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Statutory Capital and Surplus (Details)
 3 Months Ended 12 Months Ended
Dec. 31, 2014
USD ($)
Dec. 31, 2015
USD ($)
yr
Dec. 31, 2014
USD ($)
Dec. 31, 2013
USD ($)
Dec. 31, 2016
Dec. 31, 2012
USD ($)
Statutory Accounting Practices [Line Items]            
Stockholders' Equity Attributable to Parent $ 3,995,700,000 $ 3,913,200,000 $ 3,995,700,000      
Amount available for dividend distributions without prior approval from regulatory authorities   $ 48,000,000        
Equity held in insurance and reinsurance subsidiaries   505,000,000        
Distributions made   $ 6,000,000        
Payments for Repurchase of Common Stock   268,600,000 128,200,000 $ 79,800,000    
Fair value investments 3,343,600,000 4,050,900,000 3,343,600,000 3,889,000,000    
Trading Securities   2,639,700,000        
Dividend Capacity            
Other long-term investments 331,900,000 315,800,000 331,900,000      
OneBeacon            
Statutory Accounting Practices [Line Items]            
Statutory net income (loss)   44,500,000 (14,200,000) 100,100,000    
Stockholders' Equity Attributable to Parent 787,500,000 755,200,000 787,500,000      
Distributions made   80,000,000   80,200,000    
Unrestricted cash   65,300,000        
Other Operations            
Statutory Accounting Practices [Line Items]            
Stockholders' Equity Attributable to Parent 1,425,500,000 1,344,300,000 1,425,500,000      
Unrestricted cash   73,700,000        
Dividend Capacity            
Other long-term investments   17,600,000        
Unregulated Operation | OneBeacon            
Statutory Accounting Practices [Line Items]            
Distributions made   5,300,000 4,800,000      
Surplus notes   101,000,000        
Unrestricted cash   104,400,000        
Lone Tree Insurance Group Ltd            
Statutory Accounting Practices [Line Items]            
Noncash distribution received       27,900,000    
Proceeds from Contributions from Affiliates   15.0        
Star & Shield Insurance Exchange [Member]            
Statutory Accounting Practices [Line Items]            
Surplus notes 17,000,000 21,000,000 17,000,000      
Star & Shield Insurance Exchange [Member] | Other Operations            
Statutory Accounting Practices [Line Items]            
Statutory capital and surplus 6,500,000 5,000,000 6,500,000      
Statutory net income (loss)   3,500,000 9,500,000      
Surplus required   1,500,000        
OneBeacon            
Statutory Accounting Practices [Line Items]            
Dividends available, net of noncontrolling interest   180,000,000        
HG Global            
Statutory Accounting Practices [Line Items]            
Surplus notes           $ 503,000,000
HG Global | HG Global-BAM            
Dividend Capacity            
Preferred stock, value   $ 613,000,000        
Ownership interest (as a percent)   96.90%        
Preferred stock dividend rate   6.00%        
HG Re | HG Global-BAM            
Statutory Accounting Practices [Line Items]            
Statutory capital and surplus   $ 460,800,000        
Collateral Held in Supplement Trust   401,900,000        
Dividend Capacity            
Accrued interest on surplus notes   $ 53,800,000        
BAM | HG Global-BAM            
Statutory Accounting Practices [Line Items]            
Statutory capital and surplus   437,300,000        
Statutory net income (loss)   32,000,000 31,800,000 29,300,000    
Surplus required   66,000,000        
Subsidiaries            
Statutory Accounting Practices [Line Items]            
Stockholders' Equity Attributable to Parent   554,000,000        
One Beacon Insurance Company | OneBeacon            
Statutory Accounting Practices [Line Items]            
Distributions made 700,500,000          
Noncash distribution received 151,200,000          
Split Rock [Member] | OneBeacon            
Statutory Accounting Practices [Line Items]            
Statutory capital and surplus 122,600,000 249,500,000 122,600,000      
Statutory net income (loss)   45,500,000 46,200,000 $ (38,700,000)    
Amount available for dividend distributions without prior approval from regulatory authorities   37,400,000        
Payments of Distributions to Affiliates   85,000,000        
White Mountains | OneBeacon            
Statutory Accounting Practices [Line Items]            
Distributions made   60,300,000        
White Mountains | Other Operations            
Statutory Accounting Practices [Line Items]            
Unrestricted cash   14,400,000        
Atlantic Speciality Insurance Company (ASIC) [Member] | OneBeacon            
Statutory Accounting Practices [Line Items]            
Surplus required   117,700,000        
Atlantic Speciality Insurance Company (ASIC) [Member] | Regulated Operation | OneBeacon            
Statutory Accounting Practices [Line Items]            
Statutory capital and surplus   622,300,000        
Amount available for dividend distributions without prior approval from regulatory authorities   26,600,000        
Distributions made   44,900,000 10,000,000      
Payments for Repurchase of Common Stock   66,000,000        
Payments of Capital Distribution     10,000,000      
Statutory accounting practices earned surplus   68,300,000        
Atlantic Speciality Insurance Company (ASIC) [Member] | Regulatory Approval [Member] | OneBeacon            
Statutory Accounting Practices [Line Items]            
Amount available for dividend distributions without prior approval from regulatory authorities   62,200,000        
White Mountains Life Re | Other Operations            
Statutory Accounting Practices [Line Items]            
Statutory capital and surplus $ 76,000,000 77,500,000 $ 76,000,000      
Surplus required   $ 500,000        
Surplus Note | BAM | HG Global-BAM            
Dividend Capacity            
Interest rate (as a percent)   8.00%        
basis points   3.00%        
Preferred stocks | HG Global | HG Global-BAM            
Dividend Capacity            
Dividends Payable   $ 139,700,000        
Preferred stocks | White Mountains | HG Global | HG Global-BAM            
Dividend Capacity            
Dividends Payable   $ 135,300,000        
SEK            
Dividend Capacity            
Exchange rate 7.7737 8.4247 7.7737 6.4339    
Common Stock [Member] | OneBeacon            
Dividend Capacity            
Other long-term investments   $ 51,500,000        
Common Equities [Member] | OneBeacon            
Statutory Accounting Practices [Line Items]            
Trading Securities   54,600,000        
Common Equities [Member] | Other Operations            
Statutory Accounting Practices [Line Items]            
Trading Securities   292,300,000        
Retained earnings            
Statutory Accounting Practices [Line Items]            
Stockholders' Equity Attributable to Parent $ 3,010,500,000 3,084,900,000 $ 3,010,500,000 $ 2,801,900,000   $ 2,542,500,000
Amount available for dividend distributions without prior approval from regulatory authorities   $ 2,600,000,000        
Retained earnings | Split Rock [Member] | OneBeacon            
Statutory Accounting Practices [Line Items]            
Statutory Accounting Practices, Statutory Capital, Percent   15.00%        
Retained earnings | Atlantic Speciality Insurance Company (ASIC) [Member] | OneBeacon            
Statutory Accounting Practices [Line Items]            
Statutory Accounting Practices, Statutory Capital, Percent   10.00%        
U.S and Bermuda [Member] | OneBeacon            
Statutory Accounting Practices [Line Items]            
Statutory capital and surplus $ 721,500,000 $ 622,300,000 $ 721,500,000      
Surplus Note | Unregulated Operation | OneBeacon            
Statutory Accounting Practices [Line Items]            
Fair value investments   $ 51,500,000        
Combination One [Member] | Surplus Note | BAM | HG Global-BAM            
Dividend Capacity            
Number of years of change in interest rate   5        
Combination Two [Member] | Surplus Note | BAM | HG Global-BAM            
Dividend Capacity            
Number of years of change in interest rate | yr   3        
US Treasury Rate [Member] | Surplus Note | BAM | HG Global-BAM            
Dividend Capacity            
Interest rate (as a percent)   3.15%        
Fixed interest rate [Member] | Surplus Note | BAM | HG Global-BAM            
Dividend Capacity            
Interest rate (as a percent)   8.00%        
Scenario, Forecast [Member] | US Treasury Rate [Member] | Surplus Note | BAM | HG Global-BAM            
Dividend Capacity            
Interest rate (as a percent)         3.54%