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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, 2017
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
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%      
Share-based Compensation Arrangement by Share-based Payment Award, 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%      
Share-based Compensation Arrangement by Share-based Payment Award, Payout for Maximum Growth Target Percentage 200.00%      
Range Of Performance Cycle From 2015-2017        
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 8.00%      
Share-based Compensation Arrangement by Share-based Payment Award, 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) 51,285      
Incentive compensation payable before forfeitures $ 46.6      
Assumed forfeitures (770)      
Assumed forfeitures in period amount (0.8)      
Shares outstanding (in shares) 50,515 80,353 93,654 111,257
Accrued incentive compensation $ 45.8 $ 42.4 $ 57.7 $ 44.4
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) 16,680      
Incentive compensation payable before forfeitures $ 8.3      
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) 16,235      
Incentive compensation payable before forfeitures $ 14.7      
White Mountains | Range Of Performance Cycle From 2015-2017        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 18,370      
Incentive compensation payable before forfeitures $ 23.6      
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%      
Minimum | Range Of Performance Cycle From 2015-2017        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 2.00%      
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%      
Maximum | Range Of Performance Cycle From 2015-2017        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 14.00%