferee of International Series A
         Preferred Stock (whether by means of a transfer or other disposition
         permitted under Section 11 of Exhibit A attached to the Hollinger/APC
         Share Exchange Agreement or as a result of any merger, consolidation,
         amalgamation, or sale, lease, transfer, assignment or other dispostion
         of all or any significant portion of its properties or assets) to
         agree in writing to be bound by the provisions of this Amendment and
         to provide a copy of that agreement in writing to International.

9.       This Amendment shall be governed by and construed in accordance with
         the laws of the State of Delaware. Each party hereto submits to the
         non-exclusive jurisdiction of the courts of competent jurisdiction of
         the State of Delaware in connection with any dispute arising out of or
         related to this Agreement.

10.      This Amendment may be executed in one or more counterparts none of
         which need contain the signatures of all parties, each of which shall
         be deemed an original, and all of which together shall constitute one
         and the same instrument.

11.      This Agreement constitutes the entire understanding among the parties
         hereto with respect to the amendment of Sections 5(h)(iii) through
         (vi) of the Hollinger/APC Share Exchange Agreement and supersedes all
         prior discussions, negotiations, agreements and understandings (both
         written and oral) between the parties with respect to the subject
         matter set out herein.

12.      As amended hereby, the Hollinger/APC Share Exchange Agreement is
         hereby reaffirmed, approved and confirmed in every respect, and
         remains in full force and effect with such changes as are required to
         be made thereto in order to take account of the Southam Consolidation,
         including the substitution of the Southam Shares for the HTH Shares
         under the Pledge and the dissolution of HTH, and to give effect to the
         amendments to that agreement set forth herein.

                                       3
<PAGE>   4


IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of the
date first written above.

                                    HOLLINGER INC.

                                    By:
                                         -------------------------------------
                                             Charles G. Cowan
                                             Vice-President and Secretary

                                    HOLLINGER INTERNATIONAL INC.

                                    By:
                                         -------------------------------------
                                             Kenneth L. Serota
                                             Vice President-Law and Finance and
                                             Secretary

                                       4

<PAGE>   1
                                                                  EXHIBIT 10.02

                 HTH/FDTH SHARE EXCHANGE AGREEMENT - AMENDMENT

THIS AGREEMENT made this 18th day of March, 1997,

BETWEEN:            HOLLINGER INC., a corporation continued under the laws of
                    Canada ("Hollinger")

AND:                HOLLINGER CANADIAN PUBLISHING HOLDINGS INC., a corporation
                    amalgamated under the laws of New Brunswick ("HCPH").

WHEREAS, Hollinger is contemplating a reorganization of certain shareholdings
and debt obligations of certain of Hollinger's subsidiaries (the "Southam
Consolidation");

WHEREAS, Hollinger and First DT Holdings Inc. ("FDTH") concluded an agreement
dated as of July 19, 1995 (the "HTH/FDTH Share Exchange Agreement") providing
for the acquisition by FDTH from Hollinger of all of Hollinger's right, title
and interest in and to 129,324,500 common shares in the capital of
Hollinger-Telegraph Holdings Inc. beneficially owned by Hollinger (the "HTH
Shares");

WHEREAS, pursuant to various corporate reorganisations, all of FDTH's rights
and obligations under the HTH/FDTH Share Exchange Agreement have been
transferred to and assumed by HCPH;

WHEREAS, Hollinger and HCPH have ongoing rights and obligations under, among
others, Sections 3(a) and (b) and Section 8(c) of the HTH/FDTH Share Exchange
Agreement pertaining to the delivery to HCPH of stock certificates representing
some or all of the HTH Shares;

WHEREAS, the HTH Shares are currently pledged to and registered in the name of
the Montreal Trust Company of Canada (the "Trustee") in its capacity as trustee
under the Trust Indenture dated December 1, 1993 relating to the 7%
Southam-Linked Debentures of Hollinger due November 1, 1998 (the "Pledge");

WHEREAS, pursuant to the terms of the proposed Southam Consolidation, among
other things, the HTH Shares pledged to the Trustee under the Pledge will be
released, 5,874,282 common shares in the capital of Southam Inc. ("Southam")
will be pledged to the Trustee pursuant to the Pledge (the "Southam Shares")
and HTH will be dissolved;

AND WHEREAS, the parties hereto have determined that it is in their best
interests to amend the HTH/FDTH Share Exchange Agreement as provided for herein
to account for the dissolution of HTH and the Southam Consolidation;


<PAGE>   2

NOW, THEREFORE, in consideration of the premises, the agreements and the
covenants contained herein and other good and valuable consideration, the
receipt and adequacy of which are hereby acknowledged, the parties hereby agree
as follows:

1.       Capitalised terms used herein which are not otherwise defined in this
         Amendment have the same meanings as are ascribed to them in the
         HTH/FDTH Share Exchange Agreement.

2.       The parties' respective rights and obligations under Sections 3 and
         8(c) of the HTH/FDTH Share Exchange Agreement are amended as provided
         for herein.

3.       Hollinger covenants that:

         (a)      prior to April 1, 1999, Hollinger upon five days' notice to
                  HCPH may from time to time deliver to HCPH stock certificates
                  representing some or all of the Southam Shares, and on or
                  before April 1, 1999, Hollinger shall deliver to HCPH stock
                  certificates representing all of the Southam Shares not
                  previously delivered to HCPH; and

         (b)      notwithstanding paragraph 3(a) hereof, HCPH may at any time,
                  on not less than 30 days' written demand, require Hollinger
                  to deliver to HCPH stock certificates representing some or
                  all of the Southam Shares;

         in each in each case free and clear of the Pledge and all Encumbrances
         whatsoever, together with:

         (c)      a certificate signed on behalf of Hollinger by the
                  Vice-President, Finance and Treasury of Hollinger
                  substantially in the form attached as Exhibit E to the
                  HTH/FDTH Share Exchange Agreements; and

         (d)      the legal opinion of counsel to Hollinger substantially in
                  the form attached as Exhibit F to the HTH/FDTH Share Exchange
                  Agreement.

4.       The parties agree that HCPH shall not be required to accept delivery
         of any Southam Shares if HCPH has notice of any adverse claim or
         interest with respect to the ownership thereof or of any Encumbrance
         with respect thereto or if Hollinger has not otherwise complied with
         its obligations under Section 3 hereof.

5.       If Hollinger shall not comply with its obligations in Section 3(a) or
         Section 3(b) hereof, Hollinger shall immediately pay to HCPH an
         amount, in Canadian dollars, equal to the greater of:

         (a)      C$119,508,770 or, if some but not all of the Southam Shares
                  have been delivered, the product of C$16.7266 (the "Southam
                  Purchase Price") and the number of Southam Shares which have
                  not been delivered; and

         (b)      the product of the Fair Market Value of a common share of
                  Southam and the number of Southam Shares which have not been
                  delivered.

         For the purposes of this Section 5, the "Fair Market Value" of a
         common share of Southam shall mean an amount per common share of
         Southam equal to the simple average of the closing price for a common
         share of Southam on The Toronto Stock Exchange for each of the
         business days in Toronto, Ontario, on which there was a closing price
         not

                                      -2-
<PAGE>   3

         falling more than 20 business days before the earlier of (A) April 1,
         1999, in the case of a failure by Hollinger to comply with its
         covenant in Section 3(a) and (B) the date on which a demand under
         Section 3(b) is made by HCPH.

6.       Upon payment in full of the amount due from Hollinger under Section 5
         hereof, HCHP shall (i) reconvey to Hollinger HCPH's right, title
         and interest in the Southam Shares not previously delivered by
         Hollinger and (ii) release Hollinger from the covenant in Section 3
         hereof in respect of that number of Southam Shares for which payment
         has been received by HCPH under Section 5 hereof provided further that
         if Southam shall pay a dividend, or make a distribution, on its common
         shares in the form of capital stock of the same or another
         corporation, or subdivide its outstanding common shares into a greater
         number of common shares, or combine its outstanding common shares into
         a smaller number of common shares, or effect a reorganisation or
         reclassification of its capital stock, or amalgamate, enter into an
         arrangement or consolidation or merge with or into another entity
         (other than an amalgamation, arrangement, consolidation or merger
         which does not result in a reclassification or change of the
         outstanding common shares of Southam), reference in this Agreement to
         "Southam Shares" or to the "common shares of Southam" shall include
         any securities distributed with respect to any such shares or into
         which any such shares shall be converted, changed or reclassified or
         for which any such shares shall be exchanged, and the "Southam
         Purchase Price" referred to in Section 5 hereof shall be adjusted, to
         the end that the rights of HCPH under Sections 5 and 6 hereof shall be
         unchanged, as nearly as may be, notwithstanding the occurrence of such
         event and provided further that if the average price of common shares
         of Southam cannot be determined in accordance with the Section 5
         definition of "Fair Market Value", such price shall be the "market
         price" of common shares of Southam otherwise determined in accordance
         with Section 183 of the Regulation to the Securities Act (Ontario).

7.       If any event shall occur which shall require the determination of the
         Fair Market Value of a Southam Share, or an adjustment under Section 6
         hereof, the determination of such value or adjustment shall be made in
         good faith by the directors of HCPH and they shall provide Hollinger
         with a certificate certifying such value or adjustment and providing
         in reasonable detail the event requiring and the manner of computing
         such value or adjustment, as the case may be. If Hollinger shall
         dispute such determination, the question shall be conclusively
         determined by such firm of independent auditors (who shall act as
         experts and not arbitrators) as may be chosen by agreement of
         Hollinger and HCPH from among the six largest firms of auditors in the
         Province of Ontario, Canada ("Eligible Auditors") or, failing such
         agreement, such firm of Eligible Auditors as shall be chosen by the
         Chief Justice of the Supreme Court of Ontario, and its determination
         of such value or adjustment shall be conclusive and binding upon both
         Hollinger and HCPH.

8.       This Amendment shall be governed by and construed in accordance with
         the laws of the Province of Ontario and of Canada applicable therein.
         Each party hereto submits to the non-exclusive jurisdiction of the
         courts of competent jurisdiction of the Province of Ontario in
         connection with any dispute arising out of or related to this
         Agreement.

9.       This Amendment may be executed in one or more counterparts none of
         which need contain the signatures of all parties, each of which shall
         be deemed an original, and all of which together shall constitute one
         and the same instrument.

                                      -3-
<PAGE>   4

10.      This Amendment constitutes the entire understanding among the parties
         hereto with respect to the amendment of Sections 3 and 8(c) of the
         HTH/FDTH Share Exchange Agreement and supersedes all prior
         discussions, negotiations, agreements and understandings (both written
         and oral) between the parties with respect to the subject matter set
         out herein.

11.      As amended hereby, the HTH/FDTH Share Exchange Agreement is hereby
         reaffirmed, approved and confirmed in every respect, and remains in
         full force and effect with such changes as are required to be made
         thereto in order to take account of the Southam Consolidation,
         including the substitution of the Southam Shares for the HTH Shares
         under the Pledge and the dissolution of HTH, and to give effect to the
         amendments to that agreement set forth herein.

IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of the
date first written above.

                                        HOLLINGER INC.

                                        By:
                                            ---------------------------------
                                            Charles G. Cowan
                                            Vice-President and Secretary

                                        HOLLINGER CANADIAN PUBLISHING HOLDINGS
                                        INC.

                                        By:
                                            ---------------------------------
                                            Charles G. Cowan
                                            Vice-President

                                   * * * * *

                                      -4-
<PAGE>   5


Pursuant to the provisions of Section 5(h)(i) of the Telegraph Share Exchange
Agreement dated July 19, 1995 between Hollinger Inc. and Hollinger
International Inc. (formerly American Publishing Company), Hollinger
International Inc. hereby consents to the amendments to the HTH/FDTH Share
Exchange Agreement provided for herein.

DATED as of the date first written above.

                                          HOLLINGER INTERNATIONAL INC.

                                          By:
                                              --------------------------------
                                              Kenneth L. Serota
                                              Vice President - Law and
                                              Finance and Secretary

                                      -5-

<PAGE>   1

                                                             Exhibit 99.01

                                     [logo]

                          HOLLINGER INTERNATIONAL INC.

- -------------------------------------------------------------------------------
                           P R E S S   R E L E A S E
- -------------------------------------------------------------------------------

Contact:
Paul B. Healy, Vice President              Jack A. Boultbee, Vice President and
Corporate Development and                  Chief Financial Officer
  Investor Relations                       Hollinger International Inc.
Hollinger International Inc.               (800) 288-1141
(212) 586-5666                             (416) 363-8721

NEW YORK, MARCH 18, 1997 - HOLLINGER INTERNATIONAL INC. (NYSE: HLR) (the 
"Company") and Hollinger International Publishing Inc. ("Publishing"), a 
wholly-owned subsidiary of the Company, announced that they have closed their 
previously announced underwritten public offering of $260,000,000 principal 
amount of 8-5/8% senior notes due March 15, 2005 ("Senior Note") and 
$290,000,000 principal amount of 9-1/4% senior subordinated notes due March 15, 
2007 (the "Senior Subordinated Notes") issued by Publishing. The Company has 
guaranteed payment of the principal of, premium, if any, and interest on the 
Senior Notes on an unsecured senior basis and the Senior Subordinated Notes on 
an unsecured senior subordinated basis.

The Senior Notes, rated Ba3 by Moody's Investor Service, Inc. and BB+ by 
Standard & Poors, are priced at 99.5% of par. The Senior Subordinated Notes, 
rated B1 by Moody's Investor Service, Inc. and BB- by Standard & Poors, are 
priced at 99.358% of par. The net proceeds to be received by the Company from 
the Offering are estimated at $523.3 million after deducting the underwriting 
discounts and estimated offering expenses to be paid by Publishing. The net 
proceeds of the Offering will be used to repay approximately $354.9 million of 
outstanding bank indebtedness of the Company and its subsidiaries. The balance 
of the total net proceeds, which is expected to be approximately $177.4 
million, will be used to redeem certain outstanding preference shares of 
English subsidiaries of the Company held by third parties (at an aggregate 
redemption price of approximately $124.2 million) at their respective 
redemption dates in May and June 1997 and for general corporate purposes.

Hollinger International Inc., through its subsidiaries and affiliated 
companies, is a leading publisher of English-language newspapers in the United 
States, the United Kingdom, Canada and Israel. Included among the 142 paid 
daily newspapers which the Company owns are the Chicago Sun-Times and The Daily 
Telegraph. These 142 newspapers have a world-wide daily combined circulation of 
4,021,000 (including approximately 2,230,000 attributable to the publications 
of affiliates in which the Company has a minority but influential equity 
interests). In addition, the Company owns or has an interest in 358 non-daily 
newspapers as well as magazines and other publications.


     For more information on Hollinger International Inc., free of charge,
          simply dial 1 800 PRO INFO and enter the company code: "HLR"




© 2022 IncJournal is not affiliated with or endorsed by the U.S. Securities and Exchange Commission