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Employee Share-Based Incentive Compensation Plans (WTM - Restricted Shares) (Details) - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2016
Mar. 31, 2015
Share-based compensation arrangement by share-based payment award    
Equity in earnings of unconsolidated affiliates, net of tax $ 0.0 $ 7.3
White Mountains | W T M Incentive Plan | Restricted Share Cliff Vesting in January 2019 [Member]    
Target Restricted Share Activity    
Issued (in shares) 21,215  
White Mountains | W T M Incentive Plan | Restricted Share Cliff Vesting in January 2018    
Target Restricted Share Activity    
Issued (in shares)   22,890
White Mountains | W T M Incentive Plan | Restricted Stock    
Target Restricted Share Activity    
Beginning of period (in shares) 70,675 83,314
Issued (in shares) 21,215 22,890
Vested (in shares) (24,620) (35,079)
Assumed forfeitures and cancellations (800) 0
Ending of period (in shares) 66,470 71,125
Unamortized grant date fair value    
Unamortized grant date fair value, beginning balance $ 15.7 $ 14.3
Issued 16.3 15.2
Assumed forfeitures and cancellations 0.2 0.0
Expense recognized (3.0) (3.0)
Unamortized grant date fair value, ending balance $ 29.2 $ 26.5
Sirius Group | W T M Incentive Plan | Restricted Stock    
Target Restricted Share Activity    
Ending of period (in shares) 2,512 3,572