X0303 4 2009-12-29 0000776867 WHITE MOUNTAINS INSURANCE GROUP LTD WTM 0001181360 BARRETTE RAYMOND JOSEPH RENE C/O WHITE MOUNTAINS INSURANCE GROUP 80 SOUTH MAIN STREET HANOVER NH 03755 1 1 0 1 Chief Executive Officer Chairman of the Board Common Shares 2009-12-29 5 G 0 410 0 D 28785 D Common Shares (restricted) 36000 D Common Shares 24768 I By Grantor Retained Annuity Trust Common Shares 11615 I By wife Common Shares 775 I by daughter Common Shares 300 I By son Common Shares 4230 I By IRA Common Shares 162 I By 401(k) Common Share Options 650.00 2014-01-19 Common Shares 200000 200000 D Since the date of Reporting Person's last filing, Reporting Person acquired 19 shares of WTM Common Shares under his Company 401(k) Plan account 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 December 31, 2009. 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. The options vest in five equal annual installments beginning January 19, 2008. Jason R. Lichtenstein, by Power of Attorney 2010-01-14