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Employee Share-Based Incentive Compensation Plans (Performance Shares Granted Under the WTM Incentive Plan) (Details) - White Mountains - Performance Share - W T M Incentive Plan - USD ($)
$ in Millions
Sep. 30, 2018
Jun. 30, 2018
Dec. 31, 2017
Sep. 30, 2017
Jun. 30, 2017
Dec. 31, 2016
Share-based compensation arrangement by share-based payment award            
Target Performance Shares Outstanding 41,235          
Accrued Expense $ 35.4          
Target Performance Shares Outstanding, Assumed forfeitures (619)          
Accrued Expense, Assumed forfeitures (0.5)          
Total Target Performance Shares Outstanding 40,616 40,616 50,515 50,319 50,575 80,353
Total Accrued Expense $ 34.9 $ 27.2 $ 45.8 $ 37.8 $ 31.2 $ 42.4
Performance Cycle 2016 to 2018            
Share-based compensation arrangement by share-based payment award            
Target Performance Shares Outstanding 13,715          
Accrued Expense $ 18.9          
Performance Cycle 2017 to 2019            
Share-based compensation arrangement by share-based payment award            
Target Performance Shares Outstanding 14,070          
Accrued Expense $ 13.3          
Performance Cycle 2018 to 2020            
Share-based compensation arrangement by share-based payment award            
Target Performance Shares Outstanding 13,450          
Accrued Expense $ 3.2