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Statutory Capital and Surplus (Details) - USD ($)
 1 Months Ended 12 Months Ended
Dec. 31, 2020
Jan. 31, 2020
Dec. 31, 2019
Dec. 31, 2020
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2021
Dec. 31, 2012
Statutory Accounting Practices [Line Items]                
Cash and investments included in collateral trust $ 434,500,000     $ 434,500,000        
Repayments of principal debt       4,500,000 $ 22,900,000 $ 15,400,000    
Other long-term investments 786,800,000     786,800,000        
BAM                
Statutory Accounting Practices [Line Items]                
Surplus notes 388,200,000   $ 457,600,000 388,200,000 457,600,000      
Interest receivable 4,400,000   7,500,000 4,400,000 7,500,000      
Accrued interest on surplus notes 155,700,000   162,700,000 155,700,000 162,700,000      
Kudu                
Statutory Accounting Practices [Line Items]                
Proceeds from borrowings     57,000,000.0          
Distributions made     53,700,000 4,000,000.0        
Other Operations                
Statutory Accounting Practices [Line Items]                
Unrestricted cash 464,200,000     464,200,000        
Other long-term investments 172,700,000     172,700,000        
HG Global                
Statutory Accounting Practices [Line Items]                
Collateral held in supplement trust 827,100,000   786,700,000 827,100,000 786,700,000      
Cash and investments included in collateral trust 434,500,000   321,600,000 434,500,000 321,600,000      
Interest receivable 155,700,000   162,700,000 155,700,000 162,700,000      
HG Re | HG Global-BAM                
Statutory Accounting Practices [Line Items]                
Statutory capital and surplus 768,100,000     768,100,000        
Surplus required 1     1        
Cash outside of collateral trusts 2,800,000     2,800,000        
Collateral held in supplement trust 827,100,000     827,100,000        
Cash and investments outside of collateral trusts 20,100,000     20,100,000        
Accrued interest held in supplemental trust 114,000,000.0     114,000,000.0        
BAM | HG Global-BAM                
Statutory Accounting Practices [Line Items]                
Statutory capital and surplus 324,700,000     324,700,000        
Surplus required 66,000,000.0     66,000,000.0        
Statutory net loss       $ (59,300,000) (38,300,000) $ (34,600,000)    
HG Global                
Statutory Accounting Practices [Line Items]                
Percent over a target trust balance       102.00%        
Supplement trust target 603,000,000.0     $ 603,000,000.0        
Surplus notes               $ 503,000,000.0
HG Global | HG Global-BAM                
Statutory Accounting Practices [Line Items]                
Preferred stock value $ 619,000,000.0     $ 619,000,000.0        
Ownership interest (as a percent) 96.90%     96.90%        
Preferred stock dividend rate (as a percent)       6.00%        
White Mountains | Kudu                
Statutory Accounting Practices [Line Items]                
Distributions made     53,300,000          
NSM | NSM                
Statutory Accounting Practices [Line Items]                
Cash $ 48,100,000     $ 48,100,000        
Kudu                
Statutory Accounting Practices [Line Items]                
Cash and short-term investments 7,800,000     7,800,000        
Surplus Note | BAM                
Statutory Accounting Practices [Line Items]                
Cash repayments on notes 30,100,000 $ 65,000,000.0 32,000,000.0   10,000,000.0      
Accrued interest on surplus notes $ 8,400,000 16,200,000 8,000,000.0 $ 8,400,000 8,000,000.0      
Surplus Note | BAM | U.S. treasury rate plus                
Statutory Accounting Practices [Line Items]                
Basis spread on variable rate       3.00%        
Surplus Note | BAM | Fixed interest rate                
Statutory Accounting Practices [Line Items]                
Interest rate 8.00%     8.00%        
Surplus Note | BAM | Forecast | U.S. treasury rate plus                
Statutory Accounting Practices [Line Items]                
Effective yield (as a percent)             3.10%  
Supplemental Trust | BAM                
Statutory Accounting Practices [Line Items]                
Cash repayments on notes $ 21,500,000 47,900,000 23,700,000          
Accrued interest on surplus notes 200,000 $ 900,000 300,000 $ 200,000 300,000      
Preferred stocks | HG Global                
Statutory Accounting Practices [Line Items]                
Dividends       23,000,000.0        
Preferred stocks | HG Global | HG Global-BAM                
Statutory Accounting Practices [Line Items]                
Dividends payable 376,600,000     376,600,000        
Preferred stocks | White Mountains | HG Global | HG Global-BAM                
Statutory Accounting Practices [Line Items]                
Dividends       22,300,000        
Dividends payable 363,900,000     363,900,000        
Common Equities | Other Operations                
Statutory Accounting Practices [Line Items]                
Distributions made       3,200,000        
Common Equities | MediaAlpha                
Statutory Accounting Practices [Line Items]                
Common equity securities, at fair value 802,200,000     802,200,000        
Surplus Note | BAM                
Statutory Accounting Practices [Line Items]                
Accrued interest held in supplemental trust 200,000   300,000 200,000 300,000      
Cash repayments on notes       30,100,000 32,000,000.0      
Repayments of principal debt       21,500,000 23,700,000      
Accrued interest on surplus notes $ 8,400,000   $ 8,000,000.0 $ 8,400,000 $ 8,000,000.0