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Debt and Standby Letter of Credit Facilities (Debt Outstanding) (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Oct. 10, 2014
Aug. 14, 2013
Debt Instrument          
Debt $ 442.4 $ 343.1      
Interest expense on debt 18.6 15.6 $ 16.2    
Draw down of debt and revolving line of credit 195.5 133.6 200.0    
WTM Bank Facility          
Debt Instrument          
Total commitment under revolving credit facility         $ 425.0
Line of Credit Facility, Fair Value of Amount Outstanding 50.0        
Interest expense on debt 0.1 0.3 $ 0.3    
Draw down of debt and revolving line of credit 125.0 65.0      
Repayments of lines of credit $ 75.0 $ 65.0      
Effective yield (as a percent) 3.74% 3.65%      
Prior W T M Bank Facility          
Debt Instrument          
Total commitment under revolving credit facility         $ 375.0
Other Debt [Member]          
Debt Instrument          
Debt $ 0.0 $ 1.0      
OneBeacon | 2012 OBH Senior Notes          
Debt Instrument          
Debt instrument at face value 275.0 275.0      
Unamortized original issue discount (0.2) (0.3)      
Debt 274.8 274.7      
White Mountains | WTM Bank Facility          
Debt Instrument          
Debt 50.0 0.0      
Tranzact [Member] | Tranzact Bank Facility          
Debt Instrument          
Total commitment under revolving credit facility 116.0        
Debt   67.4      
Line of Credit Facility, Fair Value of Amount Outstanding 104.7     $ 70.0  
Interest expense on debt 4.0 0.7      
Line of Credit Facility, Amount Outstanding 104.7 68.7      
Unamortized Debt Issuance Expense (1.8) (1.3)      
Draw down of debt and revolving line of credit 24.0        
Repayments of lines of credit 13.0        
MediaAlpha [Member] | MediaAlpha Bank Facility [Member]          
Debt Instrument          
Total commitment under revolving credit facility 20.0        
Line of Credit Facility, Fair Value of Amount Outstanding   0.0      
Line of Credit Facility, Amount Outstanding 15.0        
Unamortized Debt Issuance Expense (0.3) 0.0      
Carrying Value | OneBeacon | 2012 OBH Senior Notes          
Debt Instrument          
Debt 274.8 274.7      
Carrying Value | Tranzact [Member] | Tranzact Bank Facility          
Debt Instrument          
Debt 102.9 $ 67.4      
Carrying Value | MediaAlpha [Member] | MediaAlpha Bank Facility [Member]          
Debt Instrument          
Debt $ 14.7