HOLLINGER INTERNATIONAL INC
S-3/A, 1996-11-29
NEWSPAPERS: PUBLISHING OR PUBLISHING & PRINTING
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<PAGE>   1
   
      As filed with the Securities and Exchange Commission on November 29, 1996

                                                     Registration No. 333-04697
===============================================================================
    

                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549

                         ______________________________

                                Amendment No. 1
                                       to
    
                                    FORM S-3
            REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933
                         _____________________________

                          HOLLINGER INTERNATIONAL INC.
             (Exact name of registrant as specified in its charter)

                   DELAWARE                                95-3518892
         (State or other jurisdiction                   (I.R.S. Employer
       of incorporation or organization)               Identification No.)

                            401 NORTH WABASH AVENUE
                            CHICAGO, ILLINOIS 60611
                                 (312) 321-3000

  (Address, including zip code, and telephone number, including area code, of
                   registrant's principal executive offices)
                         ______________________________

   
                               KENNETH L. SEROTA
                        VICE PRESIDENT--LAW AND FINANCE
                                  AND SECRETARY
                          HOLLINGER INTERNATIONAL INC.
                            401 NORTH WABASH AVENUE
                            CHICAGO, ILLINOIS 60611
                                 (312) 321-2299
 (Name, address, including zip code, and telephone number, including area code,
                             of agent for service)
                         ______________________________
    

                                    Copy to:

                               MICHAEL C. MCLEAN
                           KIRKPATRICK & LOCKHART LLP
                              1500 OLIVER BUILDING
                      PITTSBURGH, PENNSYLVANIA 15222-2312
                                 (412) 355-6458

  APPROXIMATE DATE OF COMMENCEMENT OF PROPOSED SALE TO PUBLIC:  From time to
time after this registration statement becomes effective.
  If the only securities being registered on this Form are being offered
pursuant to dividend or interest reinvestment plans, please check the following
box. [ ]
  If any of the securities being registered on this Form are to be offered on a
delayed or continuous basis pursuant to Rule 415 under the Securities Act of
1933, other than securities offered only in connection with dividend or
interest reinvestment plans, check the following box.  [x]
  If this Form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, please check the following
box and list the Securities Act registration statement number of the earlier
effective registration statement for the same offering.[ ]
  If this Form is a post-effective amendment filed pursuant to Rule 462(c)
under the Securities Act, please check the following box and list the
Securities Act registration statement number of the earlier effective
registration statement for the same offering. [ ]
  If delivery of the prospectus is expected to be made pursuant to Rule 434,
please check the following box. [ ]

   
                       ---------------------------------

                   CALCULATION OF ADDITIONAL REGISTRATION FEE

<TABLE>
<CAPTION>
===============================================================================================================
     TITLE OF EACH
       CLASS OF                                PROPOSED MAXIMUM      PROPOSED MAXIMUM
   SECURITIES TO BE        AMOUNT TO BE       OFFERING PRICE PER    AGGREGATE OFFERING     AMOUNT OF ADDITIONAL
      REGISTERED          REGISTERED (1)           SHARE (2)             PRICE (2)         REGISTRATION FEE (1)
- ---------------------------------------------------------------------------------------------------------------
  <S>                    <C>                           <C>                   <C>                   <C>
  Class A Common
  Stock, par value
  $.01 per
  share.....              14,990,000 shares             $10.625              $159,268,750          $48,264
==============================================================================================================
</TABLE>

(1)  This registration statement was originally filed on May 29, 1996 covering
     33,610,754 shares of Class A Common Stock.  A registration fee of $140,528
     was paid in connection with the filing of this registration statement on
     May 29, 1996 with respect to those 33,610,754 shares of Class A Common
     Stock.  An additional 14,990,000 shares of Class A Common Stock are being
     registered hereby and an additional registration fee with respect to such
     14,990,000 shares of Class A Common Stock is being paid.

(2)  Estimated solely for the purpose of calculating the registration fee.
     Computed in accordance with Rule 457(c) on the basis of the average of the
     high and low sales prices for the Class A Common Stock on November 21, 1996
     as reported on the New York Stock Exchange Composite Tape.

                       ---------------------------------
    

  THE REGISTRANT HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE OR
DATES AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT
SHALL FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION
STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTION 8(A) OF
THE SECURITIES ACT OF 1933 OR UNTIL THIS REGISTRATION STATEMENT SHALL BECOME
EFFECTIVE ON SUCH DATE AS THE COMMISSION, ACTING PURSUANT TO SAID SECTION 8(A),
MAY DETERMINE.

===============================================================================
<PAGE>   2
Information contained herein is subject to completion or amendment. A 
registration statement relating to these securities has been filed with the 
Securities and Exchange Commission. These securities may not be sold nor may 
offers to buy be accepted prior to the time the registration statement becomes 
effective. This Prospectus shall not constitute an offer to sell or the 
solicitation of an offer to buy nor shall there be any sale of these securities 
in any State in which such offer, solicitation or sale would be unlawful prior 
to registration or qualification under the securities laws of any such State.

   
                   SUBJECT TO COMPLETION, DATED NOVEMBER 29, 1996
    

                               48,600,754 SHARES

                          HOLLINGER INTERNATIONAL INC.

                              CLASS A COMMON STOCK
                           (PAR VALUE $.01 PER SHARE)
                             _____________________
   
  This prospectus provides for the offering by certain Canadian bank lenders
(the Pledgees, as more fully defined below) of up to an aggregate of 48,600,754
shares (the "Pledged Shares") of the Class A Common Stock, par value $.01 per
share ("Class A Common Stock"), of Hollinger International Inc. (the "Company")
owned by Hollinger Inc. ("Hollinger Inc."), a Canadian corporation and the
parent corporation of the Company, which Pledged Shares may in the future be
owned of record by such Pledgees subject to the terms of the pledge 
arrangements. See "Terms of the Pledge Arrangements" below. 

  Of the Pledged Shares, 33,610,754 of such shares (the "Outstanding Pledged
Shares") were acquired by Hollinger Inc. on October 13, 1995 pursuant to the
terms of a Share Exchange Agreement dated as of July 19, 1995 (the "Share
Exchange Agreement") entered into between Hollinger Inc. and the Company as part
of the corporate reorganization of the international newspaper operations of the
Company and Hollinger Inc. (the "Reorganization").  See "Background--Hollinger
Inc." The remaining 14,990,000 of the Pledged Shares (the "Conversion Pledged
Shares") are the shares of Class A Common Stock into which all of the
outstanding shares of the Company's Class B Common Stock, par value $.01 per
share ("Class B Common Stock," and together with Class A Common Stock, "Common
Stock"), all owned by Hollinger Inc., would be automatically converted into,
pursuant to the terms of the Company's Restated Certificate of Incorporation, as
amended, upon transfer of such shares of Class B Common Stock to the Pledgees.
See "Risk Factors--Control by Hollinger Inc.," "Background--Hollinger Inc.," and
"Background--Pledges." 

  The Outstanding Pledged Shares are being registered under the Securities Act
of 1933, as amended (the "Securities Act"), pursuant to the terms of a
Registration Rights Agreement dated February 29, 1996, as amended on May 24,
1996 (the "Registration Rights Agreement"), described under
"Background--Pledges." The Conversion Pledged Shares are being registered under
the Securities Act pursuant to the terms of agreements among the Company,
Hollinger Inc. and CIBC, including, without limitation, the terms of the CIBC
Letter Agreement dated October 13, 1995, as amended on May 24, 1996 (the "CIBC
Letter Agreement"), as described under "Background--Pledges." 
    
  
  UNTIL SUCH TIME AS THE PLEDGEES HAVE FORECLOSED UPON THE OUTSTANDING PLEDGED
SHARES AND THE CLASS B COMMON STOCK IN ACCORDANCE WITH THE PLEDGES, THE TERMS OF
THE HOLLINGER INC.  INDEBTEDNESS (AS DEFINED BELOW) AND APPLICABLE LAW, AND
RECORD OWNERSHIP OF THE PLEDGED SHARES HAS BEEN TRANSFERRED FROM HOLLINGER INC.
TO THE PLEDGEES, NO PLEDGED SHARES WILL BE SOLD PURSUANT TO THIS PROSPECTUS.  

   
  TERMS OF PLEDGE ARRANGEMENTS.  Pursuant to the terms of the Hypothecation of
Specific Securities dated October 13, 1995 (the "Hypothecation") by Hollinger
Inc. in favor of the Canadian Imperial Bank of Commerce ("CIBC"), Hollinger Inc.
pledged the Outstanding Pledged Shares, the Class B Common Stock and certain
other securities of the Company held by Hollinger Inc. to CIBC as collateral
security for all present and future obligations of Hollinger Inc. and certain
affiliated companies under a demand operating facility and a revolving debt
facility (together, the "CIBC Facility").  See "Background--Pledges."
    

   
  Hollinger Inc. subsequently transferred, subject to the Hypothecation,
beneficial ownership of 7,539,028 of the Outstanding Pledged Shares to 3184081
Canada Limited, a wholly owned subsidiary of Hollinger Inc. ("Canada Limited"),
and registered and beneficial ownership of 15,950,000 of the Outstanding Pledged
Shares and all of the Class B Common Stock to 1159670 Ontario Limited, an
indirect wholly owned subsidiary of Hollinger Inc. ("Ontario Limited"). Canada
Limited has since been continued under the laws of New Brunswick with the name
503264 N.B. Inc. ("N.B. Inc."). As used in this Prospectus, unless the context
otherwise requires, "Hollinger Inc." refers to Hollinger Inc. and its direct and
indirect wholly owned subsidiaries, including but not limited to N.B. Inc.,
(formerly named 3184081 Canada Limited) and Ontario Limited.
    

   
  Pursuant to the terms of a Securities Pledge Agreement dated February 29, 1996
(the "Securities Pledge Agreement"), Ontario Limited has pledged the 15,950,000
Outstanding Pledged Shares held by it (the "Ontario Limited Shares") as
collateral security for its obligations under a Cdn.$90,000,000 Credit Agreement
dated as of February 29, 1996 (as amended, supplemented, restated or replaced
from time to time, the "Ontario Limited Credit Agreement") among Ontario
Limited, Hollinger Inc., CIBC, as agent for the Lenders, and CIBC, The
Toronto-Dominion Bank and The Bank of Nova Scotia (collectively, the "Lenders").
As used in this Prospectus, unless the context otherwise requires, "Pledgees"
refers to (i) CIBC as agent under the Ontario Limited Credit Agreement and the
Securities Pledge Agreement, (ii) CIBC in its own capacity under the
Hypothecation and the CIBC Facility and (iii) CIBC as agent under the N.B. Inc.
Guarantees (as defined below), the N.B. Inc. Securities Pledge Agreements (as
defined below), the Ontario Limited Guarantees (as defined below) and the
Ontario Limited Securities Pledge Agreements (as defined below).
    

   
  Pursuant to the terms of a Securities Pledge Agreement dated May 24, 1996, a
second Securities Pledge Agreement dated as of July 17, 1996 to reflect the
syndication on July 17, 1996 of the Southam Facility (as defined below) equally
between CIBC and The Bank of Nova Scotia and a third Securities Pledge Agreement
dated as of November 15, 1996 to reflect the continuance of Canada Limited in
New Brunswick as N.B. Inc. (the "N.B. Inc. Securities Pledge Agreements"), N.B.
Inc. has pledged the 7,539,028 Outstanding Pledged Shares held by it (the "N.B.
Inc. Shares") as collateral security for its obligations to CIBC and The Bank of
Nova Scotia under a Guarantee of the Southam Facility dated as of May 24, 1996,
a second Guarantee dated as of July 17, 1996 to reflect the syndication of the
Southam Facility equally between CIBC and The Bank of Nova Scotia and a third
Guarantee of the Southam Facility dated as of November 15, 1996 to reflect the
continuance of Canada Limited in New Brunswick as N.B. Inc. (the "N.B. Inc.
Guarantees"). The maturity date of the Southam Facility has been extended to
February 28, 1997 or earlier upon the occurrence of certain events (as more 
fully described below). See "Background--Southam."
    

   
  Pursuant to the terms of a Securities Pledge Agreement dated as of May 24,
1996, and a second Securities Pledge Agreement dated as of July 17, 1996 to
reflect the syndication on July 17, 1996 of the Southam Facility equally between
CIBC and The Bank of Nova Scotia (the "Ontario Limited Securities Pledge
Agreements"), Ontario Limited has pledged the Class B Common Stock as collateral
security for its obligations to CIBC and The Bank of Nova Scotia under a
Guarantee of the Southam Facility dated as of May 24, 1996, and a second
Guarantee dated as of July 17, 1996 to reflect the syndication of the Southam
Facility equally between CIBC and The Bank of Nova Scotia (the "Ontario Limited
Guarantees"). The maturity date of the Southam Facility has been extended to
February 28, 1997 or earlier upon the occurrence of certain events (as more 
fully described below). See "Background--Southam."
    

     
  As used in this Prospectus, the "Southam Facility" means the Cdn.$300 million
bank credit facility established pursuant to a credit commitment agreement
titled "Summary of Terms and Conditions" dated May 24, 1996 among the Company,
Hollinger Inc. and CIBC, as supplemented by an assignment agreement dated as of
July 17, 1996 among the Company, CIBC and The Bank of Nova Scotia, as replaced
by a credit agreement dated as of November 15, 1996 among CIBC as agent, CIBC,
The Bank of Nova Scotia, the Company, Hollinger Inc., Ontario Limited, N.B.
Inc., 3230767 Canada Limited and Hollinger Eastern Publishing Inc. as amended,
supplemented, restated or replaced from time to time. 
    
<PAGE>   3
   
  In addition to the Pledges, Hollinger Inc. may pledge the Outstanding Pledged
Shares and the Class B Common Stock, subject to the Pledges and/or upon release
from one or more of the Pledges, to secure other present or future indebtedness
of Hollinger Inc. ("Other Indebtedness") to one or more of the Pledgees or to
parties other than the Pledgees.  As used in this Prospectus, unless the context
otherwise requires: (i) "Pledges" refers to the Pledges, any additional pledges
of the Pledged Shares to the Pledgees or other parties as described above; (ii)
"Hollinger Inc. Indebtedness" refers to the CIBC Facility, the Ontario Limited
Credit Agreement, the N.B. Inc. Guarantees, the Ontario Limited Guarantees and
Other Indebtedness, so long as such indebtedness continues to be collateralized
by a pledge of the Pledged Securities ("See Background--Pledges"); and (iii)
"Pledgees" refers to both the Pledgees and any additional pledgees. 
    

  MANNER OF SALE OF PLEDGED SHARES.  Upon a default by Hollinger Inc. under
Hollinger Inc. Indebtedness and a foreclosure upon the Outstanding Pledged
Shares and/or the Class B Common Stock by one or more Pledgees in accordance
with the Pledges, the terms of the Hollinger Inc. Indebtedness and applicable
law (a "Foreclosure"), such resulting Pledged Shares may be offered or sold by
or for the account of the Pledgees, or their transferees, from time to time or
at one time, at prices and on terms to be determined at the time of sale, to
purchasers directly or by or through brokers, dealers, underwriters or agents
who may receive compensation in the form of discounts, commissions or
concessions.  The Pledgees, or their transferees, and any brokers, dealers,
underwriters or agents that participate in the distribution of the Pledged
Shares may be deemed to be "underwriters" within the meaning of the Securities
Act and any discounts, concessions and commissions received by any such broker,
dealer, underwriter or agent may be deemed to be underwriting commissions or
discounts under the Securities Act.  The Company will not receive any of the
proceeds from any sale of the Pledged Shares that may be offered hereby.  See
"Use of Proceeds," "Background -- Pledges" and "Plan of Distribution."

   
  The Class A Common Stock is listed on the New York Stock Exchange (the "NYSE")
and traded under the symbol "HLR."  The last sale price of the Class A Common
Stock as reported on the NYSE Composite Tape on November 27, 1996 was $11.00 per
share.
    
                             _____________________

   
  SEE "RISK FACTORS" BEGINNING ON PAGE 4 FOR CERTAIN CONSIDERATIONS RELEVANT TO
AN INVESTMENT IN THE CLASS A COMMON STOCK.
    

                             _____________________

   THESE SECURITIES HAVE NOT BEEN APPROVED OR DISAPPROVED BY THE SECURITIES
    AND EXCHANGE COMMISSION OR ANY STATE SECURITIES COMMISSION NOR HAS THE
    SECURITIES AND EXCHANGE COMMISSION OR ANY STATE SECURITIES COMMISSION
         PASSED UPON THE ACCURACY OR ADEQUACY OF THIS PROSPECTUS. ANY
            REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENSE.

                             _____________________

   

             The date of this Prospectus is [date].

    
<PAGE>   4
                             AVAILABLE INFORMATION

   
  The Company is subject to the informational requirements of the Securities
Exchange Act of 1934, as amended (the "Exchange Act"), and in accordance
therewith files periodic reports, proxy solicitation materials and other
information with the Securities and Exchange Commission (the "Commission"). Such
reports, proxy solicitation materials and other information can be inspected and
copied at the public reference facilities maintained by the Commission at
Judiciary Plaza, 450 Fifth Street, N.W., Washington, D.C. 20549, and at the
Commission's Regional Offices located at Seven World Trade Center, Suite 1300,
New York, New York 10048 and 500 West Madison Street, Suite 1400, Chicago,
Illinois 60661.  Copies of such materials can be obtained from the Public
Reference Section of the Commission, 450 Fifth Street, N.W., Washington, D.C.
20549, at prescribed rates.  The Commission maintains a Web site that contains
reports, proxy and information statements and other information regarding
registrants that file electronically with the Commission. The address of the
Commission's Web site is http://www.sec.gov. The Class A Common Stock is listed
on the NYSE.  Such reports, proxy solicitation materials and other information
can also be inspected and copied at the NYSE at 20 Broad Street, New York, New
York 10005.
    

  The Company has filed with the Commission a registration statement on Form
S-3 (herein, together with all amendments and exhibits, referred to as the
"Registration Statement") under the Securities Act with respect to the offering
made hereby.  This Prospectus does not contain all of the information set forth
in the Registration Statement, certain portions of which are omitted in
accordance with the rules and regulations of the Commission.  Such additional
information may be obtained from the Commission's principal office in
Washington, D.C. as set forth above.  For further information, reference is
hereby made to the Registration Statement, including the exhibits filed as a
part thereof or otherwise incorporated herein.  Statements made in this
Prospectus as to the contents of any documents referred to are not necessarily
complete, and in each instance reference is made to such exhibit for a more
complete description and each such statement is modified in its entirety by
such reference.

                INCORPORATION OF CERTAIN DOCUMENTS BY REFERENCE

  The following documents filed by the Company with the Commission (File No.
0-24004) pursuant to the Exchange Act are incorporated herein by reference:

  1.  the Company's Annual Report on Form 10-K for the year ended December 31,
      1995;

   
  2.  the Company's Quarterly Report on Form 10-Q for the quarters ended March
      31, 1996, June 30, 1996 and September 30, 1996;
    

  3.  the Company's Current Reports on Form 8-K dated February 7, 1996, 
      April 24, 1996 and August 7, 1996; and

  4.  the description of the Class A Common Stock contained in the Company's
      Registration Statement on Form 8-A, as the same may be amended.

  All reports and other documents filed by the Company pursuant to Section
13(a), 13(c), 14 or 15(d) of the Exchange Act subsequent to the date of this
Prospectus and prior to the termination of the offering made by this Prospectus
shall be deemed to be incorporated by reference herein.  Any statement
contained herein or in a document incorporated or deemed to be incorporated by
reference herein shall be deemed to be modified or superseded for purposes of
this Prospectus to the extent that a statement contained herein or in any other
subsequently filed document which also is incorporated or deemed to be
incorporated by reference herein modifies or supersedes such statement.  Any
such statement so modified or superseded shall not be deemed, except as
modified or superseded, to constitute a part of this Prospectus.

  The Company will provide without charge to each person to whom a copy of this
Prospectus is delivered, upon the written or oral request of such person, a
copy of any or all of the documents that are incorporated herein by reference,
other than exhibits to such information (unless such exhibits are specifically
incorporated by reference into such documents).  Requests should be directed to
Hollinger International Inc., 401 North Wabash Avenue, Chicago, Illinois 60611,
Attention:  Secretary, telephone number (312) 321-2299.

                                       2
<PAGE>   5
                                  THE COMPANY

   
  The Company, through subsidiaries and affiliated companies, is a leading
publisher of English-language newspapers in the United States, the United
Kingdom, Australia, Canada and Israel.  Included among the 145 paid daily
newspapers which the Company owns or has an interest are the Chicago Sun-Times
and The Daily Telegraph.  These 145 newspapers have a world-wide daily combined
circulation of approximately 4,530,000 (including 2,230,000 attributable to the
publications in which the Company has a minority equity interest).  In addition,
the Company owns or has an interest in 405 non-daily newspapers as well as
magazines and other publications.  The Company's strategy is to achieve growth
through acquisitions and improvements in the cash flow and profitability of its
newspapers, principally through cost reductions.  Since the Company's formation
in 1986, the existing senior management team has acquired over 404 newspapers
and related publications in the United States, Telegraph Group Limited in the
United Kingdom and the Jerusalem Post in Israel, and has made significant
investments in newspapers in Australia and Canada. 
    

  The Company was incorporated in the State of Delaware on December 28, 1990
and its executive offices are located at 401 North Wabash Avenue, Chicago,
Illinois 60611, telephone number (312) 321-3000.  References herein to the
Company refer to Hollinger International Inc. and its subsidiaries, unless the
context requires otherwise.


                                       3
<PAGE>   6

                                  RISK FACTORS

   
  Prospective investors should carefully consider the following factors
relating to the business of the Company, together with the other factors,
information and financial data included or incorporated by reference in this
Prospectus, or in any Prospectus Supplement, before acquiring any of the 
Pledged Shares that may be offered hereby.
    

INTERNATIONAL HOLDING COMPANY STRUCTURE

   
  The Company is an international holding company and its assets consist solely
of investments in its subsidiaries and affiliated companies. As a result, the
Company's ability to meet its future financial obligations is dependent upon the
availability of cash flows from its United States and foreign subsidiaries and
affiliated companies (subject to applicable withholding taxes) through
dividends, intercompany advances, management fees and other payments. Similarly,
the Company's ability to pay dividends on its Common Stock, its preferred stock
or its Preferred Redeemable Increased Dividend Equity Security PRIDES(SM)
("PRIDES") will be limited as a result of its dependence upon the distribution
of earnings of its subsidiaries and affiliated companies. The Company's
subsidiaries and affiliated companies are under no obligation to pay dividends
and, in the case of Hollinger International Publishing Inc., a Delaware
corporation and a wholly owned subsidiary of the Company through which the
Company holds all the shares of its other subsidiaries ("Publishing"), and its
principal United States and foreign subsidiaries, are subject to statutory
restrictions and restrictions in debt agreements that may limit their ability to
pay dividends. See "Restrictions in Debt Agreements" below. Substantially all of
the shares of the subsidiaries of the Company have been pledged to lenders of
the Company. The Company's and Hollinger Inc.'s combined interests in Southam
Inc. ("Southam") are pledged to lenders of the Company and Hollinger Inc. The
Company's right to participate in the distribution of assets of any subsidiary
or affiliated company upon its liquidation or reorganization will be subject to
the prior claims of the creditors of such subsidiary or affiliated company,
including trade creditors, except to the extent that the Company may itself be a
creditor with recognized claims against such subsidiary or affiliated company.
    
 
GROWTH STRATEGY
 
   
  The Company's strategy is to achieve growth through acquisitions and
improvements in the cash flow and profitability of its newspapers, principally
through cost reductions. The Company's growth strategy presents risks inherent
in assessing the value, strengths and weaknesses of acquisition opportunities,
in evaluating the costs of new growth opportunities at existing operations and
in managing the numerous publications it has acquired and improving their
operating efficiency. While the Company believes that there are significant
numbers of potential acquisition candidates, the Company is unable to predict
the number or timing of future acquisition opportunities or whether any such
opportunities will meet the Company's acquisition criteria or, if such
acquisitions occur, whether the Company will be able to achieve improved
operating efficiencies or enhanced profitability. Accordingly, there can be no
assurance that the Company will continue to experience the rate of growth that
it has had in the past. In addition, the Company's acquisition strategy is
largely dependent on the Company's ability to obtain additional debt or other
financing on acceptable terms. See "Restrictions in Debt Agreements", "Other
Restrictive Arrangements" and "Substantial Leverage" below.
    

   
SUBSTANTIAL LEVERAGE
 
  The Company and its subsidiaries have substantial leverage and have
substantial debt service obligations, as well as obligations under the Series A
Convertible Redeemable Preferred Stock, par value $.01 per share ("Series A
Preferred Stock") of the Company (which is convertible into shares of Class A
Common Stock), the PRIDES, which each represent one-half share of Series B
Convertible Preferred Stock, par value $.01 per share of the Company ("Series B
Preferred Stock") (which is convertible into shares of Class A Common Stock),
and the redeemable preferred shares of its subsidiaries. The instruments
governing the terms of the principal indebtedness and redeemable preferred stock
of the Company and its principal United States and foreign subsidiaries contain
various covenants, events of default and other provisions that could limit the
financial flexibility of the Company, including the payment of dividends with
respect to outstanding Common Stock and Preferred Stock and the implementation
of its growth strategy. A substantial portion of the obligations of the Company
and its subsidiaries become due within six months (unless refinanced or
extended), including the Company's Southam Facility which is secured by
Hollinger Inc.'s guarantees pursuant to which the N.B. Inc. Shares and the
Shares of Class B Common Stock, among other Securities, have been pledged. As of
September 30, 1996, the Company's total short-term debt was $587.3 million. At
September 30, 1996, the amount outstanding under the Southam Facility was
approximately $155.9 million. The Southam Facility is guaranteed by Hollinger
Inc. and matures on February 28, 1997 or earlier upon the occurrence of certian
events, namely (i) one banking day prior to the maturity date of the Amended and
Restated Credit Agreement dated May 30, 1996, as amended (the "Publishing Credit
Facility") among Publishing and certain lenders, which is currently scheduled to
mature on February 7, 1997; (ii) one banking day prior to the maturity date of
the Credit Agreement dated May 30, 1996, as amended (the "First DT Credit
Agreement") among FDTH and certian lenders, which is currently scheduled to
mature on February 7, 1997; or (iii) the closing date of any equity issue, debt
financing, public or private placement or high yield financing completed by the
Company or any of its subsidiaries or by Hollinger Inc. or certain of its
Canadian subsidiaries. All net proceeds of any financing referred to in (iii)
above, must be applied as a permanent prepayment of the Southam Facility. Unless
extended, the First DT Credit Agreement matures on February 7, 1997, under which
$306.9 million is currently outstanding, and the Publishing Credit Facility also
matures on February 7, 1997, under which $130.0 million is currently
outstanding. 
    

   
  The substantial leveraged position of the Company could make it vulnerable to
a downturn in the operating performance of its business or a downturn in
economic conditions and could have the following consequences: (i) the Company's
ability to obtain additional debt financing on attractive terms for corporate or
other purposes, including the financing of future acquisitions, may be limited;
(ii) the funds available to the Company for its operations and for dividends on
its Common Stock and its PRIDES may be reduced as a result of the use of an
increased portion of available cash flow to pay debt service; (iii) certain of
the Company's borrowings are and will continue to be at variable rates of
interest, which could result in higher interest expenses in the event of
increases in interest rates; and (iv) such indebtedness and outstanding
redeemable preferred stock contain financial and restrictive covenants
(including certain change of control provisions related to Hollinger Inc.'s
control of the Company discussed below), the failure to comply with which may
result in an event of default which, if not cured or waived, could have a
material adverse effect on the Company. See "Restrictions in Debt Agreements"
and "Other Restrictive Arrangements" below.
    

  In addition, the instruments governing the terms of the principal
indebtedness of the Company and its principal United States and foreign
subsidiaries contain customary events of default, including, without
limitation, certain "change of control" provisions.  Generally, a "change of
control" is defined in the instruments governing the terms of the principal
indebtedness of the Company and its principal United States and foreign
subsidiaries to include, without limitation, any person other than Conrad M.
Black beneficially owning voting stock representing more than 50% of the total
voting power of the Company.  A Foreclosure could result in the triggering of
these "change of control" event of default provisions.  See "Risk
Factors--Control by Hollinger Inc." and "Background--Pledges."

RESTRICTIONS IN DEBT AGREEMENTS
 
   
  The instruments governing the terms of the principal indebtedness and
redeemable preferred stock of the Company and its principal subsidiaries contain
various covenants, events of default and other provisions that could limit the
flexibility of the Company. Such provisions include requirements to maintain
compliance with certain financial ratios, limitations on the ability of the
Company and certain of its subsidiaries to make acquisitions or investments
without the consent of the lenders and limitations on the ability of the
Company's principal subsidiaries to incur indebtedness, make dividend and other
payments to the Company and take
    

                                       4
<PAGE>   7
 
   
certain other actions. In addition, such indebtedness is secured by, among other
things, pledges of the stock of the Company's principal subsidiaries.
    
 
   
  The amount available for the payment of dividends by the Company at any time
is a function of (i) restrictions in agreements binding the Company limiting its
ability to pay dividends and (ii) restrictions in agreements binding the
Company's subsidiaries limiting their ability to pay dividends to the Company.
The Southam Facility, among other things, limits dividends on the Company's
Class A Common Stock and Class B Common Stock to their current levels and on the
Company's Series A Preferred Stock and PRIDES in accordance with their existing
terms. In addition, certain agreements binding subsidiaries of the Company,
including Publishing, American Publishing (1991) Inc. and FDTH, contain
provisions that limit their respective abilities to pay dividends to the
Company.
    
 
OTHER RESTRICTIVE ARRANGEMENTS
 
   
  The Company's equity interests in The Telegraph and Fairfax are currently held
through intermediate English holding companies, DT Holdings Limited ("DTH") and
First DT Holdings Limited ("FDTH"), and the Company's and Hollinger Inc.'s
combined equity interests in Southam are currently held through a new Canadian
holding Company and The Telegraph. DTH and FDTH have outstanding preference
shares held by persons other than the Company and its affiliates (the "DTH
Preference Shares," the "FDTH Preference Shares," and, collectively, the "DTH
and FDTH Preference Shares") which require the payment of quarterly dividends
with a current effective dividend cost of 5.5% per annum (after giving effect to
certain interest rate and currency exchange agreements). In addition, DTH owns
all 165,000,000 non-cumulative redeemable preference shares of L1 per share
issued by FDTH and 23,801,420 non-cumulative redeemable preference shares of
Cdn.$1 per share issued by FDTH which were transferred by Hollinger Inc. to DTH
pursuant to the HTH/FDTH Share Exchange Agreement dated July 19, 1995 (the
"HTH/FDTH Share Exchange Agreement"). All of the outstanding DTH Preference
Shares are held by unrelated parties and a portion of the outstanding FDTH
Preference Shares are held by unrelated third parties, with an aggregate
redemption price of approximately $221.2 million.
    

   
  On December 29, 1995, DTH transferred all outstanding FDTH Preference Shares
which it then held (with an aggregate redemption amount of Cdn.$140 million) to
a wholly owned English subsidiary ("Argsub") of Argus Corporation Limited
("Argus"), a Canadian corporation all the voting stock of which is indirectly
owned or controlled by Mr. Black (See "Risk Factors--Control by Hollinger
Inc."), in exchange for newly issued preference shares (with an aggregate
redemption amount of Cdn.$140 million) of such English subsidiary. Such
preference shares have terms substantially identical to those of the FDTH
Preference Shares and constitute the entire issued and outstanding preference
share capital of such subsidiary. The transaction was structured to eliminate
economic gain or loss to Argus and Argsub on the preference shares. Argus owns
directly and indirectly approximately 31.3% of the common shares of Hollinger
Inc. 

  On September 30, 1996, FDTH issued 600 Fourth Preference Shares, Series 1996
of FDTH (with an aggregate redemption amount of $300 million) to Argsub in
exchange for 600 newly issued Second Preference Shares, Series 1996 of Argsub
(with an aggregate redemption amount of $300 million).  The newly issued Second
Preference Shares, Series 1996 of Argsub have terms substantially identical to
those of the newly issued Fourth Preference Shares Series 1996 of FDTH for which
they were exchanged and constitute, together with the preference shares issued
by Argsub to DTH on December 29, 1995, the entire issued and outstanding
preference share capital of Argsub.  The preference shares issued by Argsub on
December 29, 1995 differ from the newly issued Second Preference Shares, Series
1996 in that the former are redeemable by the holder while the latter are not
and the latter carry a fixed, rather than a variable, dividend rate.  These
transactions were structured to eliminate economic gain or loss to Argus and
Argsub on the preference shares. The issuance of additional preference shares 
by FDTH to Argsub may occur prior to the redemption or repayment of outstanding 
FDTH preference shares. Argsub owns directly and indirectly approximately 31.3% 
of the common shares of Hollinger Inc.

  The DTH Preference Shares are redeemable at the option of the holder at any
time on four days' notice at a redemption price discounted in accordance with an
agreed formula, and the FDTH Preference Shares and the DTH Preference Shares are
redeemable by the issuer or the holders on the fifth anniversary of their
issuance (May or June 1997, respectively), each five year anniversary thereafter
and at other prescribed times and in prescribed circumstances, including where
the consolidated debt of Hollinger Inc. is more than two
     

                                       5
<PAGE>   8
 
   
times its consolidated equity (the "Debt to Equity Ratio"). The Debt to Equity
Ratio is affected by, among other things, Hollinger Inc.'s consolidated results
of operations, as well as changes in the levels of consolidated debt of
Hollinger Inc. and its subsidiaries, including the Company. Accordingly, there
can be no assurance that Hollinger Inc. will be in compliance with the Debt to
Equity Ratio as of any future date. The Company has been informed by Hollinger
Inc. that, based on preliminary calculations as of September 30, 1996, Hollinger
Inc. believes that it is in Compliance with the Debt to Equity Ratio at
September 30, 1996. There can be no assurance, however, that Hollinger Inc. will
remain in compliance with the Debt to Equity Ratio or that in the event of
non-compliance that holders of the DTH or FDTH Preference Shares will not
exercise their retraction rights against DTH or FDTH or Hollinger Inc. pursuant
to contractual arrangements with the holders under which Hollinger Inc. has
agreed to purchase the DTH and FDTH Preference Shares. In the event Hollinger
Inc. is required to purchase any DTH and FDTH Preference Shares under these
circumstances, Hollinger Inc. shall have the right, following written notice, to
require the Company to purchase such shares at the then retraction price. 
    
 
   
  Hollinger Inc. has indemnified the holders of the DTH and FDTH Preference
Shares and agreed to purchase these preference shares if DTH or FDTH fails to
pay the full amount of dividends or redemption prices on such shares and in
certain other events. The Company has entered into an agreement to compensate
Hollinger Inc. for any payments made by Hollinger Inc. to holders of the DTH and
FDTH Preference Shares and to purchase any DTH and FDTH Preference Shares which
Hollinger Inc. is required to purchase in accordance with the terms thereof. The
timing of any such payments by the Company to Hollinger Inc. will be determined
by Hollinger Inc.
    
 
   
  Substantially all of the Company's indirect 19.5% equity interest in Southam
is currenlty held through Hollinger-Telegraph Holdings Inc. ("HTH") (18.9%), a
Canadian corporation which is jointly owned by FDTH and The Telegraph. The
balance of the Company's indirect interest in Southam is owned directly by FDTH
(0.3%) and The Telegraph (0.3%). The 21.5% equity interest in Southam formerly
held by Power Corporation is held by Hollinger Eastern Publishing Inc.
("Hollinger Eastern"), a Canadian corporation in which the Company holds all
outstanding non-voting common shares, one-half of the outstanding voting
preference shares and Cdn.$30 million in non-voting preference shares, and
Hollinger Inc. holds the remaining one-half of the voting preference shares. The
shares representing FDTH's one-half interest in HTH are subject to a pledge
securing certain Hollinger Inc. debentures in the principal amount of Cdn.$125
million due November 1, 1998 (the "Southam-Linked Debentures"). In the event
Hollinger Inc. does not deliver clear legal title to such HTH shares on or prior
to April 1, 1999, or upon demand by FDTH, approximately one-half of the
Company's indirect equity interest in Southam would be subject to the rights of
the holders of the Southam-Linked Debentures. For information concerning a
planned reorganization of the interests of the Company and Hollinger Inc. in
Southam, see "Background--Southam."
    

                                       6
<PAGE>   9
 
   
CONTROL BY HOLLINGER INC.

  Hollinger Inc. owns the Outstanding Pledged Shares and all of the Class B
Common Stock, constituting approximately 57.4% of the combined equity interest
in the Company and approximately 83.6% of the combined voting power of the
outstanding Common Stock (without giving effect to the issuance of shares of
Class A Common Stock upon conversion of the Series A Preferred Stock or in
connection with the PRIDES), and 46.1% and 76.4%, respectively, upon the 
issuance of up to approximately 20,700,000 shares of Class A Common Stock in 
connection with the PRIDES (without giving effect to the issuance of shares of 
Class A Common Stock upon conversion of the Series A Preferred Stock).
    


                                       7
<PAGE>   10
   
  As a result, Hollinger Inc. is in a position to control the outcome of
substantially all actions requiring stockholder approval, including the election
of the entire Board of Directors. The retention by Hollinger Inc. of securities
representing more than 50% of the voting power of the Company's outstanding
Common Stock will preclude any acquisition of control of the Company not favored
by Hollinger Inc.  Subject to the fiduciary responsibilities of the directors of
the Company to all stockholders and the terms of agreements defining the ongoing
relationships between Hollinger Inc. and the Company, Hollinger Inc., through
its ability to control the outcome of any election of directors, will continue
to be able to direct management policy, strategic direction and financial
decisions of the Company.  Hollinger Inc. is effectively controlled by Mr.
Conrad M. Black, Chairman of the Board and Chief Executive Officer of Hollinger
Inc. and the Company, through his direct and indirect ownership and control of
Hollinger Inc.'s securities. Mr. Black has advised the Company that Hollinger
Inc. does not presently intend to reduce its voting power in the Company's
outstanding Common Stock to less than 50%.  Furthermore, Mr. Black has advised
the Company that he does not presently intend to reduce his voting control over
Hollinger Inc. such that a third party would be able to exercise effective
control over it. 
    

   
  If the Pledgees were to effect a Foreclosure upon all of the Outstanding
Pledged Shares (excluding the shares of Class B Common Stock), Hollinger Inc.
would continue to own 17.7% of the combined equity interest and 68.3% of the
combined voting power of the outstanding Common Stock of the Company (without
giving effect to the issuance of shares of Class A Common Stock upon conversion
of the Series A Preferred Stock or in connection with the PRIDES).  As a result,
Hollinger Inc. would continue to be able to control the outcome of any election
of directors and to direct management policy, strategic direction and financial
decisions of the Company. Also, a default by Ontario Limited under the Credit
Agreement and a foreclosure upon only the Ontario Limited Shares in accordance
with the Securities Pledge Agreement, the terms of the Ontario Limited Credit
Agreement and applicable law is not expected to result in a change of control of
the Company; provided, however, that CIBC may determine that such a default
constitutes a default under the CIBC Facility, the Southam Facility and the
related Ontario Limited Guarantees and N.B. Inc. Guarantees or Other
Indebtedness, which in turn could result in a change of control of the Company. 

  If the Company were to be in default under the Southam Facility, a default by
N.B. Inc. under the N.B. Inc. Guarantees and a foreclosure upon only the N.B.
Inc. Shares in accordance with the N.B. Inc. Pledge Agreements, the N.B. Inc.
Guarantees and applicable law is not expected to result in a change of control
of the Company; provided, however, that CIBC may determine, in its discretion,
that a default under the Southam Facility and/or the N.B. Inc. Guarantees
constitutes a default under the CIBC Facility, the Southam Facility and the
related Ontario Limited Guarantee or Other Indebtedness, which in turn could
result in a change of control of the Company.

  However, if the Company were to be in default under the Southam Facility, a
default by Ontario Limited under the Ontario Limited Guarantees and a
foreclosure upon the Class B Common Stock in accordance with the Ontario Limited
Securities Agreements, the Ontario Limited Guarantees and applicable law could
result in a change of control of the Company.  Such a foreclosure would trigger
the change of control event of default provisions contained in the instruments
governing the terms of the principal indebtedness of the Company and its
principal United States and foreign subsidiaries.  See "Risk
Factors--Substantial Leverage."

  A default by Hollinger Inc. under the CIBC Facility and a foreclosure upon the
Outstanding Pledged Shares, the Class B Common Stock and the other securities of
Company owned by Hollinger Inc. that are subject to the Hypothecation, in
accordance with the Hypothecation, the terms of the CIBC Facility and applicable
law could result in a change of control of the Company. Such a foreclosure would
trigger the change of control event of default provisions contained in the
instruments governing the terms of the principal indebtedness of the Company and
its principal United States and foreign subsidiaries.  See "Risk
Factors--Substantial Leverage."
    

                                       8
<PAGE>   11
DIVIDEND POLICY
 
   
  The Company has paid quarterly dividends on its Common Stock since the third
quarter of 1994. The quarterly dividend was previously $0.025 per share of
Common Stock and was increased to $0.10 per share of Common Stock in the first
quarter of 1996. As an international holding company, the Company's ability to
declare and pay dividends in the future with respect to its Common Stock, its
Series A Preferred Stock and the PRIDES will be dependent, among other factors,
upon its results of operations, financial condition and cash requirements, the
ability of its United States and foreign subsidiaries to pay dividends and make
other payments to the Company under applicable law and subject to restrictions
contained in existing and future loan agreements, the prior payment of dividends
to holders of PRIDES and Series A Preferred Stock, the preference share terms
and other financing obligations to third parties relating to such United States
or foreign subsidiaries or the Company, as well as foreign and United States tax
liabilities with respect to dividends and other payments from those entities.
See "International Holding Company Structure," "Restrictions in Debt Agreements"
and "Other Restrictive Agreements" above. 
    

                                       9

<PAGE>   12
 
POTENTIAL CONFLICTS OF INTEREST
 
  The Company and Hollinger Inc. have entered into agreements for the purpose of
defining their ongoing relationships, including a Services Agreement (to which
Publishing is also a party) and a Business Opportunities Agreement. These
agreements were developed in the context of a parent-subsidiary relationship
and, therefore, were not the result of arms-length negotiations between
independent parties. 

                                       10
<PAGE>   13
 
   
  Services Agreement.  The Services Agreement governs the provision by Hollinger
Inc. of certain advisory, consultative, procurement and administrative services
to the Company. The Services Agreement also contemplates that the Company may
provide services to Hollinger Inc. The services to be provided pursuant to the
Services Agreement include, among other things, strategic advice and planning
and financial services (including advice and assistance with respect to
acquisitions); assistance in operational matters; participation in group
insurance programs; and guarantees of indebtedness of the Company or other forms
of credit enhancements. The party receiving the services will reimburse the
party rendering the services for its allocable costs in providing those
services, as determined by the provider thereof or, in the case of a guarantee,
for an amount equal to the cost to the party of obtaining a bank letter of
credit in the amount of such guarantee. The party allocating its costs will
consider the salaries or other compensation payable to directors, officers and
employees actually providing services, out-of-pocket costs, the cost of
obtaining substantially equivalent services from a third party and other factors
as may be deemed appropriate. The Services Agreement will be in effect for so
long as Hollinger Inc. holds at least 50% of the voting power of the Company,
subject to termination by either party under certain specified circumstances.
Payments made pursuant to the Services Agreement are subject to the review and
approval of the Audit Committee of the Board of Directors of the Company.
    
 
   
  In addition, Hollinger Inc. and The Telegraph are parties to a separate
services agreement under which The Telegraph bears two-thirds of the cost of the
office of the Chairman incurred by Hollinger Inc. as long as Mr. Black remains
Chairman of the Board of The Telegraph, and requires that other services will be
provided at cost, including the arrangement of insurance, assistance in the
arrangement of financing and assistance and advice on acquisitions, dispositions
and joint venture arrangements. Hollinger Inc. has assigned its rights and
obligations under The Telegraph services agreement to the Company and Publishing
on May 9, 1996 with the consent of The Telegraph.
 
  Business Opportunities.  The Business Opportunities Agreement provides that
the Company will be Hollinger Inc.'s principal vehicle for engaging in and
effecting acquisitions in newspaper businesses and in related media businesses
in the United States, Israel and, through The Telegraph, the European Community,
Australia and New Zealand (the "Telegraph Territory"). Hollinger Inc. has
reserved to itself the ability to pursue newspaper and all media acquisition
opportunities outside the United States, Israel and the Telegraph Territory, and
media acquisition opportunities unrelated to the newspaper business in the
United States, Israel and the Telegraph Territory, except that the Company is
permitted to increase its indirect investment in Southam. The Business
Opportunities Agreement does not restrict newspaper companies in which Hollinger
Inc. has a minority investment from acquiring newspaper or media businesses in
the United States, Israel or the Telegraph Territory, nor does it restrict
subsidiaries of Hollinger Inc. from acquiring up to 20% interests in publicly
held newspaper businesses in the United States. The Business Opportunities
Agreement will be in effect for so long as Hollinger Inc. holds at least 50% of
the voting power of the Company, subject to termination by either party under
specified circumstances.
 
  Continuing Agreements Relating to the Reorganization.  In connection with the
Company's October 1995 Reorganization, Hollinger Inc. and the Company entered
into the Share Exchange Agreement (the "Share Exchange Agreement"). Under the
Share Exchange Agreement, Hollinger Inc. and the Company have agreed that if the
Company proposes to effect a public offering of its equity or equity-linked
securities for cash, or to issue equity-linked securities in any acquisition by
the Company of the stock or assets of an unrelated corporation or entity, at any
time during the 24 months following the closing date of such agreement, the
Company's efforts to raise capital through such offering shall have priority
over any proposal by Hollinger Inc. to effect a public offering or sale of the
Company's equity securities by Hollinger Inc., unless a majority of the
disinterested members of an Independent Committee of the Company's Board of
Directors shall otherwise agree. For these purposes, an "Independent Committee"
means a committee of the Company's Board the majority of the members of which
are not employees or directors of Hollinger Inc. or employees of the Company, or
another committee of the Company's Board whose membership satisfies any more
restrictive requirements of independence of any securities exchange or market in
which the Company's equity securities are traded or listed. If during such
period Hollinger Inc. proposes to sell or otherwise dispose of any shares of
    
 
                                       11
<PAGE>   14
   
Series A Preferred Stock (other than certain transfers to Hollinger Inc.
subsidiaries or affiliates and pledges) or to offer or sell publicly any shares
of Class A Common Stock held by it or its affiliates, it shall first consult
with the Independent Committee so as not to interfere with any planned capital
market activities of the Company to be undertaken within this period.
    
 
   
  The Share Exchange Agreement includes a covenant by Hollinger Inc. to limit
the exercise of its redemption rights as a holder of shares of Series A
Preferred Stock to a number of shares proportionate to the number of HTH shares
or Southam common shares that at the time of such exercise have been delivered
to FDTH free and clear of encumbrances. The Company also agreed that so long as
any of the HTH shares are subject to the pledge under the Southam-Linked
Debentures, the Company will use reasonable commercial efforts not to take any
action, without the consent of Hollinger Inc., which itself would constitute an
event of default by Hollinger Inc. under the trust indenture relating to the
Southam-Linked Documents. Hollinger Inc. has agreed to deliver to FDTH legal
title to the HTH shares free and clear of pledges, liens or encumbrances other
than certain permitted encumbrances.
    
 
   
  Under the agreement between the Company and Hollinger Inc. with respect to the
DTH and FDTH Preference Shares (the "DTH/FDTH Preference Share Agreement"), the
Company has agreed to compensate Hollinger Inc. for any payments made by
Hollinger Inc. to holders of the DTH and FDTH Preference Shares and to purchase
any DTH and FDTH Preference Shares which Hollinger Inc. is required to purchase
in accordance with the terms thereof. The timing of any such payments by the
Company to Hollinger Inc. will be determined by Hollinger Inc.
    

                                       12
<PAGE>   15

                                USE OF PROCEEDS

  None of the net proceeds from any sale of the Pledged Shares offered hereby
will be available for use by the Company or otherwise for the Company's
benefit.

                                   BACKGROUND

HOLLINGER INC.

  Hollinger Inc. owns the Outstanding Pledged Shares and all of the 14,990,000 
outstanding shares of Class B Common Stock of the Company.

  The Company's Restated Certificate of Incorporation, as amended, provides
that holders of Class B Common Stock are entitled to ten votes per share and
holders of Class A Common Stock are entitled to one vote per share.  The
holders of Class A Common Stock and Class B Common Stock vote together as a
single class on all matters on which stockholders may vote, except when class
voting is required by applicable law or on a vote to issue or increase the
authorized number of shares of Class B Common Stock.  Each share of Class B
Common Stock is convertible at any time at the option of the holder into one
share of Class A Common Stock and is automatically convertible into one 
share of Class A Common Stock upon the happening of certain events. 
See "Background--Pledges."

   
  As a result, Hollinger Inc. owns approximately 57.4% of the combined equity
interest in the Company and approximately 83.6% of the combined voting power of
the outstanding Common Stock (without giving effect to the issuance of shares of
Class A Common Stock upon conversion of the Series A Preferred Stock or in
connection with the Company's 9 3/4% Preferred Redeemable Increased Dividend
Equity Securities PRIDES(SM) ("PRIDES"), and 46.1% and 76.4%, respectively, upon
the issuance of up to approximately 20,700,000 shares of Class A Common Stock in
connection with the PRIDES (without giving effect to the issuance of shares of
Class A Common Stock upon conversion of the Series A Preferred Stock)) and is in
a position to control the outcome of substantially all actions requiring
stockholder approval, including the election of the entire Board of Directors.
In addition, Hollinger Inc. owns all outstanding shares of Series A Preferred
Stock of the Company, which are convertible at any time into shares of Class A
Common Stock at the initial conversion price of $14 per share.  Based on the
initial conversion price, 5,791,043 shares (the "Initial Conversion Shares") of
Class A Common Stock would have been issuable upon the conversion of the Series
A Preferred Stock as of October 13, 1995, the date on which the shares of Series
A Preferred Stock were acquired pursuant to the Share Exchange Agreement (with
each share of Series A Preferred Stock having a redemption price of Cdn.$146.625
and assuming an exchange rate of $1.00 per Cdn.$1.3374, as in effect on October
13, 1995).  The number of shares of Class A Common Stock into which the Series A
Preferred Stock may be converted will fluctuate from time to time based on
changes in the conversion rate and/or the exchange rate.
    

  Hollinger Inc. is effectively controlled by Mr. Conrad M. Black, Chairman of
the Board and Chief Executive Officer of Hollinger Inc. and the Company,
through his direct and indirect ownership and control of Hollinger Inc.'s
securities.  Mr. Black has advised the Company that Hollinger Inc. does not
presently intend to reduce its voting power in the Company's outstanding Common
Stock to less than 50%.  Furthermore, Mr. Black has advised the Company that he
does not presently intend to reduce his voting control over Hollinger Inc. such
that a third party would be able to exercise effective control over it.

   
  If the Pledgees were to effect a Foreclosure upon all of the Outstanding
Pledged Shares, Hollinger Inc. would continue to own 17.7% of the combined
equity interest and 68.3% of the combined voting power of the outstanding Common
Stock of the Company (without giving effect to the issuance of shares of Class A
Common Stock upon conversion of the Series A Preferred Stock or in connection
with the PRIDES).  As a result, Hollinger Inc. would continue to be able to
control the outcome of any election of directors and to direct management
policy, strategic direction and financial decisions of the Company after such a
Foreclosure. However, if the Pledgees were to effect a Foreclosure upon all of
the Class B Common Stock, a change of control of the Company could result, such
that Hollinger Inc. would no longer be able to control the outcome of any
election of directors nor to direct management policy, strategic direction 
and financial decisions of the Company after such a Foreclosure.  Such a 
Foreclosure would trigger the change of control event of default provisions 
contained in the instruments governing the terms of the principal indebtedness 
of the Company and its principal United States and foreign subsidiaries.  
See "Risk Factors--Substantial Leverage."
    

  In addition to being convertible at any time at the option of the holder into
one share of Class A Common Stock, each share of Class B Common Stock is
transferable by Hollinger Inc. to a subsidiary or an affiliate of

                                       13
<PAGE>   16
Hollinger Inc.  In addition, each share of Class B Common Stock is
automatically convertible into a share of Class A Common Stock at the time it
is sold, transferred or otherwise disposed of by Hollinger Inc. or a subsequent
permitted transferee to any third party (other than a subsidiary or an
affiliate of Hollinger Inc. or such subsequent permitted transferee) unless
such purchaser or transferee offers to purchase all shares of Class A Common
Stock from the holders thereof for an amount per share equal to the amount per
share received by the holder of the Class B Common Stock (a "Permitted
Transaction").

  Accordingly, Hollinger Inc. may sell or transfer shares of Class B Common
Stock, and thus potentially voting control of the Company, to an unaffiliated
third person provided such purchaser or transferee offers to purchase all
shares of Class A Common Stock from the holders thereof for an amount per share
equal to the amount per share received by Hollinger Inc. for the Class B Common
Stock.

PLEDGES

  Notwithstanding the restrictions on permitted transfers, any holder of Class
B Common Stock may pledge his or its shares of Class B Common Stock to a
pledgee pursuant to a bona fide pledge of such shares as collateral security
for indebtedness due to the pledgee, provided that such shares shall not be
transferred to or registered in the name of the pledgee and shall remain
subject to the transfer restrictions described above.  In the event that shares
of Class B Common Stock are so pledged, the pledged shares shall not be
converted automatically into Class A Common Stock.  However, if any such
pledged shares become subject to any foreclosure, realization or other similar
action of the pledgee, such shares shall be converted automatically into shares
of Class A Common Stock unless they are sold in a Permitted Transaction.

  The Company's Restated Certificate of Incorporation, as amended, also
provides that no sale, transfer or other disposition of the Series A Preferred
Stock shall be valid unless made to a subsidiary or affiliate of Hollinger Inc.
or unless the Company, by resolution adopted by its Board of Directors, shall
first have consented to the proposed transfer and approved the proposed
transferee (the "Series A Transfer Restriction").  Notwithstanding the
foregoing sentence, any holder of Series A Preferred Stock may pledge such
shares to a pledgee pursuant to a bona fide pledge of such shares as collateral
security for indebtedness or other obligations due to the pledgee, provided
that such shares shall remain subject to, and upon foreclosure, realization or
other similar action by the pledgee, shall be transferred only in accordance
with, the Series A Transfer Restriction.

  Pursuant to the terms of the Hypothecation, Hollinger Inc. has pledged the
Outstanding Pledged Shares, the Class B Common Stock and the Series A Preferred
Stock (together, the "Pledged Securities") to CIBC as collateral security for
the obligations of Hollinger Inc. and certain affiliated companies under the
CIBC Facility.  The CIBC Facility requires compliance by Hollinger Inc. with
certain financial and other covenants and is subject to customary default and
other provisions.  A default by Hollinger Inc. under the CIBC Facility and a
foreclosure upon the Pledged Securities in accordance with the Hypothecation,
the terms of the CIBC Facility and applicable law could result in a change of
control of the Company.  Such a foreclosure would trigger the change of control
event of default provisions contained in the instruments governing the terms of
the principal indebtedness of the Company and its principal United States and
foreign subsidiaries.  See "Risk Factors--Substantial Leverage."

   
  In connection with the Hypothecation, Hollinger Inc. entered into the CIBC
Letter Agreement, pursuant to which Hollinger Inc. has agreed that, in the event
that Hollinger Inc. or the Company is in default under any present or future
indebtedness and CIBC intends to effect foreclosure upon such securities or to
exercise its power of sale rights under any applicable security documents,
Hollinger Inc. will, at the written request of CIBC, use its reasonable best
efforts to cause the Company to effect the registration under the Securities Act
of all or part of the Outstanding Pledged Shares, the Class B Common Stock
(including the Conversion Pledged Shares) and the shares of Class A Common Stock
into which the Series A Preferred Stock is convertible (but not less than
5,000,000 shares of Class A Common Stock), unless certain exemptions from the
registration provisions of the Securities Act are applicable to the transactions
proposed by CIBC.  Hollinger Inc. has further agreed to pay all registration
expenses (including any underwriting discounts or commissions and reasonable
fees and disbursements of counsel to the Pledgees) in connection with such a
registration.  Hollinger Inc.'s undertakings in the CIBC Letter Agreement are
subject to Hollinger Inc.'s obligations under the Share Exchange Agreement
(including those described above) and were modified by the Registration Rights
Agreement. While the CIBC Letter Agreement by its terms does not require the
Company to register the Conversion Pledged Shares at this time, pursuant to a
subsequent agreement the Company, Hollinger Inc. and CIBC have agreed that the
Company will register such shares at this time.
    

                                       14
<PAGE>   17
   
  On February 29, 1996 Hollinger Inc. transferred the Ontario Limited Shares and
the Class B Common Stock, subject to the Hypothecation, to Ontario Limited.
Pursuant to the terms of the Securities Pledge Agreement, Ontario Limited has
pledged the Ontario Limited Shares as collateral security for its obligations
under the Ontario Limited Credit Agreement.  The obligations of Ontario Limited
under the Ontario Limited Credit Agreement are guaranteed by Hollinger Inc. and
certain of its Canadian subsidiaries.  The Credit Agreement requires compliance
by Hollinger and Ontario Limited with certain financial and other covenants and
is subject to customary default and other provisions.  A default by Ontario
Limited under the Ontario Limited Credit Agreement and a foreclosure upon only
the Ontario Limited Shares in accordance with the Securities Pledge Agreement,
the Ontario Limited Credit Agreement and applicable law is not expected to
result in a change of control of the Company; provided, however, that CIBC may
determine, in its discretion, that a default under the Credit Agreement
constitutes a default under the CIBC Facility, the Southam Facility and the
related Ontario Limited Guarantees and N.B. Inc. Guarantees or Other
Indebtedness, which in turn could result in a change of control of the Company.
    

   
  In connection with the Securities Pledge Agreement, Ontario Limited, Hollinger
Inc. and the Lenders entered into the Registration Rights Agreement. The
Registration Rights Agreement provides that Hollinger and Ontario Limited will
use their reasonable best efforts to cause the Company to effect a "shelf
registration" under the Securities Act of the Outstanding Pledged Shares
(consisting of the 10,121,726 shares held directly by Hollinger Inc., the
7,539,028 shares held by Canada Limited and the 15,950,000 shares held by
Ontario Limited) at the earliest possible date, but, in any case, not later than
May 29, 1996.  In connection with such registration, Hollinger Inc. agreed to
pay all registration expenses ([other than] [including] any underwriting
discounts or commissions [and reasonable fees and disbursements of counsel to
the Pledgees]), and all other selling expenses incurred by the Lenders will be
borne by Hollinger Inc. and the Company.  In accordance with the Registration
Rights Agreement, this Registration Statement is being used to register the
Outstanding Pledged Shares pledged as collateral to both CIBC and the Lenders.
The Registration Rights Agreement also provides that with respect to the Class B
Common Stock and the Series A Preferred Stock the registration rights
undertaking by Hollinger Inc. pursuant to the CIBC Letter Agreement shall remain
in full force and effect.
    

   
SOUTHAM

  On May 24, 1996, Hollinger Inc.'s wholly owned Canadian subsidiary, Hollinger
Eastern, purchased from a subsidiary of Power Corporation of Canada ("Power")
the 16,349,743 common shares (the "Power Shares") of Southam held by Power
representing approximately 21.5% of Southam's outstanding common shares, at a
price of Cdn.$18.00 per share. This purchase increased the Company's and
Hollinger Inc.'s combined holdings in Southam to approximately 41% of Southam's
outstanding common shares, including 19.5% which is currently held indirectly by
the Company. Subsequent to the acquisition of the Power Shares, on July 22,
1996, following a request by Hollinger Inc., Southam held a special shareholders
meeting at which five new directors proposed by Hollinger Inc. were elected to
replace five of the existing directors of Southam.  On August 8, 1996 Hon.
Conrad M. Black, Chairman of the Board and Chief Executive Officer of the
Company, became Chairman and Chief Executive Officer of Southam, and F. David
Radler, President and Chief Operating Officer of the Company, was appointed
Deputy Chairman and Associate Chief Executive Officer of Southam.  In addition,
Daniel W. Colson, Deputy Chairman and Chief Executive of The Telegraph and
Deputy Chairman of Fairfax, was appointed a Director of Southam.  The Company
believes that the reconstituted Board of Directors of Southam, together with
announced changes involving its corporate and newspaper executives, has
positioned Southam to implement steps designed to enhance operating performance
through reduced costs and improved editorial quality, including the acquisition
of additional Canadian newspapers and the disposition of non-newspaper assets.
The Company subsequently acquired all of the outstanding non-voting common
shares, one-half of the outstanding voting preference shares and Cdn. $30
million in non-voting preference shares of Hollinger Eastern. Hollinger Inc.
holds the remaining one-half of the voting preference shares of Hollinger
Eastern. 
    

   
  On October 24, 1996, the Company announced an offer to Southam shareholders
(the "Southam Offer") to purchase pro rata, through a wholly owned indirect
subsidiary, 7,000,000 common shares of Southam at Cdn. $18.75 per share. The
Company increased the per share offer price in the Southam Offer to Cdn. $20.00
on November 15, 1996. On November 28, 1996, the expiration date of the Southam
offer, a total of approximately 22,443,600 common shares of Southam had been
tendered pursuant to the Southam Offer and not withdrawn. Under the terms of the
Southam offer, the Company is obligated to purchase at least 7,000,000 of the
tendered Southam common shares on a pro rata basis but has the right at its
option to purchase a number of the tendered Southam common shares that is
greater than 7,000,000 but less than 8,500,000 shares on a pro rata basis. The
Company is obligated under the Southam Offer to give notice to the depository of
the number of tendered Southam common shares to be purchased not later than 10
days from the expiry of the Southam Offer on November 28, 1996 and to close the
purchase of such Southam common shares as soon as possible thereafter, but in
any event not later than three days after giving such notice. The Company
intends to give notice to the depository of the exercise of the option to
purchase 8,000,000 Southam common shares on a pro rata basis on December 8, 1996
and to close such purchase on December 11, 1996. As a result of the acquisition
of 8,000,000 Southam common shares, the Company, Hollinger Inc. and their
affiliates will hold 50.7% of the currently outstanding 77,132,069 common shares
of Southam. When the completion of the Company's pending Southam Offer to
acquire additional common shares of Southam results in the Company's and
Hollinger Inc's ownership of more than 50% of the outstanding common shares of
Southam, the Company intends to consolidate Southam's results of operations with
the Company's for accounting purposes. 
    

   
  The purchase of the Power Shares was financed through the Southam Facility in
the amount of Cdn.$300 million between the Company and CIBC. The Southam
Facility was syndicated equally between CIBC and The Bank of Nova Scotia on July
17, 1996. At September 30, 1996, the amount outstanding under the Southam
Facility was approximately $155.9 million. The Southam Facility is guaranteed by
Hollinger Inc. and matures on February 28, 1997 or earlier upon the occurrence
of certain events, namely (i) one banking day prior to the maturity date of the
Amended and Restated Credit Agreement dated May 30, 1996, as amended (the
"Publishing Credit Facility") among Publishing and certain lenders, which is
currently scheduled to mature on February 7, 1997; (ii) one banking day prior to
the maturity date of the Credit Agreement dated May 30, 1996, as amended (the
"First DT Credit Agreement") among FDTH and certain lenders, which is currently
scheduled to mature on February 7, 1997; or (iii) the closing date of any equity
issue, debt financing, public or private placement or high yield financing
completed by the Company or any of its subsidiaries or by Hollinger Inc. or
certain of its Canadian subsidiaries. All net proceeds of any financing referred
to in (iii) above, must be applied as a permanent prepayment of the Southam
Facility. Unless extended, the First DT Credit Agreement matures on February 7,
1997, under which $306.9 million is currently outstanding, and the Publishing
Credit Facility also matures on February 7, 1997, under which $130.0 million is
currently outstanding. The funds under the Southam Facility were advanced by the
Company to Hollinger Eastern as an intercompany loan which was canceled in
connection with the Company's acquisition of equity interests in Hollinger
Eastern. The Hollinger Inc. guarantee of the Southam Facility is secured by
among other things, a pledge of the Power Shares, the Canada Limited Shares and
the 14,990,000 shares of Class B Common Stock held by Hollinger Inc. The CIBC
Letter Agreement (as defined herein) and the Registration Rights Agreement (as
defined herein) have been amended to reflect the pledges under the Southam
Facility.
    

   
    

   
  In connection with the Southam Facility, pursuant to the terms of the N.B.
Inc. Securities Pledge Agreements, N.B. Inc. has pledged the N.B. Inc. Shares as
collateral security for its obligations to CIBC and The Bank of Nova Scotia
under the N.B. Inc. Guarantees. If the Company were to be in default under the
Southam Facility, a default by N.B. Inc. under the N.B. Inc. Guarantees and a
foreclosure upon only the N.B. Inc. Shares in accordance with the N.B. Inc.
Securities Pledge Agreements, the N.B. Inc. Guarantees and applicable law is not
expected to result in a change of control of the Company; provided, however,
that CIBC may determine, in its discretion, that a default under the Southam
Facility and/or the N.B. Inc. Guarantees constitutes a default under the CIBC
Facility or Other Indebtedness, which in turn could result in a change of
control of the Company.
    

  In connection with the Southam Facility, pursuant to the terms of the Ontario
Limited Securities Pledge Agreements, Ontario Limited has pledged the Class B
Common Stock as collateral security for its obligations to CIBC and The Bank of
Nova Scotia under the Ontario Limited Guarantees.  If the Company were to be in
default under the Southam Facility, a default by Ontario Limited under the
Ontario Limited Guarantees and a foreclosure upon the Class B Common Stock in
accordance with the Ontario Limited Securities Agreements, the Ontario Limited
Guarantees and applicable law could result in a change of control of the
Company.  Such a foreclosure would trigger the change of control event of
default provisions contained in the instruments governing the terms of the
principal indebtedness of the Company and its principal United States and
foreign subsidiaries.  See "Risk Factors--Substantial Leverage."

   
  The CIBC Letter Agreement and the Registration Rights Agreement were amended
on May 24, 1996 in connection with the Southam Facility. In addition to any
changes to the CIBC Letter Agreement and the Registration Rights Agreement
reflected above, the principal effects of the May 24, 1996 amendments were 
(i) to make the Company and Canada Limited parties to the CIBC Letter Agreement 
and the Registration Rights Agreement, (ii) to provide that the registration
undertakings set forth in the CIBC Letter Agreement apply to any default under
any indebtedness of Hollinger Inc. or the Company to CIBC secured by a pledge of
the Company's securities, including the Southam Facility and (iii) to reflect
that the Canada Limited Shares and the 14,990,000 shares of Class B Common Stock
held by Hollinger Inc. were pledged to CIBC in connection with guarantees of 
the Southam Facility. In addition, as of November 15, 1996, the Company, 
Hollinger Inc., Ontario Limited, N.B. Inc., CIBC, The Toronto-Dominion Bank 
and The Bank of Nova Scotia entered into a letter agreement to clarify and 
confirm certain rights and obligations of the parties thereto under the 
Registration Rights Agreement and the CIBC Letter Agreement.
    

                                       15
<PAGE>   18
  In addition to any present Pledges, Hollinger Inc. may pledge the Pledged
Shares, subject to the Pledges and/or upon release from one or more of the
Pledges, to secure Other Indebtedness to one or more of the Pledgees or to
parties other than the Pledgees.

                              PLAN OF DISTRIBUTION

   
  In the event a Foreclosure occurs, Pledged Shares registered hereby may be
sold from time to time by or for the account of the Pledgees, or their
transferees, on one or more exchanges or otherwise; directly to purchasers in
negotiated transactions; by or through brokers or dealers, in ordinary brokerage
transactions or transactions in which the broker solicits purchasers; in block
trades in which the broker or dealer will attempt to sell Pledged Shares as
agent but may position and resell a portion of the block as principal; in
transactions in which a broker or dealer purchases as principal for resale for
its own account; through underwriters or agents; or in any combination of the
foregoing methods. Pledged Shares may be sold at a fixed offering price, which
may be changed, at the prevailing market price at the time of sale, at prices
related to such prevailing market price or at negotiated prices.  Any brokers,
dealers, underwriters or agents may arrange for others to participate in any
such transaction and may receive compensation in the form of discounts,
commissions or concessions from the Pledgees, or their transferees, and/or the
purchasers of Pledged Shares. If required at the time that a particular offer of
Pledged Shares is made, a supplement to this Prospectus will be delivered that
describes any material arrangements for the distribution of Pledged Shares and
the terms of the offering, including, without limitation, the names of any
underwriters, brokers, dealers or agents and any discounts, commissions or
concessions and other items constituting compensation. The Company may
agree to indemnify any such brokers, dealers, underwriters, or agents against
certain civil liabilities, including liabilities under the Securities Act.
    

  The Pledgees, or their transferees, and any brokers, dealers, underwriters or
agents that participate with the Pledgees, or their transferees, in the
distribution of Pledged Shares may be deemed to be "underwriters" within the
meaning of the Securities Act, in which event any discounts, commissions or
concessions received by any such brokers, dealers, underwriters or agents and
any profit on the resale of the Pledged Shares purchased by them may be deemed
to be underwriting commissions or discounts under the Securities Act.

  Hollinger Inc. has informed the Pledgees that the provisions of Rules 10b-6
and 10b-7 under the Exchange Act may apply to its sales of Pledged Shares and
has furnished the Pledgees with a copy of these rules.  Hollinger Inc. has
advised the Pledgees of the requirement for delivery of a prospectus in
connection with any sale of the Pledged Shares.

  Any Pledged Shares covered by this Prospectus which qualify for sale pursuant
to Rule 144 under the Securities Act may be sold under Rule 144 rather than
pursuant to this Prospectus.  There is no assurance that the Pledgees, or their
transferees, will sell any or all of the Pledged Shares.  The Pledgees, or
their transferees, may transfer, devise or gift such Pledged Shares by other
means not described herein.

   
  Hollinger Inc. will pay all of the expenses, including, but not limited to,
fees and expenses of compliance with state securities or "blue sky" laws,
incident to the registration of the Pledged Shares, including any underwriting 
discounts and selling commissions and reasonable fees and disbursements of 
counsel to the Pledgees.
    

                                 LEGAL MATTERS

  Certain legal matters in connection with the Pledged Shares offered hereby
will be passed upon for the Company by Kirkpatrick & Lockhart LLP, Pittsburgh,
Pennsylvania.

                                    EXPERTS

   
  The consolidated financial statements of Hollinger International Inc. and
subsidiaries as of December 31, 1995 and 1994, and for each of the years in the
three-year period ended December 31, 1995, incorporated by reference herein 
from the Company's 1995 Form 10-K, have been included therein and incorporated 
by reference herein in reliance upon the report of KPMG Peat Marwick LLP,
independent certified public accountants and upon the authority of said firm 
as experts in accounting and auditing.
    

                                       16
<PAGE>   19

=============================================================

     NO PERSON HAS BEEN AUTHORIZED TO GIVE ANY INFORMATION
OR TO MAKE ANY REPRESENTATIONS OTHER THAN THOSE CONTAINED IN
THIS PROSPECTUS, AND, IF GIVEN OR MADE,SUCH INFORMATION OR
REPRESENTATIONS MUST NOT BE RELIED UPON AS HAVING BEEN
AUTHORIZED. THIS PROSPECTUS DOES NOT CONSTITUTE AN OFFER TO
SELL OR THE SOLICITATION OF AN OFFER TO BUY ANY SECURITIES
OTHER THAN THE SECURITIES TO WHICH IT RELATES OR AN OFFER TO
SELL OR THE SOLICITATION OF AN OFFER TO BUY SUCH SECURITIES
IN ANY CIRCUMSTANCES IN WHICH SUCH OFFER OR SOLICITATION IS
UNLAWFUL. NEITHER THE DELIVERY OF THIS PROSPECTUS NOR ANY
SALE MADE HEREUNDER SHALL, UNDER ANY CIRCUMSTANCES, CREATE
ANY IMPLICATION THAT THERE HAS BEEN NO CHANGE IN THE AFFAIRS
OF THE COMPANY SINCE THE DATE HEREOF OR THAT THE INFORMATION
CONTAINED HEREIN IS CORRECT AS OF ANY TIME SUBSEQUENT TO ITS
DATE.


                        _____________


                      TABLE OF CONTENTS

<TABLE>
<CAPTION>
                                                            Page
                                                            ----
<S>                                                         <C>
Available Information . . . . . . . . . . . . . . . . . . .    2     
Incorporation of Certain Documents by Reference . . . . . .    2           
The Company . . . . . . . . . . . . . . . . . . . . . . . .    3       
Risk Factors  . . . . . . . . . . . . . . . . . . . . . . .    4
Use of Proceeds . . . . . . . . . . . . . . . . . . . . . .   13
Background  . . . . . . . . . . . . . . . . . . . . . . . .   13
Plan of Distribution  . . . . . . . . . . . . . . . . . . .   16
Legal Matters   . . . . . . . . . . . . . . . . . . . . . .   16
Experts . . . . . . . . . . . . . . . . . . . . . . . . . .   16
</TABLE>

=============================================================

                             48,600,754 SHARES

                         HOLLINGER INTERNATIONAL INC.

                             CLASS A COMMON STOCK


                                  ----------

                                  PROSPECTUS

                                  ----------


   
                                     [date]
    

=============================================================
<PAGE>   20
                                    PART II

                     INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 14.  OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION.

   
     The estimated expenses to be paid by Hollinger Inc., Ontario Limited,
  Canada Limited and/or the Company in connection with the distribution of the
  securities being registered, other than underwriting discounts and
  commissions, are as follows:

<TABLE>
         <S>                                                                                <C>
         Securities and Exchange Commission Filing Fee  . . . . . . . . . . .               $188,792
         *Legal Fees and Expenses . . . . . . . . . . . . . . . . . . . . . .                250,000
         *Printing Expenses . . . . . . . . . . . . . . . . . . . . . . . . .                115,000
         *Miscellaneous Expenses  . . . . . . . . . . . . . . . . . . . . . .                 26,208
                                                                                            --------

                                  Total                                                     $580,000
</TABLE>
    

_______________________
         *Estimated.

ITEM 15.  INDEMNIFICATION OF DIRECTORS AND OFFICERS.

         The Company's Restated Certificate of Incorporation provides that no
director of the Company will be personally liable to the Company or any of its
stockholders for monetary damages arising from the director's breach of the
duty of care as a director, with certain limited exceptions.

         Pursuant to the provisions of Section 145 of the Delaware General
Corporation Law, every Delaware corporation has the power to indemnify any
person who was or is a party or is threatened to be made a party to any
threatened, pending or completed action, suit or proceeding (other than an
action by or in the right of the corporation) by reason of the fact that he is
or was a director, officer, employee or agent of any corporation, partnership,
joint venture, trust or other enterprise, against any and all expenses,
judgments, fines and amounts paid in settlement and reasonably incurred in
connection with such action, suit or proceeding.  The power to indemnify
applies only if such person acted in good faith and in a manner he reasonably
believed to be in the best interest, or not opposed to the best interest, of
the corporation and with respect to any criminal action or proceeding, had no
reasonable cause to believe his conduct was unlawful.

         The power to indemnify applies to actions brought by or in the right
of the corporation as well, but only to the extent of defense and settlement
expenses and to any satisfaction of a judgment or settlement of the claim
itself, and with the further limitation that in such actions no indemnification
shall be made in the event of any adjudication or liability unless the court,
in its discretion, believes that in light of all the circumstances
indemnification should apply.

         To the extent any of the persons referred to in the two immediately
preceding paragraphs is successful in the defense of the actions referred to
therein, such person is entitled, pursuant to Section 145, to indemnification
as described above.

         The Company's Restated Certificate of Incorporation and Amended and
Restated Bylaws provide for indemnification to officers and directors of the
Company to the fullest extent permitted by the Delaware General Corporation
Law.

         The Company maintains a policy of liability insurance which insures
its officers and directors against losses resulting from certain wrongful acts
committed by them in their capacity as officers and directors of the Company.
<PAGE>   21
ITEM 16.  EXHIBITS AND FINANCIAL STATEMENT SCHEDULES.

         (a)     Exhibits.  The following exhibits are filed as part of this
registration statement:

   
<TABLE>
<CAPTION>
         EXHIBIT
         NUMBER                                   DESCRIPTION
         -------     -------------------------------------------------------------------------------- 
          <S>        <C>
           5.01      Opinion of Kirkpatrick & Lockhart LLP
         
          23.01      Consent of Kirkpatrick & Lockhart LLP (included in Exhibit 5.01)

          23.02      Consent of KPMG Peat Marwick LLP
         
          24.01      Powers of Attorney (previously filed)

          99.01      Hypothecation of Specific Securities dated October 13, 1995 by Hollinger Inc.
                     in favor of the Canadian Imperial Bank of Commerce (previously filed)
         
          99.02      Letter Agreement dated October 13, 1995 between Hollinger Inc. and the
                     Canadian Imperial Bank of Commerce (previously filed)

          99.03      Securities Pledge Agreement dated February 29, 1996 by 1159670 Ontario Limited
                     in favor of the Canadian Imperial Bank of Commerce, as agent for the Lenders,
                     and the Canadian Imperial Bank of Commerce, The Toronto-Dominion Bank and The Bank 
                     of Nova Scotia (previously filed)
         
          99.04      Registration Rights Agreement dated February 29, 1996 among Hollinger Inc.,
                     1159670 Ontario Limited and the Canadian Imperial Bank of Commerce, The
                     Toronto-Dominion Bank and The Bank of Nova Scotia (previously filed)

          99.05      Letter Agreement dated May 24, 1996 by Hollinger Inc., Hollinger International Inc.,
                     1159670 Ontario Limited, 3184081 Canada Limited and the Canadian Imperial Bank of 
                     Commerce amending the Letter Agreement dated October 13, 1995 and the  Registration
                     Rights Agreement dated February 29, 1996

          99.06      Securities Pledge Agreement dated May 24, 1996 by 3184081 Canada Limited in favor of 
                     the Canadian Imperial Bank of Commerce      

          99.07      Securities Pledge Agreement dated May 24, 1996 by 1159670 Ontario
                     Limited in favor of the Canadian Imperial Bank of Commerce

          99.08      Securities Pledge Agreement dated as of July 17, 1996 by 3184081 Canada
                     Limited in favor of the Canadian Imperial Bank of Commerce, as agent for
                     the Canadian Imperial Bank of Commerce and The Bank of Nova Scotia

          99.09      Securities Pledge Agreement dated as of July 17, 1996 by 1159670 Ontario
                     Limited in favor of the Canadian Imperial Bank of Commerce, as agent for
                     the Canadian Imperial Bank of Commerce and The Bank of Nova Scotia

          99.10      Securities Pledge Agreement dated as of November 15, 1996 by 503264 N.B.
                     Inc. in favor of the Canadian Imperial Bank of Commerce, as agent for
                     the Canadian Imperial Bank of Commerce and The Bank of Nova Scotia

          99.11      Letter Agreement dated as of November 15, 1996 among Hollinger Inc., Hollinger
                     International Inc., 1159670 Ontario Limited, 503264 N.B. Inc., the
                     Canadian Imperial Bank of Commerce, The Toronto-Dominion Bank and The
                     Bank of Nova Scotia
</TABLE>
    

ITEM 17.  UNDERTAKINGS.

         The undersigned registrant hereby undertakes:

         (1)     To file, during any period in which offers or sales are being
                 made, a post-effective amendment to this registration
                 statement:

                 (i)      To include any prospectus required by Section
                          10(a)(3) of the Securities Act of 1933;

                 (ii)     To reflect in the prospectus any facts or events
                          arising after the effective date of the registration
                          statement (or the most recent post-effective
                          amendment thereof) which, individually or in the
                          aggregate, represent a fundamental change in the
                          information set forth in the registration statement;

                 (iii)    To include any material information with respect to
                          the plan of distribution not previously disclosed in
                          the registration statement or any material change to
                          such information in the registration statement.

         Provided, however, that paragraphs (i) and (ii) do not apply if the
information required to be included in a post-effective amendment by those
paragraphs is contained in periodic reports filed with or furnished to the
Commission by the registrant pursuant to Section 13 or Section 15(d) of the
Securities Exchange Act of 1934 that are incorporated by reference in the
registration statement.

         (2)     That, for the purpose of determining any liability under the
Securities Act of 1933, each such post-effective amendment shall be deemed to
be a new registration statement relating to the securities offered therein, and
the offering of such securities at the time shall be deemed to be the initial
bona fide offering thereof.


                                      II-2
<PAGE>   22
         (3)     To remove from registration by means of a post-effective
amendment any of the securities being registered which remain unsold at the
termination of the offering.

         (4)     That, for purposes of determining any liability under the
Securities Act of 1933, each filing of the registrant's annual report pursuant
to Section 13(a) or Section 15(d) of the Securities Exchange Act of 1934 that
is incorporated by reference in the registration statement shall be deemed to
be a new registration statement relating to the securities offered therein, and
the offering of such securities at that time shall be deemed to be the initial
bona fide offering thereof.

         Insofar as indemnification for liabilities arising under the
Securities Act of 1933 may be permitted to directors, officers and controlling
persons of the registrant pursuant to the foregoing provisions, or otherwise,
the registrant has been advised that in the opinion of the Securities and
Exchange Commission such indemnification is against public policy as expressed
in the Act and is, therefore, unenforceable.  In the event that a claim for
indemnification against such liabilities (other than the payment by the
registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant in the successful defense of any action, suit or
proceeding) is asserted by such director, officer or controlling person in
connection with the securities being registered, the registrant will, unless in
the opinion of its counsel the matter has been settled by controlling
precedent, submit to a court of appropriate jurisdiction the question whether
such indemnification by it is against public policy as expressed in the Act and
will be governed by the final adjudication of such issue.





                                      II-3
<PAGE>   23
                                   SIGNATURES

   
   Pursuant to the requirements of the Securities Act of 1933, the registrant
certifies that it has reasonable grounds to believe that it meets all of the
requirements for filing on Form S-3 and has duly caused this amendment to
registration statement to be signed on its behalf by the undersigned, thereunto
duly authorized, in the City of Chicago, State of Illinois, on November 29, 
1996.
    

                                        HOLLINGER INTERNATIONAL INC.

                                        By: /s/ CONRAD M. BLACK
                                            --------------------------
                                            Conrad M. Black,
                                            Chairman of the Board
                                              and Chief Executive Officer
   
    

   
   Pursuant to the requirements of the Securities Act of 1933, this amendment to
registration statement has been signed by the following persons in the
capacities and on the dates indicated.
    

   
<TABLE>
<CAPTION>
             SIGNATURE                                     TITLE                             DATE
             ---------                                     -----                             ----
<S>                                      <C>                                             <C>
        /s/ CONRAD M. BLACK              Chairman of the Board, Chief Executive          November 29, 1996
- -----------------------------------      Officer and Director (Principal
          Conrad M. Black                Executive Officer)


                 *                       President, Chief Operating Officer and          November 29, 1996
- -----------------------------------      Director
          F. David Radler


         /s/ J. A. BOULTBEE              Vice President and Chief Financial Officer      November 29, 1996
- -----------------------------------      (Principal Financial Officer)
           J. A. Boultbee


      /s/ FREDERICK A. CREASEY           Group Corporate Controller (Principal           November 29, 1996
- -----------------------------------      Accounting Officer)
        Frederick A. Creasey


                 *                       Director                                        November 29, 1996
- -----------------------------------
        Barbara Amiel Black


                 *                       Director                                        November 29, 1996
- -----------------------------------
         Dwayne O. Andreas


                 *                       Director                                        November 29, 1996
- -----------------------------------
            Richard Burt


                                         Director                                                   , 1996
- -----------------------------------                                                          
        Raymond G. Chambers


                  *                      Director                                        November 29, 1996
- -----------------------------------
          Daniel W. Colson
</TABLE>
    
<PAGE>   24
   
<TABLE>
<CAPTION>
             SIGNATURE                                     TITLE                             DATE
             ---------                                     -----                             ----
<S>                                      <C>                                             <C>
                 * 
- -----------------------------------      Director                                        November 29, 1996
         Henry A. Kissinger


- -----------------------------------      Director                                                   , 1996
         Marie-Josee Kravis                                                                  


                 *
- -----------------------------------      Director                                        November 29, 1966
           Shmuel Meitar


- -----------------------------------      Director                                                   , 1966
          Richard N. Perle                                                                   


                 *
- -----------------------------------      Director                                        November 29, 1996
         Robert S. Strauss


                 *
- -----------------------------------      Director                                        November 29, 1966
           Alfred Taubman


                 *
- -----------------------------------      Director                                        November 29, 1966
         James R. Thompson


                 *
- -----------------------------------      Director                                        November 29, 1966
          Lord Weidenfeld


                 *
- -----------------------------------      Director                                        November 29, 1996
          Leslie H. Wexner


*By:     /s/ KENNETH L. SEROTA
      -----------------------------
         Kenneth L. Serota,
         Attorney-in-fact, pursuant to
         power of attorney previously
         filed as part of this
         Registration Statement.
</TABLE>
    
<PAGE>   25
                                 EXHIBIT INDEX

   
<TABLE>
<CAPTION>
EXHIBIT                                                                       SEQUENTIAL PAGE
 NUMBER                              DESCRIPTION                                   NUMBER
- -------       -----------------------------------------------------------     ---------------
  <S>         <C>
   5.01       Opinion of Kirkpatrick & Lockhart LLP

  23.01       Consent of Kirkpatrick & Lockhart LLP (included in
              Exhibit 5.01)

  23.02       Consent of KPMG Peat Marwick LLP

  24.01       Powers of Attorney (previously filed)

  99.01       Hypothecation of Specific Securities dated October 13,
              1995 by Hollinger Inc. in favor of the Canadian Imperial
              Bank of Commerce (previously filed)

  99.02       Letter Agreement dated October 13, 1995 between Hollinger
              Inc. and the Canadian Imperial Bank of Commerce (previously filed)

  99.03       Securities Pledge Agreement dated February 29, 1996 by
              1159670 Ontario Limited in favor of the Canadian Imperial
              Bank of Commerce, as agent for the Lenders, and the Canadian 
              Imperial Bank of Commerce, The Toronto-Dominion Bank and 
              The Bank of Nova Scotia (previously filed)

  99.04       Registration Rights Agreement dated February 29, 1996
              among Hollinger Inc., 1159670 Ontario Limited and the
              Canadian Imperial Bank of Commerce, The Toronto-Dominion
              Bank and The Bank of Nova Scotia (previously filed)

  99.05       Letter Agreement dated May 24, 1996 by Hollinger Inc., 
              Hollinger International Inc., 1159670 Ontario Limited, 
              3184081 Canada Limited, and the Canadian Imperial Bank of
              Commerce amending the Letter Agreement dated October 13, 1995 
              and the Registration Rights Agreement dated February 29, 1996

  99.06       Securities Pledge Agreement dated May 24, 1996 by 3184081 
              Canada Limited in favor of the Canadian Imperial Bank of Commerce

  99.07       Securities Pledge Agreement dated May 24, 1996 by 1159670 Ontario
              Limited in favor of the Canadian Imperial Bank of Commerce

  99.08       Securities Pledge Agreement dated as of July 17, 1996 by 3184081 Canada
              Limited in favor of the Canadian Imperial Bank of Commerce, as 
              agent for the Canadian Imperial Bank of Commerce and The Bank of 
              Nova Scotia

  99.09       Securities Pledge Agreement dated as of July 17, 1996 by 1159670 Ontario
              Limited in favor of the Canadian Imperial Bank of Commerce, as 
              agent for the Canadian Imperial Bank of Commerce and The Bank of 
              Nova Scotia

  99.10       Securities Pledge Agreement dated as of November 15, 1996 by 503264 N.B.
              Inc. in favor of the Canadian Imperial Bank of Commerce, as agent for
              the Canadian Imperial Bank of Commerce and The Bank of Nova Scotia

  99.11       Letter Agreement dated as of November 15, 1996 among Hollinger Inc., Hollinger
              International Inc., 1159670 Ontario Limited, 503264 N.B. Inc., the
              Canadian Imperial Bank of Commerce, The Toronto-Dominion Bank and The
              Bank of Nova Scotia

- ---------------                                                         
</TABLE>
    


<PAGE>   1
                                                                   EXHIBIT 5.01

   
                               November 29, 1996
    

Hollinger International Inc.
401 North Wabash Avenue
Chicago, Illinois  60611

Ladies and Gentlemen:
   
    We are acting as counsel to Hollinger International Inc., a Delaware
corporation (the "Company"), in connection with the Registration Statement on
Form S-3 (No. 333-04697), originally filed by the Company with the Securities
and Exchange Commission on May 29, 1996, as amended (the "Registration
Statement"), in connection with the registration pursuant to the Securities Act
of 1933, as amended, of 48,600,754 shares of Class A Common Stock, par value
$0.01, of the Company (the "Shares") comprised of (i) 33,610,754 Shares (the
"Outstanding Shares") held by Hollinger Inc., a Canadian corporation and the
parent corporation of the Company, or its subsidiaries ("Hollinger Inc.") that
are currently outstanding and (ii) the 14,990,000 Shares (the "Conversion
Shares") into which all 14,990,000 of the outstanding shares of the Company's
Class B Common Stock, par value $.01 per share ("Class B Common Stock"), held by
Hollinger Inc. are automatically convertible into, pursuant to the terms of the
Company's Restated Certificate of Incorporation, as amended, upon transfer of
such shares in any transaction other than a Permitted Transaction, as defined in
the Company's Restated Certificate of Incorporation, as amended.
    

   We have examined the Registration Statement and we have examined the
Company's Restated Certificate of Incorporation and By-laws, each as amended to
date.  We have also examined such other public and corporate documents,
certificates, instruments and corporate records, and such questions of law, as
we have deemed necessary for purposes of this opinion.

   
     Based on the foregoing, we are of the opinion that (i) the Outstanding
Shares have been validly issued and are fully paid and non-assessable and (ii)
assuming that (a) there has been a default (a "Default") under any indebtedness 
secured by a pledge of the 14,990,000 shares of Class B Common Stock held by 
Hollinger Inc., (b) the party whose interests are secured by such a pledge of 
the Class B Common Stock has foreclosed upon the Class B Common Stock in 
accordance with the terms of the pledge documents, the terms of the documents 
evidencing such indebtedness and applicable law (a "Foreclosure") and (c) there 
are no existing disputes regarding such Default or Foreclosure, then (x) the 
issuance of the Conversion Shares upon such a Foreclosure has been duly 
authorized by the Company and (y) the Conversion Shares if and when sold by 
the Pledgees as contemplated by the Prospectus contained in the Registration 
Statement will be validly issued, fully paid and non-assessable.
    

   We consent to the use of this opinion as Exhibit 5.01 to the Registration
Statement and to the reference to the undersigned in the Prospectus that forms
part of the Registration Statement.

                                        Yours truly,


                                        /s/ KIRKPATRICK & LOCKHART LLP



<PAGE>   1

                                                                   EXHIBIT 23.02

                         INDEPENDENT AUDITORS' CONSENT


The Board of Directors
Hollinger International Inc.:


   
We consent to the use of our report dated February 27, 1996, relating to the 
consolidated balance sheets of Hollinger International Inc. and subsidiaries 
as of December 31, 1995 and 1994, and the related consolidated statements of 
operations, stockholders' equity and cash flows for each of the years in the 
three-year period ended December 31, 1995, incorporated herein by reference 
from the Company's Annual Report on Form 10-K for the year ended December 31, 
1995 and to the reference to our firm under the heading "Experts" in the 
Prospectus.
    

                                     /s/ KPMG Peat Marwick LLP

   
Chicago, Illinois
November 29, 1996
    



<PAGE>   1
                                                                  Exhibit 99.05

Canadian Imperial Bank of Commerce
Commerce Court West, 7th Floor
Toronto, Ontario
M5H 3T7


Dear Sirs:

   Re:  Registration Rights 
   ------------------------

   Reference is made to a registration rights undertaking made by Hollinger
Inc. in favour of Canadian Imperial Bank of Commerce ("CIBC") dated October 13,
1995 (the "1995 Agreement") and attached hereto as Schedule A and a
registration rights undertaking dated February 29, 1996 (the "1996 Agreement")
made by Hollinger Inc. and 1159670 Ontario Limited ("Ontario") in favour of
CIBC, The Toronto-Dominion Bank and the Bank of Nova Scotia and attached hereto
as Schedule B.

   Each of the undersigned agree that the 1995 Agreement is hereby amended as
follows:

  (i)   Clause (i), (ii) and (iii) of the first full paragraph of page 2 shall
        be deleted and the following substituted therefor:

         "(i) Hollinger or Ontario or the U.S. Subsidiary is in default under
         any present or future indebtedness or liabilities to the Bank secured
         by the Pledged Securities, (ii) you have or intend to effect
         foreclosure upon the Pledged Securities in accordance with your rights
         under any applicable security documents or to exercise your power of
         sale rights under any applicable security documents, as follows:".

  (ii)  The fourth line of page 2 shall be amended by adding immediately after
        the word "Hollinger" the following ", the U.S. Subsidiary or 1159670
        Ontario Limited ("Ontario").

  (iii) The last full paragraph of the 1995 Agreement shall be deleted in its
        entirety.

   Each of the undersigned agree that the 1996 Agreement is hereby amended
vis-a-vis the undersigned and CIBC as follows:

  (i)   The definition of "Pledged Shares" shall be amended to include 7,539,028
        shares of Class A Common Stock pledged by 3184081 Canada Limited
        ("Canada") to CIBC


<PAGE>   2
                                     - 2 -

        pursuant to a securities pledge agreement dated on or about the date
        hereof, such shares having been transferred directly or indirectly, by
        Hollinger to Canada subject to the 1995 Pledge (as defined in the 1996
        Agreement).

  (ii)  All references to "Hollinger and Ontario" shall be deemed to be
        references to "Hollinger, Ontario, Canada and the U.S. Subsidiary".

  (iii) All references to "Hollinger Inc. or its subsidiaries" shall be
        deemed to be references to "Hollinger, Ontario, Canada and the U.S.
        Subsidiary or their respective subsidiaries".

  (iv)  All references to the "Banks" shall be deemed to be references to the 
        "Banks (including CIBC)".

  (v)   The last full paragraph of page 2 shall be amended by inserting
        immediately after the "," in the second line, the following:  "and the
        U.S. Subsidiary agrees to effect".

  (vi)  The registration referred to in the last full paragraph of page 2 and
        the last full paragraph of page 3 shall be effected no later that 90
        days following the 29th day of February, 1996 provided that any
        amendment to such registration required to effect a registration which
        extends to the 7,539,028 shares of Class A Common Stock pledged by
        Canada as referred to above shall be effected within 60 days of the date
        hereof.

  (vii) The last paragraph of the 1996 Agreement shall be amended by (1) adding
        "and the pledge by Ontario of 14,990,000 shares of Class B Common Stock
        to the Bank pursuant to a securities pledge agreement made by Ontario on
        or about the date hereof" immediately after the "," in the third line,
        (2) adding "as amended by this Agreement" after "1995" in the third
        line; and (3) by deleting the reference to Hollinger in the first line
        on page 5 and substituting therefore "Hollinger, Ontario and the U.S.
        subsidiary".
<PAGE>   3
                               DATED May 24, 1996


HOLLINGER INC.                           HOLLINGER INTERNATIONAL INC.

By:  /s/  C.G. COWAN                     By:  /s/  C.G. COWAN       
    ------------------------                 -------------------------


1159670 ONTARIO LIMITED                  3184081 CANADA LIMITED

By:  /s/  C.G. COWAN                     By:  /s/  C.G. COWAN       
    ------------------------                 -------------------------
<PAGE>   4
                                   Schedule A


                                   Hollinger


                                                       Telephone: (416) 363-8721
                                                             Fax: (416) 364-2088


                                October 13, 1995


Canadian Imperial Bank of Commerce
Commerce Court
Toronto, Canada M5H 3T7

   Re:  Registration Rights Undertaking
        -------------------------------

Gentlemen:

   Upon consummation of the transactions contemplated by the Share Exchange
Agreement dated as of July 19, 1995 ("Share Exchange Agreement") between
Hollinger Inc. ("Hollinger") and Hollinger International Inc., a Delaware
corporation formerly named American Publishing Company (the "U.S. Subsidiary"),
Hollinger owns, as of the date hereof, the following securities issued by the
U.S. Subsidiary:

      (i)   33, 610, 754 shares of Class A Common Stock, par value $.01 per
   share ("Class A Common Stock");

      (ii)  14,990,000 shares of Class B Common Stock, par value $.01 per share
   ("Class B Common Stock"); and

      (iii) 739,500 shares of non-voting Series A Redeemable Convertible
   Preferred Stock, par value $.01 per share ("Series A Preferred Stock").

   This is to confirm our understanding and agreement with respect to certain
registration rights relating to the above shares of Class A Common Stock, the
above shares of Class B Common Stock (and the shares of Class A Common Stock
into which the Class B Common Stock is automatically convertible upon transfer
of such shares to you pursuant to the terms of the Restated Certificate of
Incorporation, as amended, of the U.S.
<PAGE>   5
Canadian Imperial Bank of Commerce
October 13, 1995
Page 2


Subsidiary), and the shares of Class A Common Stock into which the above shares
of Series A Preferred Stock are convertible (collectively, the "Pledged
Securities"), which have been pledged to you to secure indebtedness of
Hollinger and certain affiliated companies now or hereafter outstanding under
existing agreements or arrangements.  The Pledged Securities are "restricted
securities" within the meaning of the U.S.  Securities Act of 1933, as amended
(the "Securities Act"), and may not be sold, transferred or disposed of in the
absence of registration under the Securities Act or an exemption thereunder.

   Accordingly, Hollinger, intending to be legally bound, agrees, if but only
if (i) Hollinger is in default on indebtedness now or hereafter outstanding
under existing agreements or arrangements and secured by the Pledged
Securities, (ii) you have effected foreclosure upon the Pledged Securities in
accordance with applicable law, and (iii) as a result you have duly become the
record owner of the Pledged Securities, as follows:  upon written request from
you, Hollinger agrees to use its reasonable best efforts to cause the U.S.
Subsidiary to effect, at the earliest possible date, the registration under the
Securities Act of all or part of the Pledged Securities (but not less than
5,000,000 shares of Class A Common Stock of the U.S. Subsidiary); provided,
however, that if the transaction to sell Pledged Securities referred to in your
written request may be accomplished pursuant to an applicable exemption from
registration under the Securities Act, Hollinger shall not be required to cause
the U.S. Subsidiary to effect the registration of such Pledged Securities.
Registration shall be on such appropriate form of the Securities Exchange
Commission as shall be reasonably selected by the U.S. Subsidiary.
Registration may be effected, if requested, by means of a "shelf registration"
pursuant to Rule 415 under the Securities Act (but only if the U.S. Subsidiary
is then eligible to use a shelf registration and the appropriate registration
form is then available to the U.S. Subsidiary).  Hollinger will pay all
registration expenses (other than any underwriting discounts or commissions) in
connection with a registration requested hereunder.

   It is understood and agreed that this undertaking by Hollinger to use its
reasonable best efforts to cause the registration of the Pledged Securities by
the U.S. Subsidiary is subject to (i) compliance by Hollinger with its
obligations under the Share Exchange Agreement (including without limitation
Sections 5(h) and 5(i) thereof), and (ii) such other terms,
<PAGE>   6
Canadian Imperial Bank of Commerce
October 13, 1995
Page 3


provisions and procedures which would customarily be contained in a standard
registration rights agreement.

                                           Very truly yours,

                                           Hollinger Inc.

                                           /s/ CHARLES G. COWAN
Acknowledged and agreed to this            ------------------------
13th day of October, 1995.                 Vice-President &
                                           Secretary


CANADIAN IMPERIAL BANK OF COMMERCE

By   /s/ PHILIP BASSETT           
     --------------------------------
Title  Director                   
     --------------------------------
<PAGE>   7
                                   Schedule B


                                 HOLLINGER INC.


                                                               February 29, 1996


Canadian Imperial Bank of Commerce
Commerce Court West, 7th Floor
Toronto, Canada M5H 3T7

The Toronto-Dominion Bank
55 King Street West, 8th Floor
Toronto, Canada M5K 1H1

The Bank of Nova Scotia
44 King Street West, 16th Floor
Toronto, Canada M5H 1H1

   Re:   Registration Rights
         -------------------

Gentlemen:

   Hollinger Inc. and certain of its subsidiaries ("Hollinger") own, as of the
date hereof, the following securities issued by Hollinger International Inc., a
Delaware corporation (the "U.S. Subsidiary"):

      (i)   33,610,754 shares of Class A Common Stock, par value $.01 per share
   ("Class A Common Stock");

     (ii)  14,900,000 shares of Class B Common Stock, par value $.01 per share
   ("Class B Common Stock"); and

     (iii) 739,500 shares of non-voting Series A Redeemable Convertible
   Preferred Stock, par value $.01 per share ("Series A Preferred Stock").

   All the foregoing securities are currently pledged to Canadian Imperial Bank
of Commerce ("CIBC") pursuant to a Hypothecation of Specific Securities dated
October 13, 1995 made by Hollinger in favor of CIBC (the "1995 Pledge") to
secure obligations of Hollinger Inc. to CIBC, subject to the following actions
which are effective as of the date hereof:

     (x)  Hollinger Inc. and CIBC have agreed, in connection with the
   execution and delivery of a new bank credit facility in the amount of
   Cdn.$90 million ("New Bank Facility"), to permit the transfer of up to
   16,000,000 shares of Class A Common Stock and 14,990,000 shares of Class B
   Common Stock
<PAGE>   8
Canadian Imperial Bank of Commerce
The Toronto-Dominion Bank
The Bank of Nova Scotia
February 29, 1996
Page 2


   owned by Hollinger Inc. to 1159670 Ontario Limited ("Ontario"), a wholly-
   owned subsidiary of Hollinger Inc., subject to the 1995 Pledge, and to cause
   Ontario to pledge up to 16,000,000 shares of Class A Common Stock to CIBC as
   Agent for itself and The Toronto-Dominion Bank and Bank of Nova Scotia
   (collectively, the "Banks") to secure Ontario's obligations under the New
   Bank Facility;

     (y)  All remaining outstanding shares of Class A Common Stock
   owned by Hollinger Inc., together with the Series A Preferred Stock owned by
   Hollinger Inc., will continue to be subject to pledge to CIBC pursuant to
   the 1995 Pledge.

All shares of Class A Common Stock owned by Hollinger Inc. or Ontario or
3184081 Canada Limited and subject to pledge are hereinafter called the
"Pledged Shares".

   This is to confirm our understanding and agreement with respect to certain
registration rights relating to the Pledged Shares.  The Pledged Shares are
"restricted securities " within the meaning of the U.S. Securities Act of 1933,
as amended (the "Securities Act"), and may not be sold, transferred or disposed
of in the absence of registration under the Securities Act or an exemption
thereunder.  The Banks acknowledge that they do not possess the Pledged Shares
with a view to any sale or distribution thereof within the meaning of the
Securities Act and the rules and regulations thereunder.

   The Banks confirm that they have had access to all information concerning
the business and financial condition of the U.S. Subsidiary that each of the
Banks requires.  Without limiting the foregoing, the Banks have been provided
copies of the principal organizational documents of the U.S. Subsidiary,
including the Restated Certificate of Incorporation, as filed on May 10, 1994
with the Secretary of State of Delaware, the Certificate of Amendment of
Restated Certificate of Incorporation as filed on October 13, 1995.

<TABLE>
<S>     <C>
   Accordingly, each of Hollinger and Ontario, intending to be legally bound, 
agrees to use its reasonable best efforts to cause the U.S. Subsidiary to effect, 
at the earliest possible date (but in any case not later than 90 days
following the date of this agreement) the registration under the Securities Act
of all of the Pledged Shares.  Registration shall be effected by means of a
"shelf registration" pursuant to Rule 415 under the Securities Act.  Hollinger
will pay all registration expenses (other than any underwriting discounts or
commissions) in connection with the registration requested hereunder.  All
selling expenses related to the Pledged Shares, including reasonable internal
costs and expenses incurred by each of you, shall be borne by Hollinger and
Ontario.
</TABLE>

   The U.S. Subsidiary may terminate such registration (x) 30 days after the
date the Banks no longer hold shares of Class A Common Stock exceeding in the
aggregate one percent
<PAGE>   9
Canadian Imperial Bank of Commerce
The Toronto-Dominion Bank
The Bank of Nova Scotia
February 29, 1996
Page 3


of the outstanding shares of Class A Common Stock (and securities convertible
into Class A Common Stock) or (y) such earlier date which concludes the holding
period for Class A Common Stock held by persons that are not deemed to be
"affiliates" of the U.S. Subsidiary as specified in Rule 144 promulgated by the
U.S.  Securities and Exchange Commission ("Commission") as then in effect.  In
addition, upon the payment or satisfaction in full of the obligations of
Hollinger Inc. or its subsidiaries, as the case may be, to the Banks under all
credit arrangements secured by the Pledged Shares and the termination of such
credit arrangements, the U.S. Subsidiary may terminate such registration.

   In connection with the registration and any subsequent offers and sales of
the Pledged Shares pursuant thereto, each of you shall furnish to the U.S.
Subsidiary such information regarding the Pledged Shares to be owned by you
after default by Hollinger under the obligations secured by such shares, the
lending arrangements and other circumstances related to the Pledged Shares, the
distribution proposed by you and other related matters as the U.S. Subsidiary
may request and as shall be required in connection with the registration,
qualification or compliance with the Securities Act and applicable state
securities laws.

   Each of you covenants that you will comply with the prospectus delivery
requirements of the Securities Act with respect to the registration statement
to be filed pursuant to this letter agreement.  Furthermore, each of you agrees
to make customary representations and warranties to Hollinger and the U.S.
Subsidiary and the underwriters, agents, or distributors, if any, in form,
substance and scope as are customarily made as to ownership of stock by selling
stockholders in underwritten public offerings, but you shall not be required to
make any representation or warranty as to the accuracy or completeness of the
registration statement (except for written information furnished to the U.S.
Subsidiary expressly for use therein).  In addition, each of you agrees that
you will refrain from offering for sale or selling any Pledged Shares if you
are not notified by Hollinger or the U.S. Subsidiary that the registration
statement is not accurate or is not complete in all material respects, and
Hollinger shall notify you of any material fact or change which results in the
registration statement not being accurate or complete in all material respects
from time to time as any such fact or change occurs.  You may make sales of the
Pledged Shares after notification by the U.S. Subsidiary that the registration
statement is current or, based on an opinion of counsel for the U.S.
Subsidiary, that the Pledged Shares could be sold in compliance with the
Securities Act and the Securities Exchange Act of 1934, as amended, without
disclosure of any nonpublic information which may be the subject of the
notification.

   With respect to the Class B Common Stock and the Series A Preferred Stock of
the U.S. Subsidiary owned by Hollinger or Ontario which are subject to the 1995
Pledge, the registration rights undertaking by Hollinger dated October 13, 1995
shall
<PAGE>   10
Canadian Imperial Bank of Commerce
The Toronto-Dominion Bank
The Bank of Nova Scotia
February 29, 1996
Page 4


remain in full force and effect and Hollinger and CIBC agree to remain 
bound by its terms.

                                           Very truly yours,

                                           HOLLINGER INC.

                                           By  /s/ PETER Y. ATKINSON 
                                               --------------------------


                                           1159670 ONTARIO LIMITED

                                           By  /s/ PETER Y. ATKINSON
                                               --------------------------


Acknowledged and agreed to this
29th day of February, 1996.

CANADIAN IMPERIAL BANK OF COMMERCE

By /s/ STEVEN SLOANE             
   ----------------------------------
Title
      -------------------------------


THE TORONTO-DOMINION BANK

By /s/ MICHAEL COLLINS           
   ----------------------------------

   /s/ JOHN COOMBS               
   ----------------------------------

Title
      -------------------------------


THE BANK OF NOVA SCOTIA

By /s/ KEN LEHNER                
   ----------------------------------
Title
      -------------------------------

<PAGE>   1
                                                                   Exhibit 99.06


                          SECURITIES PLEDGE AGREEMENT


TO:  CANADIAN IMPERIAL BANK OF COMMERCE
     Commerce Court West - 7th Floor
     Toronto, Ontario
     M5L 1A2

  WHEREAS in order to secure the due payment and performance of the Obligations
(as defined below), the undersigned (the "Debtor") has agreed to pledge the
Pledged Securities (as defined below) to Canadian Imperial Bank of Commerce
(the "Bank");

  THEREFORE, for good and valuable consideration, the receipt and sufficiency
of which are conclusively acknowledged by the parties hereto, the Debtor hereby
agrees as follows:

1. DEFINED TERMS.  In this Agreement, the following words have the following
meanings:

  "Companies" means the corporations, companies, partnerships, limited
partnerships, trusts and other entities listed under the heading "Companies" in
Schedule "A" and their respective successors;

  "Default" means a failure to pay any of the Obligations when due;

  "Lien" means a mortgage, hypothec, title retention, pledge, lien, charge,
security interest or other encumbrance whatsoever, whether fixed or floating
and howsoever created or arising;

  "Obligations" means all present and future indebtedness and liabilities of
every kind, nature and description (whether direct or indirect, joint or
several, absolute or contingent, matured or unmatured) of the Debtor to the
Bank under or pursuant to the guarantee dated the date hereof made by the
Debtor in favour of the Bank in respect of Hollinger International Inc. and any
unpaid balance thereof; and

  "Pledged Securities" means the securities listed under the heading "Pledged
Securities" in Schedule "A", together with any other securities in the capital
of the Companies owned by the Debtor from time to time (other than 15,950,000
Class A Common Stock of Hollinger International Inc. presently owned by the
Debtor and evidenced or represented by share certificate #A0358).


<PAGE>   2
                                     - 2 -

2. PLEDGE.  As general and continuing collateral security for the payment and
performance of all Obligations, the Debtor hereby assigns and pledges to and in
favour of the Bank, and the Debtor hereby grants to the Bank a continuing
security interest in the following (collectively, the "Collateral"):  (i) the
Pledged Securities, together with any replacements thereof and substitutions
therefor, and all certificates and instruments evidencing or representing such
securities; (ii) all dividends, whether in cash, kind or stock, received or
receivable upon or in respect of any of the Pledged Securities and all moneys
or other property payable or paid on account of any return or repayment of
capital in respect of any of the Pledged Securities or otherwise distributed in
respect thereof or which will in any way be charged to, or payable or paid out
of, the capital of any of the Companies on account of the Pledged Securities;
(iii) all other property that may at any time be received or receivable by or
otherwise distributed to the Debtor in respect of, or in substitution for, or
in exchange for, any of the foregoing; and (iv) all cash, securities and other
proceeds of the foregoing and all rights and interests of the Debtor in respect
thereof or evidenced thereby, including all moneys received from time to time
by the Debtor in connection with the sale or other disposition of any of the
Pledged Securities; provided, however, that the Debtor will not sell or
otherwise dispose of any of the Pledged Securities or purport to do any of the
foregoing without the prior written consent of the Bank.

3. DELIVERY OF PLEDGED SECURITIES.  The certificates representing the Pledged
Securities duly endorsed by the appropriate person in blank for transfer or
accompanied by powers of attorney satisfactory to the Bank will forthwith be
delivered to and remain in the custody of the Bank or its nominee.  All Pledged
Securities may, at the option of the Bank, be registered in the name of the
Bank or its nominee.  If the Bank so requests, the certificates representing
the Pledged Securities will also be guaranteed by a Canadian chartered bank.

4. REPRESENTATIONS AND WARRANTIES.  The Debtor hereby represents and warrants
to the Bank and acknowledges that the Bank is relying thereon, notwithstanding
any investigation by the Bank or otherwise, that:  (i) the Debtor is the lawful
owner of the Collateral, free and clear of any and all Liens or claims of
others other than any Lien granted by the Debtor to the Bank hereunder or Liens
in favour of Canadian Imperial Bank of Commerce, with full right to deliver,
assign, pledge and charge the Collateral to the Bank pursuant hereto; (ii) the
Pledged Securities represent all of the issued and outstanding shares in the
capital of each of the Companies held by the Debtor (other than 15,950,000
Class A Common Stock of Hollinger International Inc. referred to in the
definition of "Pledged Securities"); (iii) the Pledged Securities are validly
issued, fully paid and non-assessable; (iv) there is no existing agreement,
option,
<PAGE>   3
                                     - 3 -

right or privilege capable of becoming an agreement or option pursuant to which
the Debtor would be required to sell or otherwise dispose of any of the Pledged
Securities; (v) except as otherwise agreed by the Bank in writing, the Liens
granted by the Debtor to the Bank pursuant to this Agreement constitute Liens
on the Collateral in favour of the Bank which are prior to all other Liens on
the Collateral other than Liens in favour of Canadian Imperial Bank of
Commerce, whether created by the Debtor or any other Person, and in existence
on the date hereof; (vi) the Debtor has the power and authority and the legal
right to execute and deliver, to perform its obligations under, and to grant
the Lien on the Collateral pursuant to, this Agreement and the Debtor has taken
all necessary corporate action to authorize its execution, delivery and
performance of, and grant of the Lien on the Collateral pursuant to, this
Agreement; (vii) this Agreement constitutes a legal, valid and binding
obligation of the Debtor, enforceable in accordance with its terms, except as
enforceability may be limited by bankruptcy, insolvency, reorganization,
moratorium or similar laws affecting the enforcement of creditors' rights
generally and by general principles of equity; (viii) the execution, delivery
and performance of this Agreement will not violate any provision or requirement
of any law or contractual obligation of the Debtor and will not result in the
creation or imposition of any Lien on any of the properties or revenues of the
Debtor pursuant to any requirement of law or contractual obligation of the
Debtor; (ix) no consent or authorization of, filing with, or other act by or in
respect of, any arbitrator or governmental authority and no consent of any
other person (including any shareholder or creditor of the Debtor), is required
in connection with the execution, delivery, performance, validity or
enforceability of this Agreement, except for such as have been obtained or made
and are in full force and effect, and the terms of which have been disclosed to
the Bank; and (x) no litigation, investigation or proceeding of or before any
arbitrator or governmental authority is pending or, to the knowledge of the
Debtor, threatened by or against the Debtor or against any of its properties or
revenues which may materially adversely affect the business, property or
financial or other condition of the Debtor.

5. COVENANTS.  The Debtor covenants and agrees with the Bank that:  (i) at any
time and from time to time, upon the written request of the Bank, and at the
sole expense of the Debtor, the Debtor will promptly and duly execute and
deliver such further instruments and documents and take such further action as
the Bank may request for the purpose of obtaining or preserving the full
benefits of this Agreement and of the rights and powers herein granted,
including the filing or execution of any financing or financing change
statements under any applicable legislation in effect in any jurisdiction with
respect to the Liens created hereby; (ii) the Debtor authorizes the Bank to
file any such financing or financing change statement without the
<PAGE>   4
                                     - 4 -

signature of the Debtor to the extent permitted by applicable law; (iii) the
Debtor will not create, incur or permit to exist, but will defend the
Collateral against, and will take such other action as is necessary to remove,
any Lien or claim on or to the Collateral, other than the Liens created hereby
and Liens in favour of Canadian Imperial Bank of Commerce and other than as
permitted in writing by the Bank; (iv) the Debtor will not sell, transfer,
lease or otherwise dispose of any of the Collateral except as permitted in
writing by the Bank; and (v) the Debtor will ensure that at the request of the
Bank, all Pledged Securities are registered in the name of the Bank or its
nominee, that the certificates representing the Pledged Securities will be
forthwith delivered to and remain in the custody of the Bank or its nominee,
and that all certificates, instruments or other documents representing or
evidencing any Pledged Securities acquired or issued subsequent to the date
hereof will be registered in the name of the Bank or its nominee and will
forthwith after issuance be delivered to, and remain in the custody of, the
Bank or its nominee.

6. RIGHTS AND DUTIES OF BANK.  The Bank will have and be entitled to exercise
all such powers hereunder as are specifically delegated to the Bank by the
terms hereof, together with such powers as are incidental thereto.  The Bank
may execute any of its duties hereunder by or through agents and will be
entitled to retain counsel and to act in reliance upon the advice of such
counsel concerning all matters pertaining to its duties hereunder.  The Bank
and any nominee on its behalf will be bound to exercise in the holding of the
Pledged Securities and other Collateral only the same degree of care as it
would exercise with respect to similar property of its own held in the same
place.  Neither the Bank, nor any nominee acting on behalf of the Bank, nor any
director, officer or employee of the Bank or such nominee, will be liable for
any action taken or admitted to be taken by it hereunder or in connection
herewith except for its own gross negligence or wilful misconduct.

7. VOTING RIGHTS.  Unless a Default has occurred and is continuing, the Debtor
will be entitled to exercise all voting power from time to time exercisable in
respect of the Pledged Securities and give consents, waivers and ratifications
in respect thereof.  Immediately upon the occurrence and during the continuance
of any Default, all such rights of the Debtor to vote and give consents,
waivers and ratifications will cease and the Bank will be entitled to exercise
all such voting rights and to give all consents, waivers and ratifications as
permitted by the Bank.

8. DIVIDENDS.  Unless a Default has occurred and is continuing, the Debtor
will, subject to any agreement with the Bank to the contrary, be entitled to
receive any and all cash dividends and other distributions on the Pledged
Securities which it is
<PAGE>   5
                                     - 5 -

otherwise entitled to receive.  If a Default has occurred and is continuing,
the Bank will have the sole and exclusive right and authority to receive and
retain the dividends and other distributions which the Debtor would otherwise
be authorized to receive.  Any money and other property paid over to or
received by the Bank pursuant to the provisions of this Section 8 will be
retained by the Bank as additional Collateral hereunder and be applied in
accordance with the provisions hereof.

9. REMEDIES.  If a Default has occurred and is continuing, the Bank may,
without notice to or the consent of the Debtor or any other person (other than
as required by applicable law), take all or any of the following actions:

(a)  transfer all or any part of the Collateral into the name of the Bank or
     any nominee on behalf of the Bank, with or without disclosing that such
     Collateral is subject to the Lien hereunder;

(b)  notify any parties obligated on any of the Collateral to make payment to
     the Bank of any amounts due or to become due thereunder;

(c)  exercise any and all rights of conversion, exchange, subscription or any
     other rights, privileges or options pertaining to any of the Pledged
     Securities as if it were the absolute owner thereof;

(d)  from time to time realize upon, collect, sell, transfer, assign, give
     options to purchase, or otherwise dispose of and deliver the Pledged
     Securities and other Collateral, or any part thereof, in such a manner as
     may seem to it advisable, and for the purposes thereof each and every
     requirement relating thereto and prescribed by law or otherwise is hereby
     waived to the extent permitted by law;

(e)  enforce collection of any of the Collateral by suit or otherwise, and
     surrender, release or exchange all or any part of any property in addition
     to the Collateral, securing any of the Obligations, or compromise or
     extend or renew for any period (whether or not longer than the original
     period) any obligations of any nature of any party with respect to any
     property; and

(f)  to the extent permitted by applicable law, the Bank may purchase any or
     all of the Pledged Securities and other Collateral, whether in connection
     with a sale made under the power of sale herein contained or pursuant to
     judicial proceedings or otherwise;
<PAGE>   6
                                     - 6 -

provided, however, that the Bank will not be bound to deal with the Pledged
Securities and other Collateral as aforesaid, and will not be liable for any
loss which may be occasioned by any failure to do so and no action of the Bank
permitted hereunder will impair or affect any rights of the Bank in and to the
Collateral.

10.  APPLICATION OF PROCEEDS.  After payment of expenses as provided in Section
11 hereof, the balance of any proceeds received by the Bank in or in connection
with realizing, collecting, selling, transferring, delivering or obtaining
payment of the Collateral or any part thereof may be held by the Bank and may,
as and when the Bank thinks fit, be applied on account of such part of the
Obligations as to the Bank seems best, without prejudice to the Bank's claims
upon the Debtor for any deficiency.

11.  PAYMENT OF EXPENSES.  The Bank may charge on its own behalf and also pay
to others all out-of-pocket expenses of the Bank and others retained by the
Bank, incurred in connection with realizing, collecting, selling, transferring,
delivering or obtaining payment of the Pledged Securities or any other
Collateral or any part thereof, or in connection with the administration or
amendment of this Agreement or incidental to the care, safe keeping, or
otherwise of any and all of the Collateral, and may deduct the amount of such
sums from any proceeds of the Collateral.  The Debtor agrees to indemnify and
hold harmless the Bank from and against any and all liability incurred by the
Bank, or any nominee, agent or employees of the Bank hereunder or in connection
herewith, unless such liability was due to wilful misconduct or gross
negligence on the part of the Bank or such nominee or agent.

12.  ASSIGNMENT.  This Agreement will be binding upon the Debtor and its
successors and permitted assigns and will enure to the benefit of and be
enforceable by the Bank and its respective successors and assigns.  The Debtor
will not assign all or any part of this Agreement without the Bank's prior
written consent.

13.  NO WAIVER; CUMULATIVE REMEDIES.  The Bank will not by any act, delay,
indulgence, omission or otherwise be deemed to have waived any right or remedy
hereunder or to have acquiesced in any breach of any of the terms and
conditions hereof.  No failure to exercise, nor any delay in exercising, on the
part of the Bank, any right, power or privilege hereunder will operate as a
waiver thereof.

14.  COMMUNICATION.  All communications provided for or permitted hereunder
shall be in writing, personally delivered to an officer or other responsible
employee of the addressee or sent by registered mail, charges prepaid, or by
telecopy, to the address or telecopy number set forth opposite the name of the
Debtor in
<PAGE>   7
                                     - 7 -

the execution pages of this Agreement, in the case of the Debtor, and to
Canadian Imperial Bank of Commerce, Head Office, Commerce Court West, 7th
Floor, Toronto, Ontario M5L 1A2 (Attention:  Vice-President, Global Media &
Telecommunications) (Telecopy:  (416) 980-2801), in the case of the Bank, or to
such other address as the applicable party hereto may from time to time
designate to the other in such manner.  Any communication so personally
delivered shall be deemed to have been validly and effectively given on the
date of such delivery.  Communications so sent by telecopy shall be deemed to
have been validly and effectively given on the business day next following the
day on which it is sent.  Communications so sent by mail shall be deemed to
have been validly and effectively given on the fifth business day next
following the day on which it is sent.

15.  DEALINGS BY BANK.  The Bank may grant extensions of time and other
indulgences, take and give up security, accept compositions, grant releases and
discharges and otherwise deal with the Debtor and any third party having
dealings with the Debtor, and with the Collateral or any part thereof, and with
other security and sureties, as the Bank may see fit, all without prejudice to
the Obligations or to the rights of the Bank under this Agreement.  The Bank
will be accountable only for amounts that the Bank actually receives as a
result of the exercise of such powers, and neither the Bank nor any of its
officers, directors, employees or agents will be responsible to the Debtor for
any act or failure to act hereunder, except for its or their own gross
negligence or wilful misconduct.

16.  NON-EXCLUSIVITY OF REMEDIES.  This Agreement and the Liens arising
hereunder are in addition to and not in substitution for any other security now
or hereafter held by the Bank in respect of the Debtor, the Obligations or the
Collateral.  No remedy for the enforcement of the rights of the Bank hereunder
will be exclusive of or dependent on any other such remedy but any one or more
of such remedies may from time to time be exercised independently or in
combination.

17.  POWER OF ATTORNEY. The Debtor hereby irrevocably constitutes and appoints
the Bank and any officer or agent thereof, with full power of substitution, as
its true and lawful attorney-in-fact, with full irrevocable power and authority
in the place and stead of the Debtor and in the name of the Debtor or in its
own name, from time to time in the Bank's discretion, for the purpose of
carrying out the terms of this Agreement, to take any and all appropriate
action, to do, make and execute any and all statements, acts, matters,
documents, instruments and things which may be necessary or desirable to
accomplish the purposes of this Agreement and from time to time to exercise all
rights and powers and to perform all acts of ownership in respect to the
Pledged Securities to the same extent as the Debtor might have done were it not
for this Agreement.  The Debtor hereby ratifies
<PAGE>   8
                                     - 8 -

all that said attorneys will lawfully do or cause to be done by virtue hereof.
This power of attorney is a power coupled with an interest and will be
irrevocable until the Obligations have been paid and performed in full.

18.  NO MERGER.  Neither the taking and holding of the Pledged Securities and
other Collateral nor the obtaining of any judgment by the Bank will operate as
a merger of any Obligation or any other indebtedness or liability of the Debtor
to the Bank or operate to prejudice the security constituted by this Agreement.

19.  SEVERABILITY.  Any provision of this Agreement which is prohibited or
unenforceable in any jurisdiction will, as to such jurisdiction, be ineffective
to the extent of such prohibition or unenforceability without invalidating the
remaining provisions hereof and any such prohibition or unenforceability in any
jurisdiction will not invalidate or render unenforceable such provision in any
other jurisdiction.

20.  GOVERNING LAW.  This Agreement will be governed by and construed in
accordance with the laws of Ontario.

21.  SURVIVAL OF REPRESENTATIONS AND WARRANTIES.  All agreements,
representations, warranties and covenants made by or on behalf of the Debtor
herein are material, will be considered to have been relied upon by the Bank
and will survive the execution and delivery of this Agreement or any
investigation made at any time by or on behalf of the Bank and any disposition
or payment of the Obligations until repayment in full thereof.

22.  ACKNOWLEDGEMENT OF RECEIPT.  The Debtor acknowledges receipt of an
executed copy of this Agreement.

DATED:  May 24, 1996.

ADDRESS                                3184081 CANADA LIMITED

10 Toronto Street
Toronto, Ontario                       By:  /s/ C.G. COWAN
M5K 1N2                                    --------------------
                                       Name:   Charles G. Cowan
Attention:  President                  Title:  Vice President &
                                               Secretary
Facsimile:  (416) 364-2088
                                       By:   /s/ J.A. BOULTBEE
                                           --------------------
                                       Name:   J. A. Boultbee
                                       Title:  President
Schedule A - Pledged Securities
<PAGE>   9



                                  SCHEDULE "A"
<TABLE>
<CAPTION>
                                                           Certificate
Companies                         Pledged Securities          Number        No.       Class  
- ---------                         ------------------       -----------      ---       -----  
<S>                                <C>                        <C>          <C>     <C>
1.  Hollinger International Inc.   7,539,028 Class A          A0499                Common Stock
</TABLE>

<PAGE>   1
                                                             EXHIBIT 99.07


                          SECURITIES PLEDGE AGREEMENT


TO:  CANADIAN IMPERIAL BANK OF COMMERCE
     Commerce Court West - 7th Floor
     Toronto, Ontario
     M5L 1A2


  WHEREAS in order to secure the due payment and performance of the Obligations
(as defined below), the undersigned (the "Debtor") has agreed to pledge the
Pledged Securities (as defined below) to Canadian Imperial Bank of Commerce
(the "Bank");

  THEREFORE, for good and valuable consideration, the receipt and sufficiency
of which are conclusively acknowledged by the parties hereto, the Debtor hereby
agrees as follows:

1. DEFINED TERMS.  In this Agreement, the following words have the following
meanings:

  "Companies" means the corporations, companies, partnerships, limited
partnerships, trusts and other entities listed under the heading "Companies" in
Schedule "A" and their respective successors;

  "Default" means a failure to pay any of the Obligations when due;

  "Lien" means a mortgage, hypothec, title retention, pledge, lien, charge,
security interest or other encumbrance whatsoever, whether fixed or floating
and howsoever created or arising;

  "Obligations" means all present and future indebtedness and liabilities of
every kind, nature and description (whether direct or indirect, joint or
several, absolute or contingent, matured or unmatured) of the Debtor to the
Bank under or pursuant to the guarantee dated the date hereof made by the
Debtor in favour of the Bank in respect of Hollinger International Inc. and any
unpaid balance thereof; and

  "Pledged Securities" means the securities listed under the heading "Pledged
Securities" in Schedule "A", together with any other securities in the capital
of the Companies owned by the Debtor from time to time.

2.  PLEDGE.  As general and continuing collateral security for the payment and
performance of all Obligations, the Debtor hereby assigns and pledges to and in
favour of the Bank, and the Debtor hereby grants to the Bank a continuing
security interest in the following (collectively, the "Collateral"):  (i) the
Pledged 
<PAGE>   2


                                      -2-

Securities, together with any replacements thereof and substitutions
therefor, and all certificates and instruments evidencing or representing such
securities; (ii) all dividends, whether in cash, kind or stock, received or
receivable upon or in respect of any of the Pledged Securities and all moneys
or other property payable or paid on account of any return or repayment of
capital in respect of any of the Pledged Securities or otherwise distributed in
respect thereof or which will in any way be charged to, or payable or paid out
of, the capital of any of the Companies on account of the Pledged Securities;
(iii) all other property that may at any time be received or receivable by or
otherwise distributed to the Debtor in respect of, or in substitution for, or
in exchange for, any of the foregoing; and (iv) all cash, securities and other
proceeds of the foregoing and all rights and interests of the Debtor in respect
thereof or evidenced thereby, including all moneys received from time to time
by the Debtor in connection with the sale or other disposition of any of the
Pledged Securities; provided, however, that the Debtor will not sell or
otherwise dispose of any of the Pledged Securities or purport to do any of the
foregoing without the prior written consent of the Bank.

3. DELIVERY OF PLEDGED SECURITIES.  The certificates representing the Pledged
Securities duly endorsed by the appropriate person in blank for transfer or
accompanied by powers of attorney satisfactory to the Bank will forthwith be
delivered to and remain in the custody of the Bank or its nominee.  All Pledged
Securities may, at the option of the Bank, be registered in the name of the
Bank or its nominee.  If the Bank so requests, the certificates representing
the Pledged Securities will also be guaranteed by a Canadian chartered bank.

4. REPRESENTATIONS AND WARRANTIES.  The Debtor hereby represents and warrants
to the Bank and acknowledges that the Bank is relying thereon, notwithstanding
any investigation by the Bank or otherwise, that:  (i) the Debtor is the lawful
owner of the Collateral, free and clear of any and all Liens or claims of
others other than any Lien granted by the Debtor to the Bank hereunder or Liens
in favour of Canadian Imperial Bank of Commerce, with full right to deliver,
assign, pledge and charge the Collateral to the Bank pursuant hereto; (ii) the
Pledged Securities represent all of the issued and outstanding shares in the
capital of each of the Companies held by the Debtor; (iii) the Pledged
Securities are validly issued, fully paid and non-assessable; (iv) there is no
existing agreement, option, right or privilege capable of becoming an agreement
or option pursuant to which the Debtor would be required to sell or otherwise
dispose of any of the Pledged Securities; (v) except as otherwise agreed by the
Bank in writing, the liens granted by the Debtor to the Bank pursuant to this
Agreement constitute Liens on the Collateral in favour of the Bank which are
prior to all other Liens on the Collateral other than Liens in favour of
Canadian 

<PAGE>   3
                                      -3-

Imperial Bank of Commerce, whether created by the Debtor or any other
Person, and in existence on the date hereof; (vi) the Debtor has the power and
authority and the legal right to execute and deliver, to perform its
obligations under, and to grant the Lien on the Collateral pursuant to, this
Agreement and the Debtor has taken all necessary corporate action to authorize
its execution, delivery and performance of, and grant of the Lien on the
Collateral pursuant to, this Agreement; (vii) this Agreement constitutes a
legal, valid and binding obligation of the Debtor, enforceable in accordance
with its terms, except as enforceability may be limited by bankruptcy,
insolvency, reorganization, moratorium or similar laws affecting the
enforcement of creditors' rights generally and by general principles of equity;
(viii) the execution, delivery and performance of this Agreement will not
violate any provision or requirement of any law or contractual obligation of
the Debtor and will not result in the creation or imposition of any Lien on any
of the properties or revenues of the Debtor pursuant to any requirement of law
or contractual obligation of the Debtor; (ix) no consent or authorization of,
filing with, or other act by or in respect of, any arbitrator or governmental
authority and no consent of any other person (including any shareholder or
creditor of the Debtor), is required in connection with the execution,
delivery, performance, validity or enforceability of this Agreement, except for
such as have been obtained or made and are in full force and effect, and the
terms of which have been disclosed to the Bank; and (x) no litigation,
investigation or proceeding of or before any arbitrator or governmental
authority is pending or, to the knowledge of the Debtor, threatened by or
against the Debtor or against any of its properties or revenues which may
materially adversely affect the business, property or financial or other
condition of the Debtor.

5. COVENANTS.  The Debtor covenants and agrees with the Bank that:  (i) at any
time and from time to time, upon the written request of the Bank, and at the
sole expense of the Debtor, the Debtor will promptly and duly execute and
deliver such further instruments and documents and take such further action as
the Bank may request for the purpose of obtaining or preserving the full
benefits of this Agreement and of the rights and powers herein granted,
including the filing or execution of any financing or financing change
statements under any applicable legislation in effect in any jurisdiction with
respect to the Liens created hereby; (ii) the Debtor authorizes the Bank to
file any such financing or financing change statement without the signature of
the Debtor to the extent permitted by applicable law; (iii) the Debtor will not
create, incur or permit to exist, but will defend the Collateral against, and
will take such other action as is necessary to remove, any Lien or claim on or
to the Collateral, other than the Liens created hereby and Liens in favour of
Canadian Imperial Bank of Commerce and other than as permitted in writing by
the Bank; (iv) the Debtor will not sell, 

<PAGE>   4
                                      -4-

transfer, lease or otherwise dispose of any of the Collateral except as
permitted in writing by the Bank; and (v) the Debtor will ensure that at the
request of the Bank, all Pledged Securities are registered in the name of the
Bank or its nominee, that the certificates representing the Pledged Securities
will be forthwith delivered to and remain in the custody of the Bank or its
nominee, and that all certificates, instruments or other documents representing
or evidencing any Pledged Securities acquired or issued subsequent to the date
hereof will be registered in the name of the Bank or its nominee and will
forthwith after issuance be delivered to, and remain in the custody of, the Bank
or its nominee.

6. RIGHTS AND DUTIES OF BANK.  The Bank will have and be entitled to exercise
all such powers hereunder as are specifically delegated to the Bank by the
terms hereof, together with such powers as are incidental thereto.  The Bank
may execute any of its duties hereunder by or through agents and will be
entitled to retain counsel and to act in reliance upon the advice of such
counsel concerning all matters pertaining to its duties hereunder.  The Bank
and any nominee on its behalf will be bound to exercise in the holding of the
Pledged Securities and other Collateral only the same degree of care as it
would exercise with respect to similar property of its own held in the same
place.  Neither the Bank, nor any nominee acting on behalf of the Bank, nor any
director, officer or employee of the Bank or such nominee, will be liable for
any action taken or admitted to be taken by it hereunder or in connection
herewith except for its own gross negligence or wilful misconduct.

7. VOTING RIGHTS.  Unless a Default has occurred and is continuing, the Debtor
will be entitled to exercise all voting power from time to time exercisable in
respect of the Pledged Securities and give consents, waivers and ratifications
in respect thereof.  Immediately upon the occurrence and during the continuance
of any Default, all such rights of the Debtor to vote and give consents,
waivers and ratifications will cease and the Bank will be entitled to exercise
all such voting rights and to give all consents, waivers and ratifications as
permitted by the Bank.

8. DIVIDENDS.  Unless a Default has occurred and is continuing, the Debtor
will, subject to any agreement with the Bank to the contrary, be entitled to
receive any and all cash dividends and other distributions on the Pledged
Securities which it is otherwise entitled to receive.  If a Default has
occurred and is continuing, the Bank will have the sole and exclusive right and
authority to receive and retain the dividends and other distributions which the
Debtor would otherwise be authorized to receive.  Any money and other property
paid over to or received by the Bank pursuant to the provisions of this Section
8 will be 
<PAGE>   5
                                      -5-

retained by the Bank as additional Collateral hereunder and be
applied in accordance with the provisions hereof.

9. REMEDIES.  If a Default has occurred and is continuing, the Bank may,
without notice to or the consent of the Debtor or any other person (other than
as required by applicable law), take all or any of the following actions:

(a)  transfer all or any part of the Collateral into the name of the Bank or
     any nominee on behalf of the Bank, with or without disclosing that such
     Collateral is subject to the Lien hereunder;

(b)  notify any parties obligated on any of the Collateral to make payment to
     the Bank of any amounts due or to become due thereunder;

(c)  exercise any and all rights of conversion, exchange, subscription or any
     other rights, privileges or options pertaining to any of the Pledged
     Securities as if it were the absolute owner thereof;

(d)  from time to time realize upon, collect, sell, transfer, assign, give
     options to purchase, or otherwise dispose of and deliver the Pledged
     Securities and other Collateral, or any part thereof, in such a manner as
     may seem to it advisable, and for the purposes thereof each and every
     requirement relating thereto and prescribed by law or otherwise is hereby
     waived to the extent permitted by law;

(e)  enforce collection of any of the Collateral by suit or otherwise, and
     surrender, release or exchange all or any part of any property in addition
     to the Collateral, securing any of the Obligations, or compromise or
     extend or renew for any period (whether or not longer than the original
     period) any obligations of any nature of any party with respect to any
     property; and

(f)  to the extent permitted by applicable law, the Bank may purchase any or
     all of the Pledged Securities and other Collateral, whether in connection
     with a sale made under the power of sale herein contained or pursuant to
     judicial proceedings or otherwise;

provided, however, that the Bank will not be bound to deal with the Pledged
Securities and other Collateral as aforesaid, and will not be liable for any
loss which may be occasioned by any failure to do so and no action of the Bank
permitted hereunder will impair or affect any rights of the Bank in and to the
Collateral.


<PAGE>   6
                                      -6-

10.  APPLICATION OF PROCEEDS.  After payment of expenses as provided in Section
11 hereof, the balance of any proceeds received by the Bank in or in connection
with realizing, collecting, selling, transferring, delivering or obtaining
payment of the Collateral or any part thereof may be held by the Bank and may,
as and when the Bank thinks fit, be applied on account of such part of the
Obligations as to the Bank seems best, without prejudice to the Bank's claims
upon the Debtor for any deficiency.

11.  PAYMENT OF EXPENSES.  The Bank may charge on its own behalf and also pay
to others all out-of-pocket expenses of the Bank and others retained by the
Bank, incurred in connection with realizing, collecting, selling, transferring,
delivering or obtaining payment of the Pledged Securities or any other
Collateral or any part thereof, or in connection with the administration or
amendment of this Agreement or incidental to the care, safe keeping, or
otherwise of any and all of the Collateral, and may deduct the amount of such
sums from any proceeds of the Collateral.  The Debtor agrees to indemnify and
hold harmless the Bank from and against any and all liability incurred by the
Bank, or any nominee, agent or employees of the Bank hereunder or in connection
herewith, unless such liability was due to wilful misconduct or gross
negligence on the part of the Bank or such nominee or agent.

12.  ASSIGNMENT.  This Agreement will be binding upon the Debtor and its
successors and permitted assigns and will enure to the benefit of and be
enforceable by the Bank and its respective successors and assigns.  The Debtor
will not assign all or any part of this Agreement without the Bank's prior
written consent.

13.  NO WAIVER; CUMULATIVE REMEDIES.  The Bank will not by any act, delay,
indulgence, omission or otherwise be deemed to have waived any right or remedy
hereunder or to have acquiesced in any breach of any of the terms and
conditions hereof.  No failure to exercise, nor any delay in exercising, on the
part of the Bank, any right, power or privilege hereunder will operate as a
waiver thereof.

14.  COMMUNICATION.  All communications provided for or permitted hereunder
shall be in writing, personally delivered to an officer or other responsible
employee of the addressee or sent by registered mail, charges prepaid, or by
telecopy, to the address or telecopy number set forth opposite the name of the
Debtor in the execution pages of this Agreement, in the case of the Debtor, and
to Canadian Imperial Bank of Commerce, Head Office, Commerce Court West, 7th
Floor, Toronto, Ontario M5L 1A2 (Attention:  Vice-President, Global Media &
Telecommunications) (Telecopy:  (416) 980-2801), in the case of the Bank, or to
such other address as the applicable party hereto may from time to time
designate to the other in such manner.  Any communication so 


<PAGE>   7
                                      -7-

personally delivered shall be deemed to have been validly and effectively given
on the date of such delivery.  Communications so sent by telecopy shall be
deemed to have been validly and effectively given on the business day next
following the day on which it is sent.  Communications so sent by mail shall be
deemed to have been validly and effectively given on the fifth business day next
following the day on which it is sent.

15.  DEALINGS BY BANK.  The Bank may grant extensions of time and other
indulgences, take and give up security, accept compositions, grant releases and
discharges and otherwise deal with the Debtor and any third party having
dealings with the Debtor, and with the Collateral or any part thereof, and with
other security and sureties, as the Bank may see fit, all without prejudice to
the Obligations or to the rights of the Bank under this Agreement.  The Bank
will be accountable only for amounts that the Bank actually receives as a
result of the exercise of such powers, and neither the Bank nor any of its
officers, directors, employees or agents will be responsible to the Debtor for
any act or failure to act hereunder, except for its or their own gross
negligence or wilful misconduct.

16.  NON-EXCLUSIVITY OF REMEDIES.  This Agreement and the Liens arising
hereunder are in addition to and not in substitution for any other security now
or hereafter held by the Bank in respect of the Debtor, the Obligations or the
Collateral.  No remedy for the enforcement of the rights of the Bank hereunder
will be exclusive of or dependent on any other such remedy but any one or more
of such remedies may from time to time be exercised independently or in
combination.

17.  POWER OF ATTORNEY.  The Debtor hereby irrevocably constitutes and appoints
the Bank and any officer or agent thereof, with full power of substitution, as
its true and lawful attorney-in-fact, with full irrevocable power and authority
in the place and stead of the Debtor and in the name of the Debtor or in its
own name, from time to time in the Bank's discretion, for the purpose of
carrying out the terms of this Agreement, to take any and all appropriate
action, to do, make and execute any and all statements, acts, matters,
documents, instruments and things which may be necessary or desirable to
accomplish the purposes of this Agreement and from time to time to exercise all
rights and powers and to perform all acts of ownership in respect to the
Pledged Securities to the same extent as the Debtor might have done were it not
for this Agreement.  The Debtor hereby ratifies all that said attorneys will
lawfully do or cause to be done by virtue hereof.  This power of attorney is a
power coupled with an interest and will be irrevocable until the Obligations
have been paid and performed in full.

18.  NO MERGER.  Neither the taking and holding of the Pledged Securities and
other Collateral nor the obtaining of any judgment 


<PAGE>   8
                                      -8-


by the Bank will operate as a merger of any Obligation or any other indebtedness
or liability of the Debtor to the Bank or operate to prejudice the security
constituted by this Agreement.

19.  SEVERABILITY.  Any provision of this Agreement which is prohibited or
unenforceable in any jurisdiction will, as to such jurisdiction, be ineffective
to the extent of such prohibition or unenforceability without invalidating the
remaining provisions hereof and any such prohibition or unenforceability in any
jurisdiction will not invalidate or render unenforceable such provision in any
other jurisdiction.

20.  GOVERNING LAW.  This Agreement will be governed by and construed in
accordance with the laws of Ontario.

21.  SURVIVAL OF REPRESENTATIONS AND WARRANTIES.  All agreements,
representations, warranties and covenants made by or on behalf of the Debtor
herein are material, will be considered to have been relied upon by the Bank
and will survive the execution and delivery of this Agreement or any
investigation made at any time by or on behalf of the Bank and any disposition
or payment of the Obligations until repayment in full thereof.

22.  ACKNOWLEDGEMENT OF RECEIPT.  The Debtor acknowledges receipt of an
executed copy of this Agreement.

  DATED:  May 24, 1996.

ADDRESS                            1159670 ONTARIO LIMITED

10 Toronto Street
Toronto, Ontario                   By: /s/ CHARLES G. COWAN
M5K 1N2                            Name: Charles G. Cowan
                                   Title: Vice President & Secretary
Attention:  President

Facsimile:  (416) 364-2088
                                   By: /s/ J.A. BOULTBEE
                                   Name: J.A. Boultbee
                                   Title:  President

Schedule A - Pledged Securities

<PAGE>   9
                                      -9-

                                  SCHEDULE "A"


<TABLE>
<CAPTION>
                                                                  CERTIFICATE
COMPANIES                           PLEDGED SECURITIES              NUMBER 
- ---------                           ------------------              ------
                                      NO.       CLASS
                                      ---       -----   
<S>                               <C>           <C>                <C>
1. Hollinger International Inc.    14,990,000    Class B            B0001
                                                 Common Stock
</TABLE>

<PAGE>   1
                                                                 EXHIBIT 99.08

                          SECURITIES PLEDGE AGREEMENT


TO:  CANADIAN IMPERIAL BANK OF COMMERCE
     Commerce Court West - 7th Floor
     Toronto, Ontario
     M5L 1A2

  WHEREAS in order to secure the due payment and performance of the Obligations
(as defined below), the undersigned (the "Debtor") has agreed to pledge the
Pledged Securities (as defined below) to Canadian Imperial Bank of Commerce, as
agent (in that capacity, the "Agent") for the benefit of the lenders
(collectively, the "Lenders", the present Lenders being Canadian Imperial Bank
of Commerce and The Bank of Nova Scotia) from time to time parties to the
credit commitment agreement titled "Summary of Terms and Conditions" dated May
24, 1996 among Hollinger International Inc., Hollinger Inc., Canadian Imperial
Bank of Commerce and the Agent (as supplemented by an assignment agreement
dated as of July 17, 1996 among Hollinger International Inc., Canadian Imperial
Bank of Commerce and The Bank of Nova Scotia and as further supplemented,
amended, restated or replaced from time to time, the "Credit Agreement").

  THEREFORE, for good and valuable consideration, the receipt and sufficiency
of which are conclusively acknowledged by the parties hereto, the Debtor hereby
agrees as follows:

1.  DEFINED TERMS.  In this Agreement, the following words have the following
meanings:

  "Companies" means the corporations, companies, partnerships, limited
partnerships, trusts and other entities listed under the heading "Companies" in
Schedule "A" and their respective successors;

  "Default" means a failure to pay any of the Obligations when due;

  "Lien" means a mortgage, hypothec, title retention, pledge, lien, charge,
security interest or other encumbrance whatsoever, whether fixed or floating
and howsoever created or arising;

  "Obligations" means all present and future indebtedness and liabilities of
every kind, nature and description (whether direct or indirect, joint or
several, absolute or contingent, matured or unmatured) of the Debtor to the
Agent and the Lenders under or pursuant to the guarantee dated the date hereof
made by the Debtor in favour of the Agent in respect of Hollinger International
Inc. and any unpaid balance thereof; and


<PAGE>   2

                                      -2-

  "Pledged Securities" means the securities listed under the heading "Pledged
Securities" in Schedule "A", together with any other securities in the capital
of the Companies owned by the Debtor from time to time (other than 15,950,000
Class A Common Stock of Hollinger International Inc. presently owned by the
Debtor and evidenced or represented by share certificate #A0358).

2.  PLEDGE.  As general and continuing collateral security for the payment and
performance of all Obligations, the Debtor hereby assigns and pledges to and in
favour of the Agent, and the Debtor hereby grants to the Agent a continuing
security interest in the following (collectively, the "Collateral"):  (i) the
Pledged Securities, together with any replacements thereof and substitutions
therefor, and all certificates and instruments evidencing or representing such
securities; (ii) all dividends, whether in cash, kind or stock, received or
receivable upon or in respect of any of the Pledged Securities and all moneys
or other property payable or paid on account of any return or repayment of
capital in respect of any of the Pledged Securities or otherwise distributed in
respect thereof or which will in any way be charged to, or payable or paid out
of, the capital of any of the Companies on account of the Pledged Securities;
(iii) all other property that may at any time be received or receivable by or
otherwise distributed to the Debtor in respect of, or in substitution for, or
in exchange for, any of the foregoing; and (iv) all cash, securities and other
proceeds of the foregoing and all rights and interests of the Debtor in respect
thereof or evidenced thereby, including all moneys received from time to time
by the Debtor in connection with the sale or other disposition of any of the
Pledged Securities; provided, however, that the Debtor will not sell or
otherwise dispose of any of the Pledged Securities or purport to do any of the
foregoing without the prior written consent of the Agent.

3.  DELIVERY OF PLEDGED SECURITIES.  The certificates representing the Pledged
Securities duly endorsed by the appropriate person in blank for transfer or
accompanied by powers of attorney satisfactory to the Agent will forthwith be
delivered to and remain in the custody of the Agent or its nominee.  All
Pledged Securities may, at the option of the Agent, be registered in the name
of the Agent or its nominee.  If the Agent so requests, the certificates
representing the Pledged Securities will also be guaranteed by a Canadian
chartered bank.

4.  REPRESENTATIONS AND WARRANTIES.  The Debtor hereby represents and warrants
to the Agent and acknowledges that the Agent is relying thereon,
notwithstanding any investigation by the Agent or any Lender or otherwise,
that:  (i) the Debtor is the lawful owner of the Collateral, free and clear of
any and all Liens or claims of others other than any Lien granted by the Debtor
to the Agent hereunder or Liens in favour of Canadian Imperial Bank of
Commerce, with full right to deliver, assign, pledge and charge the 


<PAGE>   3
                                      -3-

Collateral to the Agent pursuant hereto; (ii) the Pledged Securities represent
all of the issued and outstanding shares in the capital of each of the Companies
held by the Debtor (other than 15,950,000 Class A Common Stock of Hollinger
International Inc. referred to in the definition of "Pledged Securities"); (iii)
the Pledged Securities are validly issued, fully paid and non-assessable; (iv)
there is no existing agreement, option, right or privilege capable of becoming
an agreement or option pursuant to which the Debtor would be required to sell or
otherwise dispose of any of the Pledged Securities; (v) except as otherwise
agreed by the Agent in writing, the Liens granted by the Debtor to the Agent
pursuant to this Agreement constitute Liens on the Collateral in favour of the
Agent which are prior to all other Liens on the Collateral other than Liens in
favour of Canadian Imperial Bank of Commerce, whether created by the Debtor or
any other Person, and in existence on the date hereof; (vi) the Debtor has the
power and authority and the legal right to execute and deliver, to perform its
obligations under, and to grant the Lien on the Collateral pursuant to, this
Agreement and the Debtor has taken all necessary corporate action to authorize
its execution, delivery and performance of, and grant of the Lien on the
Collateral pursuant to, this Agreement; (vii) this Agreement constitutes a
legal, valid and binding obligation of the Debtor, enforceable in accordance
with its terms, except as enforceability may be limited by bankruptcy,
insolvency, reorganization, moratorium or similar laws affecting the enforcement
of creditors' rights generally and by general principles of equity; (viii) the
execution, delivery and performance of this Agreement will not violate any
provision or requirement of any law or contractual obligation of the Debtor and
will not result in the creation or imposition of any Lien on any of the
properties or revenues of the Debtor pursuant to any requirement of law or
contractual obligation of the Debtor; (ix) no consent or authorization of,
filing with, or other act by or in respect of, any arbitrator or governmental
authority and no consent of any other person (including any shareholder or
creditor of the Debtor), is required in connection with the execution, delivery,
performance, validity or enforceability of this Agreement, except for such as
have been obtained or made and are in full force and effect, and the terms of
which have been disclosed to the Agent; and (x) no litigation, investigation or
proceeding of or before any arbitrator or governmental authority is pending or,
to the knowledge of the Debtor, threatened by or against the Debtor or against
any of its properties or revenues which may materially adversely affect the
business, property or financial or other condition of the Debtor.

5.  COVENANTS.  The Debtor covenants and agrees with the Agent that:  (i) at
any time and from time to time, upon the written request of the Agent, and at
the sole expense of the Debtor, the Debtor will promptly and duly execute and
deliver such further instruments and documents and take such further action as
the Agent may request for the purpose of obtaining or preserving the full


<PAGE>   4
                                      -4-

benefits of this Agreement and of the rights and powers herein granted,
including the filing or execution of any financing or financing change
statements under any applicable legislation in effect in any jurisdiction with
respect to the Liens created hereby; (ii) the Debtor authorizes the Agent to
file any such financing or financing change statement without the signature of
the Debtor to the extent permitted by applicable law; (iii) the Debtor will not
create, incur or permit to exist, but will defend the Collateral against, and
will take such other action as is necessary to remove, any Lien or claim on or
to the Collateral, other than the Liens created hereby and Liens in favour of
Canadian Imperial Bank of Commerce and other than as permitted in writing by
the Agent; (iv) the Debtor will not sell, transfer, lease or otherwise dispose
of any of the Collateral except as permitted in writing by the Agent; and (v)
the Debtor will ensure that at the request of the Agent, all Pledged Securities
are registered in the name of the Agent or its nominee, that the certificates
representing the Pledged Securities will be forthwith delivered to and remain
in the custody of the Agent or its nominee, and that all certificates,
instruments or other documents representing or evidencing any Pledged
Securities acquired or issued subsequent to the date hereof will be registered
in the name of the Agent or its nominee and will forthwith after issuance be
delivered to, and remain in the custody of, the Agent or its nominee.

6.  RIGHTS AND DUTIES OF AGENT.  The Agent will have and be entitled to
exercise all such powers hereunder as are specifically delegated to the Agent
by the terms hereof, together with such powers as are incidental thereto.  The
Agent may execute any of its duties hereunder by or through agents and will be
entitled to retain counsel and to act in reliance upon the advice of such
counsel concerning all matters pertaining to its duties hereunder.  The Agent
and any nominee on its behalf will be bound to exercise in the holding of the
Pledged Securities and other Collateral only the same degree of care as it
would exercise with respect to similar property of its own held in the same
place.  Neither the Agent, nor any Lender, nor any nominee acting on behalf of
the Agent or any Lender, nor any director, officer or employee of the Agent or
any Lender or such nominee, will be liable for any action taken or admitted to
be taken by it hereunder or in connection herewith except for its own gross
negligence or wilful misconduct.

7.  VOTING RIGHTS.  Unless a Default has occurred and is continuing, the Debtor
will be entitled to exercise all voting power from time to time exercisable in
respect of the Pledged Securities and give consents, waivers and ratifications
in respect thereof.  Immediately upon the occurrence and during the continuance
of any Default, all such rights of the Debtor to vote and give consents,
waivers and ratifications will cease and the Agent will be entitled to exercise
all such voting rights and to give all consents, waivers and ratifications as
permitted by the Agent.
<PAGE>   5
                                      -5-

8.  DIVIDENDS.  Unless a Default has occurred and is continuing, the Debtor
will, subject to any agreement with the Agent to the contrary, be entitled to
receive any and all cash dividends and other distributions on the Pledged
Securities which it is otherwise entitled to receive.  If a Default has
occurred and is continuing, the Agent will have the sole and exclusive right
and authority to receive and retain the dividends and other distributions which
the Debtor would otherwise be authorized to receive.  Any money and other
property paid over to or received by the Agent pursuant to the provisions of
this Section 8 will be retained by the Agent as additional Collateral hereunder
and be applied in accordance with the provisions hereof.

9.  REMEDIES.  If a Default has occurred and is continuing, the Agent may,
without notice to or the consent of the Debtor or any other person (other than
as required by applicable law), take all or any of the following actions:

(a)  transfer all or any part of the Collateral into the name of the Agent or
     any Lender or any nominee on behalf of the Agent or any Lender, with or
     without disclosing that such Collateral is subject to the Lien hereunder;

(b)  notify any parties obligated on any of the Collateral to make payment to
     the Agent or any Lender of any amounts due or to become due thereunder;

(c)  exercise any and all rights of conversion, exchange, subscription or any
     other rights, privileges or options pertaining to any of the Pledged
     Securities as if it were the absolute owner thereof;

(d)  from time to time realize upon, collect, sell, transfer, assign, give
     options to purchase, or otherwise dispose of and deliver the Pledged
     Securities and other Collateral, or any part thereof, in such a manner as
     may seem to it advisable, and for the purposes thereof each and every
     requirement relating thereto and prescribed by law or otherwise is hereby
     waived to the extent permitted by law;

(e)  enforce collection of any of the Collateral by suit or otherwise, and
     surrender, release or exchange all or any part of any property in addition
     to the Collateral, securing any of the Obligations, or compromise or
     extend or renew for any period (whether or not longer than the original
     period) any obligations of any nature of any party with respect to any
     property; and

(f)  to the extent permitted by applicable law, the Agent or any Lender may
     purchase any or all of the Pledged Securities and other Collateral,
     whether in connection with a sale made under the power of sale herein
     contained or pursuant to judicial proceedings or otherwise;
<PAGE>   6
                                      -6-


provided, however, that the Agent and the Lenders will not be bound to deal
with the Pledged Securities and other Collateral as aforesaid, and will not be
liable for any loss which may be occasioned by any failure to do so and no
action of the Agent or any Lender permitted hereunder will impair or affect any
rights of the Agent or any Lender in and to the Collateral.

10.  APPLICATION OF PROCEEDS.  After payment of expenses as provided in Section
11 hereof, the balance of any proceeds received by the Agent in or in
connection with realizing, collecting, selling, transferring, delivering or
obtaining payment of the Collateral or any part thereof may be held by the
Agent and may, as and when the Agent thinks fit, be applied on account of such
part of the Obligations as to the Agent seems best, without prejudice to the
Agent's and the Lenders' claims upon the Debtor for any deficiency.

11.  PAYMENT OF EXPENSES.  The Agent may charge on its own behalf and also pay
to others all out-of-pocket expenses of the Agent and others retained by the
Agent, incurred in connection with realizing, collecting, selling,
transferring, delivering or obtaining payment of the Pledged Securities or any
other Collateral or any part thereof, or in connection with the administration
or amendment of this Agreement or incidental to the care, safe keeping, or
otherwise of any and all of the Collateral, and may deduct the amount of such
sums from any proceeds of the Collateral.  The Debtor agrees to indemnify and
hold harmless the Agent and the Lenders from and against any and all liability
incurred by the Agent, any Lender or any nominee, agent or employees of the
Agent or any Lender hereunder or in connection herewith, unless such liability
was due to wilful misconduct or gross negligence on the part of the Agent or
Lender or such nominee or agent.

12.  ASSIGNMENT.  This Agreement will be binding upon the Debtor and its
successors and permitted assigns and will enure to the benefit of and be
enforceable by the Agent and the Lenders and their respective successors and
assigns.  The Debtor will not assign all or any part of this Agreement without
the Agent's prior written consent.

13.  NO WAIVER:  CUMULATIVE REMEDIES.  Neither the Agent nor any Lender will by
any act, delay, indulgence, omission or otherwise be deemed to have waived any
right or remedy hereunder or to have acquiesced in any breach of any of the
terms and conditions hereof.  No failure to exercise, nor any delay in
exercising, on the part of the Agent or any Lender, any right, power or
privilege hereunder will operate as a waiver thereof.




<PAGE>   7
                                      -7-

hereunder shall be in writing, personally delivered to an officer or other
responsible employee of the addressee or sent by registered mail, charges
prepaid, or by telecopy, to the address or telecopy number set forth opposite
the name of the Debtor in the execution pages of this Agreement, in the case of
the Debtor, and to Canadian Imperial Bank of Commerce, Head Office, Commerce
Court West, 7th Floor, Toronto, Ontario M5L 1A2 (Attention:  Vice-President,
Global Media & Telecommunications) (Telecopy:  (416) 980-2801), in the case of
the Agent and the Lenders, or to such other address as the applicable party
hereto may from time to time designate to the other in such manner.  Any
communication so personally delivered shall be deemed to have been validly and
effectively given on the date of such delivery.  Communications so sent by
telecopy shall be deemed to have been validly and effectively given on the
business day next following the day on which it is sent.  Communications so sent
by mail shall be deemed to have been validly and effectively given on the fifth
business day next following the day on which it is sent.

15.  DEALINGS BY AGENT AND LENDERS.  The Agent and the Lenders may grant
extensions of time and other indulgences, take and give up security, accept
compositions, grant releases and discharges and otherwise deal with the Debtor
and any third party having dealings with the Debtor, and with the Collateral or
any part thereof, and with other security and sureties, as the Agent and the
Lenders may see fit, all without prejudice to the Obligations or to the rights
of the Agent and the Lenders under this Agreement.  The Agent and the Lenders
will be accountable only for amounts that the Agent or any Lender actually
receives as a result of the exercise of such powers, and neither the Agent nor
any Lender nor any of their officers, directors, employees or agents will be
responsible to the Debtor for any act or failure to act hereunder, except for
its or their own gross negligence or wilful misconduct.

16.  NON-EXCLUSIVITY OF REMEDIES.  This Agreement and the Liens arising
hereunder are in addition to and not in substitution for any other security now
or hereafter held by the Agent or any Lender in respect of the Debtor, the
Obligations or the Collateral.  No remedy for the enforcement of the rights of
the Agent and the Lenders hereunder will be exclusive of or dependent on any
other such remedy but any one or more of such remedies may from time to time be
exercised independently or in combination.

17.  POWER OF ATTORNEY.  The Debtor hereby irrevocably constitutes and appoints
the Agent and any officer or agent thereof, with full power of substitution, as
its true and lawful attorney-in-fact, with full irrevocable power and authority
in the place and stead of the Debtor and in the name of the Debtor or in its
own name, from time to time in the Agent's discretion, for the purpose of
carrying out the terms of this Agreement, to take any and all appropriate
action, to do, make and execute any and all statements, acts, matters,
documents, instruments and things which may be necessary 
<PAGE>   8
                                      -8-

14.  COMMUNICATION.  All communications provided for or permitted or desirable
to accomplish the purposes of this Agreement and from time to time to exercise
all rights and powers and to perform all acts of ownership in respect to the
Pledged Securities to the same extent as the Debtor might have done were it not
for this Agreement.  The Debtor hereby ratifies all that said attorneys will
lawfully do or cause to be done by virtue hereof.  This power of attorney is a
power coupled with an interest and will be irrevocable until the Obligations
have been paid and performed in full.

18.  NO MERGER.  Neither the taking and holding of the Pledged Securities and
other Collateral nor the obtaining of any judgment by the Agent or any Lender
will operate as a merger of any Obligation or any other indebtedness or
liability of the Debtor to the Agent or any Lender or operate to prejudice the
security constituted by this Agreement.

19.  SEVERABILITY.  Any provision of this Agreement which is prohibited or
unenforceable in any jurisdiction will, as to such jurisdiction, be ineffective
to the extent of such prohibition or unenforceability without invalidating the
remaining provisions hereof and any such prohibition or unenforceability in any
jurisdiction will not invalidate or render unenforceable such provision in any
other jurisdiction.

20.  GOVERNING LAW.  This Agreement will be governed by and construed in
accordance with the laws of Ontario.

21.  SURVIVAL OF REPRESENTATIONS AND WARRANTIES.  All agreements,
representations, warranties and covenants made by or on behalf of the Debtor
herein are material, will be considered to have been relied upon by the Agent
and the Lenders and will survive the execution and delivery of this Agreement
or any investigation made at any time by or on behalf of the Agent or any
Lender and any disposition or payment of the Obligations until repayment in
full thereof.

22.  ACKNOWLEDGEMENT OF RECEIPT.  The Debtor acknowledges receipt of an
executed copy of this Agreement.

  DATED:  As of July 17, 1996.

ADDRESS                                  3184081 CANADA LIMITED
- -------
10 Toronto Street
Toronto, Ontario                         By: /s/ J.A. BOULTBEE
M5K 1N2                                  Name:  J.A. Boultbee
                                         Title: Vice-President,
Attention:  President                           Finance & Treasury

Facsimile:  (416) 364-2088


                                         By:______________________c/s
                                         Name:
                                         Title:

Schedule A - Pledged Securities

<PAGE>   9
                                      -9-

                                  SCHEDULE "A"

                                                              CERTIFICATE
COMPANIES                               PLEDGED SECURITIES       NUMBER    
- ---------                               ------------------       ------
                                       NO.            CLASS       
                                       --------------------
1.  Hollinger International Inc.     7,539,028      Class A       A0499
                                                    Common Stock

<PAGE>   1
                                                                   EXHIBIT 99.09

                           SECURITIES PLEDGE AGREEMENT


TO:  CANADIAN IMPERIAL BANK OF COMMERCE
     Commerce Court West - 7th Floor
     Toronto, Ontario
     M5L 1A2


  WHEREAS in order to secure the due payment and performance of the Obligations
(as defined below), the undersigned (the "Debtor") has agreed to pledge the
Pledged Securities (as defined below) to Canadian Imperial Bank of Commerce, as
agent (in that capacity, the "Agent") for the benefit of the lenders
(collectively, the "Lenders", the present Lenders being Canadian Imperial Bank
of Commerce and The Bank of Nova Scotia) from time to time parties to the
credit commitment agreement titled "Summary of Terms and Conditions" dated May
24, 1996 among Hollinger International Inc., Hollinger Inc., Canadian Imperial
Bank of Commerce and the Agent (as supplemented by an assignment agreement
dated as of July 17, 1996 among Hollinger International Inc., Canadian Imperial
Bank of Commerce and The Bank of Nova Scotia and as further supplemented,
amended or restated from time to time, the "Credit Agreement").

  THEREFORE, for good and valuable consideration, the receipt and sufficiency
of which are conclusively acknowledged by the parties hereto, the Debtor hereby
agrees as follows:

1. DEFINED TERMS.  In this Agreement, the following words have the following
meanings:

  "Companies" means the corporations, companies, partnerships, limited
partnerships, trusts and other entities listed under the heading "Companies" in
Schedule "A" and their respective successors;

  "Default" means a failure to pay any of the Obligations when due;

  "Lien" means a mortgage, hypothec, title retention, pledge, lien, charge,
security interest or other encumbrance whatsoever, whether fixed or floating
and howsoever created or arising;

  "Obligations" means all present and future indebtedness and liabilities of
every kind, nature and description (whether direct or indirect, joint or
several, absolute or contingent, matured or unmatured) of the Debtor to the
Agent and the Lenders under or pursuant to the guarantee dated the date hereof
made by the Debtor in favour of the Agent in respect of Hollinger International
Inc. and any unpaid balance thereof; and


<PAGE>   2
                                      -2-

  "Pledged Securities" means the securities listed under the heading "Pledged
Securities" in Schedule "A", together with any other securities in the capital
of the Companies owned by the Debtor from time to time.

2. PLEDGE.  As general and continuing collateral security for the payment and
performance of all Obligations, the Debtor hereby assigns and pledges to and in
favour of the Agent, and the Debtor hereby grants to the Agent a continuing
security interest in the following (collectively, the "Collateral"):  (i) the
Pledged Securities, together with any replacements thereof and substitutions
therefor, and all certificates and instruments evidencing or representing such
securities; (ii) all dividends, whether in cash, kind or stock, received or
receivable upon or in respect of any of the Pledged Securities and all moneys
or other property payable or paid on account of any return or repayment of
capital in respect of any of the Pledged Securities or otherwise distributed in
respect thereof or which will in any way be charged to, or payable or paid out
of, the capital of any of the Companies on account of the Pledged Securities;
(iii) all other property that may at any time be received or receivable by or
otherwise distributed to the Debtor in respect of, or in substitution for, or
in exchange for, any of the foregoing; and (iv) all cash, securities and other
proceeds of the foregoing and all rights and interests of the Debtor in respect
thereof or evidenced thereby, including all moneys received from time to time
by the Debtor in connection with the sale or other disposition of any of the
Pledged Securities; provided, however, that the Debtor will not sell or
otherwise dispose of any of the Pledged Securities or purport to do any of the
foregoing without the prior written consent of the Agent.

3. DELIVERY OF PLEDGED SECURITIES.  The certificates representing the Pledged
Securities duly endorsed by the appropriate person in blank for transfer or
accompanied by powers of attorney satisfactory to the Agent will forthwith be
delivered to and remain in the custody of the Agent or its nominee.  All
Pledged Securities may, at the option of the Agent, be registered in the name
of the Agent or its nominee.  If the Agent so requests, the certificates
representing the Pledged Securities will also be guaranteed by a Canadian
chartered bank.

4. REPRESENTATIONS AND WARRANTIES.  The Debtor hereby represents and warrants
to the Agent and acknowledges that the Agent is relying thereon,
notwithstanding any investigation by the Agent or any Lender or otherwise,
that: (i) the Debtor is the lawful owner of the Collateral, free and clear of
any and all Liens or claims of others other than any Lien granted by the Debtor
to the Agent hereunder or Liens in favour of Canadian Imperial Bank of
Commerce, with full right to deliver, assign, pledge and charge the Collateral
to the Agent pursuant hereto; (ii) the Pledged Securities represent all of the
issued and outstanding shares in

<PAGE>   3
                                      -3-


the capital of each of the Companies held by the Debtor; (iii) the Pledged
Securities are validly issued, fully paid and non-assessable; (iv) there is no
existing agreement, option, right or privilege capable of becoming an agreement
or option pursuant to which the Debtor would be required to sell or otherwise
dispose of any of the Pledged Securities; (v) except as otherwise agreed by the
Agent in writing, the Liens granted by the Debtor to the Agent pursuant to this
Agreement constitute Liens on the Collateral in favour of the Agent which are
prior to all other Liens on the Collateral other than Liens in favour of
Canadian Imperial Bank of Commerce, whether created by the Debtor or any other
Person, and in existence on the date hereof; (vi) the Debtor has the power and
authority and the legal right to execute and deliver, to perform its obligations
under, and to grant the Lien on the Collateral pursuant to, this Agreement and
the Debtor has taken all necessary corporate action to authorize its execution,
delivery and performance of, and grant of the Lien on the Collateral pursuant
to, this Agreement; (vii) this Agreement constitutes a legal, valid and binding
obligation of the Debtor, enforceable in accordance with its terms, except as
enforceability may be limited by bankruptcy, insolvency, reorganization,
moratorium or similar laws affecting the enforcement of creditors' rights
generally and by general principles of equity; (viii) the execution, delivery
and performance of this Agreement will not violate any provision or requirement
of any law or contractual obligation of the Debtor and will not result in the
creation or imposition of any Lien on any of the properties or revenues of the
Debtor pursuant to any requirement of law or contractual obligation of the
Debtor; (ix) no consent or authorization of, filing with, or other act by or in
respect of, any arbitrator or governmental authority and no consent of any other
person (including any shareholder or creditor of the Debtor), is required in
connection with the execution, delivery, performance, validity or enforceability
of this Agreement, except for such as have been obtained or made and are in full
force and effect, and the terms of which have been disclosed to the Agent; and
(x) no litigation, investigation or proceeding of or before any arbitrator or
governmental authority is pending or, to the knowledge of the Debtor, threatened
by or against the Debtor or against any of its properties or revenues which may
materially adversely affect the business, property or financial or other
condition of the Debtor.

5. COVENANTS.  The Debtor covenants and agrees with the Agent that: (i) at any
time and from time to time, upon the written request of the Agent, and at the
sole expense of the Debtor, the Debtor will promptly and duly execute and
deliver such further instruments and documents and take such further action as
the Agent may request for the purpose of obtaining or preserving the full
benefits of this Agreement and of the rights and powers herein granted,
including the filing or execution of any financing or financing change
statements under any applicable legislation in effect in any jurisdiction with
respect to the Liens created 

<PAGE>   4
                                      -4-

hereby; (ii) the Debtor authorizes the Agent to file any such financing or
financing change statement without the signature of the Debtor to the extent
permitted by applicable law; (iii) the Debtor will not create, incur or permit
to exist, but will defend the Collateral against, and will take such other
action as is necessary to remove, any Lien or claim on or to the Collateral,
other than the Liens created hereby and Liens in favour of Canadian Imperial
Bank of Commerce and other than as permitted in writing by the Agent; (iv) the
Debtor will not sell, transfer, lease or otherwise dispose of any of the
Collateral except as permitted in writing by the Agent; and (v) the Debtor will
ensure that at the request of the Agent, all Pledged Securities are registered
in the name of the Agent or its nominee, that the certificates representing the
Pledged Securities will be forthwith delivered to and remain in the custody of
the Agent or its nominee, and that all certificates, instruments or other
documents representing or evidencing any Pledged Securities acquired or issued
subsequent to the date hereof will be registered in the name of the Agent or its
nominee and will forthwith after issuance be delivered to, and remain in the
custody of, the Agent or its nominee.

6. RIGHTS AND DUTIES OF AGENT.  The Agent will have and be entitled to exercise
all such powers hereunder as are specifically delegated to the Agent by the
terms hereof, together with such powers as are incidental thereto.  The Agent
may execute any of its duties hereunder by or through agents and will be
entitled to retain counsel and to act in reliance upon the advice of such
counsel concerning all matters pertaining to its duties hereunder.  The Agent
and any nominee on its behalf will be bound to exercise in the holding of the
Pledged Securities and other Collateral only the same degree of care as it
would exercise with respect to similar property of its own held in the same
place.  Neither the Agent, nor any Lender, nor any nominee acting on behalf of
the Agent or any Lender, nor any director, officer or employee of the Agent or
any Lender or such nominee, will be liable for any action taken or admitted to
be taken by it hereunder or in connection herewith except for its own gross
negligence or wilful misconduct.

7. VOTING RIGHTS.  Unless a Default has occurred and is continuing, the Debtor
will be entitled to exercise all voting power from time to time exercisable in
respect of the Pledged Securities and give consents, waivers and ratifications
in respect thereof.  Immediately upon the occurrence and during the continuance
of any Default, all such rights of the Debtor to vote and give consents,
waivers and ratifications will cease and the Agent will be entitled to exercise
all such voting rights and to give all consents, waivers and ratifications as
permitted by the Agent.

8. DIVIDENDS.  Unless a Default has occurred and is continuing, the Debtor
will, subject to any agreement with the Agent to the contrary, be entitled to
receive any and all cash dividends and 

<PAGE>   5
                                      -5-

other distributions on the Pledged Securities which it is otherwise entitled to
receive.  If a Default has occurred and is continuing, the Agent will have the
sole and exclusive right and authority to receive and retain the dividends and
other distributions which the Debtor would otherwise be authorized to receive.
Any money and other property paid over to or received by the Agent pursuant to
the provisions of this Section 8 will be retained by the Agent as additional
Collateral hereunder and be applied in accordance with the provisions hereof.

9. REMEDIES.  If a Default has occurred and is continuing, the Agent may,
without notice to or the consent of the Debtor or any other person (other than
as required by applicable law), take all or any of the following actions:

(a)  transfer all or any part of the Collateral into the name of the Agent or
     any Lender or any nominee on behalf of the Agent or any Lender, with or
     without disclosing that such Collateral is subject to the Lien hereunder;

(b)  notify any parties obligated on any of the Collateral to make payment to
     the Agent or any Lender of any amounts due or to become due thereunder;

(c)  exercise any and all rights of conversion, exchange, subscription or any
     other rights, privileges or options pertaining to any of the Pledged
     Securities as if it were the absolute owner thereof;

(d)  from time to time realize upon, collect, sell, transfer, assign, give
     options to purchase, or otherwise dispose of and deliver the Pledged
     Securities and other Collateral, or any part thereof, in such a manner as
     may seem to it advisable, and for the purposes thereof each and every
     requirement relating thereto and prescribed by law or otherwise is hereby
     waived to the extent permitted by law;

(e)  enforce collection of any of the Collateral by suit or otherwise, and
     surrender, release or exchange all or any part of any property in addition
     to the Collateral, securing any of the Obligations, or compromise or
     extend or renew for any period (whether or not longer than the original
     period) any obligations of any nature of any party with respect to any
     property; and

(f)  to the extent permitted by applicable law, the Agent or any Lender may
     purchase any or all of the Pledged Securities and other Collateral,
     whether in connection with a sale made under the power of sale herein
     contained or pursuant to judicial proceedings or otherwise;

provided, however, that the Agent and the Lenders will not be bound 

<PAGE>   6
                                      -6-

to deal with the Pledged Securities and other Collateral as aforesaid, and will
not be liable for any loss which may be occasioned by any failure to do so and
no action of the Agent or any Lender permitted hereunder will impair or affect
any rights of the Agent or any Lender in and to the Collateral.

10.  APPLICATION OF PROCEEDS.  After payment of expenses as provided in Section
11 hereof, the balance of any proceeds received by the Agent in or in
connection with realizing, collecting, selling, transferring, delivering or
obtaining payment of the Collateral or any part thereof may be held by the
Agent and may, as and when the Agent thinks fit, be applied on account of such
part of the Obligations as to the Agent seems best, without prejudice to the
Agent's and the Lenders' claims upon the Debtor for any deficiency.

11.  PAYMENT OF EXPENSES.  The Agent may charge on its own behalf and also pay
to others all out-of-pocket expenses of the Agent and others retained by the
Agent, incurred in connection with realizing, collecting, selling,
transferring, delivering or obtaining payment of the Pledged Securities or any
other Collateral or any part thereof, or in connection with the administration
or amendment of this Agreement or incidental to the care, safe keeping, or
otherwise of any and all of the Collateral, and may deduct the amount of such
sums from any proceeds of the Collateral. The Debtor agrees to indemnify and
hold harmless the Agent and the Lenders from and against any and all liability
incurred by the Agent, any Lender or any nominee, agent or employees of the
Agent or any Lender hereunder or in connection herewith, unless such liability
was due to wilful misconduct or gross negligence on the part of the Agent or
Lender or such nominee or agent.

12.  ASSIGNMENT.  This Agreement will be binding upon the Debtor and its
successors and permitted assigns and will enure to the benefit of and be
enforceable by the Agent and the Lenders and their respective successors and
assigns.  The Debtor will not assign all or any part of this Agreement without
the Agent's prior written consent.

13.  NO WAIVER; CUMULATIVE REMEDIES.  Neither the Agent nor any Lender will by
any act, delay, indulgence, omission or otherwise be deemed to have waived any
right or remedy hereunder or to have acquiesced in any breach of any of the
terms and conditions hereof. No failure to exercise, nor any delay in
exercising, on the part of the Agent or any Lender, any right, power or
privilege hereunder will operate as a waiver thereof.

14.  COMMUNICATION.  All communications provided for or permitted hereunder
shall be in writing, personally delivered to an officer or other responsible
employee of the addressee or sent by registered mail, charges prepaid, or by
telecopy, to the address or telecopy number set forth opposite the name of the
Debtor in the 

<PAGE>   7
                                      -7-

execution pages of this Agreement, in the case of the Debtor, and to Canadian
Imperial Bank of Commerce, Head Office, Commerce Court West, 7th Floor, Toronto,
Ontario M5L 1A2 (Attention: Vice-President, Global Media & Telecommunications)
(Telecopy: (416) 980-2801), in the case of the Agent and the Lenders, or to such
other address as the applicable party hereto may from time to time designate to
the other in such manner.  Any communication so personally delivered shall be
deemed to have been validly and effectively given on the date of such delivery.
Communications so sent by telecopy shall be deemed to have been validly and
effectively given on the business day next following the day on which it is
sent.  Communications so sent by mail shall be deemed to have been validly and
effectively given on the fifth business day next following the day on which it
is sent.

15.  DEALINGS BY AGENT AND LENDERS.  The Agent and the Lenders may grant
extensions of time and other indulgences, take and give up security, accept
compositions, grant releases and discharges and otherwise deal with the Debtor
and any third party having dealings with the Debtor, and with the Collateral or
any part thereof, and with other security and sureties, as the Agent and the
Lenders may see fit, all without prejudice to the Obligations or to the rights
of the Agent and the Lenders under this Agreement.  The Agent and the Lenders
will be accountable only for amounts that the Agent or any Lender actually
receives as a result of the exercise of such powers, and neither the Agent nor
any Lender nor any of their officers, directors, employees or agents will be
responsible to the Debtor for any act or failure to act hereunder, except for
its or their own gross negligence or wilful misconduct.

16.  NON-EXCLUSIVITY OF REMEDIES.  This Agreement and the Liens arising
hereunder are in addition to and not in substitution for any other security now
or hereafter held by the Agent or any Lender in respect of the Debtor, the
Obligations or the Collateral.  No remedy for the enforcement of the rights of
the Agent and the Lenders hereunder will be exclusive of or dependent on any
other such remedy but any one or more of such remedies may from time to time be
exercised independently or in combination.

17.  POWER OF ATTORNEY.  The Debtor hereby irrevocably constitutes and appoints
the Agent and any officer or agent thereof, with full power of substitution, as
its true and lawful attorney-in-fact, with full irrevocable power and authority
in the place and stead of the Debtor and in the name of the Debtor or in its
own name, from time to time in the Agent's discretion, for the purpose of
carrying out the terms of this Agreement, to take any and all appropriate
action, to do, make and execute any and all statements, acts, matters,
documents, instruments and things which may be necessary or desirable to
accomplish the purposes of this Agreement and from time to time to exercise all
rights and powers and to perform all acts of ownership in respect to the
Pledged Securities to the same extent as the Debtor might have done were it not
for this 

<PAGE>   8
                                      -8-

Agreement.  The Debtor hereby ratifies all that said attorneys will lawfully do
or cause to be done by virtue hereof.  This power of attorney is a power coupled
with an interest and will be irrevocable until the Obligations have been paid
and performed in full.

18.  NO MERGER.  Neither the taking and holding of the Pledged Securities and
other Collateral nor the obtaining of any judgment by the Agent or any Lender
will operate as a merger of any Obligation or any other indebtedness or
liability of the Debtor to the Agent or any Lender or operate to prejudice the
security constituted by this Agreement.

19.  SEVERABILITY.  Any provision of this Agreement which is prohibited or
unenforceable in any jurisdiction will, as to such jurisdiction, be ineffective
to the extent of such prohibition or unenforceability without invalidating the
remaining provisions hereof and any such prohibition or unenforceability in any
jurisdiction will not invalidate or render unenforceable such provision in any
other jurisdiction.

20.  GOVERNING LAW.  This Agreement will be governed by and construed in
accordance with the laws of Ontario.

21.  SURVIVAL OF REPRESENTATIONS AND WARRANTIES.  All agreements,
representations, warranties and covenants made by or on behalf of the Debtor
herein are material, will be considered to have been relied upon by the Agent
and the Lenders and will survive the execution and delivery of this Agreement
or any investigation made at any time by or on behalf of the Agent or any
Lender and any disposition or payment of the Obligations until repayment in
full thereof.

22.  ACKNOWLEDGEMENT OF RECEIPT.  The Debtor acknowledges receipt of an
executed copy of this Agreement.

     DATED:  As of July 17, 1996.

ADDRESS                                          1159670 ONTARIO LIMITED

10 Toronto Street
Toronto, Ontario                                 By: /s/ J. A. BOULTBEE
M5K 1N2                                          Name:   J. A. Boultbee

                                                 Title: Vice-President, Finance
                                                        & Treasury
Attention:  President

Facsimile:  (416) 364-2088
                                                                            c/s
                                                  By: _________________________
                                                  Name: 
                                                  Title:

Schedule A - Pledged Securities


<PAGE>   9
                                      -9-

                                  SCHEDULE "A"

<TABLE>
<CAPTION>

                                                                     CERTIFICATE
COMPANIES                                  PLEDGED SECURITIES           NUMBER              
- ---------                                  ------------------        -----------            
                                            NO.        CLASS
                                            ---        -----
<S>                                     <C>           <C>              <C>   
1.  Hollinger  International Inc.        14,990,000    Class B          B0001
                                                       Common Stock
</TABLE>

<PAGE>   1
                                                                   EXHIBIT 99.10


                          SECURITIES PLEDGE AGREEMENT

TO: CANADIAN IMPERIAL BANK OF COMMERCE
    Commerce Court West - 7th Floor
    Toronto, Ontario
    M5L 1A2


     WHEREAS in order to secure the due payment and performance of the
Obligations (as defined below), the undersigned (the "Debtor") has agreed to
pledge the Pledged Securities (as defined below) to Canadian Imperial Bank of
Commerce, as agent (in that capacity, the "Agent") for the benefit of the
lenders (collectively, the "Lenders", the present Lenders being Canadian
Imperial Bank of Commerce and The Bank of Nova Scotia) from time to time parties
to the credit agreement dated on or about the date hereof between, among others,
Hollinger International Inc., Hollinger Inc., the Debtor, the Lenders and the
Agent (as amended, supplemented, restated or replaced from time to time, the
"Credit Agreement").

     THEREFORE, for good and valuable consideration, the receipt and sufficiency
of which are conclusively acknowledged by the parties hereto, the Debtor hereby
agrees as follows:


1.  DEFINED TERMS.  In this Agreement, the following words have the following
meanings:

     "Companies" means the corporations, companies, partnerships, limited
partnerships, trusts and other entities listed under the heading "Companies" in
Schedule "A" and their respective successors;

     "Default" means a failure to pay any of the Obligations when due;

     "Lien" means a mortgage, hypothec, title retention, pledge, lien, charge,
security interest or other encumbrance whatsoever, whether fixed or floating and
howsoever created or arising;

     "Obligations" means all present and future indebtedness and liabilities of
every kind, nature and description (whether direct or indirect, joint or
several, absolute or contingent, matured or unmatured) of the Debtor to the
Agent and the Lenders under or pursuant to the guarantee dated the date hereof
made by the Debtor in favour of the Agent in respect of Hollinger International
Inc. and any unpaid balance thereof; and

     "Pledged Securities" means the securities listed under the heading "Pledged
Securities" in Schedule "A", together with any

<PAGE>   2

other securities in the capital of the Companies owned by the Debtor from time
to time.


2.  PLEDGE.  As general and continuing collateral security for the payment and
performance of all Obligations, the Debtor hereby assigns and pledges to and in
favour of the Agent, and the Debtor hereby grants to the Agent a continuing
security interest in the following (collectively, the "Collateral"):  (i) the
Pledged Securities, together with any replacements thereof and substitutions
therefor, and all certificates and instruments evidencing or representing such
securities; (ii) all dividends, whether in cash, kind or stock, received or
receivable upon or in respect of any of the Pledged Securities and all moneys
or other property payable or paid on account of any return or repayment of
capital in respect of any of the Pledged Securities or otherwise distributed in
respect thereof or which will in any way be charged to, or payable or paid out
of, the capital of any of the Companies on account of the Pledged Securities;
(iii) all other property that may at any time be received or receivable by or
otherwise distributed to the Debtor in respect of, or in substitution for, or
in exchange for, any of the foregoing; and (iv) all cash, securities and other
proceeds of the foregoing and all rights and interests of the Debtor in respect
thereof or evidenced thereby, including all moneys received from time to time
by the Debtor in connection with the sale or other disposition of any of the
Pledged Securities; provided, however, that the Debtor will not sell or
otherwise dispose of any of the Pledged Securities or purport to do any of the
foregoing without the prior written consent of the Agent.


3.  DELIVERY OF PLEDGED SECURITIES.  The certificates representing the Pledged
Securities duly endorsed by the appropriate person in blank for transfer or
accompanied by powers of attorney satisfactory to the Agent will forthwith be
delivered to and remain in the custody of the Agent or its nominee.  All
Pledged Securities may, at the option of the Agent, be registered in the name
of the Agent or its nominee.  If the Agent so requests, the certificates
representing the Pledged Securities will also be guaranteed by a Canadian
chartered bank.


4.  REPRESENTATIONS AND WARRANTIES.  The Debtor hereby represents and warrants
to the Agent and acknowledges that the Agent is relying thereon,
notwithstanding any investigation by the Agent or any Lender or otherwise,
that:  (i) the Debtor is the lawful owner of the Collateral, free and clear of
any and all Liens or claims of others other than any Lien granted by the Debtor
to the Agent hereunder or Liens in favour of Canadian Imperial Bank of
Commerce, with full right to deliver, assign, pledge and charge the Collateral
to the Agent pursuant hereto; (ii) the Pledged

                                     - 2 -
<PAGE>   3
Securities represent all of the issued and outstanding shares in the capital of
each of the Companies held by the Debtor; (iii) the Pledged Securities are
validly issued, fully paid and non-assessable; (iv) there is no existing
agreement, option, right or privilege capable of becoming an agreement or
option pursuant to which the Debtor would be required to sell or otherwise
dispose of any of the Pledged Securities; (v) except as otherwise agreed by
the Agent in writing, the Liens granted by the Debtor to the Agent pursuant to
this Agreement constitute Liens on the Collateral in favour of the Agent which
are prior to all other Liens on the Collateral other than Liens in favour of
Canadian Imperial Bank of Commerce, whether created by the debtor or any other
Person, and in existence on the date hereof; (vi) the Debtor has the power and
authority and the legal right to execute and deliver, to perform its
obligations under, and to grant the Lien on the Collateral pursuant to, this
Agreement and the Debtor has taken all necessary corporate action to authorize
its execution, delivery and performance of, and grant of the Lien on the
Collateral pursuant to, this Agreement; (vii) this Agreement constitutes a
legal, valid and binding obligation of the Debtor, enforceable in accordance
with its terms, except as enforceability may be limited by bankruptcy,
insolvency, reorganization, moratorium or similar laws affecting the
enforcement of creditors, rights generally and by general principles of equity;
(viii) the execution, delivery and performance of this Agreement will not
violate any provision or requirement of any law or contractual obligation of
the Debtor and will not result in the creation or imposition of any Lien on any
of the properties or revenues of the Debtor pursuant to any requirement of law
or contractual obligation of the Debtor; (ix) no consent or authorization of,
filing with, or other act by or in respect of, any arbitrator or governmental
authority and no consent of any other person (including any shareholder or
creditor of the Debtor), is required in connection with the execution,
delivery, performance, validity or enforceability of this Agreement, except for
such as have been obtained or made and are in full force and effect, and the
terms of which have been disclosed to the Agent; and (x) no litigation,
investigation or proceeding of or before any arbitrator or governmental
authority is pending or, to the knowledge of the Debtor, threatened by or
against the Debtor or against any of its properties or revenues which may
materially adversely affect the business, property or financial or other
condition of the Debtor.

5.  COVENANTS.  The Debtor covenants and agrees with the Agent that:  (i) at
any time and from time to time, upon the written request of the Agent, and at
the sole expense of the Debtor, the Debtor will promptly and duly execute and
deliver such further instruments and documents and take such further action as
the Agent may request for the purpose of obtaining or preserving the full
benefits of this Agreement and of the rights and powers

                                     - 3 -
<PAGE>   4
herein granted, including the filing or execution of any financing or financing
change statements under any applicable legislation in effect in any
jurisdiction with respect to the Liens created hereby; (ii) the Debtor
authorizes the Agent to file any such financing or financing change statement
without the signature of the Debtor to the extent permitted by applicable law;
(iii) the Debtor will not create, incur or permit to exist, but will defend the
Collateral against, and will take such other action as is necessary to remove,
any Lien or claim on or to the Collateral, other than the Liens created hereby
and Liens in favour of Canadian Imperial Bank of Commerce and other than as
permitted in writing by the Agent; (iv) the Debtor will not sell, transfer,
lease or otherwise dispose of any of the Collateral except as permitted in
writing by the Agent; and (v) the Debtor will ensure that at the request of the
Agent, all Pledged Securities are registered in the name of the Agent or its
nominee, that the certificates representing the Pledged Securities will be
forthwith delivered to and remain in the custody of the Agent or its nominee,
and that all certificates, instruments or other documents representing or
evidencing any Pledged Securities acquired or issued subsequent to the date
hereof will be registered in the name of the Agent or its nominee and will
forthwith after issuance be delivered to, and remain in the custody of, the
Agent or its nominee.


6.  RIGHTS AND DUTIES OF AGENT.  The Agent will have and be entitled to
exercise all such powers hereunder as are specifically delegated to the Agent
by the terms hereof, together with such powers as are incidental thereto.  The
Agent may execute any of its duties hereunder by or through agents and will be
entitled to retain counsel and to act in reliance upon the advice of such
counsel concerning all matters pertaining to its duties hereunder.  The Agent
and any nominee on its behalf will be bound to exercise in the holding of the
Pledged Securities and other Collateral only the same degree of care as it
would exercise with respect to similar property of its own held in the same
place.  Neither the Agent, nor any Lender, nor any nominee acting on behalf of
the Agent or any Lender, nor any director, officer or employee of the Agent or
any Lender or such nominee, will be liable for any action taken or admitted to
be taken by it hereunder or in connection herewith except for its own gross
negligence or wilful misconduct.


7.  VOTING RIGHTS.  Unless a Default has occurred and is continuing, the Debtor
will be entitled to exercise all voting power from time to time exercisable in
respect of the Pledged Securities and give consents, waivers and ratifications
in respect thereof.  Immediately upon the occurrence and during the continuance
of any Default, all such rights of the Debtor to vote and give consents,
waivers and ratifications will cease and the

                                     - 4 -
<PAGE>   5
Agent will be entitled to exercise all such voting rights and to give all
consents, waivers and ratifications as permitted by the Agent.


8.  DIVIDENDS.  Unless a Default has occurred and is continuing, the Debtor
will, subject to any agreement with the Agent to the contrary, be entitled to
receive any and all cash dividends and other distributions on the Pledged
Securities which it is otherwise entitled to receive.  If a Default has
occurred and is continuing, the Agent will have the sole and exclusive right
and authority to receive and retain the dividends and other distributions which
the Debtor would otherwise be authorized to receive.  Any money and other
property paid over to or received by the Agent pursuant to the provisions of
this Section 8 will be retained by the Agent as additional Collateral hereunder
and be applied in accordance with the provisions hereof.


9.  REMEDIES.  If a Default has occurred and is continuing, the Agent may,
without notice to or the consent of the Debtor or any other person (other than
as required by applicable law), take all or any of the following actions:

(a)  transfer all or any part of the Collateral into the name of the Agent or
any Lender or any nominee on behalf of the Agent or any Lender, with or without
disclosing that such Collateral is subject to the Lien hereunder;

(b)  notify any parties obligated on any of the Collateral to make payment to
the Agent or any Lender of any amounts due or to become due thereunder;

(c)  exercise any and all rights of conversion, exchange, subscription or any
other rights, privileges or options pertaining to any of the Pledged Securities
as if it were the absolute owner thereof;

(d)  from time to time realize upon, collect, sell, transfer, assign, give
options to purchase, or otherwise dispose of and deliver the Pledged Securities
and other Collateral, or any part thereof, in such a manner as may seem to it
advisable, and for the purposes thereof each and every requirement relating
thereto and prescribed by law or otherwise is hereby waived to the extent
permitted by law;

(e)  enforce collection of any of the Collateral by suit or otherwise, and
surrender, release or exchange all or any part of any property in addition to
the Collateral, securing any of the Obligations, or compromise or extend or
renew for any period (whether or not longer than the original period) any
obligations of any nature of any party with respect to any property; and

                                     - 5 -
<PAGE>   6
(f)  to the extent permitted by applicable law, the Agent or any Lender may
purchase any or all of the Pledged Securities and other Collateral, whether in
connection with a sale made under the power of sale herein contained or
pursuant to judicial proceedings or otherwise;

provided, however, that the Agent and the Lenders will not be bound to deal
with the Pledged Securities and other Collateral as aforesaid, and will not be
liable for any loss which may be occasioned by any failure to do so and no
action of the Agent or any Lender permitted hereunder will impair or affect any
rights of the Agent or any Lender in and to the Collateral.


10.  APPLICATION OF PROCEEDS.  After payment of expenses as provided in Section
11 hereof, the balance of any proceeds received by the Agent in or in
connection with realizing, collecting, selling, transferring, delivering or
obtaining payment of the Collateral or any part thereof may be held by the
Agent and may, as and when the Agent thinks fit, be applied on account of such
part of the Obligations as to the Agent seems best, without prejudice to the
Agent's and the Lenders' claims upon the Debtor for any deficiency.


11.  PAYMENT OF EXPENSES.  The Agent may charge on its own behalf and also pay
to others all out-of-pocket expenses of the Agent and others retained by the
Agent, incurred in connection with realizing, collecting, selling,
transferring, delivering or obtaining payment of the Pledged Securities or any
other Collateral or any part thereof, or in connection with the administration
or amendment of this Agreement or incidental to the care, safekeeping, or
otherwise of any and all of the Collateral, and may deduct the amount of such
sums from any proceeds of the Collateral.  The Debtor agrees to indemnify and
hold harmless the Agent and the Lenders from and against any and all liability
incurred by the Agent, any Lender or any nominee, agent or employees of the
Agent or any Lender hereunder or in connection herewith, unless such liability
was due to willful misconduct or gross negligence on the part of the Agent or
Lender or such nominee or agent.


12.  ASSIGNMENT.  This Agreement will be binding upon the Debtor and its
successors and permitted assigns and will enure to the benefit of and be
enforceable by the Agent and the Lenders and their respective successors and
assigns.  The Debtor will not assign all or any part of this Agreement without
the Agent's prior written consent.

                                     - 6 -
<PAGE>   7
13.  NO WAIVER; CUMULATIVE REMEDIES.  Neither the Agent nor any Lender will by
any act, delay, indulgence, omission or otherwise be deemed to have waived any
right or remedy hereunder or to have acquiesced in any breach of any of the
terms and conditions hereof.  No failure to exercise, nor any delay in
exercising, on the part of the Agent or any Lender, any right, power or
privilege hereunder will operate as a waiver thereof.


14.  COMMUNICATION.  All communications provided for or permitted hereunder
shall be in writing, personally delivered to an officer or other responsible
employee of the addressee or sent by registered mail, charges prepaid, or by
telecopy, to the address or telecopy number set forth opposite the name of the
Debtor in the execution pages of this Agreement, in the case of the Debtor, and
to Canadian Imperial Bank of Commerce, Head Office, Commerce Court West, 7th
Floor, Toronto, Ontario M5L 1A2 (Attention:  Vice-President, Global Media &
Telecommunications) (Telecopy: (416) 980-2801), in the case of the Agent and
the Lenders, or to such other address as the applicable party hereto may from
time to time designate to the other in such manner.  Any communication so
personally delivered shall be deemed to have been validly and effectively given
on the date of such delivery.  Communications so sent by telecopy shall be
deemed to have been validly and effectively given on the business day next
following the day on which it is sent.  Communications so sent by mail shall be
deemed to have been validly and effectively given on the fifth business day
next following the day on which it is sent.


15.  DEALINGS BY AGENT AND LENDERS.  The Agent and the Lenders may grant
extensions of time and other indulgences, take and give up security, accept
compositions, grant releases and discharges and otherwise deal with the Debtor
and any third party having dealings with the Debtor, and with the Collateral or
any part thereof, and with other security and sureties, as the Agent and the
Lenders may see fit, all without prejudice to the Obligations or to the rights
of the Agent and the Lenders under this Agreement.  The Agent and the Lenders
will be accountable only for amounts that the Agent or any Lender actually
receives as a result of the exercise of such powers, and neither the Agent nor
any Lender nor any of their officers, directors, employees or agents will be
responsible to the Debtor for any act or failure to act hereunder, except for
its or their own gross negligence or willful misconduct.


16.  NON-EXCLUSIVITY OF REMEDIES.  This Agreement and the Liens arising
hereunder are in addition to and not in substitution for any other security now
or hereafter held by the Agent or any Lender in respect to the Debtor, the
Obligations or the Collateral.  No remedy for the enforcement of the rights of
the

                                     - 7 -
<PAGE>   8
Agent and the Lenders hereunder will be exclusive of or dependent on any
other such remedy but any one or more of such remedies may from time to time be
exercised independently or in combination.


17.  POWER OF ATTORNEY.  The Debtor hereby irrevocably constitutes and appoints
the Agent and any officer or agent thereof, with full power of substitution, as
its true and lawful attorney-in-fact, with full irrevocable power and authority
in the place and stead of the Debtor and in the name of the Debtor or in its
own name, from time to time in the Agent's discretion, for the purpose of
carrying out the terms of this Agreement, to take any and all appropriate
action, to do, make and execute any and all statements, acts, matters,
documents, instruments and things which may be necessary or desirable to
accomplish the purposes of this Agreement and from time to time to exercise all
rights and powers and to perform all acts of ownership in respect to the
Pledged Securities to the same extent as the Debtor might have done were it not
for this Agreement.  The Debtor hereby ratifies all that said attorneys will
lawfully do or cause to be done by virtue hereof.  This power of attorney is a
power coupled with an interest and will be irrevocable until the Obligations
have been paid and performed in full.


18.  NO MERGER.  Neither the taking and holding of the Pledged Securities and
other Collateral nor the obtaining of any judgment by the Agent or any Lender
will operate as a merger of any Obligation or any other indebtedness or
liability of the Debtor to the Agent or any Lender or operate to prejudice the
security constituted by this Agreement.


19.  SEVERABILITY.  Any provision of this Agreement which is prohibited or
unenforceable in any jurisdiction will, as to such jurisdiction, be ineffective
to the extent of such prohibition or unenforceability without invalidating the
remaining provisions hereof and any such prohibition or unenforceability in any
jurisdiction will not invalidate or render unenforceable such provision in any
other jurisdiction.


20.  GOVERNING LAW.  This Agreement will be governed by and construed in
accordance with the laws of Ontario.


21.  SURVIVAL OF REPRESENTATIONS AND WARRANTIES.  All agreements,
representations, warranties and covenants made by or on behalf of the Debtor
herein are material, will be considered to have been relied upon by the Agent
and the Lenders and will survive the execution and delivery of this Agreement
or any investigation

                                     - 8 -
<PAGE>   9
made at any time by or on behalf of the Agent or any Lender and any disposition
or payment of the Obligations until repayment in full thereof.


22.  ACKNOWLEDGEMENT OF SECURITIES PLEDGE AGREEMENT.  The Debtor acknowledges
receipt of a copy of the hypothecation of specific securities agreement dated
October 13, 1995 made by Hollinger Inc. in favour of Canadian Imperial Bank of
Commerce (the "Prior Securities Pledge") and agrees to be bound by the terms
thereof. The Debtor acknowledges that it acquired its beneficial interest in
the Pledged Securities from Hollinger Inc. and Domgroup Limited subject to the
Prior Securities Pledge and the rights of Canadian Imperial Bank of Commerce
under the Prior Securities Pledge and in relation to the Pledged Securities.


23.  ACKNOWLEDGEMENT OF RECEIPT.  The Debtor acknowledges receipt of an
executed copy of this Agreement.


  DATED: As of November 15, 1996.

   
ADDRESS                              503264 N.B. INC.

10 Toronto Street
Toronto, Ontario                     By: /s/ J.A. BOULTBEE
M5K 1N2                              Name:   J.A. Boultbee
                                     Title: President
Attention: President

Facsimile: (416) 364-2088                                  c/s
                                     By: /s/ CHARLES G. COWAN
                                     Name:   Charles G. Cowan
                                     Title: Vice President & Secretary
    

Schedule A - Pledged Securities

                                     - 9 -
<PAGE>   10
                                  SCHEDULE "A"


COMPANIES                          PLEDGED SECURITIES               CERTIFICATE
                                                                    NUMBER
                                   No.               Class

1.  Hollinger International        7,539,028         Class A
    Inc.                                             Common
                                                     Stock

<PAGE>   1
                                                                   EXHIBIT 99.11

                                                         As of November 15, 1996

Canadian Imperial Bank of Commerce
Commerce Court West, 7th Floor
Toronto, Ontario
M5H 3T7

- - and -

The Bank of Nova Scotia
44 King Street West, 16th Floor
Toronto, Ontario
M5H 1H1

- - and -

The Toronto-Dominion Bank
55 King Street West, 8th Floor
Toronto, Ontario
M5K 1H1

Dear Sirs:

                       Registration Rights Understanding

     Pursuant to the terms of the Hypothecation of Specific Securities dated
October 13, 1995 (the "Hypothecation") by Hollinger Inc. in favour of Canadian
Imperial Bank of Commerce ("CIBC"), Hollinger Inc. pledged 33,610,754 shares of
Class A Common Stock (the "Outstanding Pledged Shares") of Hollinger
International Inc. ("HII"), 14,990,000 shares of Class B Common Stock of HII
and certain other securities of HII held by Hollinger Inc. to CIBC as
collateral security for all present and future obligations of Hollinger Inc. to
CIBC.

     Hollinger Inc. subsequently transferred, subject to the Hypothecation,
beneficial ownership of 7,539,028 of the Outstanding Pledged Shares to 3184081
Canada Limited (now 503264 N.B. Inc.), a wholly-owned subsidiary of Hollinger
Inc. ("N.B. Inc."), registered and beneficial ownership of 15,950,00 of the
Outstanding Pledged Shares and beneficial ownership of all of the Class B
Common Stock to 1159670 Ontario Limited, a wholly-owned subsidiary of Hollinger
Inc.  ("Ontario Limited"). As used in this agreement, unless the context
otherwise requires, "Hollinger Inc." refers to Hollinger Inc. and its
wholly-owned subsidiaries, including but not limited to N.B. Inc. and Ontario
Limited.

     Pursuant to the terms of a Securities Pledge Agreement dated February 29,
1996 (the "Ontario Limited Securities Pledge Agreement"), Ontario Limited has
pledged the 15,950,000

<PAGE>   2

                                     - 2 -

Outstanding Pledged Shares held by it (the "Ontario Limited Shares") as
collateral security for its obligations under a $90,000,000 Credit Agreement
dated as of February 29, 1996 (as amended, supplemented, restated or replaced
from time to time, the "Ontario Limited Facility") among Ontario Limited,
Hollinger Inc., CIBC as agent for the Lenders, and CIBC, The Toronto-Dominion
Bank and The Bank of Nova Scotia (collectively, the "Lenders"). CIBC as agent
under the Ontario Limited Facility together with (i) CIBC in its own capacity
under the Hypothecation and (ii) CIBC as agent under the Southam Facility (as
defined herein) are hereinafter referred to as the "Pledgees".

     Pursuant to the terms of a Securities Pledge Agreement dated as of May 24,
1996, a second Securities Pledge Agreement dated as of July 17, 1996 to reflect
the syndication on July 17, 1996 of the Southam Facility (as defined herein)
equally between CIBC and The Bank of Nova Scotia and a third Securities Pledge
Agreement dated on or about the date hereof to reflect the continuance of
3184081 Canada Limited in New Brunswick (the "N.B. Inc. Securities Pledge
Agreements"), N.B. Inc. has pledged the 7,539,028 Outstanding Pledged Shares
held by it (the "N.B. Inc. Shares") as collateral security for its obligations
to CIBC and The Bank of Nova Scotia under a Guarantee of the Southam Facility
dated as of May 24, 1996, a second Guarantee dated as of July 17, 1996 to
reflect the syndication of the Southam Facility equally between CIBC and The
Bank of Nova Scotia and a third guarantee of the Southam Facility dated on or
about the date hereof to reflect the continuance of 3184081 Canada Limited in
New Brunswick (the "N.B. Inc. Guarantees").

     Pursuant to the terms of a Securities Pledge Agreement dated as of May 24,
1996, and a second Securities Pledge Agreement dated as of July 17, 1996 to
reflect the syndication on July 17, 1996 of the Southam Facility equally
between CIBC and The Bank of Nova Scotia (the "Ontario Limited Securities
Pledge Agreements"), Ontario Limited has pledged the Class B Common Stock as
collateral security for its obligations to CIBC and The Bank of Nova Scotia
under a Guarantee of the Southam Facility dated as of May 24, 1996, and a
second Guarantee dated as of July 17, 1996 to reflect the syndication of the
Southam Facility equally between CIBC and The Bank of Nova Scotia (the "Ontario
Limited Guarantees"). For purposes hereof, the "Southam Facility" means the
credit facility established pursuant to a credit commitment agreement titled
"Summary of Terms and Conditions" dated May 24, 1996 between Hollinger Inc.,
HII and CIBC, as supplemented by an assignment agreement dated as of July 17,
1996 among HII, CIBC and The Bank of Nova Scotia, as replaced by a credit
agreement dated on or about the date hereof between, among others, CIBC as
agent, CIBC, The Bank of Nova Scotia, HII, Hollinger, Ontario Limited and N.B.
Inc. and as amended, supplemented, restated, replaced from time to time.

<PAGE>   3

                                     - 3 -

     A registration statement (including a prospectus) on Form S-3 (No.
333-04697) has been filed under the Securities Act of 1933, as amended (the
"Securities Act") with the Securities and Exchange Commission on May 29, 1996
and will shortly be amended by Amendment No. 1 thereto to be filed by the
undersigned on or about November 25, 1996 (the "Registration Statement") that
relates to an aggregate of 48,600,754 shares (the "Pledged Shares") of Class A
Common Stock of HII. HII hereby agrees to use its best efforts to have the
Registration Statement declared effective by the Securities and Exchange
Commission on or before November 30, 1996. The Pledged Shares comprise the
Outstanding Pledged Shares and 14,990,000 Pledged Shares (the "Conversion
Pledged Shares"), the shares of Class A Common Stock into which all of the
outstanding shares of HII's Class B Common Stock, all owned of record by
Hollinger Inc. (and beneficially owned by Ontario Limited), would be
automatically converted into, pursuant to the terms of HII's Restated
Certificate of Incorporation, as amended, upon transfer of such shares of Class
B Common Stock to the Pledgees. The Outstanding Pledged Shares were registered
under the Securities Act pursuant to the terms of a Registration Rights
Agreement dated February 29, 1996, as amended on May 24, 1996 (the
"Registration Rights Agreement"). The Conversion Pledged Shares will be
registered under the Securities Act on or before November 30, 1996 pursuant to
the terms of agreements among the Company, Hollinger Inc. and CIBC, including,
without limitation, the terms of the CIBC Letter Agreement dated October 13,
1995, as amended on May 24, 1996 (the "CIBC Letter Agreement").

     No offers or sales of the Pledged Shares may be made by the Pledgees
pursuant to the Registration Statement, and prospectus included therein, unless
appropriate post-effective amendments or supplements are made to reflect facts
or events arising after the effective date of the Registration Statement (or
the most recent post-effective amendment thereof) which, individually or in the
aggregate, represent a fundamental change in the information set forth in the
Registration Statement and to include any material information with respect to
the plan of distribution not previously disclosed in the Registration Statement
or any material change to such information in the Registration Statement. HII
may require each Pledgee to furnish HII such information regarding such Pledgee
and the distribution of the Pledged Shares as HII may from time to time
reasonably request in writing.

     This is to confirm our undertaking and agreement that if (i) Hollinger
Inc.  or HII or Ontario Limited or N.B. Inc. or any other person is in default
on indebtedness now or hereafter outstanding under agreements or arrangements
secured by the Pledged Shares and (ii) the Pledgees have or intend to effect
foreclosure upon the Pledged Shares in accordance with their rights under any
applicable security documents or to exercise

<PAGE>   4

                                     - 4 -

their power of sale rights under any applicable security documents, upon
written request from any of the Pledgees, the undersigned (HII, Hollinger Inc.,
Ontario Limited and N.B. Inc.) shall take all further steps necessary,
including filing the necessary amendments or supplements to the Registration
Statement and the prospectus included therein, to permit the sale of all or any
part of the Pledged Shares pursuant to the prospectus included in the
Registration Statement, as amended.

     The Pledgees agree that, upon receipt of any notice from HII of the
happening of any event as a result of which the prospectus included in the
Registration Statement, as then in effect, includes an untrue statement of a
material fact or omits to state any material fact required to be stated therein
or necessary to make the statements therein not misleading, in the light of the
circumstances under which they were made, they will forthwith discontinue the
Pledgees' disposition of Pledged Shares pursuant to the Registration Statement
until the Pledgees' receipt of the copies of the amended or supplemented
Registration Statement (or prospectus included therein) contemplated by the
preceding sentence of this letter agreement (which the undersigned shall file
as a contemplated by the preceding sentence of this Agreement).

     Hollinger and HII will pay all reasonable expenses incurred by the
Pledgees in connection with the sale of the Pledged Shares, including
underwriting discounts or commission and reasonable fees and disbursements of
counsel to the Pledgees.

                                       Yours very truly,

                                       Hollinger Inc.

                                       By: /s/ PETER Y. ATKINSON
                                       Name: Peter Y. Atkinson
                                       Title: Vice-President & General Counsel


                                       Hollinger International Inc.

                                       By: /s/ J.A. BOULTBEE
                                       Name: J.A. Boultbee
                                       Title: Vice President and
                                                Chief Financial Officer

<PAGE>   5

                                     - 5 -

                                       1159670 Ontario Limited

                                       By: /s/ PETER Y. ATKINSON
                                       Name: Peter Y. Atkinson
                                       Title: Vice-President & General Counsel


                                       503264 N.B. Inc.

                                       By: /S/ J.A. BOULTBEE
                                       Name: J.A. Boultbee
                                       Title: President

Acknowledged and agreed to this 15th day of November, 1996.

Canadian Imperial Bank of Commerce

By: /s/ ILLEGIBLE
Name:
Title:


The Toronto-Dominion Bank

By: /S/ M. F. COLLINS
Name: M. F. Collins
Title: Manager, Communications Finance


The Bank of Nova Scotia

By: /s/ ILLEGIBLE
Name:
Title:


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