ALLEGHANY CORP /DE
S-8, 1999-04-13
TITLE INSURANCE
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<PAGE>   1
     As filed with the Securities and Exchange Commission on April 13, 1999
                                                 Registration Number 333-_______


                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549




                                    FORM S-8
                             REGISTRATION STATEMENT
                                      UNDER
                           THE SECURITIES ACT OF 1933




                              ALLEGHANY CORPORATION
             (Exact name of registrant as specified in its charter)

                Delaware                               51-0283071
            (State or other                         (I.R.S. Employer
            jurisdiction of                      Identification Number)
            incorporation or
             organization)

            375 Park Avenue                               10152
           New York, New York                          (Zip Code)
(Address of Principal Executive Offices)

               UNDERWRITERS RE GROUP, INC. 1998 STOCK OPTION PLAN
                            (Full Title of the Plan)

                              Robert M. Hart, Esq.
                     Senior Vice President, General Counsel
                                  and Secretary
                              Alleghany Corporation
                                 375 Park Avenue
                            New York, New York 10152
                                 (212) 752-1356
            (Name, address and telephone number of agent for service)


                                   Copies to:
                              Linda E. Ransom, Esq.
                              Dewey Ballantine LLP
                           1301 Avenue of the Americas
                          New York, New York 10019-6092
                                 (212) 259-8000
<PAGE>   2
                         CALCULATION OF REGISTRATION FEE

<TABLE>
<CAPTION>
==========================================================================================================================
                                                     PROPOSED MAXIMUM        PROPOSED MAXIMUM
 TITLE OF SECURITIES TO        AMOUNT TO BE         OFFERING PRICE PER      AGGREGATE OFFERING           AMOUNT OF
      BE REGISTERED           REGISTERED (1)             UNIT (2)                PRICE (2)            REGISTRATION FEE
- --------------------------------------------------------------------------------------------------------------------------
<S>                           <C>                   <C>                     <C>                       <C>
Common Stock,
     par value $1.00
     per share                    42,097                $79.22192               $3,335,005                $927.13
==========================================================================================================================
</TABLE>

(1)   This Registration Statement shall also cover any additional shares of
      Common Stock which become issuable under the Underwriters Re Group, Inc.
      1998 Stock Option Plan (the "Plan") by reason of any stock dividend, stock
      split, recapitalization, merger, consolidation or reorganization of or by
      the Registrant which results in an increase in the number of the
      Registrant's outstanding shares of Common Stock or shares issuable
      pursuant to the options.

(2)   Pursuant to Rule 457(h) of the Securities Act of 1933, as amended, solely
      for the purpose of computing the registration fee, the proposed maximum
      offering price per unit was computed by multiplying the exercise price of
      each option granted under the Plan by the number of shares issuable upon
      exercise of such option, adding those results together and dividing that
      sum by the total number of shares issuable upon exercise of all options
      granted under the Plan.
<PAGE>   3
                                     PART II


               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.     INCORPORATION OF DOCUMENTS BY REFERENCE.

            The following documents filed with the Securities and Exchange
Commission by Alleghany Corporation ("Alleghany") (File No. 1-9371) are
incorporated herein by reference and made a part hereof:

      (a)   Alleghany's Annual Report on Form 10-K for the fiscal year ended
            December 31, 1998; and

      (b)   the description of the Common Stock of Alleghany contained in its
            Registration Statement on Form 10 filed pursuant to Section 12 of
            the Securities Exchange Act of 1934, as amended (the "Exchange
            Act"), which incorporates by reference certain portions of
            Alleghany's Proxy Statement dated November 26, 1986 relating to its
            Special Meeting of Stockholders held on December 19, 1986; such
            description is qualified in its entirety by reference to the (i)
            Restated Certificate of Incorporation of Alleghany, as amended by
            Amendment accepted and received for filing by the Secretary of State
            of the State of Delaware on June 23, 1988, filed as Exhibit 20 to
            Alleghany's Quarterly Report on Form 10-Q for the quarter ended June
            30, 1988, and (ii) By-Laws of Alleghany, as amended April 18, 1995,
            filed as Exhibit 3.1 to Alleghany's Quarterly Report on Form 10-Q
            for the quarter ended March 31, 1995, and any amendment or report
            filed for the purpose of updating that description.

            All documents filed by Alleghany pursuant to Sections 13(a), 13(c),
14 and 15(d) of the Exchange Act subsequent to the date of this Registration
Statement and prior to the filing of a post-effective amendment which indicates
that all securities offered have been sold or which deregisters all securities
then remaining unsold, shall be deemed to be incorporated by reference in this
Registration Statement and to be part hereof from the date of filing of such
documents.

            The consolidated financial statements and financial statement
schedules of Alleghany and its subsidiaries included in or incorporated by
reference in Alleghany's Annual Report on Form 10-K for the fiscal year ended
December 31, 1998 have been incorporated herein by reference in reliance upon
the reports, also incorporated herein by reference, of KPMG LLP, independent
auditors, given on their authority as experts in auditing and accounting.

ITEM 4.     DESCRIPTION OF SECURITIES.

            Not Applicable.

ITEM 5.     INTERESTS OF NAMED EXPERTS AND COUNSEL.

            Not Applicable.


                                      II-1
<PAGE>   4
ITEM 6.     INDEMNIFICATION OF DIRECTORS AND OFFICERS.

            Alleghany is a Delaware corporation. Reference is made to Section
145 of the Delaware General Corporation Law as to indemnification by Alleghany
of its officers and directors. The general effect of such law is to empower a
corporation to indemnify any of its officers and directors against certain
expenses (including attorneys' fees), judgments, fines and amounts paid in
settlement actually and reasonably incurred by the person to be indemnified in
connection with certain actions, suits or proceedings (threatened, pending or
completed) if the person to be indemnified acted in good faith and in a manner
he reasonably believed to be in, or not opposed to, the best interests of the
corporation and, with respect to any criminal action or proceeding, had no
reasonable cause to believe his conduct was unlawful.

            Article Tenth of Alleghany's Restated Certificate of Incorporation,
as amended, provides for the indemnification of Alleghany's officers and
directors in accordance with the Delaware General Corporation Law, and includes,
as permitted by the Delaware General Corporation Law, certain limitations on the
potential personal liability of members of Alleghany's Board of Directors for
monetary damages as a result of actions taken in their capacity as Board
members.

            The directors and officers of Alleghany are covered by insurance
policies indemnifying them against certain liabilities arising under the
Securities Act of 1933, as amended, which might be incurred by them in such
capacities.

ITEM 7.     EXEMPTION FROM REGISTRATION CLAIMED.

            Not applicable.

ITEM 8.     EXHIBITS.

            The documents listed hereunder are filed as exhibits hereto.


<TABLE>
<CAPTION>
Exhibit Number            Description
- --------------            -----------
<S>                       <C>
     4                    Underwriters Re Group, Inc. 1998 Stock Option Plan.

     5                    Opinion and Consent of Dewey Ballantine LLP.

    23.1                  Consent of Dewey Ballantine LLP (included in Exhibit
                          5 hereto).

    23.2                  Consent of KPMG LLP.

    23.3                  Consent of Wilde Sapte.

    24                    Powers of Attorney.
</TABLE>


                                      II-2
<PAGE>   5
ITEM 9.     UNDERTAKINGS

      (a)   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; and

                  (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 (a)(1)(i) and (a)(1)(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
Securities and Exchange 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 that time shall be deemed to be the initial bona
fide offering thereof.

            (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.

      (b) The undersigned registrant hereby undertakes 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 (and, where applicable, each filing of an
employee benefit plan's annual report pursuant to Section 15(d) of the
Securities Exchange Act of 1934) that is incorporated by reference in this
Registration Statement shall be deemed to be a new registration statement
relating to the securities offered herein, and the offering of such securities
at that time shall be deemed to be the initial bona fide offering thereof.

      (c) 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


                                      II-3
<PAGE>   6
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-4
<PAGE>   7
                                   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-8 and has duly caused this Registration
Statement to be signed on its behalf by the undersigned, thereunto duly
authorized, in the City of New York, State of New York, on the 13th day of
April, 1999.

                                    ALLEGHANY CORPORATION


                                    By:  /s/ John J. Burns, Jr.
                                         ---------------------------------------
                                                John J. Burns, Jr.
                                                    President

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


Date: April 13, 1999                     By:     /s/ John J. Burns, Jr.
                                            ------------------------------------
                                                   John J. Burns, Jr.
                                                 President and Director
                                              (principal executive officer)


Date: April 13, 1999                     By:                           *
                                            ------------------------------------
                                                    Dan R. Carmichael
                                                        Director


Date: April 13, 1999                     By:     /s/ David B. Cuming
                                            ------------------------------------
                                                     David B. Cuming
                                                  Senior Vice President
                                              (principal financial officer)


Date: April 13, 1999                     By:                           *
                                            ------------------------------------
                                                    Thomas S. Johnson
                                                        Director


Date: April 13, 1999                     By:                           *
                                            ------------------------------------
                                                   Allan P. Kirby, Jr.
                                                        Director
<PAGE>   8
Date: April 13, 1999
                                         By:                           *
                                            ------------------------------------
                                                       F.M. Kirby
                                           Chairman of the Board and Director


Date: April 13, 1999                     By:                           *
                                            ------------------------------------
                                                    William K. Lavin
                                                        Director


Date: April 13, 1999                     By:                           *
                                            ------------------------------------
                                                       Roger Noall
                                                        Director


Date: April 13, 1999                     By:    /s/ Peter R. Sismondo
                                            ------------------------------------
                                                    Peter R. Sismondo
                                               Vice President, Controller,
                                            Treasurer and Assistant Secretary
                                             (principal accounting officer)


Date: April 13, 1999                     By:                           *
                                            ------------------------------------
                                                      James F. Will
                                                        Director


Date: April 13, 1999                     By:                           *
                                            ------------------------------------
                                                    Paul F. Woodberry
                                                        Director


                       *By:     /s/ John J. Burns, Jr.
                           ------------------------------------
                                   John J. Burns, Jr.
                                   Attorney-in-Fact
<PAGE>   9
                                INDEX TO EXHIBITS

<TABLE>
<CAPTION>
Exhibit Number            Description
- --------------            -----------
<S>                       <C>
     4                    Underwriters Re Group, Inc. 1998 Stock Option Plan.

     5                    Opinion and Consent of Dewey Ballantine LLP.

    23.1                  Consent of Dewey Ballantine LLP (included in Exhibit
                          5 hereto).

    23.2                  Consent of KPMG LLP.

    23.3                  Consent of Wilde Sapte.

    24                    Powers of Attorney.
</TABLE>


<PAGE>   1
                                                                       Exhibit 4


                           UNDERWRITERS RE GROUP, INC.
                             1998 STOCK OPTION PLAN

1.    Definitions.

            In this Plan, except where the context otherwise indicates, the
following definitions apply:

            a. "Alleghany" means Alleghany Corporation, a Delaware corporation.

            b. "Board" means the Board of Directors of the Corporation.

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

            d. "Committee" means the compensation committee of the Board,
consisting of directors who are not employees of the Corporation or a
Subsidiary.

            e. "Common Stock" means the common stock, par value $1.00 per share,
of Alleghany.

            f. "Corporation" means Underwriters Re Group, Inc., a Delaware
corporation, and any successor thereto.

            g. "Date of Exercise" means the date on which the Corporation
receives notice of the exercise of an Option and payment therefor in accordance
with the terms of Article 6.

            h. "Exercise Price" means the price per share of Alleghany Common
Stock at which an Option may be exercised.

            i. "Fair Market Value" means the mean of the high and low sales
prices of Alleghany Common Stock on the relevant date as reported on the New
York Stock Exchange, or, if no sale is made on such date, the average of the
mean of the high and low sales prices of Alleghany Common Stock on the next
preceding day and the next succeeding day on which sales were made as reported
on the New York Stock Exchange.

            j. "Option" means an option to purchase shares of Alleghany Common
Stock granted in accordance with the terms of Article 5.

            k. "Option Agreement" means the written agreement evidencing the
grant of an Option hereunder.

            l. "Optionee" means an employee of Venton to whom an Option is
granted.

            m. "Permanent disability" means the inability of the Optionee, as a
result of physical or mental illness or incapacity, to perform his duties with
the
<PAGE>   2
Corporation or a Subsidiary for a period of four consecutive months or for an
aggregate of more than six months in any twelve-month period.

            n. "Plan" means the Underwriters Re Group, Inc. 1998 Stock Option
Plan.

            o. "Predecessor Option" to an Option means a warrant or an option to
purchase Class C shares of Venton, which is exchanged for such Option and
cancelled prior to the issuance of such Option.

            p. "Subsidiary" means a corporation at least 50 percent of the total
combined voting power of all classes of stock of which is owned by the
Corporation, either directly or through one or more other Subsidiaries.

            q. "Venton" means Venton Holdings Ltd., a wholly owned Subsidiary.

2. Purpose.

            The Plan is intended to provide Options in exchange for Predecessor
Options, for the purpose of implementing the provisions of the agreement
relating to the acquisition of Venton by the Corporation, which contemplated
such exchange, and to eliminate the minority interests in Venton and provide a
more marketable security to the Optionees.

3. Administration.

            The Plan shall be administered by the Committee. In addition to any
other powers granted to the Committee, it shall have the following powers,
subject to the express provisions of the Plan:

            a. to select Optionees, determine the amount of Options granted to
them in accordance with the terms of Article 5 and determine the terms and
conditions of such grants;

            b. to construe and interpret the Plan and the Option Agreements;

            c. to provide for income tax withholding, including, without
limitation, through retention of shares of Alleghany Common Stock otherwise
issuable upon the exercise of an Option or by delivery of shares of Alleghany
Common Stock to the Corporation by the Optionee, to the extent and under such
terms and conditions as the Committee deems appropriate; and

            d. to make all other determinations and take all other actions
necessary or advisable for the administration of the Plan.

            Any determinations made or actions taken by the Committee pursuant
to the Plan shall be binding and final. Any powers granted to the Committee 
shall also be exercisable by  the Board.


                                      -2-
<PAGE>   3
4. Eligibility.

            Options may be granted only to employees of Venton and its
subsidiaries as of October 23, 1998 who hold Predecessor Options.

5. Awards.

            a. There may be issued under the Plan pursuant to the exercise of
Options an aggregate of not more than 42,097 shares of Alleghany Common Stock,
subject to adjustment as provided in the Plan.

            b. Options shall be forfeited by the Optionee to the extent not
exercisable upon termination of the Optionee's employment with the Corporation
or a Subsidiary for any reason.

            c. To the extent not inconsistent with the terms of their
Predecessor Options, Options shall expire if not exercised prior to the earliest
of (i) the expiration date of the Predecessor Option, (ii) three months after
termination of the Optionee's employment with the Corporation or a Subsidiary
for any reason except death or permanent disability, and (iii) one year after
termination of the Optionee's employment with the Corporation or a Subsidiary by
reason of death or permanent disability.

            d. The Exercise Price may be paid in cash, shares of Alleghany
Common Stock valued at the Fair Market Value thereof on the Date of Exercise, or
a combination of cash and shares of Alleghany Common Stock so valued.

            e. No Option may be granted as an incentive stock option under
Section 422 of the Code.

            f. Each grant of Options under the Plan shall be evidenced by an
Option Agreement substantially in the form of Appendix I to the Plan, and shall
be executed by any officer of the Corporation and by the Optionee.

            g. Subject to the terms of the Plan, all other terms of Options
shall be as determined by the Committee in its sole discretion and Options shall
contain such other conditions, not inconsistent with the foregoing, as may be
determined by the Committee.

6. Exercise.

            An Option may, subject to the provisions of the Option Agreement
under which it was granted (including withholding provisions), be exercised in
whole or in part by delivery to the Corporation of written notice of exercise,
in such form as the Committee may prescribe, accompanied by full payment for the
shares of Alleghany Common Stock with respect to which such Option is exercised.


                                      -3-
<PAGE>   4
7. Restrictions on Transfer and Exercise.

            Options shall be subject to such restrictions on transfer and
exercise as provided in the Option Agreement.

8. Capital Adjustments.

            The number and class of shares of Alleghany Common Stock subject to
each Option and the Exercise Price thereof shall be subject to such adjustment,
if any, as the Committee in its sole discretion deems appropriate to reflect
such events as stock dividends, stock splits, recapitalizations, mergers,
consolidations or reorganizations of or by Alleghany, subject to the approval of
the Compensation Committee of the Board of Directors of Alleghany.

9. Termination and Amendment.

            The Board shall have the power to terminate the Plan and to amend it
in any respect, provided that no such termination or amendment shall adversely
affect the rights or obligations of an Optionee with respect to any Option
previously granted under the Plan.

10. Modification, Extension and Renewal of Options.

            Subject to the terms and conditions of the Plan, the Committee may
modify, extend or renew outstanding Options or accept the surrender of
outstanding Options (to the extent not theretofore exercised) granted under the
Plan and authorize the granting of new Options in substitution therefor on such
terms consistent with the Plan as the Committee may specify; provided, however,
that no modification of an Option granted under the Plan shall, without the
consent of the Optionee, alter or impair any of such Optionee's rights or
obligations.

11. General Provisions.

            a. The establishment of the Plan shall not confer upon any Optionee
any legal or equitable right against the Corporation, any Subsidiary, Alleghany
or the Committee, except as expressly provided in the Plan.

            b. The Plan does not constitute inducement or consideration for the
employment or service of any Optionee, nor is it a contract between the
Corporation, any Subsidiary or Alleghany and any Optionee. Participation in the
Plan shall not give an Optionee any right to be retained in the service or
employ of the Corporation, any Subsidiary or Alleghany.

            c. The interests of any Optionee under the Plan or any Option are
not subject to the claims of creditors and may not, in any way, be assigned,
alienated or encumbered.

            d. The Plan shall be governed, construed and administered in
accordance with the laws of the State of Delaware.


                                      -4-
<PAGE>   5
                                                                      Appendix I


                           UNDERWRITERS RE GROUP, INC.

                       Nonstatutory Stock Option Agreement
                                      Under
                             1998 Stock Option Plan


Option Agreement No:

Optionee:

Date of Grant:  October 23, 1998

Exercise Price:

Number of Shares of
Alleghany Common Stock:

1.    Definitions. This Option Agreement evidences the grant of an Option under
      the 1998 Stock Option Plan (the "Plan") adopted by Underwriters Re Group,
      Inc. (the "Corporation"). All terms used in this Option Agreement which
      are not defined herein shall have the meanings given to them in the Plan.

2.    Grant of Option. Pursuant to the Plan and subject to the terms and
      conditions of this Option Agreement, the Corporation hereby grants to
      _______ (the "Optionee") the right ("Option") to purchase ________shares
      of common stock, par value $1.00 per share ("Common Stock"), of Alleghany
      Corporation ("Alleghany") from the Corporation at the purchase price of
      $___ per share (the "Option Price"), as the same may be adjusted from time
      to time pursuant to the terms of the Plan. This Option has been granted in
      exchange for and upon cancellation of Predecessor Options to purchase ____
      Class C shares of Venton.

3.    Subject to the Plan. The Option evidenced by this Option Agreement and the
      exercise thereof are subject to the terms and conditions of the Plan,
      which is incorporated herein by reference and made a part hereof.

4.    Terms of the Option.

            a.    Type of Option. The Option is intended to be a nonstatutory
                  stock option, and is not an incentive stock option within the
                  meaning of section 422 of the Code.

            b.    Option Period. The Option may be exercised with respect to
                  full shares of Alleghany Common Stock (and no fractional
                  shares shall be issued) as follows:
<PAGE>   6
                  (i)   in addition to the terms set forth herein, the Option
                        shall have all of the terms of its Predecessor Option;

                  (ii)  the Option shall be forfeited by the Optionee to the
                        extent not exercisable upon termination of the
                        Optionee's employment with the Corporation or a
                        Subsidiary for any reason; and

                  (iii) to the extent not inconsistent with the terms of its
                        Predecessor Option, the Option shall expire if not
                        exercised prior to the earliest of (1) the expiration
                        date of the Predecessor Option, (2) three months after
                        termination of the Optionee's employment with the
                        Corporation or a Subsidiary for any reason except death
                        or permanent disability, and (3) one year after
                        termination of the Optionee's employment with the
                        Corporation or a Subsidiary by reason of death or
                        permanent disability. For purposes hereof, the term
                        "permanent disability" means the inability of the
                        Optionee, as a result of physical or mental illness or
                        incapacity, to perform his duties with the Corporation
                        or a Subsidiary for a period of four consecutive months
                        or for an aggregate of more than six months in any
                        twelve-month period.

5.    Restrictions on the Transfer of Options.

      The Optionee shall not, and no action taken by the Optionee shall be
      effective to, directly or indirectly, sell, distribute, transfer, assign,
      pledge, hypothecate or otherwise dispose of or encumber the Option or any
      interest therein (all of which acts shall be deemed included in the term
      "transfer" as used in this Option, Agreement), except that transfer of the
      Option is permitted (i) to the Corporation or Alleghany upon their
      consent, or (ii) to the Optionee's executors, administrators, testamentary
      trustees, legatees or beneficiaries (collectively, the "Optionee's
      Estate") upon the Optionee's death, provided that the Optionee's Estate
      agrees to be bound by the terms of this Option Agreement.

6.    Exercise.

            a.    Notice. The Option shall be exercised, in whole or in part, by
                  the delivery to the Corporation of written notice of such
                  exercise, in such form as the Committee may from time to time
                  prescribe, accompanied by (i) full payment of the Exercise
                  Price with respect to that portion of the Option being
                  exercised, and (ii) full payment of any amounts required to be
                  withheld pursuant to applicable income tax laws in connection
                  with such exercise. The date that such notice and the required
                  payments are received by the Corporation shall be the Date of
                  Exercise of such Option. Until


                                      -2-
<PAGE>   7
                  the Committee notifies the Optionee to the contrary, the form
                  attached to this Option Agreement as Exhibit A shall be used
                  to exercise the Option.

            b.    Payment of the Exercise Price. Upon exercise of the Option, in
                  whole or in part, the Optionee may pay the Exercise Price in
                  cash, by delivering duly endorsed certificates representing
                  whole shares of Alleghany Common Stock having a Fair Market
                  Value on the Date of Exercise equal to that portion of the
                  Exercise Price being paid by delivery of such shares, or
                  through a combination of cash and shares of Alleghany Common
                  Stock so valued.

            c.    Payment of Withholding. An Optionee may elect in the notice of
                  exercise to satisfy applicable income tax withholding
                  requirements by payment of cash or, subject to such terms and
                  conditions as the Committee may from time to time establish,
                  through retention by the Corporation of shares of Alleghany
                  Common Stock otherwise issuable upon exercise of the Option or
                  by delivery to the Corporation of previously acquired shares
                  of Alleghany Common Stock.

7.    Restrictions on the Exercise of Options and the Sale of Shares.
      Notwithstanding any other provision of this Option Agreement, the Optionee
      agrees, for such Optionee and such Optionee's Estate, that the Option may
      not be exercised, and the shares of Alleghany Common Stock issued upon
      exercise may not be sold, at any time that Alleghany does not have in
      effect a registration statement under the Securities Act of 1933, as
      amended, relating to the offer of shares of Alleghany Common Stock to the
      Optionee under the Plan, unless the Optionee furnishes to the Corporation
      an opinion of counsel reasonably satisfactory to the Corporation to the
      effect that such registration is not required, or unless the Corporation
      agrees to permit such exercise. The certificates representing such shares
      of Alleghany Common Stock may set forth a legend to such effect.

8.    Rights as Stockholder. The Optionee shall have no rights as a stockholder
      with respect to any shares of Alleghany Common Stock subject to the Option
      until and unless a certificate or certificates representing such shares
      are issued to the Optionee pursuant to this Option Agreement. Except as
      the Committee may determine in accordance with the terms of the Plan, no
      adjustment shall be made for dividends or other rights for which the
      record date is prior to the issuance of such certificate or certificates.

9.    Employment. Neither the granting of the Option evidenced by this Option
      Agreement nor any term or provision of this Option Agreement shall
      constitute or be evidence of any understanding, express or implied, on the
      part of the Corporation, a Subsidiary or Alleghany to employ the Optionee
      for any period.


                                      -3-
<PAGE>   8
            IN WITNESS WHEREOF, the Corporation has caused this Option Agreement
to be signed on its behalf effective as of the Date of Grant.

                                    UNDERWRITERS RE GROUP, INC.



                                    By:_________________________________
                                       Name:  Stuart M. de Haaff
                                       Title: General Counsel and Secretary

Accepted and agreed to as of
the Date of Grant:


________________________________
Optionee


                                      -4-
<PAGE>   9
                                                                       Exhibit A

                               EXERCISE OF OPTION


Secretary
Underwriters Re Group, Inc.

            The undersigned Optionee under the Nonstatutory Stock Option
Agreement identified as Option Agreement No. ___ (the "Option Agreement"),
granted pursuant to the Underwriters Re Group, Inc. 1998 Stock Option Plan (the
"Plan"), hereby irrevocably elects to exercise the Option granted in the Option
Agreement to purchase ___ shares of common stock, par value $1.00 per share, of
Alleghany Corporation, and herewith makes payment of the option price of $______
in the form of ______ [cash, shares, cash plus shares (indicate amount of
each)].

            [IF APPLICABLE, INCLUDE] [In addition, the undersigned hereby elects
to have the income tax withholding requirements imposed upon this exercise of
the Option met by:

<TABLE>
<S>                                                <C>
            / /  Payment of cash                   $_________
                                                    

            / /  Retention of shares otherwise
                 issuable upon such exercise       $_________
                                                   

            / /  Delivery of shares                $_________
                                                    
</TABLE>

            Check the applicable boxes, and indicate the amount of each.]

                                    Signature of Optionee:  ________________

                                    Date:  _________________________________



                                    Received by Underwriters Re Group Inc.

                                    By:  __________________________________

                                    Date of Receipt:  _____________________



Note: Shares being delivered in payment of all or any part of the Exercise Price
      or income tax withholding requirements must be represented by a
      certificate or certificates registered in the name of the Optionee and
      duly endorsed by the Optionee and by each and every other co-owner in
      whose name the shares may also be registered.


<PAGE>   1
                                                                       Exhibit 5

                              DEWEY BALLANTINE LLP

                           1301 Avenue of the Americas
                               New York 10019-6092
                        TEL 212 259-8000 FAX 212 259-6333





                                    April 13, 1999


Alleghany Corporation
375 Park Avenue
New York, New York  10152


            Re:  Registration Statement on Form S-8 Filed with the
                 Securities and Exchange Commission on April 13, 1999
                 -----------------------------------------------------

Gentlemen:

            We are acting as counsel for Alleghany Corporation, a Delaware
corporation ("Alleghany"), in connection with the registration by Alleghany
under the Securities Act of 1933, as amended (the "Act"), of 42,097 shares of
common stock, par value $1.00 per share (the "Shares"), of Alleghany to be
offered pursuant to the Underwriters Re Group, Inc. 1998 Stock Option Plan (the
"Plan") under the Registration Statement on Form S-8 filed with the Securities
and Exchange Commission on April 13, 1999 (the "Registration Statement").

            We are familiar with the proceedings of Alleghany relating to the
authorization and issuance of the Shares. In addition, we have made such further
examinations of law and fact as we have deemed appropriate in connection with
the opinion hereinafter set forth. We express no opinion as to the law of any
jurisdiction other than the laws of the State of New York and the corporate laws
of the State of Delaware.

            Based upon the foregoing, we are of the opinion that the Shares to
be offered pursuant to the Plan have been duly authorized and, when issued in
accordance with the resolutions of the Board of Directors of Alleghany
authorizing such issuance, will be validly issued, fully paid and nonassessable.
<PAGE>   2
Alleghany Corporation
April 13, 1999
Page 2


            We hereby consent to the filing of this opinion as an exhibit to the
Registration Statement. In giving such consent, we do not thereby admit that we
come within the category of persons whose consent is required under Section 7 of
the Act, or under the rules and regulations of the Securities and Exchange
Commission thereunder.

                                    Very truly yours,

                                    /s/ Dewey Ballantine LLP


<PAGE>   1
                                                                    Exhibit 23.2


                         CONSENT OF INDEPENDENT AUDITORS


The Board of Directors
Alleghany Corporation:


We consent to the incorporation by reference in the registration statement on
Form S-8 of Alleghany Corporation of our reports dated February 19, 1999 which
are incorporated by reference or included in the 1998 Annual Report on Form 10-K
of Alleghany Corporation, and to the reference to our firm as experts in the
registration statement.


                                          /s/ KPMG LLP

New York, New York
April 8, 1999


<PAGE>   1
                                                                    Exhibit 23.3


                               CONSENT OF COUNSEL


The Board of Directors
Alleghany Corporation:

We consent to the reference to our firm and the inclusion of our advice in the 
document, dated April 13, 1999, constituting part of a prospectus covering 
securities that have been registered under the United States Securities Act of 
1933, as amended, pursuant to a Registration Statement on Form S-8 relating to 
the Underwriters Re Group, Inc. 1998 Stock Option Plan.




                                             /s/ Wilde Sapte



London
April 13, 1999

<PAGE>   1
                                                                      Exhibit 24


                                POWER OF ATTORNEY



            KNOW ALL MEN BY THESE PRESENTS, that the undersigned does hereby
constitute and appoint JOHN J. BURNS, JR. and ROBERT M. HART, and each of them,
with full powers of substitution, his true and lawful attorneys-in-fact and
agents to do any and all acts and things and to execute any and all instruments
which said attorneys-in-fact and agents may deem necessary or advisable to
enable Alleghany Corporation, a Delaware corporation, to comply with the
Securities Act of 1933, as amended, and any rules, regulations and requirements
of the Securities and Exchange Commission in respect thereof, in connection with
the registration under said Act of the number of shares of Common Stock, par
value $1.00 per share, of Alleghany Corporation that may be issued upon the
exercise of options granted under the Underwriters Re Group, Inc. 1998 Stock
Option Plan, including specifically, but without limitation thereof, power and
authority to sign the undersigned's name as director of Alleghany Corporation to
the Registration Statement to be filed with the Securities and Exchange
Commission and any amendment, supplement or update thereto in respect of such
shares of Common Stock of Alleghany Corporation and to any documents filed as
part of or in connection with said Registration Statement or amendments,
supplements or updates; and the undersigned does hereby ratify and confirm all
that said attorneys-in-fact and agents shall do or cause to be done by virtue
hereof.

            IN WITNESS WHEREOF, the undersigned has subscribed these presents on
the 15th day of December, 1998.




                                             /s/ Dan R. Carmichael
                                         ---------------------------------
                                                    Dan R. Carmichael
<PAGE>   2
                                POWER OF ATTORNEY



            KNOW ALL MEN BY THESE PRESENTS, that the undersigned does hereby
constitute and appoint JOHN J. BURNS, JR. and ROBERT M. HART, and each of them,
with full powers of substitution, his true and lawful attorneys-in-fact and
agents to do any and all acts and things and to execute any and all instruments
which said attorneys-in-fact and agents may deem necessary or advisable to
enable Alleghany Corporation, a Delaware corporation, to comply with the
Securities Act of 1933, as amended, and any rules, regulations and requirements
of the Securities and Exchange Commission in respect thereof, in connection with
the registration under said Act of the number of shares of Common Stock, par
value $1.00 per share, of Alleghany Corporation that may be issued upon the
exercise of options granted under the Underwriters Re Group, Inc. 1998 Stock
Option Plan, including specifically, but without limitation thereof, power and
authority to sign the undersigned's name as director of Alleghany Corporation to
the Registration Statement to be filed with the Securities and Exchange
Commission and any amendment, supplement or update thereto in respect of such
shares of Common Stock of Alleghany Corporation and to any documents filed as
part of or in connection with said Registration Statement or amendments,
supplements or updates; and the undersigned does hereby ratify and confirm all
that said attorneys-in-fact and agents shall do or cause to be done by virtue
hereof.

            IN WITNESS WHEREOF, the undersigned has subscribed these presents on
the 15th day of December, 1998.




                                              /s/ Thomas S. Johnson
                                         ---------------------------------
                                                     Thomas S. Johnson
<PAGE>   3
                                POWER OF ATTORNEY



            KNOW ALL MEN BY THESE PRESENTS, that the undersigned does hereby
constitute and appoint JOHN J. BURNS, JR. and ROBERT M. HART, and each of them,
with full powers of substitution, his true and lawful attorneys-in-fact and
agents to do any and all acts and things and to execute any and all instruments
which said attorneys-in-fact and agents may deem necessary or advisable to
enable Alleghany Corporation, a Delaware corporation, to comply with the
Securities Act of 1933, as amended, and any rules, regulations and requirements
of the Securities and Exchange Commission in respect thereof, in connection with
the registration under said Act of the number of shares of Common Stock, par
value $1.00 per share, of Alleghany Corporation that may be issued upon the
exercise of options granted under the Underwriters Re Group, Inc. 1998 Stock
Option Plan, including specifically, but without limitation thereof, power and
authority to sign the undersigned's name as director of Alleghany Corporation to
the Registration Statement to be filed with the Securities and Exchange
Commission and any amendment, supplement or update thereto in respect of such
shares of Common Stock of Alleghany Corporation and to any documents filed as
part of or in connection with said Registration Statement or amendments,
supplements or updates; and the undersigned does hereby ratify and confirm all
that said attorneys-in-fact and agents shall do or cause to be done by virtue
hereof.

            IN WITNESS WHEREOF, the undersigned has subscribed these presents on
the 15th day of December, 1998.




                                              /s/ Allan P. Kirby, Jr.
                                         ---------------------------------
                                                    Allan P. Kirby, Jr.
<PAGE>   4
                                POWER OF ATTORNEY



            KNOW ALL MEN BY THESE PRESENTS, that the undersigned does hereby
constitute and appoint JOHN J. BURNS, JR. and ROBERT M. HART, and each of them,
with full powers of substitution, his true and lawful attorneys-in-fact and
agents to do any and all acts and things and to execute any and all instruments
which said attorneys-in-fact and agents may deem necessary or advisable to
enable Alleghany Corporation, a Delaware corporation, to comply with the
Securities Act of 1933, as amended, and any rules, regulations and requirements
of the Securities and Exchange Commission in respect thereof, in connection with
the registration under said Act of the number of shares of Common Stock, par
value $1.00 per share, of Alleghany Corporation that may be issued upon the
exercise of options granted under the Underwriters Re Group, Inc. 1998 Stock
Option Plan, including specifically, but without limitation thereof, power and
authority to sign the undersigned's name as director of Alleghany Corporation to
the Registration Statement to be filed with the Securities and Exchange
Commission and any amendment, supplement or update thereto in respect of such
shares of Common Stock of Alleghany Corporation and to any documents filed as
part of or in connection with said Registration Statement or amendments,
supplements or updates; and the undersigned does hereby ratify and confirm all
that said attorneys-in-fact and agents shall do or cause to be done by virtue
hereof.

            IN WITNESS WHEREOF, the undersigned has subscribed these presents on
the 16th day of December, 1998.




                                              /s/ F.M. Kirby
                                         ---------------------------------
                                                       F.M. Kirby
<PAGE>   5
                                POWER OF ATTORNEY


            KNOW ALL MEN BY THESE PRESENTS, that the undersigned does hereby
constitute and appoint JOHN J. BURNS, JR. and ROBERT M. HART, and each of them,
with full powers of substitution, his true and lawful attorneys-in-fact and
agents to do any and all acts and things and to execute any and all instruments
which said attorneys-in-fact and agents may deem necessary or advisable to
enable Alleghany Corporation, a Delaware corporation, to comply with the
Securities Act of 1933, as amended, and any rules, regulations and requirements
of the Securities and Exchange Commission in respect thereof, in connection with
the registration under said Act of the number of shares of Common Stock, par
value $1.00 per share, of Alleghany Corporation that may be issued upon the
exercise of options granted under the Underwriters Re Group, Inc. 1998 Stock
Option Plan, including specifically, but without limitation thereof, power and
authority to sign the undersigned's name as director of Alleghany Corporation to
the Registration Statement to be filed with the Securities and Exchange
Commission and any amendment, supplement or update thereto in respect of such
shares of Common Stock of Alleghany Corporation and to any documents filed as
part of or in connection with said Registration Statement or amendments,
supplements or updates; and the undersigned does hereby ratify and confirm all
that said attorneys-in-fact and agents shall do or cause to be done by virtue
hereof.

            IN WITNESS WHEREOF, the undersigned has subscribed these presents on
the 15th day of December, 1998.




                                             /s/ William K. Lavin
                                         ---------------------------------
                                                   William K. Lavin
<PAGE>   6
                                POWER OF ATTORNEY



            KNOW ALL MEN BY THESE PRESENTS, that the undersigned does hereby
constitute and appoint JOHN J. BURNS, JR. and ROBERT M. HART, and each of them,
with full powers of substitution, his true and lawful attorneys-in-fact and
agents to do any and all acts and things and to execute any and all instruments
which said attorneys-in-fact and agents may deem necessary or advisable to
enable Alleghany Corporation, a Delaware corporation, to comply with the
Securities Act of 1933, as amended, and any rules, regulations and requirements
of the Securities and Exchange Commission in respect thereof, in connection with
the registration under said Act of the number of shares of Common Stock, par
value $1.00 per share, of Alleghany Corporation that may be issued upon the
exercise of options granted under the Underwriters Re Group, Inc. 1998 Stock
Option Plan, including specifically, but without limitation thereof, power and
authority to sign the undersigned's name as director of Alleghany Corporation to
the Registration Statement to be filed with the Securities and Exchange
Commission and any amendment, supplement or update thereto in respect of such
shares of Common Stock of Alleghany Corporation and to any documents filed as
part of or in connection with said Registration Statement or amendments,
supplements or updates; and the undersigned does hereby ratify and confirm all
that said attorneys-in-fact and agents shall do or cause to be done by virtue
hereof.

            IN WITNESS WHEREOF, the undersigned has subscribed these presents on
the 15th day of December, 1998.




                                              /s/ Roger Noall
                                         ---------------------------------
                                                    Roger Noall
<PAGE>   7
                                POWER OF ATTORNEY



            KNOW ALL MEN BY THESE PRESENTS, that the undersigned does hereby
constitute and appoint JOHN J. BURNS, JR. and ROBERT M. HART, and each of them,
with full powers of substitution, his true and lawful attorneys-in-fact and
agents to do any and all acts and things and to execute any and all instruments
which said attorneys-in-fact and agents may deem necessary or advisable to
enable Alleghany Corporation, a Delaware corporation, to comply with the
Securities Act of 1933, as amended, and any rules, regulations and requirements
of the Securities and Exchange Commission in respect thereof, in connection with
the registration under said Act of the number of shares of Common Stock, par
value $1.00 per share, of Alleghany Corporation that may be issued upon the
exercise of options granted under the Underwriters Re Group, Inc. 1998 Stock
Option Plan, including specifically, but without limitation thereof, power and
authority to sign the undersigned's name as director of Alleghany Corporation to
the Registration Statement to be filed with the Securities and Exchange
Commission and any amendment, supplement or update thereto in respect of such
shares of Common Stock of Alleghany Corporation and to any documents filed as
part of or in connection with said Registration Statement or amendments,
supplements or updates; and the undersigned does hereby ratify and confirm all
that said attorneys-in-fact and agents shall do or cause to be done by virtue
hereof.

            IN WITNESS WHEREOF, the undersigned has subscribed these presents on
the 15th day of December, 1998.




                                               /s/ James F. Will
                                         ---------------------------------
                                                     James F. Will
<PAGE>   8
                                POWER OF ATTORNEY



            KNOW ALL MEN BY THESE PRESENTS, that the undersigned does hereby
constitute and appoint JOHN J. BURNS, JR. and ROBERT M. HART, and each of them,
with full powers of substitution, his true and lawful attorneys-in-fact and
agents to do any and all acts and things and to execute any and all instruments
which said attorneys-in-fact and agents may deem necessary or advisable to
enable Alleghany Corporation, a Delaware corporation, to comply with the
Securities Act of 1933, as amended, and any rules, regulations and requirements
of the Securities and Exchange Commission in respect thereof, in connection with
the registration under said Act of the number of shares of Common Stock, par
value $1.00 per share, of Alleghany Corporation that may be issued upon the
exercise of options granted under the Underwriters Re Group, Inc. 1998 Stock
Option Plan, including specifically, but without limitation thereof, power and
authority to sign the undersigned's name as director of Alleghany Corporation to
the Registration Statement to be filed with the Securities and Exchange
Commission and any amendment, supplement or update thereto in respect of such
shares of Common Stock of Alleghany Corporation and to any documents filed as
part of or in connection with said Registration Statement or amendments,
supplements or updates; and the undersigned does hereby ratify and confirm all
that said attorneys-in-fact and agents shall do or cause to be done by virtue
hereof.

            IN WITNESS WHEREOF, the undersigned has subscribed these presents on
the 15th day of December, 1998.




                                              /s/ Paul F. Woodberry
                                         ---------------------------------
                                                    Paul F. Woodberry




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