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WHITE MOUNTAINS INSURANCE GROUP LTD Director's Dealing 2012

May 29, 2012

31060_dirs_2012-05-29_b3f6a713-1a58-48b3-9fe4-2c1a2a7f6714.zip

Director's Dealing

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SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: WHITE MOUNTAINS INSURANCE GROUP LTD (WTM)
CIK: 0000776867
Period of Report: 2012-05-24

Reporting Person: GILLESPIE JOHN DAVIES (Director)

Non-Derivative Transactions

Date Security Code Shares Price A/D Holdings After Ownership
2012-05-24 Common Shares A 200 Acquired 2625 Direct

Holdings (Non-Derivative)

Security Shares Ownership
Common Shares 50000 Indirect
Common Shares 14 Indirect

Footnotes

F1: Annual Director Share Award.

F2: Prospector Partners Fund L.P. ("Prospector") is the beneficial owner of 29,122 Common Shares; Prospector Offshore Fund (Bermuda) Ltd. ("Prospector Offshore") is the beneficial owner of 16,720 Common Shares; and Prospector Partners Small Cap Fund L.P. ("Prospector Small Cap") is the beneficial owner of 4,158 Common Shares. Mr. Gillespie disclaims beneficial ownership of the Common Shares owned by Prospector, Prospector Offshore and Prospector Small Cap except to the extent of his pecuniary interest therein. Mr. Gillespie's interest is limited to that as the principal of the general partner of each of Prospector and Prospector Small Cap and as principal of the investment manager of Prospector Offshore.