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Debt (Details) - USD ($)
$ in Millions
1 Months Ended 3 Months Ended 9 Months Ended
Nov. 30, 2012
Sep. 30, 2016
Sep. 30, 2015
Dec. 31, 2012
Sep. 30, 2016
Sep. 30, 2015
Dec. 31, 2015
Jul. 23, 2015
Aug. 14, 2013
Debt Instrument                  
Incremental Common Shares Attributable to Dilutive Effect of Share-based Payment Arrangements   11,943     8,208        
Total debt   $ 288.5     $ 288.5   $ 337.6    
Repayments of Debt         401.8 $ 84.5      
Draw down of debt and revolving line of credit         $ 352.5 $ 98.5      
MediaAlpha Bank Facility [Member]                  
Debt Instrument                  
Debt Instrument, Basis Spread on Variable Rate         1.50%        
2012 OBH Senior Notes                  
Debt Instrument                  
Proceeds from Issuance of Debt       $ 275.0          
WTM Bank Facility                  
Debt Instrument                  
Debt Instrument, Interest Rate, Effective Percentage             3.90%    
Total commitment under revolving credit facility                 $ 425.0
Debt, Weighted Average Interest Rate   3.85%     3.85%        
Repayments of Debt   $ 250.0     $ 400.0        
Proceeds from Issuance of Debt     $ 250.0   350.0        
Term Loan [Member]                  
Debt Instrument                  
Repayments of Debt   0.8     0.8        
Revolving Credit Facility [Member]                  
Debt Instrument                  
Repayments of Debt   0.5     1.0        
Proceeds from Issuance of Debt         2.5        
OB Bank Facility [Member]                  
Debt Instrument                  
Total commitment under revolving credit facility   65.0     65.0        
One Beacon Holdings Inc [Member] | 2012 OBH Senior Notes                  
Debt Instrument                  
Debt Instrument, Interest Rate, Effective Percentage 4.70%                
Proceeds from Issuance of Debt $ 272.9                
Debt Instrument, Interest Rate, Stated Percentage 4.60%                
Debt Instrument, Issue Price as Percentage of Par Value 99.90%                
OneBeacon [Member] | OneBeacon Bank Facility [Member]                  
Debt Instrument                  
Long-term Line of Credit   0.0     0.0        
OneBeacon [Member] | 2012 OBH Senior Notes                  
Debt Instrument                  
Debt instrument at face value   275.0     275.0   $ 275.0    
Unamortized original issue discount   (1.9)     (1.9)   (2.1)    
Total debt   $ 273.1     $ 273.1   $ 272.9    
Debt Instrument, Interest Rate, Effective Percentage   4.70%     4.70%   4.70%    
White Mountains | WTM Bank Facility                  
Debt Instrument                  
Total debt   $ 0.0     $ 0.0   $ 50.0    
Tranzact [Member] | OneBeacon Bank Facility [Member]                  
Debt Instrument                  
Long-term Line of Credit             0.0    
MediaAlpha [Member] | MediaAlpha Bank Facility [Member]                  
Debt Instrument                  
Total debt   1.5     1.5        
Long-term Line of Credit   $ 15.6     $ 15.6   $ 15.0    
Debt Instrument, Interest Rate, Effective Percentage   5.80%     5.80%   5.50%    
Unamortized Debt Issuance Expense   $ (0.2)     $ (0.2)   $ (0.3)    
Line of Credit Facility, Fair Value of Amount Outstanding   15.4     15.4   $ 14.7    
Total commitment under revolving credit facility               $ 20.0  
Notional amount   14.2     14.2        
Line of Credit Facility, Remaining Borrowing Capacity   5.0     5.0        
Failure to pay principal and interest [Member] | OneBeacon [Member] | 2012 OBH Senior Notes                  
Debt Instrument                  
Total debt   $ 75.0     $ 75.0