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Employee Share-Based Incentive Compensation Plans (Restricted Shares) (Details) - W T M Incentive Plan - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2018
Mar. 31, 2017
White Mountains | Restricted Share Cliff Vesting in January 2021    
Target Restricted Share Activity    
Issued (in shares) 13,450  
White Mountains | Restricted Stock    
Target Restricted Share Activity    
Beginning of period (in shares) 53,755 70,620
Issued (in shares) 14,105 16,735
Vested (in shares) (25,381) (22,015)
Assumed forfeitures and cancellations (969) (5,200)
Ending of period (in shares) 41,510 60,140
Unamortized grant date fair value    
Unamortized grant date fair value, beginning balance $ 14.3 $ 19.7
Issued 11.4 15.8
Assumed forfeitures and cancellations (0.2) (2.8)
Expense recognized (3.3) (3.6)
Unamortized grant date fair value, ending balance $ 22.2 $ 29.1
White Mountains | Restricted Share Cliff Vesting in January 2019    
Target Restricted Share Activity    
Issued (in shares) 365  
White Mountains | Restricted Share Cliff Vesting in January 2020    
Target Restricted Share Activity    
Issued (in shares) 290 16,735
Sirius Group | Restricted Stock    
Target Restricted Share Activity    
Ending of period (in shares)   2,195