Notice of 2008

Annual General Meeting

of Members and

Proxy Statement

White Mountains Insurance Group, Ltd. (the “Company” or the “Registrant”) is an exempted Bermuda limited liability company whose principal businesses are conducted through its property and casualty insurance and reinsurance subsidiaries and affiliates.  Within this report, the term “White Mountains” is used to refer to one or more entities within the consolidated organization, as the context requires.

White Mountains’ property and casualty insurance and reinsurance operations principally include: (1) OneBeacon Insurance Group, Ltd. (“OneBeacon”), a 73%-owned Bermuda-based company which, through its U.S.-based subsidiaries, offers a wide range of specialty, commercial and personal products and services sold primarily through select independent agents and brokers; (2) White Mountains Re Group, Ltd. (“White Mountains Re”), a wholly-owned Bermuda-based company which, through its principal reinsurance subsidiaries, Folksamerica Reinsurance Company (“Folksamerica Re”) and Sirius International Insurance Corporation (“Sirius International”), offers reinsurance capacity for property, liability, accident & health, agriculture, aviation and space and certain other exposures on a worldwide basis, and (3) Esurance Holdings Ltd. (“Esurance”), a wholly-owned Bermuda-based company which, through its U.S.-based subsidiaries, sells personal auto insurance directly to customers online and through select online agents.  White Mountains’ invested assets are managed by White Mountains Advisors LLC (“WM Advisors”), the Company’s wholly-owned investment management subsidiary.

The 2008 Annual General Meeting will be confined to a Member vote on the proposals set forth in this Proxy Statement and on such other matters properly brought before the meeting.

1

WHITE MOUNTAINS INSURANCE GROUP, LTD.

NOTICE OF 2008 ANNUAL GENERAL MEETING OF MEMBERS

TO BE HELD MAY 29, 2008

March [31], 2008

Notice is hereby given that the 2008 Annual General Meeting of Members of White Mountains Insurance Group, Ltd. will be held on Thursday, May 29, 2008, at 12:00 noon Atlantic Time at the Fairmont Hamilton Princess Hotel, Hamilton, Bermuda.  At this meeting you will be asked to consider and vote upon the following proposals:

1)        to elect four of the Company’s directors to Class II with a term ending in 2011,

2)        to approve an amendment to the Company’s Bye-law 62 that, in order to protect the Company’s tax attributes, would require prior Board approval for any transfer of Company shares that would result in the creation of a new 5% shareholder or an increase in the ownership percentage of any 5% shareholder,

3)        to approve amendments to the Company’s Bye-laws 39 and 52 to permit the Company, to the extent permitted by Bermuda law, to utilize the new ‘Notice and Access’ rules of the Securities and Exchange Commission in connection with providing proxy materials to Members,

4)        to elect the Board of Directors of Sirius International, a wholly-owned reinsurance company organised under the laws of Sweden,

5)        to elect the Boards of Directors of White Mountains Re Bermuda Ltd. (“WMRe BDA”), Scandinavian Reinsurance Company Ltd. (“Scandinavian Re”) and Helicon Re Insurance Company, Ltd., each wholly-owned reinsurance companies organised under the laws of Bermuda,

6)        to elect the Board of Directors of White Mountains Life Reinsurance (Bermuda) Ltd. (“WM Life Re”) a wholly- owned reinsurance company organised under the laws of Bermuda,

7)        to elect the Board of Directors of Galileo Weather Risk Management Ltd. (“Galileo”), a wholly-owned reinsurance company organised under the laws of Bermuda,

8)        to elect the Board of Directors of any new non-United States operating subsidiary, as designated by the Company’s Board of Directors, and

9)        to approve the appointment of PricewaterhouseCoopers LLP (“PwC”) as the Company’s Independent Registered Public Accounting Firm for 2008.

The Company’s audited financial statements for the year ended December 31, 2007, as approved by the Company’s Board of Directors, will be presented at this Annual General Meeting.

Members of record of common shares on the record date, Monday, March 31, 2008, (1) who are individuals, may attend and vote at the meeting in person or by proxy or (2) which are corporations or other entities, may have their duly authorised representative attend and vote at the meeting in person or by proxy.  A list of all Members entitled to vote at the meeting will be open for public examination during regular business hours beginning on or about April 5, 2008 at the Company’s registered office located at Clarendon House, 2 Church Street, Hamilton HM 11, Bermuda.

All Members are invited to attend this meeting.

By Order of the Board of Directors,

Jennifer L. Pitts

Corporate Secretary

Members are invited to complete and sign the accompanying proxy card to be returned to White Mountains Insurance Group, Ltd., c/o Computershare, P.O. Box 8069, Edison, New Jersey, 08818-8069, in the envelope provided, whether or not they expect to attend the meeting. Members may also vote their shares by telephone or via the internet in accordance with the instructions on your proxy card.

2

WHITE MOUNTAINS INSURANCE GROUP, LTD.

PROXY STATEMENT

This Proxy Statement is being furnished in connection with the solicitation of proxies on behalf of the Company’s Board of Directors (the “Board”) for the 2008 Annual General Meeting of Members (the “2008 Annual Meeting”), to be held on Thursday, May 29, 2008 at the Fairmont Hamilton Princess Hotel, Hamilton, Bermuda.  The solicitation of proxies will be made primarily by mail, and the Proxy Statement and related proxy materials will be distributed to registered Members on or about April 5, 2008.

Holders of the Company’s common shares (“Members”), par value $1.00 per share, as of the close of business on Monday, March 31, 2008, the record date, are entitled to vote at the meeting.

You can ensure that your common shares are properly voted at the meeting by completing, signing, dating, and returning the enclosed proxy card in the envelope provided.  Members may also vote their shares by telephone or via the internet in accordance with the instructions on your proxy card. A Member has the right to appoint another person (who need not be a Member) to represent the Member at the meeting by completing an alternative form of proxy which can be obtained from the Corporate Secretary or by notifying the Inspectors of Election (see page 42).  Every Member entitled to vote has the right to do so either in person or by one or more persons authorised by a written proxy executed by such Member and filed with the Corporate Secretary.  Any proxy duly executed will continue in full force and effect unless revoked by the person executing it in writing or by the filing of a subsequent proxy.

Sending in a signed proxy will not affect your right to attend the meeting and vote.  If a Member attends the meeting and votes in person, his or her signed proxy is considered revoked.

3

PROPOSAL 1 - ELECTION OF THE COMPANY’S DIRECTORS

THE BOARD OF DIRECTORS

The Board is divided into three classes (each a “Class”).  Each Class serves a three-year term.

At the 2008 Annual General Meeting, Messrs. Barrette, Brouillette, G. Gillespie and J. Gillespie are nominated to be elected to Class II with a term ending in 2011.  The Board recommends a vote FOR Proposal 1 which calls for the election of the 2008 nominees.

The current members of the Board and terms of each Class are set forth below:

*  Nominated to be elected at the 2008 Annual Meeting to Class II with a term ending in 2011.

Of the nominees for election at the 2008 Annual Meeting, Messrs. Barrette, G. Gillespie and J. Gillespie were previously elected by Members and Mr. Brouillette was recommended by Mr. Barrette to the Nominating and Governance Committee for its consideration in appointing such individual to the Board.

The following information presents the principal occupation, business experience, recent business activities involving White Mountains and other affiliations of the current directors:

4

Class II - Term Ending in 2008 (up for re-election)

Raymond Barrette has served as Chairman and CEO of the Company since January 2007 and has been a director since August 2006.  He previously served as a director of the Company from 2000 to 2005, as President and CEO of the Company from 2003 to 2005, as CEO of OneBeacon from 2001 to 2002, as President of the Company from 2000 to 2001 and as Executive Vice President and Chief Financial Officer of the Company from 1997 to 2000.  Prior to joining the Company in 1997, Mr. Barrette had 23 years of experience in the insurance business, mostly at Fireman’s Fund Insurance Company. Mr. Barrette is also Chairman of White Mountains Re and Esurance and a director of OneBeacon.  See “Transactions With Related Persons, Promoters and Certain Control Persons.”

Yves Brouillette was appointed to the Board in August 2007. He has been the President of Beluca Investment, Inc. since 2005.  Previously, Mr. Brouillette served in many leadership positions at ING companies including most recently as the CEO for ING Latin America operations in Mexico, Brazil, Chile and Peru from 2002 to 2005. Mr. Brouillette is a Director of ING Canada and was Chairman of the Board from 2003 to 2007. He joined ING in 1989.  Mr Brouillette has over 30 years experience in the property and casualty insurance industry.

George J. Gillespie, III has been a director of the Company since 1986 and served as the Company’s Chairman from 2003 to May 2006.  Mr. Gillespie serves as Special Counsel to the law firm of Cravath, Swaine & Moore LLP (“CS&M”) and was a partner of CS&M from 1963 to 2005.  Mr. Gillespie’s son, John Gillespie, is also a director of the Company. See “Transactions With Related Persons, Promoters and Certain Control Persons.”

John D. Gillespie has been a director of the Company since 1999.  Mr. Gillespie is the founder and Managing Member of Prospector Partners, LLC (“Prospector”).  Mr. Gillespie served as Chairman and President of WM Advisors from 2003 to 2005 and as a Managing Director of OneBeacon from 2001 to 2003.  Prior to forming Prospector, Mr. Gillespie was President of the T. Rowe Price Growth Stock Fund and the New Age Media Fund, Inc. Mr. Gillespie’s father, George Gillespie, is also a director of the Company. See “Transactions With Related Persons, Promoters and Certain Control Persons.”

Class III - Term Ending in 2009

Howard L. Clark, Jr. was a director of the Company from 1986 to 1990, an advisor to the Board from 1990 to 1993, and was re-elected as a director in 1993.  Mr. Clark has served as Vice Chairman of Lehman Brothers, Inc. (“Lehman”) since 1993 and served as Chairman and CEO of Shearson Lehman Brothers, Inc. from 1990 to 1993.  Prior to joining Shearson Lehman Brothers, Inc., Mr. Clark was Executive Vice President and Chief Financial Officer of the American Express Company.  He is also a director of United Rentals, Inc., Walter Industries, Inc. and Mueller Water Products, Inc.  See “Transactions With Related Persons, Promoters and Certain Control Persons.”

Robert P. Cochran has been a director of the Company since 1994 and serves as its Deputy Chairman.  Mr. Cochran is a founding principal of Financial Security Assurance Holdings, Ltd. (“FSA”) and has served as FSA’s CEO since 1990 and as its Chairman and CEO since 1997.  He is also Chairman of Financial Security Assurance Inc. and Financial Security Assurance (U.K.) Ltd.

A. Michael Frinquelli has been a director of the Company since June 2005.  Mr. Frinquelli is co-founder and Manager of Renaissance Fund Advisors, Inc.  Until 2004, Mr. Frinquelli was a general partner of Renaissance Executive Partners, which he co-founded in April 1997. Prior to that, he was a managing director at Merrill Lynch and a managing director at Salomon Brothers.

Allan L. Waters was appointed President and CEO of White Mountains Re in March 2007.  He served as a director of the Company from 2003 to 2004 and was re-elected a director in November 2005.  Mr. Waters was the founder and Managing Member of Mulherrin Capital Advisors, LLC, which he managed from 1998 to 2007.  Mr. Waters formerly served as Senior Vice President and Chief Financial Officer of the Company from 1993 to 1997, as Vice President and Controller from 1990 to 1993, as Vice President of Finance from 1987 to 1990 and as Assistant Vice President of Finance from 1985 to 1987.  See “Transactions With Related Persons, Promoters and Certain Control Persons.”

5

Class I - Term Ending in 2010

Bruce R. Berkowitz has been a director of the Company since 2004.  Mr. Berkowitz is the founder and Managing Member of Fairholme Capital Management, LLC (“Fairholme”), a registered investment adviser, and is President and Director of Fairholme Funds, Inc.  Prior to founding Fairholme in 1997, Mr. Berkowitz was a portfolio manager at Smith Barney, Inc. and Lehman Brothers Holdings, Inc.  Mr. Berkowitz also serves as a director of Winthrop Realty Trust and TAL International Group, Inc. See “Transactions With Related Persons, Promoters and Certain Control Persons.”

Morgan W. Davis was appointed as a director in November 2006.  Mr. Davis serves as a director and President of American Centennial Insurance Company (“ACIC”), a wholly-owned subsidiary of the Company.  Mr. Davis was formerly a Managing Director of OneBeacon from 2001 to 2005 and served in a variety of capacities for White Mountains from 1994 to 2001.  Prior to joining the Company in 1994, Mr. Davis had 21 years of experience in the insurance business, mostly at Fireman’s Fund Insurance Company and INA/Cigna.  Mr. Davis also serves as a director of OneBeacon, Esurance and Montpelier Re Holdings, Ltd.  See “Transactions With Related Persons, Promoters and Certain Control Persons.”

Edith E. Holiday has been a director of the Company since 2004.  Ms. Holiday formerly served as Operating Trustee for TWE Holdings I and II Trusts from 2002 to 2007.  Ms. Holiday formerly served as Assistant to the President of the United States and Secretary of the Cabinet from 1990 to 1993 and as General Counsel to the United States Treasury Department from 1989 to 1990.  She is also a director of Hess Corporation, Canadian National Railway Company, H. J. Heinz Company and RTI International Metals, Inc. and is a director or trustee of 42 investment companies in the Franklin Templeton Group of Mutual Funds.

Lowndes A. Smith has been a director of the Company since 2003. Mr. Smith serves as Managing Partner of Whittington Gray Associates.  Mr. Smith formerly served as Vice Chairman of The Hartford Financial Services Group, Inc., (“The Hartford”) and President and CEO of Hartford Life Insurance Company.  He joined The Hartford in 1968.  Mr. Smith also serves as Chairman of OneBeacon and is a director of 85 investment companies in the mutual funds of The Hartford.

CORPORATE GOVERNANCE

Corporate governance is the system by which companies are directed and controlled and involves the distribution of rights and responsibilities among the Board, management and the Company’s Members.  The Company has established Corporate Governance Guidelines that spell out its overall approach towards corporate governance.

The Company also has a Code of Business Conduct that applies to all directors, officers and employees in carrying out their responsibilities to, and on behalf of, the Company. No waivers of the Code of Business Conduct were requested of, or granted by, the Board for any director or executive officer during 2007.

The Company’s Corporate Governance Guidelines and Code of Business Conduct are available at www.whitemountains.com. These documents are available in print, free of charge, to any Member upon request.

The Board

The day-to-day management of the Company, including preparation of financial statements and short-term and long-term strategic planning, is the responsibility of management. The primary responsibility of the Board is to oversee and review management’s performance of these functions in order to advance the long-term interests of the Company and its Members.

In fulfilling this responsibility, directors must exercise common sense business judgment and act in what they reasonably believe to be in the best interests of the Company and its Members. Directors are entitled to rely on the honesty and integrity of senior management and the Company’s outside advisors and auditors. However, it is the Board’s responsibility to establish that they have a reasonable basis for such reliance by ensuring that they have a strong foundation for trusting the integrity, honesty and undivided loyalty of the senior management team upon whom they are relying and the independence and expertise of outside advisors and auditors.

6

At each meeting of the Board, non-management directors meet in separate executive session without Company management present. Mr. Cochran, the Deputy Chairman of the Board, presides over these meetings.

Director Independence

The Board has determined that a majority of the Company’s current directors are independent, as defined in Section 303A of the New York Stock Exchange (“NYSE”) Listed Company Manual.  Those directors determined to be independent are Messrs. Berkowitz, Brouillette, Clark, Cochran, Frinquelli, and Smith and Ms. Holiday.  For a director to be independent, the Board must determine that the director has no relationship with the Company (other than being a director or shareholder of the Company) or has only immaterial relationships with the Company.  The Company does not apply categorical standards as a basis for determining director independence.  Accordingly, the Board considers all relevant facts and circumstances, on a case-by-case basis, in making an independence determination.

The Board notes no relationships (other than being directors or shareholders) with Messrs. Brouillette, Cochran, Frinquelli, or Smith or Ms. Holiday.  The Board notes relationships with Messrs. Berkowitz and Clark, as disclosed herein under “Transactions with Related Persons, Promoters and Certain Control Persons”, that it concluded are immaterial and do not impair their independence.  In making its independence determinations, the Board considered all such relationships in light of NYSE standards as well as the attributes it believes should be possessed by independent-minded directors.  Those attributes include the relative impact of the transactions to the director’s personal finances, the perceived degree of dependence by the director or the Company upon the relationship or transactions continuing in the future and whether the transactions were on terms that were reasonable and competitive.  The Board concluded that Messrs. Berkowitz and Clark’s relationships do not impair their ability to remain independent.

Board Meetings and Committees; Annual Meeting Attendance

During 2007, the following meetings of the Board were held: four meetings of the full Board, eight meetings of the Audit Committee, seven meetings of the Compensation Committee, three meetings of the Nominating and Governance Committee, and one meeting of the Executive Committee.  During 2007, each director attended more than 75% of the aggregate of: (1) the total number of meetings of the Board (held during the period for which he or she has been a director); and (2) the total number of meetings held by all committees of the Board on which he or she served (during the periods that he or she served).

Directors are encouraged, but are not required, to attend annual meetings.  All of the Company’s directors at the time were in attendance at the 2007 Annual General Meeting, which was held on May 24, 2007.

Committees of the Board

Nominating and Governance Committee

The primary purposes of the Nominating and Governance Committee are to: (1) identify individuals qualified to become Board members and recommend such individuals to the Board for nomination for election to the Board; (2) make recommendations to the Board concerning committee appointments; (3) develop, recommend and annually review corporate governance guidelines applicable to the Company and oversee corporate governance matters and (4) oversee the evaluation of the Board and management.

The Nominating and Governance Committee is currently comprised of Messrs. Clark (as Chairman), Cochran and Frinquelli. The Board has determined that each current member of the Nominating and Governance Committee satisfies applicable NYSE requirements.

The Nominating and Governance Committee Charter, which outlines the duties and responsibilities of the Nominating and Governance Committee, is available at www.whitemountains.com.  The Nominating and Governance Committee Charter is available in print, free of charge, to any Member upon request.

7

General Criteria and Process for Selection of Director Candidates.  In identifying and evaluating director candidates, the Nominating and Governance Committee does not set specific criteria for directors.  Under its charter, the Committee is responsible for determining desired Board skills and attributes such as independence, integrity, expertise, breadth of experience, knowledge about the Company’s business or industry and ownership interest in the Company.  Directors must be willing to devote adequate time and effort to Board responsibilities.  As set forth in the Company’s Corporate Governance Guidelines and its Charter, the Committee is responsible for recommending director candidates to the Board.

Consideration of Director Candidates Nominated by Members.  The Company has not adopted a specific policy regarding consideration of director candidates from Members.  Members who wish to recommend candidates for consideration by the Committee may submit their nominations in writing to the Corporate Secretary at the address provided in this Proxy Statement.  The Committee may consider such Member recommendations when it evaluates and recommends candidates to the Board for submission to Members at each annual general meeting.  In addition, Members may nominate director candidates for election without consideration by the Committee by complying with the eligibility, advance notice and other provisions of our Bye-laws as described below.

Procedures for Nominating Director Candidates.  Member proposals will be eligible for consideration for inclusion in the proxy statement and proxy relating to the Company’s 2009 Annual Meeting of Members pursuant to Rule 14a-8 promulgated under the Exchange Act if all applicable requirements of Rule 14a-8 are satisfied and such proposals are received timely by the Corporate Secretary as outlined below.

Under the Company’s Bye-laws, nominations for the election of directors may be made by the Board or by any Member entitled to vote for the election of directors (a “Qualified Member”).  A Qualified Member may nominate persons for election as directors only if written notice of such Qualified Member’s intent to make such nomination is delivered to the Secretary not later than: (1) with respect to an election to be held at an annual general meeting, 90 days prior to the anniversary date of the immediately preceding annual general meeting or not later than 10 days after notice or public disclosure of the date of the annual general meeting is given or made available to Qualified Members, whichever date is earlier, and (2) with respect to an election to be held at a special general meeting for the election of directors, the close of business on the seventh day following the date on which notice of such meeting is first given to Qualified Members.  Each such notice shall set forth:  (a) the name and address of the Qualified Member who intends to make the nomination and of the person or persons to be nominated; (b) a representation that the Qualified Member is a holder of record of common shares entitled to vote at such meeting and intends to appear in person or by proxy at the meeting to nominate the person or persons specified in the notice; (c) a description of all arrangements or understandings between the Qualified Member and each such candidate and any other person or persons (naming such person or persons) pursuant to which the nomination or nominations are to be made by the Qualified Member; (d) such other information regarding each candidate proposed by such Qualified Member as would have been required to be included in a proxy statement filed pursuant to the proxy rules of the United States Securities and Exchange Commission (the “SEC”) had each such candidate been nominated, or intended to be nominated, by the Board; and (e) the consent of each such candidate to serve as a director of the Company if so elected.

8

Audit Committee

The primary purposes of the Audit Committee are to: (1) assist Board oversight of: the integrity of the Company’s financial statements; the qualifications and independence of the independent auditors; the performance of the internal audit function and the independent auditors; and the Company’s compliance with legal and regulatory requirements; (2) provide an avenue of communication among the independent auditors, management, the internal auditors and the Board; (3) approve certain related or affiliated person transactions and review disclosures thereof, and (4) prepare the Audit Committee Report (which appears on page 31).

The Audit Committee is comprised of Messrs. Smith (as Chairman), Berkowitz, and Frinquelli, and Ms. Holiday. The Board has determined that, of the persons on the Audit Committee, at a minimum Mr. Smith meets the requirements of being an Audit Committee Financial Expert as defined in Item 401(h) of Regulation S-K of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). The Board has also determined that each current member of the Audit Committee satisfies applicable NYSE requirements as well as the separate independence standards set forth by the SEC.

The Audit Committee Charter, which outlines the duties and responsibilities of the Audit Committee, is available at www.whitemountains.com.  The Audit Committee Charter is available in print, free of charge, to any Member upon request.

Compensation Committee

The primary purposes of the Compensation Committee are to: (1) review and make recommendations on director compensation; (2) discharge the Board’s responsibilities relating to the compensation of executives; (3) oversee the administration of the Company’s compensation plans, (and, to the extent the Compensation Committee deems appropriate, the plans of the Company’s major subsidiaries), in particular the incentive compensation and equity-based plans and (4) reviews and discusses the Compensation Discussion and Analysis with management and prepares the Compensation Committee Report (which appears on page 19).

The Compensation Committee is currently comprised of Messrs. Cochran (Chairman), Berkowitz, Frinquelli and Smith. The Board has determined that each current member of the Compensation Committee satisfies applicable NYSE requirements.

The Compensation Committee Charter, which outlines the duties and responsibilities of the Compensation Committee, is available at www.whitemountains.com.  The Compensation Committee Charter is available in print, free of charge, to any Member upon request.

Compensation Committee Interlocks and Insider Participation

No member of the Compensation Committee has served as an officer or employee of White Mountains.  The Board notes a relationship with Mr. Berkowitz, as disclosed herein under “Transactions with Related Persons, Promoters and Certain Control Persons”, that it concluded is immaterial and does not impair his independence as a director or as a member of the Compensation Committee.

Shareholder Communications

Members, employees and others interested in communicating directly with the Board, any of the Board’s Committees or any individual member of the Board should write to the addressee, c/o the Corporate Secretary, at the address presented under “Available Information” (which appears on page 43).

VOTING SECURITIES AND PRINCIPAL HOLDERS THEREOF

Voting Rights of Members

As of March 17, 2008 there were 10,570,234 common shares outstanding.  Members of record of common shares shall be entitled to one vote per common share, provided that if, and so long as, the votes conferred by “Controlled” common shares (as defined below) of any person constitute ten percent (10%) or more of the votes conferred by the outstanding common shares of the Company, each outstanding common share comprised in such Controlled common shares shall confer only a fraction of a vote that would otherwise be applicable according to the following formula:

[(T divided by 10)-1] divided by C

Where: “T” is the aggregate number of votes conferred by all the outstanding common shares; and “C” is the number of votes conferred by the Controlled common shares of such person.

“Controlled” common shares in reference to any person means:

(1)                                  all common shares directly, indirectly, or constructively owned by such person within the meaning of Section 958 of the Internal Revenue Code of 1986, as amended, of the United States; and

(2)                                  all common shares directly, indirectly, or constructively owned by any person or “group” of persons within the meaning of Section 13(d)(3) of the Exchange Act and the rules and regulations promulgated thereunder; provided that this clause (ii) shall not apply to (a) any person (or any group that includes any person) that has been exempted from the provisions of this clause or (b) any person or group that the Board, by the affirmative vote of at least seventy-five percent (75%) of the entire Board, may exempt from the provisions of this clause.

The limitations set forth above do not apply to any Member which is a “Byrne Entity” (as defined below) for any matter submitted to the vote of Members, except with respect to the election of directors.  “Byrne Entity” means Mr. Byrne and any foundation or trust established by any associate or affiliate of him (or any group of which he is a part), as defined under Section 13(d) of the Exchange Act.

If, as a result of giving effect to the foregoing provisions or otherwise, the votes conferred by the Controlled common shares of any person would otherwise represent 10% or more of the votes conferred by all the outstanding common shares, the votes conferred by the Controlled common shares of such person shall be reduced in accordance with the foregoing provisions.  Such process shall be repeated until the votes conferred by the Controlled common shares of each person represent less than 10% of the votes conferred by all common shares.

10

Security Ownership of Certain Beneficial Owners

To the knowledge of the Company, there was no person or entity beneficially owning more than 5% of the common shares outstanding as of March 17, 2008, except as shown below.

(a)              Franklin Mutual Advisers, LLC (“Franklin”) has advised the Company that the common shares it is reported to beneficially own were acquired for investment purposes on behalf of client investment advisory accounts.

(b)             Includes 705,375 common shares over which Mr. Barrette has voting power and Mr. Byrne has dispositve power.  See note (c) below

(c)              Mr. Byrne has, or shares with his spouse, dispositive power over a total of 736,947 common shares of which 31,572 common shares are owned by trusts and charitable foundations in which Mr. Byrne has no pecuniary interest.

11

Security Ownership of Management

The following table sets forth, as of March 21, 2008, beneficial ownership of common shares by each director, the Named Executive Officers (as defined on page 20) and all other executive officers as a group:

(a)          The common shares shown as beneficially owned by (1) Mr. Barrette and (2) all directors, Named Executive Officers and all other executive officers as a group represent 7.9% and 9.1% of the total common shares outstanding at March 17, 2008, respectively.  No other director or executive officer beneficially owned 1% or more of the total common shares outstanding at that date. Beneficial ownership has been determined in accordance with Rule 13d-3(d)(1) of the Exchange Act.  To the Company’s knowledge, no common shares shown as beneficially owned above have been pledged as security.

(b)         Common shares shown as economically owned (1) include common shares beneficially owned, target unearned performance share and phantom performance share awards, unvested stock option awards and deferred compensation phantom share balances and (2) exclude, in the case of Mr. Barrette, common shares in which he has no pecuniary interest.

(c)          Mr. Barrette has, or shares with his spouse, dispositive power over a total of 49,154 common shares of which 314 common shares are owned by a charitable organization in which Mr. Barrette has no pecuniary interest.  Mr. Barrette has, or shares with his spouse, voting power over a total of 837,529 common shares consisting of: (1) the 49,154 common shares described above, (2) 705,375 common shares for which full proxy to vote was granted to Mr. Barrette in January 2007 by Mr. Byrne - - see “Security Ownership of Certain Beneficial Owners”; (3) 43,000 unvested restricted common shares granted to Mr. Barrette by the Company in January 2007, and (4) 40,000 vested but unexercised stock options.

(d)         Includes 7,074 common shares owned by East Lane L.L.C. Mr. Berkowitz is the Managing Member of East Lane, LLC.

(e)          Includes 50,000 common shares owned by various funds of Prospector in which Mr. Gillespie is either general manager or investment manager.  Mr. Gillespie disclaims beneficial ownership of such common shares except to the extent of his pecuniary interest in such funds.

(f)            Includes 120 common shares held in trusts for the benefit of Mr. Waters’ minor children that are voted and controlled by a third party. Mr. Waters has no pecuniary interest in such common shares.

12

EXECUTIVE COMPENSATION

Compensation Discussion and Analysis

Philosophy

Our executive compensation policies are designed with one primary goal in mind, maximization of shareholder value over long periods of time.  We believe that this goal is best pursued by utilising a pay-for-performance program that closely aligns the financial interests of management with those of our shareholders.  We accomplish this by emphasizing highly variable long-term compensation that is contingent on performance over a number of years rather than entitlements (such as base salary, pensions and employee benefits).  To that end, the Compensation Committee has established base salaries and target annual bonuses for our executives that tend to be lower than those paid by other property and casualty insurers and reinsurers, while granting the bulk of an executive’s target compensation as long-term incentive compensation.

We design our long-term incentive compensation programs to share with management on average roughly 15% of the value added above a risk-free return on our shareholders’ equity.  We have utilised this targeted sharing percentage for many years.  We take this approach because producing a rate of return equal to a risk free rate does not add value to the heavy capital owners put in the business—our shareholders would be better off putting their money in the bank and avoiding entirely the risk of owning a portion of a business.  We share 15% because we compete for talent and deals where such sharing is common.

In the case of our Chairman & CEO, Mr. Barrette, to induce him to re-join the Company and to incent him as an owner, in January 2007 he was granted a package of escalating strike price options and restricted shares, each of which vests in annual installments over five years.  Mr. Barrette also received a tranche of restricted shares that are structured to vest in the event of a change in control within five years of grant. These grants are intended to be the only equity grants made to Mr. Barrette over the seven years following his January 2007 election as Chairman & CEO.

Other than in the case of Mr. Barrette, we have generally structured our long-term incentive compensation as performance shares and performance units.  At our parent company, long-term compensation is typically in the form of WTM performance shares whose value is equal to the market value of our common shares.  Performance shares reward company-wide performance.  The number of shares harvested, which can be from 0x to 2x the target number granted, is tied to our after-tax growth in intrinsic business value per share as defined by the Committee with respect to each performance cycle.  At OneBeacon, which became a public company in November 2006, long-term compensation now is structured primarily in the form of OneBeacon performance shares whose value is equal to the market value of OneBeacon’s common shares.  OneBeacon performance shares reward OneBeacon’s performance.  The number of shares harvested, which can be from 0x to 2x the target number granted, is tied to its after-tax growth in intrinsic business value per share as defined by the OneBeacon Committee (as defined below) with respect to each performance cycle.  At our non-public operating subsidiaries, such as White Mountains Re and Esurance, long-term incentive compensation is typically in the form of performance units whose value is derived from the performance of the particular operating group.  Performance units reward the performance of the particular operating group.  The number of units harvested, which can be from 0x to 2x the target number granted, is tied to those elements of performance for which the operating group’s management has primary responsibility.  As an example, because the parent company keeps responsibility for investing the assets of our non-public operating subsidiaries, in calculating performance the operating subsidiaries are credited with a “standard” return on their investible assets.  In addition, for the most senior non-public operating group executives, including our Named Executive Officers at our wholly owned operating companies, in order to better align their interests with our shareholders, we typically denominate a portion of their long-term incentives in WTM performance shares that reward company-wide performance.

13

Generally, we have set our performance target for a 100% harvest of WTM performance shares at 700 basis points above the risk-free rate, a level consistent with the risk premium that the market has demanded for investing in equities.  In the last few years, given the combination of the low interest rate environment (the yield on the 10-year treasury has been under 5% for several years) and hard insurance market conditions, our Compensation Committee had set a floor on our target growth in intrinsic business value per share of 13% annually.  However, considering the softening insurance markets and continuing low interest rate environment, for the 2008-2010 performance cycle the Committee set the target at 11%, which was 700 basis points above the yield on the 10-year treasury at the beginning of 2008, with growth of 4% or less resulting in a harvest of 0% and growth of 18% or more resulting in a harvest of 200%.

In order to test our beliefs about the variable nature of our plans, from time to time our Compensation Committee has had management review the public disclosure of other property and casualty insurers and reinsurers about their compensation practices and assess the variability of their compensation programs based on differing levels of performance (6%, 13% and 20%, which was consistent with the threshold, target and maximum for the 2007-2009 performance cycle).  The results of these reviews have supported the Committee’s view that our compensation programs are more variable than most other insurers and reinsurers, have fewer fixed elements of compensation and perquisites and do not lead to sizable rewards for poor performance as can happen with long-term options granted with a fixed exercise price equal to the market price on the date of grant.

Our Compensation Process

Our Compensation Committee is responsible for approving our compensation practices that affect executive officers and it specifically approves all compensation for our executive officers and for any employee with target annual compensation in excess of $1.5 million.  Our CEO annually presents the Compensation Committee with his evaluation of our executives, their individual performances, responsibilities and the contributions they made to the Company’s accomplishments over the past year as well as over the last long-term incentive plan cycle and his expectations for the future.  In connection with this evaluation, the CEO presents the Compensation Committee with his recommendations for establishing the compensation for these executives for its consideration.  The Compensation Committee assesses the performance, responsibilities and contributions of the CEO and sets the compensation of the CEO.

With the exception of significant promotions and new hires, compensation matters are usually addressed at the first meeting of the Compensation Committee each year (typically the third week of February) following the availability of financial results for the prior year.  This allows us to determine the results of prior period grants and to set targets for the current year and newest long-term performance cycle.  Performance cycles for long-term compensation typically run for three years beginning on January 1st of the year of grant.

Following the OneBeacon initial public offering (the “OB IPO”) in November 2006, our Compensation Committee determined that it would fully delegate to the OneBeacon Compensation Committee (the “OneBeacon Committee”) authority for the compensation of OneBeacon’s officers, including those who might be Named Executive Officers of the Company.  Accordingly, compensation actions for OneBeacon personnel following the date of the OB IPO (including new annual and long-term incentives and approval of payouts on existing annual and long-term incentives) have been taken by the OneBeacon Committee (which is currently comprised of Lowndes Smith (Chair), Lois Grady and Kent Urness).

2007 Chairman and CEO Inducement Grant

In January 2007, the Company hired Ray Barrette as its Chairman and CEO.  As described above, to induce Mr. Barrette to re-join the Company and to incent him as an owner of the Company, he was granted (1) 200,000 seven-year options that vest in equal annual installments over five years and that have an initial exercise price of $650 per share that escalates each year by 5% less the annual regular dividend rate, (2) 35,000 Restricted Shares that vest in equal annual installments over five years, and (3) 15,000 Restricted Shares that vest in the event of a change in control of the Company within five years of grant.  On January 19, 2007, the last trading day prior to the Committee’s approval of these grants, the closing price of the Company’s common shares was $578.25.  These grants are intended to be the only equity grants made to Mr. Barrette over the seven years following his January 2007 election as Chairman and CEO.

14

The Committee arrived at the structure and value of this grant based on the Board’s desire that, with the retirement of Jack Byrne as Chairman of the Company and as a director, the Company secure Mr. Barrette’s services as Chairman and CEO for a substantial period of time.  In negotiating with Mr. Barrette, the Committee sought to balance its desire to ensure that, before Mr. Barrette is able to realize substantial value, the Company’s owners will have first had the benefit of substantial share price gains with Mr. Barrette’s requirement of a certain level of assured equity compensation. The Committee believes it struck this balance with the combination of options that will not be in the money unless the Company’s share price increases by more than 6.5% per year over the seven-year life of the options and the first tranche of Restricted Shares that vest in annual installments over five years. The second tranche of Restricted Shares, which was structured to vest in the event of a change in control within five years, was designed to replace the lost time value of Mr. Barrette’s options if a change of control were to occur in the first five years.  If no change in control occurs within five years and the grant has not otherwise vested, this tranche of Restricted Shares will be cancelled.

Compensation for 2007

The principal elements of compensation for our executives are long-term incentive compensation, base salary, and annual incentive bonuses.

Long-Term Incentive Compensation

Except as described above with respect to Mr. Barrette, we typically provide long-term incentive opportunities to our executive officers through awards of performance shares and performance units.  We occasionally issue stock options and restricted common shares (“Restricted Shares”).

CEO Compensation.  Mr. Barrette’s long-term incentive compensation is discussed above under “2007 Chairman and CEO Inducement Grant”.

Named Executive Officer Compensation

White Mountains.  For the performance cycle from 2007-2009, we awarded our Named Executive Officers (other than the CEO and other than Mr. Miller) 16,800 WTM performance shares.  For each of these executives, their grants reflect levels that the Committee determined, based on the Committee’s general experience and the recommendation of the CEO, were appropriate to reflect each such executive’s expected contribution to the Company.  In the case of Messrs. Foy and Lusardi, the 2007 grants were in-line with the grant date value of their 2006 long-term incentive grants. In the case of Mr. Campbell, the 2007 grant was an increase over the grant for the 2006-2008 performance cycle that the Committee believed was appropriate to reflect his increased responsibilities and greater contributions to the Company.

For each recipient of a WTM performance share grant for the 2007-2009 performance cycle, the Committee established 13% growth in intrinsic business value per share as the performance target that would result in a harvest of 100% of the target shares.  Growth of 6% or less would result in a harvest of 0% and growth of 20% or more would result in a harvest of 200%. The targets were consistent with the Company’s compensation philosophy described above.

For many years, to measure growth in intrinsic business value per share, the Committee had looked to growth in economic value per share (weighted 50%), growth in tangible GAAP book value per share (weighted 25%) and growth in market value per share (weighted 25%), in each case including dividends.  Economic value is calculated by starting with our tangible GAAP book value, then adjusting our assets and liabilities to their underlying economic value (such as through the discounting of reserves).  In February 2008, however, the Committee determined to eliminate growth in market value per share as one of the factors and instead to look only to growth in economic value per share (weighted 50%) and growth in tangible GAAP book value per share (weighted 50%), in each case including dividends.  This change applies to all performance cycles starting with the 2006-2008 performance cycle.  The Committee made this change to reduce the leverage that market value has on the evaluation of management performance.  Market value remains the currency used to measure the value of the performance shares awarded.

15

In evaluating its conclusion that eliminating market value as a performance measure was fair to all parties, the Committee reviewed the impact of market value on all performance cycles from 1999-2001 through 2005-2007.  The cumulative impact of market value on the aggregate harvests over this period was minus 25 percentage points (which equated to about a 2.5% reduction of the total number of performance shares harvested from these cycles in the aggregate).  The Committee concluded that a fair adjustment was to increase the 2005-2007 harvest by 25 percentage points (from 39% to 64%) in exchange for management giving up the future upside (and some less likely downside) for all future performance cycles starting with 2006-2008.  The Committee believes that this is “rough justice” as the cumulative impact of market value is brought to roughly zero, though the impact on individuals varies greatly.  The Committee believes that the weighting of the performance factors going forward better reflects the elements that the Committee and Board want management to focus on.

In 2007, in addition to Mr. Barrette’s Restricted Share grant, the Committee granted 2,000 Restricted Shares to Mr. Campbell.  This grant was made to recognize Mr. Campbell’s contributions to the Company over many years and, in particular, his contributions in restructuring OneBeacon in anticipation of the OB IPO.

OneBeacon.  For Michael Miller, CEO of OneBeacon, the OneBeacon Committee granted his long-term incentive compensation for the 2007-2009 performance cycle in the form of OneBeacon performance shares.  The performance target for a 100% harvest was set at 13% growth in intrinsic business value per share with a range of 6% to 20%.  Growth in intrinsic business value per share is measured based on (1) underwriting return on equity (weighted 40%), (2) growth in adjusted book value per share (weighted 40%), and (3) growth in market value per share (weighted 20%), including dividends in the case of (2) and (3).  Underwriting return on equity and adjusted book value per common share are non-GAAP financial measures that OneBeacon uses to measure its performance.  Underwriting return on equity means OneBeacon’s GAAP net income minus after tax investment income and realized gains (losses), plus standardized investment income divided by average tangible GAAP shareholders’ equity for the period minus any remaining accretion to face value related to preferred stock instruments.  Standardized investment income is the 10-year Treasury yield plus 100 basis points times OneBeacon’s average invested assets times one minus OneBeacon’s actual tax rate on investment income and realized and unrealized gains (losses) for the period.  OneBeacon’s average invested assets excludes the assets held to economically defease its preferred stock obligations.  Growth in adjusted book value per share means OneBeacon’s GAAP shareholders’ equity (on a fully converted basis) at the end of the period minus accretion to face value of preferred stock divided by the number of OneBeacon common shares outstanding (on a fully converted basis) at the end of the period plus compounded dividends divided by the fully converted tangible book value at the beginning of the period minus one.

For the 2008-2010 performance cycle, the OneBeacon Committee set 11% annual growth in intrinsic business value per share as target performance, with a range of 4% to 18%.  The OneBeacon Committee set the target at this level for the same reasons as the Compensation Committee set the White Mountains target at 11%.  In addition, for 2008-2010 the OneBeacon Committee determined to eliminate growth in market value per share as one of the factors used to calculate OneBeacon’s growth in intrinsic business value per share, and to instead calculate it using underwriting return on equity (weighted 50%) and growth in adjusted book value per share (weighted 50%).  The OneBeacon Committee made this change to reduce the leverage that market value has on the evaluation of management performance. Market value remains the currency used to measure the value of the OneBeacon performance shares awarded.

In 2006, in connection with the OB IPO, the OneBeacon Committee approved a stock option grant for executives and other selected senior managers (the “IPO Options”) that was intended to have a value at target of $22.5 million in aggregate.  While it was intended that the target value should be realized if the total return to OneBeacon’s shareholders (stock price appreciation and dividends) was 13% per year, no mechanism was included in the options to reflect the contribution to total return from the expected regular quarterly dividend.  As a result, without a correction, OneBeacon would have had to achieve a total return (including expected regularly quarterly dividends) of more than 16% per year for the $22.5 million target value to be realized.  Accordingly, the OneBeacon Committee approved a grant of OneBeacon restricted stock units (“RSUs”) with a targeted value that makes up the shortfall described above.   Awards of RSUs were made proportionately to each of the original IPO Option recipients, including to Mr. Miller.  The RSUs are subject to the same vesting requirements as the IPO Options, but also have an additional performance hurdle for vesting of 4% growth in OneBeacon’s adjusted book value per common share to ensure deductibility under 162(m) of the Internal Revenue Code.  Upon vesting, the RSUs will be mandatorily deferred into a OneBeacon non-qualified deferred compensation plan and will be paid out in 2012 in cash or OneBeacon shares at the discretion of the OneBeacon Committee.

16

Base Salary 

We pay our executive officers salaries that we believe to be below-market. In 2007, we limited base salaries to a maximum of $400,000, which was the salary each of our Named Executive Officers received, other than Mr. Campbell, who received a salary of $350,000.  For 2008, the Committee determined that it was appropriate to raise the salary cap to $500,000 as it had been seven years since the last adjustment.  Each Named Executive Officer received a salary increase of $100,000 for 2008.

Annual Incentive Bonuses

We provide annual bonus opportunities to our executive officers.  Each Named Executive Officer participates in the annual bonus pool of his respective business unit.  In 2007, the annual bonus target for each of our Named Executive Officers was equal to 50% of his base salary and the aggregate bonus pool size for each business unit could range from 0% to 200% of target, depending upon performance.  Individual bonuses can vary widely around the pool average based on individual performance and no cap (other than the size of the pool) applies to any single individual. Typically, the head of a business unit receives the average bonus percentage applicable to their business unit.

At our parent companies (including for our Named Executive Officers at the parent companies), we reward company-wide performance.  For 2007, the performance required to achieve a bonus pool of 100% of target was set at 13% growth in intrinsic business value per share. Based on the Company’s performance, the Committee awarded a bonus pool of 67% of target for 2007.  The Compensation Committee approved Mr. Barrette’s recommendation that his bonus be allocated to other key employees.

For our operating subsidiaries (including for our Named Executive Officers at operating subsidiaries), we design our annual incentives to reward performance of the applicable subsidiary operating group.  For more junior operating subsidiary executives, a portion of their annual incentives is tied to the performance of specific business units under their control.  For OneBeacon in 2007, including for Mr. Miller, the primary performance objective required to achieve a bonus pool of 100% of target was the achievement of a combined ratio of 96%.  Based on OneBeacon’s performance, the OneBeacon Committee awarded a OneBeacon bonus pool of 125% of target.

For 2008, the OneBeacon Committee approved an increase in Mr. Miller’s annual bonus target to 75% of his salary.

Other Elements of Compensation

Retirement Benefits

We have no active U.S. pension plans.  Benefit accruals under all our U.S. qualified pension plans and all our U.S. supplemental pension plans were frozen for all employees in 2002.

Our Named Executive Officers may participate in our voluntary non-qualified deferred compensation plans whereby they may defer all or a portion of their compensation. Investment options in these plans are those available in our 401(k) plans, including White Mountains common shares, and Berkshire common shares.  None of the investment options offered under these plans provides an above-market rate of interest.  In 2008, in connection with an election previously made in compliance with Section 409A of the Internal Revenue Code, Mr. Barrette received a full distribution of his non-qualified deferred compensation balances.  As part of this distribution, Mr. Barrette received 15,000 WTM common shares in lieu of cash.  Mr. Barrette has agreed not to transfer these shares for a period of two years following the distribution.

Our employees may participate in our qualified 401(k) plans and eligible employees can participate in a qualified employee stock ownership plan.  We do not provide supplemental retirement benefits to any employees in connection with these plans.

Perquisites

We review the perquisites that our senior management receives.  The primary perquisites include housing allowances in special circumstances and personal use of corporate aircraft.

17

We allow our Named Executive Officers to use our corporate aircraft from time to time for personal reasons. The aggregate incremental cost to the Company is included, for proxy reporting purposes, as compensation to the Named Executive Officer.  For tax purposes, we comply with IRS regulations.  We do not “gross-up” our Named Executive Officers for their taxes associated with personal use of our aircraft.

Our Named Executive Officers also participate in our other benefit plans on the same terms as our other employees.  These plans include medical and health insurance, company paid life insurance (which is currently capped at $150,000 in coverage at our parent companies) and charitable gift matching.

Certain Board Fees

Our Named Executive Officers do not receive director fees for serving on the Company’s board of directors or for serving on the boards of directors of our wholly-owned or majority-owned subsidiaries.  However, those Named Executive Officers who serve on the boards of directors of other companies in which we have a minority interest may receive director fees.  We consider those board fees when evaluating the compensation of our Named Executive Officers.

Employment and Severance Agreements; Change in Control

We have no long-term employment agreements with our Named Executive Officers although, from time to time we have entered into short-term arrangements with newly hired executives governing their compensation and severance during up to their first three years with the Company. No such arrangements are in effect with our Named Executive Officers.

At our parent company, severance benefits, if any, are determined by our Compensation Committee in its sole discretion.  At our operating subsidiaries, our Named Executive Officers participate in the severance plans, if any, generally applicable at those companies.

If any of our most senior executives were to retire from the Company, we generally will consider entering into a one to three year consulting agreement with the executive that would permit the executive to earn some or all of such executive’s performance shares that were then outstanding and would enable the Company to ensure a smooth transition, to receive a non-compete/non-solicit from the executive and to retain access to valuable knowledge, talents and relationships.

While the Company has no employment or severance agreement with Mr. Barrette, pursuant to the terms of his stock option and Restricted Share grants that are discussed above under “2007 Chairman and CEO Inducement Grant”, if Mr. Barrette is terminated without cause, any of these grants that are outstanding but unvested at that time would vest in such circumstance.

We have no change in control agreements with our Named Executive Officers.  Under our long-term incentive plans, if a change in control of the Company (or a business unit, as applicable) were to occur, certain events, such as involuntary or constructive employment termination or amendments to our incentive plans which are materially adverse to its participants, may cause stock options to become fully exercisable, Restricted Shares to become immediately vested and performance shares and performance units to become payable in full or in part.  Our plans do not provide for tax gross-ups for excess parachute payments that may result from a change in control.

As discussed above under “2007 Chairman and CEO Inducement Grant”, the stock option and Restricted Share grants made to Mr. Barrette include provisions pursuant to which such grants vest upon the occurrence of a change in control.  While as described above the Company typically has “double-trigger” change in control provisions in its long-term incentive plans, the Committee determined that, in light of the design of Mr. Barrette’s grants (principally stock options with an escalating exercise price set initially well above the current market price) and as an inducement to Mr. Barrette, immediate vesting upon a change in control was appropriate.

18

Tax Considerations

As a Bermuda-domiciled company, we do not receive a tax deduction for compensation paid to employees of White Mountains Insurance Group, Ltd. and, accordingly, the limitation of Section 162(m) of the Internal Revenue Code does not impact compensation paid to our Named Executive Officers who are employees of White Mountains (Messrs. Barrette and Foy).  However, in the case of Named Executive Officers who are employees of subsidiaries that are organized in the United States (Messrs. Lusardi, Miller and Campbell), Section 162(m) would limit the deductibility of their compensation to $1,000,000 per individual to the extent that such compensation is not “performance-based” as defined in Section 162(m).  The Company is cognizant of Section 162(m) and generally seeks to structure its long-term incentive programs to permit the full deductibility of such compensation paid to these Named Executive Officers.  However, in certain situations, the Compensation Committee may approve compensation that will not meet the Section 162(m) requirements if, in the Committee’s judgment, structuring compensation in such manner better promotes the Company’s interests (such as with a grant of Restricted Shares).

Compensation Committee Report

The Compensation Committee of the Company has reviewed and discussed the Compensation Discussion and Analysis required by Item 402(b) of Regulation S-K with management and, based on such review and discussions, the Compensation Committee recommended to the Board that the Compensation Discussion and Analysis be included in this Proxy Statement.

19

Summary Compensation Table

The following table presents compensation earned during 2007 and 2006 by the Company’s CEO, CFO, its three other most highly compensated executive officers and its Former CEO (collectively, the “Named Executive Officers”).

(a)    Represents annual incentive bonuses earned for the years ended December 31, 2007 and 2006.  For 2006, Mr. Miller also earned a $500,000 sign-on bonus installment from his 2005 hiring, a $750,000 special bonus relating to the OB IPO and a payment of $400,815 pursuant to a special 2006 OneBeacon bonus program.

(b)    Represents amounts recorded during 2007 and 2006 as compensation expense under FAS 123(R) for outstanding performance share and Restricted Share awards without regard to estimated forfeitures.  Compensation expense for Mr. Barrette’s 15,000 Restricted Shares that vest in the event of a change in control of the Company before January 20, 2012, is $0.  Amount for Mr. Miller in 2007 includes the effect of WTM shares forfeited (3,000 shares for the 2005-2007 performance cycle and 3,300 shares for the 2006-2008 performance cycle) in exchange for OB performance shares.  See “Grants of Plan-Based Awards.”  Amount for Mr. Fass in 2007 includes the effect of shares forfeited (5,000 shares for the 2005-2007 performance cycle and 9,000 shares for the 2006-2007 performance cycle). See “Outstanding Equity Awards at Fiscal Year End.”  For a discussion of the assumptions used in calculating the fair value of the awards under FAS 123(R), see Note 12 of the Notes to Consolidated Financial Statements included in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2007 as filed with the Securities and Exchange Commission on February 29, 2008 (“Note 12”).

(c)    Represents amounts recorded during 2007 and 2006 as compensation expense under FAS 123(R) for outstanding option awards without regard to forfeitures.  Compensation expense for Mr. Campbell’s Incentive Options in 2007 and Mr. Fass’ Incentive Options in 2006 is $0.  See “Outstanding Equity Awards at Fiscal Year End.”  For a discussion of the assumptions used in calculating the fair value of the awards under FAS 123(R), see Note 12.

(d)    Amounts in 2007 represent performance units earned for the 2005-2007 performance cycle and amounts in 2006 represent performance units earned for the 2004-2006 performance cycle.  Performance units are incentive awards that are payable upon completion of pre-defined business goals, are settled in cash and do not fall within the scope of FAS 123(R).

(e)    Represents the aggregate change in the present value of the accumulated benefit under a tax-qualified defined benefit pension plan for 2007 and 2006.  The aggregate change in the present value of the accumulated benefit under a tax-qualified defined benefit pension plan for Mr. Fass in 2007 was a loss of $2,059 before he elected to receive a lump-sum payment of $633,076 on March 2, 2007.  See “Pension Benefits.”

(f)    See below for details of All Other Compensation.

20

All Other Compensation

The following table presents a breakout of “All Other Compensation” included in the Summary Compensation Table for 2007 and 2006:

(a)     Represents director fees paid to Mr. Foy and Mr. Lusardi by Symetra.

(b)     Amounts represent the aggregate incremental cost to the Company.  For aircraft leased by the Company, the incremental cost was computed based upon a direct cost per hour multiplied by the number of hours of use.  For chartered flights, the incremental cost to the Company was the actual cost of the flight.

(c)     In 2007, Mr. Fass received $5,200,000 in severance pay.  In 2006, Mr. Miller received $97,261 (which includes $41,161 of related tax gross-up) for corporate provided housing and Mr. Fass received a $12,000 monthly housing allowance associated with his relocation to Bermuda (which was made at the Company’s request).

21

Grants of Plan-Based Awards

The following table presents grants of plan-based awards made, except as otherwise noted, under the White Mountains Long-Term Incentive Plan (the “WTM Incentive Plan”) to the Named Executive Officers during 2007.

(a)        On February 21, 2007, Messrs. Foy, Lusardi and Campbell were granted WTM performance shares for the 2007-2009 performance cycle. Target performance, which would result in a payout of 100% of the target shares, is growth in intrinsic business value per share of 13%.  Growth of 6% or less (Threshold) would result in a payout of 0% and growth of 20% or more (Maximum) would result in a payout of 200%.

(b)        On February 20, 2007, Mr. Miller was granted OB performance shares for the 2007-2009 performance cycle.  Mr. Miller’s WTM performance shares outstanding with respect to the 2005-2007 and 2006-2008 performance cycles were cancelled.  The cancelled WTM performance shares were replaced with grants of 68,700 OB performance shares for a one-year 2007 performance cycle and 75,570 OB performance shares for a two-year 2007-2008 performance cycle. The grants of OB performance shares for the 2007 and 2007-2008 performance cycles at the date of grant had the same value as the WTM performance shares forfeited, as determined in accordance with FAS 123(R) without regard to forfeitures.

(c)        On January 20, 2007, Mr. Barrette was granted 35,000 Restricted Shares that vest in equal installments over five years and 15,000 Restricted Shares that vest in the event of a change in control of the Company before January 20, 2012.  The second tranche of Restricted Shares was designed to replace the lost time value of Mr. Barrette’s options if a change in control were to occur in the five years following their grant.

(d)        On February 21, 2007, Mr. Campbell was granted 2,000 Restricted Shares that vest after a three year restricted period.

(e)        On January 20, 2007, Mr. Barrette was granted 200,000 seven-year options that vest in equal installments over five years and that have an initial exercise price of $650 per share that escalates each year by 5% less the annual regular dividend rate.

(f)         Represents the grant date fair value as determined in accordance with FAS 123(R) without regard to forfeitures.  Assuming a maximum 200% payout, the grant date fair value of the WTM performance shares granted to Messrs. Foy, Lusardi and Campbell is $7,430,280, $7,430,280 and $4,343,856.  Assuming a maximum 200% payout, the grant date fair value of the OB performance shares granted to Mr. Miller is $3,833,460 for the 2007 performance cycle, $4,216,806 for the 2007-2008 performance cycle and $5,937,734 for the 2007-2009 performance cycle.

22

Outstanding Equity Awards at Fiscal Year-End

The following table presents outstanding equity awards made, except as otherwise noted, under the WTM Incentive Plan to the Named Executive Officers as of December 31, 2007.

(a)        As of December 31, 2007, Mr. Barrette had 200,000 Non-Qualified Options to acquire the Company’s common shares which were awarded to him on January 20, 2007.  See “Grants of Plan-Based Awards.”

(b)        As of December 31, 2007, Mr. Miller had 277,826 OB Options outstanding that were awarded to him on October 18, 2006 under the OB Incentive Plan.  The OB Options vest in equal installments on each of the third, fourth and fifth anniversaries of the date of the OB IPO and their term is 66 months.

(c)        As of December 31, 2007, Mr. Campbell had 1,800 Incentive Options to acquire the Company’s common shares that were awarded to him on February 28, 2000.  The Incentive Options were issued at an exercise price equal to the market price of the Company’s common shares on the date of grant and the exercise price escalates by 6% per annum over the life of the instrument.

(d)        Stock awards not yet vested at December 31, 2007 represent WTM Restricted Shares awarded to Mr. Barrette in January 2007 and Mr. Campbell in February 2007.  Market values are based on the year-end closing market price.  See “Grants of Plan-Based Awards.”

(e)        Equity incentive plan awards not yet vested at December 31, 2007 include: (i) WTM performance shares awarded for the 2007-2009 performance cycle to Mr. Foy (6,500 target performance shares), Mr. Lusardi (6,500 target performance shares) and Mr. Campbell (3,800 target performance shares), (ii) WTM performance shares awarded for the 2006-2008 performance cycle to Mr. Foy (6,850 target performance shares), Mr. Lusardi (6,850 target performance shares) and Mr. Campbell (3,130 target performance shares) and (iii) OB performance shares awarded to Mr. Miller for the 2007-2009 performance cycle (106,411 target performance shares) and the 2007-2008 performance cycle (75,570 target performance shares).  Payout values for WTM performance shares are based on the year-end closing market price at an estimated payout of 100% of target for the 2007-2009 performance cycle and 125% of target for the 2006-2008 performance cycle.  Payout values for OB performance shares are based on the year-end closing market price at an estimated payout of 100% for the 2007-2009 performance cycle and 132.3% of target for the 2007-2008 performance cycle.

(f)         Excludes performance shares awarded for the 2005-2007 performance cycle which became fully vested at December 31, 2007 and were paid in March 2008.  See “Option Exercises and Stock Vested” below.

23

Option Exercises and Stock Vested

The following table presents option exercises and stock awards vesting in 2007 for each of the Named Executive Officers.

(a)    Represents 6,000, 6,000 and 2,000 target WTM performance shares awarded for the 2005-2007 performance cycle to Messrs. Foy, Lusardi and Campbell, respectively, which became fully vested on December 31, 2007 at 64% of target.  Values realized on vesting were determined based on the average of the high and low market values of common shares ($498.00) on February 27, 2008, the date the awards were determined by the Compensation Committee, plus dividends accrued since February 2007 of $8.00 per common share.

(b)   Represents 68,700 target OB performance shares awarded for the 2007 performance cycle to Mr. Miller, which became fully vested on December 31, 2007 at 62.9% of target.  Values realized on vesting were determined based on the average of the high and low market values of common shares ($21.94) on February 26, 2008, the date the awards were determined by the OneBeacon Compensation Committee.

(c)    On December 27, 2007, Mr. Campbell exercised 900 Incentive Options to acquire the Company’s common shares which were awarded to him on February 28, 2000.  The value realized on exercise was determined based on the closing market value on the exercise date of $500.00 less the strike price of $167.60.

(d)   On July 5, 2007, Mr. Fass exercised 6,300 Incentive Options to acquire the Company’s common shares which were awarded to him on February 28, 2000.  The value realized on exercise was determined based on the closing market value on the exercise date of $594.89 less the strike price of $162.22.

(e)    Represents 10,000 WTM Restricted Shares awarded to Mr. Fass in February 2004 which fully vested on February 25, 2007.

Pension Benefits

The following table presents the present value of accumulated benefits payable as of December 31, 2007 under the OneBeacon Pension Plan and the OneBeacon Excess Plan (collectively the “OneBeacon Plans”) to each of the Named Executive Officers, including the number of years of service credited to each such Named Executive Officer, determined using interest rate and mortality rate assumptions consistent with those used in the Company’s financial statements.

(a)    The OneBeacon Plans were frozen effective December 31, 2002.  Since inception, several predecessor plans have been merged in to the OneBeacon Pension Plan including the Folksamerica Holding Company, Inc. Employees Retirement Plan.   White Mountains does not sponsor any other defined benefit pension plans.  Messrs. Barrette, Foy, Miller and Lusardi are not entitled to receive pension benefits under the OneBeacon Plans.

(b)   Due to the freeze, Messrs. Campbell’s and Fass’ number of years of credited service and average annual compensation remain the same as they were on December 31, 2002.

(c)    On March 2, 2007, Mr. Fass retired and elected to receive a lump-sum payment of $633,076.

24

 Nonqualified Deferred Compensation

The following table presents the contributions, earnings, withdrawals and ending account balances for the Named Executive Officers under White Mountains’ various unfunded, nonqualified deferred compensation plans (the “Deferral Plans”) for 2007.