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Segment Information (Assets) (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2012
Segment reporting information      
Total investments $ 3,380.7 $ 2,714.4  
Assets held for sale   3,606.4  
Assets 3,659.2 6,520.2  
Liabilities held for sale   2,569.3  
Liabilities 298.4 2,804.2  
White Mountains’ common shareholders’ equity 3,492.5 3,582.7  
Non-controlling interests (131.7) 133.3  
HG Global BAM      
Segment reporting information      
Total investments 693.4 629.7  
Assets held for sale   0.0  
Assets 747.4 677.6  
Liabilities held for sale   0.0  
Liabilities 394.9 289.1  
White Mountains’ common shareholders’ equity 499.8 522.8  
Non-controlling interests (147.3) (134.3)  
BAM      
Segment reporting information      
Surplus notes 499.0 300.0  
Accrued interest on surplus notes 126.0 108.0  
MediaAlpha      
Segment reporting information      
Total investments 0.0 0.0  
Assets held for sale   0.0  
Assets 96.5 57.6  
Liabilities held for sale   0.0  
Liabilities 59.8 28.3  
White Mountains’ common shareholders’ equity 23.6 17.6  
Non-controlling interests 13.1 11.7  
Other Operations      
Segment reporting information      
Total investments 2,687.3 2,084.7  
Assets held for sale   0.0  
Assets 3,039.9 2,358.8  
Liabilities held for sale   0.0  
Liabilities 71.6 97.7  
White Mountains’ common shareholders’ equity 2,965.8 2,258.1  
Non-controlling interests 2.5 3.0  
Total Capital Contributed to Subsidiary 727.7 703.0  
Eliminations      
Segment reporting information      
Assets (227.9) (180.2)  
Liabilities (227.9) (180.2)  
Discontinued Operations, Held-for-sale      
Segment reporting information      
Total investments 0.0 0.0  
Assets held for sale   3,606.4  
Assets 3.3 3,606.4  
Liabilities held for sale   2,569.3  
Liabilities 0.0 2,569.3  
White Mountains’ common shareholders’ equity 3.3 784.2  
Non-controlling interests 0.0 252.9  
Continuing Operations      
Segment reporting information      
Non-controlling interests (131.7) 133.3  
HG Global      
Segment reporting information      
Non-controlling interests 15.9 16.6  
Surplus notes     $ 503.0
HG Global | BAM      
Segment reporting information      
Surplus notes 499.0 503.0  
Preferred Dividends Payable | HG Global | Other Operations      
Segment reporting information      
Accounts Payable and Accrued Liabilities $ 227.9 $ 180.2