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Employee Share-Based Incentive Compensation Plans (WTM Performance Shares Granted Under the WTM Incentive Plan) (Details) - W T M Incentive Plan - Performance Shares - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Range Of Performance Cycle 2018 to 2020        
Share-based compensation arrangement by share-based payment award        
Targeted performance goal for personnel expressed as percentage of growth in intrinsic business value per share 6.00%      
Payout for maximum growth target percentage 200.00%      
Range Of Performance Cycle From 2017-2019        
Share-based compensation arrangement by share-based payment award        
Targeted performance goal for personnel expressed as percentage of growth in intrinsic business value per share 5.00%      
Payout for maximum growth target percentage 200.00%      
Range Of Performance Cycle From 2016-2018        
Share-based compensation arrangement by share-based payment award        
Targeted performance goal for personnel expressed as percentage of growth in intrinsic business value per share 4.00%      
Payout for maximum growth target percentage 200.00%      
White Mountains        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 41,235      
Incentive compensation payable before forfeitures $ 32.2      
Assumed forfeitures (shares) (619)      
Assumed forfeitures in period amount (0.5)      
Shares outstanding (in shares) 40,616 50,515 80,353 93,654
Accrued incentive compensation $ 31.7 $ 45.8 $ 42.4 $ 57.7
White Mountains | Range Of Performance Cycle 2018 to 2020        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 13,450      
Incentive compensation payable before forfeitures $ 3.8      
White Mountains | Range Of Performance Cycle From 2017-2019        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 14,070      
Incentive compensation payable before forfeitures $ 11.9      
White Mountains | Range Of Performance Cycle From 2016-2018        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 13,715      
Incentive compensation payable before forfeitures $ 16.5      
Minimum | Range Of Performance Cycle 2018 to 2020        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 2.00%      
Minimum | Range Of Performance Cycle From 2017-2019        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 1.00%      
Minimum | Range Of Performance Cycle From 2016-2018        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 0.00%      
Maximum | Range Of Performance Cycle 2018 to 2020        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 10.00%      
Maximum | Range Of Performance Cycle From 2017-2019        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 9.00%      
Maximum | Range Of Performance Cycle From 2016-2018        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 8.00%