Ownership Submission
FORM 4
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940
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(Print or Type Responses)
1. Name and Address of Reporting Person *
BARRETTE RAYMOND JOSEPH RENE
   2. Issuer Name and Ticker or Trading Symbol
WHITE MOUNTAINS INSURANCE GROUP LTD [WTM] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
__X__ Director _____ 10% Owner
__X__ Officer (give title below) __X__ Other (specify below)
Chief Executive Officer / Chairman of the Board
(Last)
(First)
(Middle)
C/O WHITE MOUNTAINS INSURANCE GROUP, 80 SOUTH MAIN STREET		 3. Date of Earliest Transaction (Month/Day/Year)
05/11/2009
(Street)

HANOVER, NH 03755		 4. If Amendment, Date Original Filed(Month/Day/Year)
 6. Individual or Joint/Group Filing(Check Applicable Line)
_X_ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person
(City)
(State)
(Zip)
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)		 2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 3. Transaction Code
(Instr. 8)		 4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)		 5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)		 6. Ownership Form: Direct (D) or Indirect (I)
(Instr. 4)		 7. Nature of Indirect Beneficial Ownership
(Instr. 4)
Code V Amount (A) or (D) Price
Common Shares 05/11/2009   P   800 (1) A $ 216.4575 28,995 D  
Common Shares 05/11/2009   P   200 (1) A $ 216.49 29,195 D  
Common Shares (restricted)               36,000 D  
Common Shares               24,768 I By Grantor Retained Annuity Trust
Common Shares               11,615 I By wife
Common Shares               775 I by daughter
Common Shares               300 I By son
Common Shares               4,230 I By IRA
Common Shares               143 (2) I By 401(k)

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Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security
(Instr. 3)		 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 4. Transaction Code
(Instr. 8)		 5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4, and 5)		 6. Date Exercisable and Expiration Date
(Month/Day/Year)		 7. Title and Amount of Underlying Securities
(Instr. 3 and 4)		 8. Price of Derivative Security
(Instr. 5)		 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 4)		 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I)
(Instr. 4)		 11. Nature of Indirect Beneficial Ownership
(Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Common Share Options $ 650 (3)               (4) 01/19/2014 Common Shares 200,000   200,000 D  

Reporting Owners

Reporting Owner Name / Address Relationships
 Director  10% Owner  Officer  Other
BARRETTE RAYMOND JOSEPH RENE
C/O WHITE MOUNTAINS INSURANCE GROUP
80 SOUTH MAIN STREET
HANOVER, NH 03755		   X     Chief Executive Officer Chairman of the Board

Signatures

 Jason R. Lichtenstein, by Power of Attorney   05/13/2009
**Signature of Reporting Person Date

Explanation of Responses:

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
(1) Common Shares acquired in open market transaction.
(2) Since April 1, 2009, the date of Reporting Person's last filing, Reporting Person has acquired 15 shares of WTM Common Shares under his 401(k) Plan. WTM Common Shares are purchased at fair market value on the date of purchase. The information in this report is based on a plan statement dated as of May 8, 2009.
(3) On January 20, 2007, the Reporting Person was granted options to purchase 200,000 Common Shares with an initial exercise price of $650 per share. The exercise price increases on a cumulative basis at an annual rate of 5% less the annualized regular dividend rate.
(4) The options vest in five equal annual installments beginning January 19, 2008.

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