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Employee Share-Based Incentive Compensation Plans (WTM Performance Shares Granted Under the WTM Incentive Plan) (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Share-based compensation arrangement by share-based payment award        
Accrued incentive compensation $ 141.7 $ 108.1    
Range Of Performance Cycle From 2015 to 2017 [Member] | W T M Incentive Plan | Performance Shares        
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%      
Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive Plan | Performance Shares        
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 9.00%      
Share-based Compensation Arrangement by Share-based Payment Award, Payout for Maximum Growth Target Percentage 200.00%      
Performance Cycle From 2013 to 2015 | W T M Incentive Plan | Performance Shares        
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%      
Performance Cycle From 2012 to 2014 | W T M Incentive and Phantom Plan [Member] | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 91.00%      
Share-based Compensation Arrangement by Share-based Payment Award, Payout for Maximum Growth Target Percentage 145.50%      
White Mountains | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 98,678      
Incentive compensation payable before forfeitures $ 59.2      
forfeitures (2,467)      
Assumed forfeitures in period amount (1.5)      
Shares outstanding (in shares) 96,211 113,198 108,605 108,065
Accrued incentive compensation $ 57.7 $ 44.4 $ 54.9 $ 26.5
White Mountains | Range Of Performance Cycle From 2015 to 2017 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 29,828      
Incentive compensation payable before forfeitures $ 8.3      
White Mountains | Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 32,557      
Incentive compensation payable before forfeitures $ 12.9      
White Mountains | Performance Cycle From 2013 to 2015 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Options nonvested, number before forfeitures (in shares) 36,293      
Incentive compensation payable before forfeitures $ 38.0      
Sirius Group | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Shares outstanding (in shares) 7,997 10,351 10,615  
Minimum | Range Of Performance Cycle From 2015 to 2017 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 2.00%      
Minimum | Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 3.00%      
Minimum | Performance Cycle From 2013 to 2015 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 2.00%      
Maximum | Range Of Performance Cycle From 2015 to 2017 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 14.00%      
Maximum | Range Of Performance Cycle From 2014-2016 [Member] | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 15.00%      
Maximum | Performance Cycle From 2013 to 2015 | W T M Incentive Plan | Performance Shares        
Share-based compensation arrangement by share-based payment award        
Performance goal percentage for minimum payout 14.00%