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Employee Share-Based Incentive Compensation Plans (Performance Shares Granted Under the WTM Incentive Plan) (Details) - Performance Share - W T M Incentive Plan - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2020
Mar. 31, 2019
Dec. 31, 2019
Dec. 31, 2018
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 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        
Share-based compensation arrangement by share-based payment award        
Target Performance Shares Outstanding 43,105      
Accrued Expense $ 10.0      
Target Performance Shares Outstanding, Assumed forfeitures (647)      
Accrued Expense, Assumed forfeitures (0.2)      
Total Target Performance Shares Outstanding 42,458 40,602 42,473 40,616
Total Accrued Expense $ 9.8 $ 23.1 $ 43.7 $ 31.7
White Mountains | Performance Cycle 2018 to 2020        
Share-based compensation arrangement by share-based payment award        
Target Performance Shares Outstanding 13,450      
Accrued Expense $ 5.1      
White Mountains | Performance Cycle 2019 to 2021        
Share-based compensation arrangement by share-based payment award        
Target Performance Shares Outstanding 15,600      
Accrued Expense $ 3.8      
White Mountains | Performance Cycle 2020 to 2022        
Share-based compensation arrangement by share-based payment award        
Target Performance Shares Outstanding 14,055      
Accrued Expense $ 1.1