<PAGE>

As filed with the Securities and Exchange Commission on October 20, 1999
                                                      Registration No. 333-_____

                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549

                                    FORM S-8

                             REGISTRATION STATEMENT
                        UNDER THE SECURITIES ACT OF 1933

                      WHITE MOUNTAINS INSURANCE GROUP, INC.
              (formerly "Fund American Enterprises Holdings, Inc.")
             (Exact name of registrant as specified in its charter)

                Delaware                               94-2708455
    (State or other jurisdiction of       (I.R.S. employer identification no.)
     incorporation or organization)

                              80 South Main Street
                        Hanover, New Hampshire 03755-2053
                                 (603) 643-1567
  (Address, including zip code, and telephone number, including area code, of
                   registrant's principal executive offices)

                              DEFERRED BENEFIT PLAN
                            (Full title of the plan)

                               Michael S. Paquette
                      Senior Vice President and Controller
                      White Mountains Insurance Group, Inc.
                              80 South Main Street
                        Hanover, New Hampshire 03755-2053
                                 (603) 643-1567
 (Name, address, including zip code, and telephone number, including area code,
                             of agent for service)

                         CALCULATION OF REGISTRATION FEE

<TABLE>
<CAPTION>
  Title of each class of          Amount to be             Proposed maximum             Proposed maximum             Amount of
securities to be registered        registered         offering price per share(1)  aggregate offering price(1)    registration fee
---------------------------        ----------         ---------------------------  ---------------------------    ----------------
      <S>                        <C>                            <C>                      <C>                         <C>
       Common Stock,             14,000 shares                  $120.75                  $1,690,500.00               $469.96
      $1.00 par value
</TABLE>

----------
      (1) Pursuant to Rule 457(h)(1) under the Securities Act, the offering
price is based upon the average high and low sales prices of the Common Stock as
reported on the New York Stock Exchange on October 19, 1999.
<PAGE>

                                     PART II

                    INFORMATION REQUIRED IN THE REGISTRATION

                                    STATEMENT

Item 3. Incorporation of Documents by Reference.

      The following documents heretofore filed by White Mountains Insurance
Group, Inc. (formerly "Fund American Enterprises Holdings, Inc.") (the
"Registrant") (Commission file no. 1-8993) pursuant to the Securities Exchange
Act of 1934, as amended (the "Exchange Act"), hereby are incorporated in this
Registration Statement by reference: (a) the Registrant's Annual Report on Form
10-K for the year ended December 31, 1998 (the "1998 Form 10-K"); (b) the
Registrant's Quarterly Reports on Form 10-Q for the quarters ended March 31,
1999 and June 30, 1999; (c) the Registrant's Current Reports on Form 8-K dated
March 10, 1999, May 27, 1999, June 1, 1999, June 8, 1999, June 17, 1999 (as
amended by a Current Report on Form 8-K/A (Amendment No. 1) filed August 17,
1999), June 29, 1999, August 5, 1999 and October 18, 1999; and (d) the
Registrant's definitive proxy materials on Schedule 14A filed March 31, 1999 and
September 27, 1999. All documents subsequently filed by Registrant pursuant to
Sections 13(a), 14, and 15(d) of the Exchange Act, 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 such documents.

Item 4. Description of Securities.

      The authorized capital stock of the Registrant consists of 15,000,000
shares of Common Stock and 1,000,000 shares of Preferred Stock, each par value
$1.00 per share. Pursuant to the Registrant's Amended Certificate of
Incorporation, a vote of at least two-thirds of the entire Board of Directors is
required to authorize the issuance of any shares of Common Stock or Preferred
Stock. Shareholders have no cumulative voting rights.

      All outstanding shares of Common Stock participate equally in
distributions when and as declared by the Registrant and upon liquidation. Each
holder of outstanding shares of Common Stock is entitled to one vote per share
of Common Stock held. The shares of Common Stock do not entitle holders thereof
to any preemptive rights, conversion rights, redemption rights or sinking fund.
The Common Stock is listed on the New York Stock Exchange, Inc.

      There is currently no Preferred Stock of the Company outstanding. Pursuant
to the Company's Amended Certificate of Incorporation, the Board of Directors is
authorized to establish and designate series of Preferred Stock and to fix the
number of shares and the relative rights, powers, preferences and
qualifications, limitations and restrictions of such respective series. Since
the Board of Directors has the power to establish the preferences and rights of
each series, it may afford the holders of any Preferred Stock preferences,
powers and rights (including voting rights) senior to the rights of the holders
of Common Stock. The Registrant has no present intention to issue additional
shares of Preferred Stock. It is possible that a new series of the Preferred
Stock could be used to discourage an unsolicited acquisition proposal if one
were made. However, the Registrant may create and issue a new series of
Preferred Stock from the authorized Preferred Stock should the Registrant
conclude that doing so is advisable.
<PAGE>

Item 5. Interests of Named Experts and Counsel.

      Not applicable.

Item 6. Indemnification of Directors and Officers.

      The General Corporation Law ("GCL") of the State of Delaware provides that
a Delaware corporation, such as the registrant, may indemnify a director or
officer against his or her expenses and judgments, fines and amounts paid in
settlement actually and reasonably incurred in connection with any action, suit
or proceeding (other than an action by or in the right of the corporation)
involving such person by reason of the fact that such person is or was a
director or officer, concerning actions taken in good faith and in a manner
reasonably believed to be in or not opposed to the best interest of the
corporation and, with respect to any criminal action or proceeding, had no
reasonable cause to believe his or her conduct was unlawful. The GCL also
provides that in a derivative action, a Delaware corporation may indemnify its
directors and officers against expenses actually and reasonably incurred to the
extent that such director or officer acted in good faith and in a manner such
director or officer reasonably believed to be in or not opposed to the best
interests of the corporation, except that no indemnification may be made with
respect to any claim, issue or matter as to which such director or officer is
adjudged to be liable to the corporation unless and only to the extent that the
court determines upon application that, despite the adjudication of liability
but in view of all the circumstances of the case, such director or officer is
fairly and reasonably entitled to indemnity for such expenses which the court
deems proper. The GCL also generally permits the advancement of a director's or
officer's expenses, including by means of a mandatory charter or bylaw provision
to that effect, in lieu of requiring the authorization of such advancement by
the Board of Directors in specific cases.

      Article XI of Registrant's Amended and Restated By-Laws contains the
indemnification provisions that follow:

                                   ARTICLE XI
                                 Indemnification

            54.   Indemnification of Directors, Officers, Agents and Employees.

                  Section 1. Right to Indemnification. The Corporation shall to
      the fullest extent permitted by applicable law as then in effect,
      indemnify any person (the "Indemnitee") unless otherwise agreed to by
      Indemnitee, who was or is involved in any manner (including, without
      limitation, as a party or a witness) or is threatened to be made so
      involved in any threatened, pending or completed investigation, claim,
      action, suit or proceeding, whether civil, criminal, administrative or
      investigative (including without limitation, any action, suit or
      proceeding by or in the right of the Corporation to procure a judgment in
      its favor) (a "Proceeding") by reason of the fact that he is or was a
      director, officer, employee or agent of the Corporation, or is or was
      serving at the request of the Corporation as a director, officer, employee
      or agent of another corporation, partnership, joint venture, trust or
      other enterprise (including, without limitation, any employee benefit
      plan) against all expenses (including attorney's fees), judgments, fines
      and amounts paid in settlement actually and reasonably incurred by him in
      connection with such Proceeding. Such indemnification shall be a

<PAGE>

      contract right and shall include the right to receive payment in advance
      of any expenses incurred by the Indemnitee in connection with such
      Proceeding, consistent with the provisions of applicable law as then in
      effect.

                  Section 2. Insurance, Contracts and Funding. The Corporation
      may purchase and maintain insurance to protect itself and any Indemnitee
      against any expenses, judgments, fines and amounts paid in settlement as
      specified in Section 1 of this Article or incurred by any Indemnitee in
      connection with any Proceeding referred to in Section 1 of this Article,
      to the fullest extent permitted by applicable law as then in effect. The
      Corporation may enter into contracts with any director, officer, employee
      or agent of the Corporation in furtherance of the provisions of this
      Article and may create a trust fund, grant a security interest or use
      other means (including without limitation, a letter of credit) to ensure
      the payment of such amounts as may be necessary to effect indemnification
      as provided in this Article.

                  Section 3. Indemnification; Not Exclusive Right. The right of
      indemnification provided in this Article shall not be exclusive of any
      other rights to which those seeking indemnification may otherwise be
      entitled, and the provisions of this Article shall inure to the benefit of
      the heirs and legal representatives of any person entitled to indemnity
      under this Article and shall be applicable to Proceedings commenced or
      continuing after the adoption of this Article, whether arising from acts
      or omissions occurring before or after such adoption.

                  Section 4. Advancement of Expenses, Procedures; Presumptions
      and Effect of Certain Proceedings; Remedies. In furtherance, but not in
      limitation of the foregoing provisions, the following procedures,
      presumptions and remedies shall apply with respect to advancement of
      expenses and the right to indemnification under this Article:

                        (a) Advancement of Expenses. All reasonable expenses
            incurred by or on behalf of the indemnitee in connection with any
            Proceeding shall be advanced to the Indemnitee by the Corporation
            within twenty (20) business days after the receipt by the
            Corporation of a statement or statements from the Indemnitee
            requesting such advance or advances from time to time, whether prior
            to or after final disposition of such Proceeding. Such statement or
            statements shall reasonably evidence the expenses incurred by the
            Indemnitee and, if required by law or requested by the Corporation
            at the time of such advance, shall include or be accompanied by an
            undertaking by or on behalf of the Indemnitee to repay the amounts
            advanced if it should ultimately be determined that the Indemnitee
            is not entitled to be indemnified against such expenses pursuant to
            this Article.

                        (b) Procedure for Determination of Entitlement to
            Indemnification.

                              (i) To obtain indemnification under this Article,
                  an Indemnitee shall submit to the Secretary of the Corporation
                  a written request, including such documentation and
                  information as

<PAGE>

                  is reasonably available to the Indemnitee and reasonably
                  necessary to determine whether and to what extent the
                  Indemnitee is entitled to indemnification (the "Supporting
                  Documentation"). The determination of the Indemnitee's
                  entitlement to indemnification shall be made not later than
                  120 days after receipt by the Corporation of the written
                  request for indemnification together with the Supporting
                  Documentation. The Secretary of the Corporation shall,
                  promptly upon receipt of such a request for indemnification,
                  advise the Board of Directors or its designee in writing that
                  the Indemnitee has requested indemnification.

                              (ii) The Indemnitee's entitlement to
                  indemnification under this Article shall be determined in one
                  of the following ways: (A) by a majority vote of the
                  Disinterested Directors (as hereinafter defined), if they
                  constitute a quorum of the Board of Directors; (B) by a
                  written opinion of Independent Counsel (as hereinafter
                  defined) if (x) a Change of Control (as hereinafter defined)
                  shall have occurred and the Indemnitee so requests or (y) a
                  quorum of the Board of Directors consisting of Disinterested
                  Directors is not obtainable or, even if obtainable, a majority
                  of such Disinterested Directors so directs; (C) by the
                  stockholders of the Corporation (but only if a majority of the
                  Disinterested Directors, if they constitute a quorum of the
                  Board of Directors, presents the issue of entitlement or
                  indemnification to the stockholders for their determination);
                  or (D) as provided in Section 4(c), below.

                              (iii) In the event the determination of
                  entitlement to indemnification is to be made by Independent
                  Counsel pursuant to Section 4(b)(ii), a majority of the
                  Disinterested Directors shall select the Independent Counsel,
                  but only an Independent Counsel to which the Indemnitee does
                  not reasonably object; provided, however, that if a Change of
                  Control shall have occurred, the Indemnitee shall select such
                  Independent Counsel, but only an Independent Counsel to which
                  the Board of Directors does not reasonably object.

                        (c) Presumption and Effect of Certain Proceedings.
            Except as otherwise expressly provided in this Article, if a Change
            of Control shall have occurred the Indemnitee shall be presumed to
            be entitled to indemnification under this Article upon submission of
            a request for indemnification together with the Supporting
            Documentation in accordance with Section 4(b)(i), thereafter the
            Corporation shall have the burden of proof to overcome that
            presumption in reaching a contrary determination. In any event, if
            the person or persons empowered under Section 4(b) to determine
            entitlement to indemnification shall not have been appointed or
            shall not have made a determination within one hundred twenty (120)
            days after receipt by the Corporation of the request, therefore
            together with the Supporting Documentation, the Indemnitee shall be
            deemed to be entitled to indemnification and the Indemnitee shall be
            entitled to such indemnification unless (A) the Indemnitee
            misrepresented

<PAGE>

            or failed to disclose a material fact in making the request for
            indemnification or in the Supporting Documentation or (B) such
            indemnification is prohibited by law. The termination of any
            Proceeding described in Section 1, or of any claim, issue or matter
            therein, by judgement, order, settlement or conviction, or upon a
            plea of nolo contendere or its equivalent, shall not, of itself,
            adversely affect the right of the Indemnitee to indemnification or
            create a presumption that the Indemnitee did not act in good faith
            and in a manner which he reasonably believed to be in or not opposed
            to the best interests of the Corporation or, with respect to any
            criminal Proceeding, that the Indemnitee had reasonable cause to
            believe that his conduct was unlawful.

                        (d) Remedies of Indemnitee.

                              (i) In the event that a determination is made
                  pursuant to Section 4(b) that the Indemnitee is not entitled
                  to indemnification under this Article, (A) the Indemnitee
                  shall be entitled to seek an adjudication of his entitlement
                  to such indemnification either, at the Indemnitee's sole
                  option, in (x) an appropriate court of the State of Delaware
                  or any other court of competent jurisdiction or (y) an
                  arbitration to be conducted by a single arbitrator pursuant to
                  the rules of the American Arbitration Association; (B) any
                  such judicial proceeding or arbitration shall be de novo and
                  the Indemnitee shall not be prejudiced by reason of such
                  adverse determination; and (C) if a Change of Control shall
                  have occurred, in any such judicial proceeding or arbitration
                  the Corporation shall have the burden of proving that the
                  Indemnitee is not entitled to indemnification under this
                  Article.

                              (ii) If a determination shall have been made or
                  deemed to have been made, pursuant to Section 4(b) or (c),
                  that the Indemnitee is entitled to indemnification, the
                  Corporation shall be obligated to pay the amounts constituting
                  such indemnification within fifteen (15) business days after
                  such determination has been made or deemed to have been made
                  and shall be conclusively bound by such determination unless
                  (A) the indemnitee misrepresented or failed to disclose a
                  material fact in making the request for indemnification or in
                  the Supporting Documentation or (B) such indemnification is
                  prohibited by law. (Subparagraph (A) and (B) are each referred
                  to hereafter as a "Disqualifying Event"). In the event that
                  (C) advancement of expenses is not timely made pursuant to
                  Section 4(a) or (D) payment of indemnification is not made
                  within fifteen (15) business days after a determination of
                  entitlement to indemnification has been made or deemed to have
                  been made pursuant to Section 4(b) or (c), the Indemnitee
                  shall be entitled to seek judicial enforcement of the
                  Corporation's obligation to pay to the Indemnitee such
                  advancement of expenses or indemnification. Notwithstanding
                  the foregoing, the Corporation may bring an action, in an
                  appropriate court in the State of Delaware or any other court
                  of competent jurisdiction, contesting the right of the
                  Indemnitee to receive indemnification hereunder

<PAGE>

                  due to the occurrence of Disqualifying Event; provided,
                  however, that in any such action the Corporation shall have
                  the burden of proving the occurrence of such Disqualifying
                  Event.

                              (iii) The Corporation shall be precluded from
                  asserting in any judicial proceeding or arbitration commenced
                  pursuant to this Section 4(d) that the procedures and
                  presumptions of this Article are not valid, binding and
                  enforceable and shall stipulate in any such court or before
                  any such arbitrator that the Corporation is bound by all the
                  provisions of this Article.

                              (iv) In the event that the Indemnitee, pursuant to
                  this Section 4(d), seeks a judicial adjudication of an award
                  in arbitration to enforce his rights under, or to recover
                  damages for breach of, this Article, the Indemnitee shall be
                  entitled to recover from the Corporation, and shall be
                  indemnified by the Corporation against, any expenses actually
                  and reasonably incurred by him if the Indemnitee prevails in
                  such judicial adjudication or arbitration. If it shall be
                  determined in such judicial adjudication or arbitration that
                  the Indemnitee is entitled to receive part but not all of the
                  indemnification or advancement of expenses sought, the
                  expenses incurred by the indemnitee in connection with such
                  judicial adjudication or arbitration shall be prorated
                  accordingly.

                  (e) Definitions. For purposes of this Section 4:

                              (i) "Change in Control" means a change in control
                  of the Corporation of a nature that would be required to be
                  reported in response to Item 5(f) of Schedule 14A of
                  Regulation 14A promulgated under the Securities Exchange Act
                  of 1934 (the "Act"), whether or not the Corporation is then
                  subject to such reporting requirement; provided that, without
                  limitation, such change in control shall be deemed to have
                  occurred if (A) any "person" (as such term is used in Section
                  13(d) and 14(d) of the Act) is or becomes the "beneficial
                  owner" (as defined in Rule 13d-3 under the Act), directly or
                  indirectly, of securities of the Corporation representing 30%
                  or more of the combined voting power of the Corporation's then
                  outstanding securities without the prior approval of at least
                  two-thirds (2/3) of the members of the Board of Directors in
                  office immediately prior to such acquisition; (b) the
                  Corporation is a party to a merger, consolidation, sale of
                  assets or other reorganization, or proxy contest, as a
                  consequence of which members of the Board of Directors in
                  office immediately prior to such transaction or event
                  constitute less than a majority of the Board of Directors
                  thereafter; or (C) during any period of two (2) consecutive
                  years, individuals who at the beginning of such period
                  constituted the Board of Directors (including for this purpose
                  any new director whose election or nomination for election by
                  the Corporation's stockholders was approved by a vote of at
                  least a majority of the directors then still in office who
                  were

<PAGE>

                  directors at the beginning of such period) cease for any
                  reason to constitute at least a majority of the Board of
                  Directors.

                              (ii) "Disinterested Director" means a director of
                  the Corporation who is not or was not a party to the
                  Proceeding in respect of which indemnification is sought by
                  the Indemnitee.

                              (iii) "Independent Counsel" means a law firm or a
                  member of a law firm that neither presently is, nor in the
                  past five (5) years has been, retained to represent: (i) the
                  Corporation or the Indemnitee in any matter material to either
                  such party or (ii) any other party to the Proceeding giving
                  rise to a claim for indemnification under this Article.
                  Notwithstanding the foregoing, the term "Independent Counsel"
                  shall not include any person who, under the applicable
                  standards of professional conduct then prevailing under the
                  law of the State of Delaware, would have a conflict of
                  interest in representing either the Corporation or the
                  Indemnitee in an action to determine the Indemnitee's rights
                  under this Article.

                  Section 5. Severability. If any provision or provisions of
      this Article shall be held to be invalid, illegal or unenforceable for any
      reason whatsoever: (a) the validity, legality and enforceability of the
      remaining provisions of this Article (including, without limitation, all
      portions of any paragraph of this Article containing any such provision
      held to be invalid, illegal or unenforceable, that are not themselves
      invalid, illegal or unenforceable) shall not in any way be affected or
      impaired thereby; and (b) to the fullest extent possible, the provisions
      of this Article (including, without limitation, all portions of any
      paragraph of this Article containing any such provision held to be
      invalid, illegal or unenforceable) shall be construed so as to give effect
      to the intent manifested by the provision held invalid, illegal or
      unenforceable.

      Section 102(b)(7) of the GCL provides that a certificate of incorporation
may contain a provision eliminating or limiting the personal liability of a
director to the corporation or its stockholders for monetary damages for breach
of fiduciary duty as a director, provided that such provision may not eliminate
or limit the liability of a director (i) for any breach of the director's duty
of loyalty to the corporation or its stockholders; (ii) for acts or omissions
not in good faith or which involve intentional misconduct or a knowing violation
of law; (iii) under Section 174 of the GCL (relating to liability for
unauthorized acquisitions or redemptions of, or dividends on, capital stock) or
(iv) for any transaction from which the director derived an improper personal
benefit.

      Article Eleventh of Registrant's Restated Certificate of Incorporation, as
amended, implements the foregoing provision and provides as follows:

      Eleventh: (a) To the fullest extent that the General Corporation Law of
      the State of Delaware (as it exists on the date hereof [March 11, 1994] or
      as it may hereafter be amended) permits the limitation or elimination of
      the liability of directors, no director of the Corporation shall be liable
      to the Corporation or its shareholders for monetary damages for breach of
      fiduciary duty as a director. No amendment to or repeal of this Article
      shall apply to or have any effect on the

<PAGE>

      liability or alleged liability of any director of the Corporation for or
      with respect to any acts or omissions of such director occurring prior to
      such amendment or repeal.

                  (b) In addition to any requirements of law and any other
      provisions herein or in the terms of any class or series of capital stock
      having preference over the common stock of the Corporation as to dividends
      or upon liquidation (and notwithstanding that a lesser percentage may be
      specified by law), the affirmative vote of the holders of seventy-five
      percent (75%) or more of the voting power of the then outstanding voting
      stock of the Corporation, voting together as a single class, shall be
      required to amend, alter or repeal any provision of this Article.

      Insurance is maintained on a regular basis (and not specifically in
connection with this offering) against liabilities arising on the part of
directors and officers out of their performance in such capacities or arising on
the part of the registrant out of its foregoing indemnification provisions,
subject to certain exclusions and to the policy limits.

Item 7. Exemption from Registration Claimed.

      Not applicable.

Item 8. Exhibits.

      The following exhibits are furnished with this Registration Statement:

            Exhibit No.                         Description
            -----------                         -----------

            (4)(a)        Amended and Restated Certificate of Incorporation of
                          Registrant (incorporated by reference to Exhibit
                          (4)(a) of the Registrant's registration statement on
                          Form S-8 filed July 9, 1999 (registration no.
                          333-82563)).*

            (4)(b)        Amended and Restated By-Laws of Registrant as
                          amended to date (filed as Exhibit 3(b) to
                          Registrant's Annual Report on Form 10-K for the
                          fiscal year ended October 31, 1993 (Commission file
                          number 1-8993) and incorporated herein by
                          reference).

            (4)(c)        Deferred Benefit Plan.*

            (4)(d)        Form of Deferred Benefit Plan Termination
                          Amendment.*

            (5)(a)        Opinion and consent of Miller, Canfield, Paddock and
                          Stone, P.L.C.*

            (23)(a)       Consent of Miller, Canfield, Paddock and Stone,
                          P.L.C. (contained in Exhibit (5)(a)).

            (23)(b)       Consent of KPMG LLP.*
<PAGE>

            (23)(c)       Consent of Ernst & Young LLP.*

            (23)(d)       Consent of PricewaterhouseCoopers LLP.*

            (24)          Powers of attorney (contained in the signature pages
                          hereto).*

----------
*     Filed herewith.

Item 9. Undertakings.

      The undersigned registrant hereby undertakes:

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

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

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

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

      Provided, however, that paragraphs (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 by the
      registrant pursuant to Section 13 or Section 15(d) of the Securities
      Exchange Act of 1934 that are incorporated by reference into 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.

      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 that is incorporated by reference in the
registration statement shall be deemed to be a new registration statement
relating to the securities offered therein, and the offering of such securities
at that time shall be deemed to be the initial bona fide offering thereof.
<PAGE>

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

                                   SIGNATURES

      The Registrant. Pursuant to the requirements of the Securities Act of
1933, 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 Town of Hanover, State of New Hampshire, on October 19,
1999.

                                    WHITE MOUNTAINS INSURANCE
                                    GROUP, INC.


                                    By    /s/
                                       ------------------------------------
                                          Name:  K. Thomas Kemp
                                          Title: Director, President and
                                                 Chief Executive Officer
<PAGE>

      The Plan. Pursuant to the requirements of the Securities Act of 1933, the
Deferred Benefit Plan (the "Plan") has duly caused this Registration Statement
to be signed on its behalf by the undersigned, thereunto duly authorized, in the
Town of Hanover, State of New Hampshire, on October 19, 1999.

                                    Deferred Benefit Plan


                                    By    /s/
                                       ------------------------------------
                                          Name:  Gordon S. Macklin
                                          Title: Member & Chairman -
                                                 Compensation Sub-Committee


                                    And:  /s/
                                        -----------------------------------
                                          Name:  Patrick M. Byrne
                                          Title: Member - Compensation
                                                 Sub-Committee

                                    And:  /s/
                                        -----------------------------------
                                          Name:  Robert P. Cochran
                                          Title: Member - Compensation
                                                 Sub-Committee

                                    And:  /s/
                                        -----------------------------------
                                          Name:  Frank A. Olson
                                          Title: Member - Compensation
                                                 Sub-Committee

                                    And:  /s/
                                        -----------------------------------
                                          Name:  Arthur Zankel
                                          Title: Member - Compensation
                                                 Sub-Committee
<PAGE>

      Directors and Officers of the Registrant. Pursuant to the requirements of
the Securities Act of 1933, this Registration Statement has been signed below by
the following persons in the capacities indicated and on the dates indicated
below. By so signing, each of the undersigned, in his capacity as a director or
officer, or both, as the case may be, of the registrant, does hereby appoint
John J. Byrne, K. Thomas Kemp, Raymond Barrette and Michael S. Paquette, and
each of them severally, his true and lawful attorney to execute in his name,
place and stead, in his capacity as a director or officer, or both, as the case
may be, of the registrant, any and all amendments to this Registration Statement
including post-effective amendments thereto and all instruments necessary or
incidental in connection therewith, and to file the same with the Securities and
Exchange Commission. Each of said attorneys shall have full power and authority
to do and perform in the name and on behalf of each of the undersigned, in any
and all capacities, every act whatsoever requisite or necessary to be done in
the premises as fully, and for all intents and purposes, as each of the
undersigned might or could do in person, the undersigned hereby ratifying and
approving the acts of said attorneys and each of them.

          Signatures                          Title                   Date
          ----------                          -----                   ----
Principal Executive Officer:

                                   President and Chief
  /s/                              Executive Officer            October 19, 1999
-------------------------------
K. Thomas Kemp

Principal Financial Officer:

                                   Executive Vice President and
  /s/                              Chief Financial Officer      October 19, 1999
-------------------------------
Raymond Barrette

Principal Accounting Officer:

                                   Senior Vice President and
  /s/                              Controller                   October 19, 1999
-------------------------------
Michael S. Paquette
<PAGE>

      Directors and Officers of the Registrant. Pursuant to the requirements of
the Securities Act of 1933, this Registration Statement has been signed below by
the following persons in the capacities indicated and on the dates indicated
below. By so signing, each of the undersigned, in his capacity as a director or
officer, or both, as the case may be, of the registrant, does hereby appoint
John J. Byrne, K. Thomas Kemp, Raymond Barrette and Michael S. Paquette, and
each of them severally, his true and lawful attorney to execute in his name,
place and stead, in his capacity as a director or officer, or both, as the case
may be, of the registrant, any and all amendments to this Registration Statement
including post-effective amendments thereto and all instruments necessary or
incidental in connection therewith, and to file the same with the Securities and
Exchange Commission. Each of said attorneys shall have full power and authority
to do and perform in the name and on behalf of each of the undersigned, in any
and all capacities, every act whatsoever requisite or necessary to be done in
the premises as fully, and for all intents and purposes, as each of the
undersigned might or could do in person, the undersigned hereby ratifying and
approving the acts of said attorneys and each of them.

          Signatures                       Title                    Date
          ----------                       -----                    ----

  /s/                                 Director                 October 19, 1999
----------------------------------
Terry L. Baxter

  /s/                                 Chairman, Director       October 19, 1999
----------------------------------
John J. Byrne

  /s/                                 Director                 October 19, 1999
----------------------------------
Patrick M. Byrne

  /s/                                 Director                 October 19, 1999
----------------------------------
Howard L. Clark, Jr.

  /s/                                 Director                 October 19, 1999
----------------------------------
Robert P. Cochran

  /s/                                 Director                 October 19, 1999
----------------------------------
George J. Gillespie III

  /s/                                 Director                 October 19, 1999
----------------------------------
John D. Gillespie

  /s/                                 Director                 October 19, 1999
----------------------------------
K. Thomas Kemp

  /s/                                 Director                 October 19, 1999
----------------------------------
Gordon S. Macklin

  /s/                                 Director                 October 19, 1999
----------------------------------
Frank A. Olson

  /s/                                 Director                 October 19, 1999
----------------------------------
Arthur Zankel
<PAGE>

                                  EXHIBIT INDEX

         Exhibit No.                      Description
         -----------                      -----------

           (4)(c)        Deferred Benefit Plan.*

           (4)(d)        Form of Deferred Benefit Plan Termination
                         Amendment.*

           (5)(a)        Opinion and consent of Miller, Canfield, Paddock and
                         Stone, P.L.C.*

           (23)(a)       Consent of Miller, Canfield, Paddock and Stone,
                         P.L.C. (contained in Exhibit (5)(a)).

           (23)(b)       Consent of KPMG LLP.*

           (23)(c)       Consent of Ernst & Young LLP.*

           (23)(d)       Consent of PricewaterhouseCoopers LLP.*

           (24)          Powers of attorney (contained in the signature pages
                         hereto).*

----------
*     Filed herewith.
[{"type": "S-8", "sequence": "1", "description": "S-8", "secsgml_size_bytes": 44348}]
{"company-data": {"conformed-name": "WHITE MOUNTAINS INSURANCE GROUP INC", "cik": "0000776867", "assigned-sic": "6331", "irs-number": "942708455", "state-of-incorporation": "DE", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-89383", "film-number": "99731189"}, "business-address": {"street1": "80 SOUTH MAIN STREET", "city": "HANOVER", "state": "NH", "zip": "03755-2053", "phone": "6036431567"}, "mail-address": {"street1": "80 SOUTH MAIN STREET", "city": "HANOVER", "state": "NH", "zip": "03755"}, "former-company": [{"former-conformed-name": "FUND AMERICAN ENTERPRISES HOLDINGS INC", "date-changed": "19920703"}, {"former-conformed-name": "FUND AMERICAN COMPANIES INC", "date-changed": "19920701"}, {"former-conformed-name": "FIREMANS FUND CORP", "date-changed": "19900211"}]}
As filed with the Securities and Exchange Commission on October 20, 1999
                                                      Registration No. 333-_____

                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549

                                    FORM S-8

                             REGISTRATION STATEMENT
                        UNDER THE SECURITIES ACT OF 1933

                      WHITE MOUNTAINS INSURANCE GROUP, INC.
              (formerly "Fund American Enterprises Holdings, Inc.")
             (Exact name of registrant as specified in its charter)

                Delaware                               94-2708455
    (State or other jurisdiction of       (I.R.S. employer identification no.)
     incorporation or organization)

                              80 South Main Street
                        Hanover, New Hampshire 03755-2053
                                 (603) 643-1567
  (Address, including zip code, and telephone number, including area code, of
                   registrant's principal executive offices)

                              DEFERRED BENEFIT PLAN
                            (Full title of the plan)

                               Michael S. Paquette
                      Senior Vice President and Controller
                      White Mountains Insurance Group, Inc.
                              80 South Main Street
                        Hanover, New Hampshire 03755-2053
                                 (603) 643-1567
 (Name, address, including zip code, and telephone number, including area code,
                             of agent for service)

                         CALCULATION OF REGISTRATION FEE
Title of each class of          Amount to be             Proposed maximum             Proposed maximum             Amount of
securities to be registered        registered         offering price per share(1)  aggregate offering price(1)    registration fee
---------------------------        ----------         ---------------------------  ---------------------------    ----------------
Common Stock,             14,000 shares                  $120.75                  $1,690,500.00               $469.96
      $1.00 par value
----------
      (1) Pursuant to Rule 457(h)(1) under the Securities Act, the offering
price is based upon the average high and low sales prices of the Common Stock as
reported on the New York Stock Exchange on October 19, 1999.
PART II

                    INFORMATION REQUIRED IN THE REGISTRATION

                                    STATEMENT

Item 3. Incorporation of Documents by Reference.

      The following documents heretofore filed by White Mountains Insurance
Group, Inc. (formerly "Fund American Enterprises Holdings, Inc.") (the
"Registrant") (Commission file no. 1-8993) pursuant to the Securities Exchange
Act of 1934, as amended (the "Exchange Act"), hereby are incorporated in this
Registration Statement by reference: (a) the Registrant's Annual Report on Form
10-K for the year ended December 31, 1998 (the "1998 Form 10-K"); (b) the
Registrant's Quarterly Reports on Form 10-Q for the quarters ended March 31,
1999 and June 30, 1999; (c) the Registrant's Current Reports on Form 8-K dated
March 10, 1999, May 27, 1999, June 1, 1999, June 8, 1999, June 17, 1999 (as
amended by a Current Report on Form 8-K/A (Amendment No. 1) filed August 17,
1999), June 29, 1999, August 5, 1999 and October 18, 1999; and (d) the
Registrant's definitive proxy materials on Schedule 14A filed March 31, 1999 and
September 27, 1999. All documents subsequently filed by Registrant pursuant to
Sections 13(a), 14, and 15(d) of the Exchange Act, 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 such documents.

Item 4. Description of Securities.

      The authorized capital stock of the Registrant consists of 15,000,000
shares of Common Stock and 1,000,000 shares of Preferred Stock, each par value
$1.00 per share. Pursuant to the Registrant's Amended Certificate of
Incorporation, a vote of at least two-thirds of the entire Board of Directors is
required to authorize the issuance of any shares of Common Stock or Preferred
Stock. Shareholders have no cumulative voting rights.

      All outstanding shares of Common Stock participate equally in
distributions when and as declared by the Registrant and upon liquidation. Each
holder of outstanding shares of Common Stock is entitled to one vote per share
of Common Stock held. The shares of Common Stock do not entitle holders thereof
to any preemptive rights, conversion rights, redemption rights or sinking fund.
The Common Stock is listed on the New York Stock Exchange, Inc.

      There is currently no Preferred Stock of the Company outstanding. Pursuant
to the Company's Amended Certificate of Incorporation, the Board of Directors is
authorized to establish and designate series of Preferred Stock and to fix the
number of shares and the relative rights, powers, preferences and
qualifications, limitations and restrictions of such respective series. Since
the Board of Directors has the power to establish the preferences and rights of
each series, it may afford the holders of any Preferred Stock preferences,
powers and rights (including voting rights) senior to the rights of the holders
of Common Stock. The Registrant has no present intention to issue additional
shares of Preferred Stock. It is possible that a new series of the Preferred
Stock could be used to discourage an unsolicited acquisition proposal if one
were made. However, the Registrant may create and issue a new series of
Preferred Stock from the authorized Preferred Stock should the Registrant
conclude that doing so is advisable.
Item 5. Interests of Named Experts and Counsel.

      Not applicable.

Item 6. Indemnification of Directors and Officers.

      The General Corporation Law ("GCL") of the State of Delaware provides that
a Delaware corporation, such as the registrant, may indemnify a director or
officer against his or her expenses and judgments, fines and amounts paid in
settlement actually and reasonably incurred in connection with any action, suit
or proceeding (other than an action by or in the right of the corporation)
involving such person by reason of the fact that such person is or was a
director or officer, concerning actions taken in good faith and in a manner
reasonably believed to be in or not opposed to the best interest of the
corporation and, with respect to any criminal action or proceeding, had no
reasonable cause to believe his or her conduct was unlawful. The GCL also
provides that in a derivative action, a Delaware corporation may indemnify its
directors and officers against expenses actually and reasonably incurred to the
extent that such director or officer acted in good faith and in a manner such
director or officer reasonably believed to be in or not opposed to the best
interests of the corporation, except that no indemnification may be made with
respect to any claim, issue or matter as to which such director or officer is
adjudged to be liable to the corporation unless and only to the extent that the
court determines upon application that, despite the adjudication of liability
but in view of all the circumstances of the case, such director or officer is
fairly and reasonably entitled to indemnity for such expenses which the court
deems proper. The GCL also generally permits the advancement of a director's or
officer's expenses, including by means of a mandatory charter or bylaw provision
to that effect, in lieu of requiring the authorization of such advancement by
the Board of Directors in specific cases.

      Article XI of Registrant's Amended and Restated By-Laws contains the
indemnification provisions that follow:

                                   ARTICLE XI
                                 Indemnification

            54.   Indemnification of Directors, Officers, Agents and Employees.

                  Section 1. Right to Indemnification. The Corporation shall to
      the fullest extent permitted by applicable law as then in effect,
      indemnify any person (the "Indemnitee") unless otherwise agreed to by
      Indemnitee, who was or is involved in any manner (including, without
      limitation, as a party or a witness) or is threatened to be made so
      involved in any threatened, pending or completed investigation, claim,
      action, suit or proceeding, whether civil, criminal, administrative or
      investigative (including without limitation, any action, suit or
      proceeding by or in the right of the Corporation to procure a judgment in
      its favor) (a "Proceeding") by reason of the fact that he is or was a
      director, officer, employee or agent of the Corporation, or is or was
      serving at the request of the Corporation as a director, officer, employee
      or agent of another corporation, partnership, joint venture, trust or
      other enterprise (including, without limitation, any employee benefit
      plan) against all expenses (including attorney's fees), judgments, fines
      and amounts paid in settlement actually and reasonably incurred by him in
      connection with such Proceeding. Such indemnification shall be a
contract right and shall include the right to receive payment in advance
      of any expenses incurred by the Indemnitee in connection with such
      Proceeding, consistent with the provisions of applicable law as then in
      effect.

                  Section 2. Insurance, Contracts and Funding. The Corporation
      may purchase and maintain insurance to protect itself and any Indemnitee
      against any expenses, judgments, fines and amounts paid in settlement as
      specified in Section 1 of this Article or incurred by any Indemnitee in
      connection with any Proceeding referred to in Section 1 of this Article,
      to the fullest extent permitted by applicable law as then in effect. The
      Corporation may enter into contracts with any director, officer, employee
      or agent of the Corporation in furtherance of the provisions of this
      Article and may create a trust fund, grant a security interest or use
      other means (including without limitation, a letter of credit) to ensure
      the payment of such amounts as may be necessary to effect indemnification
      as provided in this Article.

                  Section 3. Indemnification; Not Exclusive Right. The right of
      indemnification provided in this Article shall not be exclusive of any
      other rights to which those seeking indemnification may otherwise be
      entitled, and the provisions of this Article shall inure to the benefit of
      the heirs and legal representatives of any person entitled to indemnity
      under this Article and shall be applicable to Proceedings commenced or
      continuing after the adoption of this Article, whether arising from acts
      or omissions occurring before or after such adoption.

                  Section 4. Advancement of Expenses, Procedures; Presumptions
      and Effect of Certain Proceedings; Remedies. In furtherance, but not in
      limitation of the foregoing provisions, the following procedures,
      presumptions and remedies shall apply with respect to advancement of
      expenses and the right to indemnification under this Article:

                        (a) Advancement of Expenses. All reasonable expenses
            incurred by or on behalf of the indemnitee in connection with any
            Proceeding shall be advanced to the Indemnitee by the Corporation
            within twenty (20) business days after the receipt by the
            Corporation of a statement or statements from the Indemnitee
            requesting such advance or advances from time to time, whether prior
            to or after final disposition of such Proceeding. Such statement or
            statements shall reasonably evidence the expenses incurred by the
            Indemnitee and, if required by law or requested by the Corporation
            at the time of such advance, shall include or be accompanied by an
            undertaking by or on behalf of the Indemnitee to repay the amounts
            advanced if it should ultimately be determined that the Indemnitee
            is not entitled to be indemnified against such expenses pursuant to
            this Article.

                        (b) Procedure for Determination of Entitlement to
            Indemnification.

                              (i) To obtain indemnification under this Article,
                  an Indemnitee shall submit to the Secretary of the Corporation
                  a written request, including such documentation and
                  information as
is reasonably available to the Indemnitee and reasonably
                  necessary to determine whether and to what extent the
                  Indemnitee is entitled to indemnification (the "Supporting
                  Documentation"). The determination of the Indemnitee's
                  entitlement to indemnification shall be made not later than
                  120 days after receipt by the Corporation of the written
                  request for indemnification together with the Supporting
                  Documentation. The Secretary of the Corporation shall,
                  promptly upon receipt of such a request for indemnification,
                  advise the Board of Directors or its designee in writing that
                  the Indemnitee has requested indemnification.

                              (ii) The Indemnitee's entitlement to
                  indemnification under this Article shall be determined in one
                  of the following ways: (A) by a majority vote of the
                  Disinterested Directors (as hereinafter defined), if they
                  constitute a quorum of the Board of Directors; (B) by a
                  written opinion of Independent Counsel (as hereinafter
                  defined) if (x) a Change of Control (as hereinafter defined)
                  shall have occurred and the Indemnitee so requests or (y) a
                  quorum of the Board of Directors consisting of Disinterested
                  Directors is not obtainable or, even if obtainable, a majority
                  of such Disinterested Directors so directs; (C) by the
                  stockholders of the Corporation (but only if a majority of the
                  Disinterested Directors, if they constitute a quorum of the
                  Board of Directors, presents the issue of entitlement or
                  indemnification to the stockholders for their determination);
                  or (D) as provided in Section 4(c), below.

                              (iii) In the event the determination of
                  entitlement to indemnification is to be made by Independent
                  Counsel pursuant to Section 4(b)(ii), a majority of the
                  Disinterested Directors shall select the Independent Counsel,
                  but only an Independent Counsel to which the Indemnitee does
                  not reasonably object; provided, however, that if a Change of
                  Control shall have occurred, the Indemnitee shall select such
                  Independent Counsel, but only an Independent Counsel to which
                  the Board of Directors does not reasonably object.

                        (c) Presumption and Effect of Certain Proceedings.
            Except as otherwise expressly provided in this Article, if a Change
            of Control shall have occurred the Indemnitee shall be presumed to
            be entitled to indemnification under this Article upon submission of
            a request for indemnification together with the Supporting
            Documentation in accordance with Section 4(b)(i), thereafter the
            Corporation shall have the burden of proof to overcome that
            presumption in reaching a contrary determination. In any event, if
            the person or persons empowered under Section 4(b) to determine
            entitlement to indemnification shall not have been appointed or
            shall not have made a determination within one hundred twenty (120)
            days after receipt by the Corporation of the request, therefore
            together with the Supporting Documentation, the Indemnitee shall be
            deemed to be entitled to indemnification and the Indemnitee shall be
            entitled to such indemnification unless (A) the Indemnitee
            misrepresented
or failed to disclose a material fact in making the request for
            indemnification or in the Supporting Documentation or (B) such
            indemnification is prohibited by law. The termination of any
            Proceeding described in Section 1, or of any claim, issue or matter
            therein, by judgement, order, settlement or conviction, or upon a
            plea of nolo contendere or its equivalent, shall not, of itself,
            adversely affect the right of the Indemnitee to indemnification or
            create a presumption that the Indemnitee did not act in good faith
            and in a manner which he reasonably believed to be in or not opposed
            to the best interests of the Corporation or, with respect to any
            criminal Proceeding, that the Indemnitee had reasonable cause to
            believe that his conduct was unlawful.

                        (d) Remedies of Indemnitee.

                              (i) In the event that a determination is made
                  pursuant to Section 4(b) that the Indemnitee is not entitled
                  to indemnification under this Article, (A) the Indemnitee
                  shall be entitled to seek an adjudication of his entitlement
                  to such indemnification either, at the Indemnitee's sole
                  option, in (x) an appropriate court of the State of Delaware
                  or any other court of competent jurisdiction or (y) an
                  arbitration to be conducted by a single arbitrator pursuant to
                  the rules of the American Arbitration Association; (B) any
                  such judicial proceeding or arbitration shall be de novo and
                  the Indemnitee shall not be prejudiced by reason of such
                  adverse determination; and (C) if a Change of Control shall
                  have occurred, in any such judicial proceeding or arbitration
                  the Corporation shall have the burden of proving that the
                  Indemnitee is not entitled to indemnification under this
                  Article.

                              (ii) If a determination shall have been made or
                  deemed to have been made, pursuant to Section 4(b) or (c),
                  that the Indemnitee is entitled to indemnification, the
                  Corporation shall be obligated to pay the amounts constituting
                  such indemnification within fifteen (15) business days after
                  such determination has been made or deemed to have been made
                  and shall be conclusively bound by such determination unless
                  (A) the indemnitee misrepresented or failed to disclose a
                  material fact in making the request for indemnification or in
                  the Supporting Documentation or (B) such indemnification is
                  prohibited by law. (Subparagraph (A) and (B) are each referred
                  to hereafter as a "Disqualifying Event"). In the event that
                  (C) advancement of expenses is not timely made pursuant to
                  Section 4(a) or (D) payment of indemnification is not made
                  within fifteen (15) business days after a determination of
                  entitlement to indemnification has been made or deemed to have
                  been made pursuant to Section 4(b) or (c), the Indemnitee
                  shall be entitled to seek judicial enforcement of the
                  Corporation's obligation to pay to the Indemnitee such
                  advancement of expenses or indemnification. Notwithstanding
                  the foregoing, the Corporation may bring an action, in an
                  appropriate court in the State of Delaware or any other court
                  of competent jurisdiction, contesting the right of the
                  Indemnitee to receive indemnification hereunder
due to the occurrence of Disqualifying Event; provided,
                  however, that in any such action the Corporation shall have
                  the burden of proving the occurrence of such Disqualifying
                  Event.

                              (iii) The Corporation shall be precluded from
                  asserting in any judicial proceeding or arbitration commenced
                  pursuant to this Section 4(d) that the procedures and
                  presumptions of this Article are not valid, binding and
                  enforceable and shall stipulate in any such court or before
                  any such arbitrator that the Corporation is bound by all the
                  provisions of this Article.

                              (iv) In the event that the Indemnitee, pursuant to
                  this Section 4(d), seeks a judicial adjudication of an award
                  in arbitration to enforce his rights under, or to recover
                  damages for breach of, this Article, the Indemnitee shall be
                  entitled to recover from the Corporation, and shall be
                  indemnified by the Corporation against, any expenses actually
                  and reasonably incurred by him if the Indemnitee prevails in
                  such judicial adjudication or arbitration. If it shall be
                  determined in such judicial adjudication or arbitration that
                  the Indemnitee is entitled to receive part but not all of the
                  indemnification or advancement of expenses sought, the
                  expenses incurred by the indemnitee in connection with such
                  judicial adjudication or arbitration shall be prorated
                  accordingly.

                  (e) Definitions. For purposes of this Section 4:

                              (i) "Change in Control" means a change in control
                  of the Corporation of a nature that would be required to be
                  reported in response to Item 5(f) of Schedule 14A of
                  Regulation 14A promulgated under the Securities Exchange Act
                  of 1934 (the "Act"), whether or not the Corporation is then
                  subject to such reporting requirement; provided that, without
                  limitation, such change in control shall be deemed to have
                  occurred if (A) any "person" (as such term is used in Section
                  13(d) and 14(d) of the Act) is or becomes the "beneficial
                  owner" (as defined in Rule 13d-3 under the Act), directly or
                  indirectly, of securities of the Corporation representing 30%
                  or more of the combined voting power of the Corporation's then
                  outstanding securities without the prior approval of at least
                  two-thirds (2/3) of the members of the Board of Directors in
                  office immediately prior to such acquisition; (b) the
                  Corporation is a party to a merger, consolidation, sale of
                  assets or other reorganization, or proxy contest, as a
                  consequence of which members of the Board of Directors in
                  office immediately prior to such transaction or event
                  constitute less than a majority of the Board of Directors
                  thereafter; or (C) during any period of two (2) consecutive
                  years, individuals who at the beginning of such period
                  constituted the Board of Directors (including for this purpose
                  any new director whose election or nomination for election by
                  the Corporation's stockholders was approved by a vote of at
                  least a majority of the directors then still in office who
                  were
directors at the beginning of such period) cease for any
                  reason to constitute at least a majority of the Board of
                  Directors.

                              (ii) "Disinterested Director" means a director of
                  the Corporation who is not or was not a party to the
                  Proceeding in respect of which indemnification is sought by
                  the Indemnitee.

                              (iii) "Independent Counsel" means a law firm or a
                  member of a law firm that neither presently is, nor in the
                  past five (5) years has been, retained to represent: (i) the
                  Corporation or the Indemnitee in any matter material to either
                  such party or (ii) any other party to the Proceeding giving
                  rise to a claim for indemnification under this Article.
                  Notwithstanding the foregoing, the term "Independent Counsel"
                  shall not include any person who, under the applicable
                  standards of professional conduct then prevailing under the
                  law of the State of Delaware, would have a conflict of
                  interest in representing either the Corporation or the
                  Indemnitee in an action to determine the Indemnitee's rights
                  under this Article.

                  Section 5. Severability. If any provision or provisions of
      this Article shall be held to be invalid, illegal or unenforceable for any
      reason whatsoever: (a) the validity, legality and enforceability of the
      remaining provisions of this Article (including, without limitation, all
      portions of any paragraph of this Article containing any such provision
      held to be invalid, illegal or unenforceable, that are not themselves
      invalid, illegal or unenforceable) shall not in any way be affected or
      impaired thereby; and (b) to the fullest extent possible, the provisions
      of this Article (including, without limitation, all portions of any
      paragraph of this Article containing any such provision held to be
      invalid, illegal or unenforceable) shall be construed so as to give effect
      to the intent manifested by the provision held invalid, illegal or
      unenforceable.

      Section 102(b)(7) of the GCL provides that a certificate of incorporation
may contain a provision eliminating or limiting the personal liability of a
director to the corporation or its stockholders for monetary damages for breach
of fiduciary duty as a director, provided that such provision may not eliminate
or limit the liability of a director (i) for any breach of the director's duty
of loyalty to the corporation or its stockholders; (ii) for acts or omissions
not in good faith or which involve intentional misconduct or a knowing violation
of law; (iii) under Section 174 of the GCL (relating to liability for
unauthorized acquisitions or redemptions of, or dividends on, capital stock) or
(iv) for any transaction from which the director derived an improper personal
benefit.

      Article Eleventh of Registrant's Restated Certificate of Incorporation, as
amended, implements the foregoing provision and provides as follows:

      Eleventh: (a) To the fullest extent that the General Corporation Law of
      the State of Delaware (as it exists on the date hereof [March 11, 1994] or
      as it may hereafter be amended) permits the limitation or elimination of
      the liability of directors, no director of the Corporation shall be liable
      to the Corporation or its shareholders for monetary damages for breach of
      fiduciary duty as a director. No amendment to or repeal of this Article
      shall apply to or have any effect on the
liability or alleged liability of any director of the Corporation for or
      with respect to any acts or omissions of such director occurring prior to
      such amendment or repeal.

                  (b) In addition to any requirements of law and any other
      provisions herein or in the terms of any class or series of capital stock
      having preference over the common stock of the Corporation as to dividends
      or upon liquidation (and notwithstanding that a lesser percentage may be
      specified by law), the affirmative vote of the holders of seventy-five
      percent (75%) or more of the voting power of the then outstanding voting
      stock of the Corporation, voting together as a single class, shall be
      required to amend, alter or repeal any provision of this Article.

      Insurance is maintained on a regular basis (and not specifically in
connection with this offering) against liabilities arising on the part of
directors and officers out of their performance in such capacities or arising on
the part of the registrant out of its foregoing indemnification provisions,
subject to certain exclusions and to the policy limits.

Item 7. Exemption from Registration Claimed.

      Not applicable.

Item 8. Exhibits.

      The following exhibits are furnished with this Registration Statement:

            Exhibit No.                         Description
            -----------                         -----------

            (4)(a)        Amended and Restated Certificate of Incorporation of
                          Registrant (incorporated by reference to Exhibit
                          (4)(a) of the Registrant's registration statement on
                          Form S-8 filed July 9, 1999 (registration no.
                          333-82563)).*

            (4)(b)        Amended and Restated By-Laws of Registrant as
                          amended to date (filed as Exhibit 3(b) to
                          Registrant's Annual Report on Form 10-K for the
                          fiscal year ended October 31, 1993 (Commission file
                          number 1-8993) and incorporated herein by
                          reference).

            (4)(c)        Deferred Benefit Plan.*

            (4)(d)        Form of Deferred Benefit Plan Termination
                          Amendment.*

            (5)(a)        Opinion and consent of Miller, Canfield, Paddock and
                          Stone, P.L.C.*

            (23)(a)       Consent of Miller, Canfield, Paddock and Stone,
                          P.L.C. (contained in Exhibit (5)(a)).

            (23)(b)       Consent of KPMG LLP.*
(23)(c)       Consent of Ernst & Young LLP.*

            (23)(d)       Consent of PricewaterhouseCoopers LLP.*

            (24)          Powers of attorney (contained in the signature pages
                          hereto).*

----------
*     Filed herewith.

Item 9. Undertakings.

      The undersigned registrant hereby undertakes:

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

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

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

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

      Provided, however, that paragraphs (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 by the
      registrant pursuant to Section 13 or Section 15(d) of the Securities
      Exchange Act of 1934 that are incorporated by reference into 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.

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

      The Registrant. Pursuant to the requirements of the Securities Act of
1933, 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 Town of Hanover, State of New Hampshire, on October 19,
1999.

                                    WHITE MOUNTAINS INSURANCE
                                    GROUP, INC.

                                    By    /s/
                                       ------------------------------------
                                          Name:  K. Thomas Kemp
                                          Title: Director, President and
                                                 Chief Executive Officer
The Plan. Pursuant to the requirements of the Securities Act of 1933, the
Deferred Benefit Plan (the "Plan") has duly caused this Registration Statement
to be signed on its behalf by the undersigned, thereunto duly authorized, in the
Town of Hanover, State of New Hampshire, on October 19, 1999.

                                    Deferred Benefit Plan

                                    By    /s/
                                       ------------------------------------
                                          Name:  Gordon S. Macklin
                                          Title: Member & Chairman -
                                                 Compensation Sub-Committee

                                    And:  /s/
                                        -----------------------------------
                                          Name:  Patrick M. Byrne
                                          Title: Member - Compensation
                                                 Sub-Committee

                                    And:  /s/
                                        -----------------------------------
                                          Name:  Robert P. Cochran
                                          Title: Member - Compensation
                                                 Sub-Committee

                                    And:  /s/
                                        -----------------------------------
                                          Name:  Frank A. Olson
                                          Title: Member - Compensation
                                                 Sub-Committee

                                    And:  /s/
                                        -----------------------------------
                                          Name:  Arthur Zankel
                                          Title: Member - Compensation
                                                 Sub-Committee
Directors and Officers of the Registrant. Pursuant to the requirements of
the Securities Act of 1933, this Registration Statement has been signed below by
the following persons in the capacities indicated and on the dates indicated
below. By so signing, each of the undersigned, in his capacity as a director or
officer, or both, as the case may be, of the registrant, does hereby appoint
John J. Byrne, K. Thomas Kemp, Raymond Barrette and Michael S. Paquette, and
each of them severally, his true and lawful attorney to execute in his name,
place and stead, in his capacity as a director or officer, or both, as the case
may be, of the registrant, any and all amendments to this Registration Statement
including post-effective amendments thereto and all instruments necessary or
incidental in connection therewith, and to file the same with the Securities and
Exchange Commission. Each of said attorneys shall have full power and authority
to do and perform in the name and on behalf of each of the undersigned, in any
and all capacities, every act whatsoever requisite or necessary to be done in
the premises as fully, and for all intents and purposes, as each of the
undersigned might or could do in person, the undersigned hereby ratifying and
approving the acts of said attorneys and each of them.

          Signatures                          Title                   Date
          ----------                          -----                   ----
Principal Executive Officer:

                                   President and Chief
  /s/                              Executive Officer            October 19, 1999
-------------------------------
K. Thomas Kemp

Principal Financial Officer:

                                   Executive Vice President and
  /s/                              Chief Financial Officer      October 19, 1999
-------------------------------
Raymond Barrette

Principal Accounting Officer:

                                   Senior Vice President and
  /s/                              Controller                   October 19, 1999
-------------------------------
Michael S. Paquette
Directors and Officers of the Registrant. Pursuant to the requirements of
the Securities Act of 1933, this Registration Statement has been signed below by
the following persons in the capacities indicated and on the dates indicated
below. By so signing, each of the undersigned, in his capacity as a director or
officer, or both, as the case may be, of the registrant, does hereby appoint
John J. Byrne, K. Thomas Kemp, Raymond Barrette and Michael S. Paquette, and
each of them severally, his true and lawful attorney to execute in his name,
place and stead, in his capacity as a director or officer, or both, as the case
may be, of the registrant, any and all amendments to this Registration Statement
including post-effective amendments thereto and all instruments necessary or
incidental in connection therewith, and to file the same with the Securities and
Exchange Commission. Each of said attorneys shall have full power and authority
to do and perform in the name and on behalf of each of the undersigned, in any
and all capacities, every act whatsoever requisite or necessary to be done in
the premises as fully, and for all intents and purposes, as each of the
undersigned might or could do in person, the undersigned hereby ratifying and
approving the acts of said attorneys and each of them.

          Signatures                       Title                    Date
          ----------                       -----                    ----

  /s/                                 Director                 October 19, 1999
----------------------------------
Terry L. Baxter

  /s/                                 Chairman, Director       October 19, 1999
----------------------------------
John J. Byrne

  /s/                                 Director                 October 19, 1999
----------------------------------
Patrick M. Byrne

  /s/                                 Director                 October 19, 1999
----------------------------------
Howard L. Clark, Jr.

  /s/                                 Director                 October 19, 1999
----------------------------------
Robert P. Cochran

  /s/                                 Director                 October 19, 1999
----------------------------------
George J. Gillespie III

  /s/                                 Director                 October 19, 1999
----------------------------------
John D. Gillespie

  /s/                                 Director                 October 19, 1999
----------------------------------
K. Thomas Kemp

  /s/                                 Director                 October 19, 1999
----------------------------------
Gordon S. Macklin

  /s/                                 Director                 October 19, 1999
----------------------------------
Frank A. Olson

  /s/                                 Director                 October 19, 1999
----------------------------------
Arthur Zankel
EXHIBIT INDEX

         Exhibit No.                      Description
         -----------                      -----------

           (4)(c)        Deferred Benefit Plan.*

           (4)(d)        Form of Deferred Benefit Plan Termination
                         Amendment.*

           (5)(a)        Opinion and consent of Miller, Canfield, Paddock and
                         Stone, P.L.C.*

           (23)(a)       Consent of Miller, Canfield, Paddock and Stone,
                         P.L.C. (contained in Exhibit (5)(a)).

           (23)(b)       Consent of KPMG LLP.*

           (23)(c)       Consent of Ernst & Young LLP.*

           (23)(d)       Consent of PricewaterhouseCoopers LLP.*

           (24)          Powers of attorney (contained in the signature pages
                         hereto).*

----------
*     Filed herewith.