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Summary of Significant Accounting Policies (Basis of Presentation) (Details) (USD $)
In Millions, except Share data, unless otherwise specified
1 Months Ended 3 Months Ended 9 Months Ended 9 Months Ended 1 Months Ended 9 Months Ended 3 Months Ended 9 Months Ended
Dec. 31, 2011
company
Sep. 30, 2012
state
Sep. 30, 2011
Sep. 30, 2012
state
Sep. 30, 2011
Sep. 30, 2012
OneBeacon Ltd.
Dec. 31, 2011
OneBeacon Ltd.
Sep. 30, 2012
White Mountains [Member]
Sep. 30, 2012
HG Global [Member]
Sep. 30, 2012
White Mountains Consolidated Limited Partnership [Member]
Dec. 31, 2011
White Mountains Consolidated Limited Partnership [Member]
Sep. 30, 2012
Hamer and Bri-Mar [Member]
Sep. 30, 2012
A W G Dewar Inc [Member]
Dec. 31, 2011
A W G Dewar Inc [Member]
Sep. 30, 2012
Passage 2 Health Limited [Member]
Dec. 31, 2011
Passage 2 Health Limited [Member]
May 31, 2007
Preferred Stock
Sirius Internation Group Ltd [Member]
May 24, 2007
Preferred Stock
Sirius Internation Group Ltd [Member]
Sep. 30, 2012
Preferred Stock
HG Global [Member]
Sep. 30, 2012
Common Stock
HG Global [Member]
Sep. 30, 2012
Non-controlling interest
Sep. 30, 2012
Non-controlling interest
Build America Mutual [Member]
Sep. 30, 2012
Non-controlling interest
HG Global [Member]
Basis of Presentation                                              
Ownership percentage in outstanding common shares           75.20% 75.50%                                
Number of small manufacturing companies owned by the Tuckerman Fund I from whom the entity received shares 2                                            
Ownership interest (as a percent)                                     97.00% 89.00%      
Percentage of par value of policy reinsured   15.00%   15.00%                               15.00%      
Number of states in which Esurance insurance directly writes insurance   30   30                                      
Noncontrolling equity percentage in OneBeacon Ltd.           24.80% 24.50%                                
Funds to Capitalized HG Global               $ 594.5                             $ 14.5
Fair Value of Net Assets Acquired                 2.2                       2.2    
Net (Income) Loss Attributable to Noncontrolling Interest   30.9 11.0 2.0 (21.2)                                 18.0  
Non-cumulative perpetual preference shares issued                                 250,000,000            
Non-cumulative perpetual preference shares per share liquidation preference (in dollars per share)                                   $ 1,000          
Proceeds from non-cumulative perpetual preference shares                                 245.7            
Non-cumulative perpetual preference shares issuance cost and commission                                   4.3          
Noncontrolling interest - other $ 57.1 $ 60.8   $ 60.8           $ 52.8 $ 54.2 $ 4.5 $ 3.2 $ 2.3 $ 0.3 $ 0.6