<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>
[{"type": "S-8", "sequence": "1", "description": "ALLEGHANY CORPORATION", "secsgml_size_bytes": 18290}]
{"company-data": {"conformed-name": "ALLEGHANY CORP /DE", "cik": "0000775368", "assigned-sic": "6361", "irs-number": "510283071", "state-of-incorporation": "DE", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-76159", "film-number": "99592714"}, "business-address": {"street1": "375 PARK AVENUE", "city": "NEW YORK", "state": "NY", "zip": "10152", "phone": "2127521356"}, "mail-address": {"street1": "375 PARK AVENUE", "city": "NEW YORK", "state": "NY", "zip": "10055"}, "former-company": {"former-conformed-name": "ALLEGHANY FINANCIAL CORP", "date-changed": "19870115"}}
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
2
                         CALCULATION OF REGISTRATION FEE
==========================================================================================================================
                                                     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
--------------------------------------------------------------------------------------------------------------------------
Common Stock,
     par value $1.00
     per share                    42,097                $79.22192               $3,335,005                $927.13
==========================================================================================================================
(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.
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
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.
Exhibit Number            Description
--------------            -----------
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.
II-2
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
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
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
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
9
                                INDEX TO EXHIBITS
Exhibit Number            Description
--------------            -----------
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.