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Employee Share-Based Incentive Compensation Plans (Performance Shares Granted Under the WTM Incentive Plan) (Details) - W T M Incentive Plan - USD ($)
$ in Millions
3 Months Ended 6 Months Ended
Jun. 30, 2020
Jun. 30, 2019
Jun. 30, 2020
Jun. 30, 2019
Mar. 31, 2020
Dec. 31, 2019
Mar. 31, 2019
Dec. 31, 2018
Performance Share | Performance Cycle 2018 to 2020                
Share-based compensation arrangement by share-based payment award                
Percentage of target payout - minimum actual     174.00%          
Percentage of target payout - maximum actual     180.00%          
Performance Share | Performance Cycle 2016 to 2018                
Share-based compensation arrangement by share-based payment award                
Percentage of target payout - minimum actual       139.00%        
Percentage of target payout - maximum actual       166.00%        
White Mountains | Restricted Share Cliff Vesting in January 2022 [Member]                
Share-based compensation arrangement by share-based payment award                
New grants (in shares)   1,900   15,600        
White Mountains | Performance Share                
Share-based compensation arrangement by share-based payment award                
Target Performance Shares Outstanding 43,105   43,105          
Accrued Expense $ 16.0   $ 16.0          
Target Performance Shares Outstanding, Assumed forfeitures (647)   (647)          
Accrued Expense, Assumed forfeitures (0.2)   (0.2)          
Total Target Performance Shares Outstanding 42,458 42,473 42,458 42,473 42,458 42,473 40,602 40,616
Total Accrued Expense $ 15.8 $ 30.8 $ 15.8 $ 30.8 $ 9.8 $ 43.7 $ 23.1 $ 31.7
New grants (in shares) 0 1,900 14,055 15,600        
White Mountains | Performance Share | Performance Cycle 2018 to 2020                
Share-based compensation arrangement by share-based payment award                
Target Performance Shares Outstanding 13,450   13,450          
Accrued Expense $ 8.0   $ 8.0          
White Mountains | Performance Share | Performance Cycle 2019 to 2021                
Share-based compensation arrangement by share-based payment award                
Target Performance Shares Outstanding 15,600   15,600          
Accrued Expense $ 5.9   $ 5.9          
White Mountains | Performance Share | Performance Cycle 2020 to 2022                
Share-based compensation arrangement by share-based payment award                
Target Performance Shares Outstanding 14,055   14,055          
Accrued Expense $ 2.1   $ 2.1