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Transactions with Related Persons (Details) - USD ($)
6 Months Ended 9 Months Ended 12 Months Ended
Jul. 16, 2012
Jun. 30, 2015
Sep. 30, 2015
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Related Party Transaction [Line Items]              
Assets       $ 10,284,500,000 $ 10,455,700,000    
Purchases       2,377,100,000 (2,868,500,000)    
Sales of common equity securities       $ 461,400,000 $ 609,800,000 $ 435,000,000  
Treasury Stock Acquired, Average Cost Per Share       $ 733 $ 617 $ 564  
OneBeacon              
Related Party Transaction [Line Items]              
Assets       $ 3,602,700,000 $ 3,559,800,000    
Prospector              
Related Party Transaction [Line Items]              
Assets under management         82,400,000    
Asset Management Fees       2,100,000 6,500,000 $ 6,500,000  
Shares paid or expired(1)       $ 5,500,000      
Percentage of fees in excess of $500,000 revenue chargeable       6.00%      
Amount of revenue over which 6% of fees chargeable       $ 500,000      
Management Fees, Base Revenue       400,000 1,100,000 1,300,000  
Incentive fees incurred       100,000 700,000 3,200,000  
Franklin Mutual Advisers [Member]              
Related Party Transaction [Line Items]              
Treasury Stock Acquired, Average Cost Per Share   $ 650.03 $ 761.50        
OneBeacon | Prospector              
Related Party Transaction [Line Items]              
Assets under management         15,800,000    
White Mountains Advisors LLC | Symetra              
Related Party Transaction [Line Items]              
Assets under management       22,100,000,000 30,900,000,000    
Asset Management Fees       8,000,000 18,400,000 16,500,000  
Oakum Bay Capital              
Related Party Transaction [Line Items]              
Ownerhsip percentage 7.50%            
Sales of common equity securities           $ 500,000  
Number of years to receive portion of revenue           10 years  
Oakum Bay Capital | Director              
Related Party Transaction [Line Items]              
Related party ownerhship percentage 67.50%            
Combination One [Member] | Prospector              
Related Party Transaction [Line Items]              
Assets       200,000,000 195,700,000    
Combination Two [Member] | Prospector              
Related Party Transaction [Line Items]              
Assets       200,000,000 431,200,000    
Combination Three [Member] | Prospector              
Related Party Transaction [Line Items]              
Assets       400,000,000      
Preferred Equity Securities | Oakum Bay Capital              
Related Party Transaction [Line Items]              
Purchases $ 2,000,000            
revenue sharing agreement | Prospector              
Related Party Transaction [Line Items]              
Fees from Revenue Sharing Agreement with Related Party         $ 400,000 $ 900,000  
Trimarc Capital Fund | Hedge funds | Oakum Bay Capital              
Related Party Transaction [Line Items]              
Trading Securities, Other       $ 8,900,000     $ 9,500,000
First Threshold Limit | White Mountains Advisors LLC | Prospector              
Related Party Transaction [Line Items]              
basis points       1.00%      
Second Threshold Limit | White Mountains Advisors LLC | Prospector              
Related Party Transaction [Line Items]              
basis points       0.50%      
Third Threshold Limit | White Mountains Advisors LLC | Prospector              
Related Party Transaction [Line Items]              
basis points       0.25%      
W T M Incentive Plan | Performance Shares | White Mountains              
Related Party Transaction [Line Items]              
Number of performance shares granted       29,828 41,580 43,660  
Shares paid or expired(1)       $ (30,800,000) $ (24,500,000) $ (10,100,000)  
W T M Incentive Plan | Performance Shares | White Mountains | Prospector              
Related Party Transaction [Line Items]              
Number of performance shares granted       7,000      
ERISA assets [Member] | Combination Two [Member] | Prospector              
Related Party Transaction [Line Items]              
Assets         $ 202,900,000    
Total              
Related Party Transaction [Line Items]              
Common shares repurchased and retired during the period       387,495 217,879 141,535  
Total | Franklin Mutual Advisers [Member]              
Related Party Transaction [Line Items]              
Common shares repurchased and retired during the period   19,688 26,300        
2014-2016 Cycle | W T M Incentive Plan | Performance Shares | White Mountains | Prospector              
Related Party Transaction [Line Items]              
Number of performance shares granted       6,250