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Derivatives Variable Annuity Reinsurance Liabilities and Derivative Instruments (Details)
$ in Millions, ¥ in Billions
3 Months Ended 6 Months Ended
Jun. 30, 2016
USD ($)
Jun. 30, 2015
USD ($)
Jun. 30, 2016
USD ($)
Jun. 30, 2015
USD ($)
Dec. 31, 2015
USD ($)
Dec. 31, 2015
JPY (¥)
Changes in derivative instruments            
Collective account values of underlying variable annuities as a percentage of the guarantee value         113.00% 113.00%
White Mountains Life Re            
Variable Annuity Reinsurance [Line Items]            
Notional amount         $ 400.0 ¥ 50.7
Fair Value Derivatives Measured on Recurring Basis, Asset Purchases $ 0.0   $ 0.0      
Changes in derivative instruments            
Beginning of period 13.1 $ 47.0 20.1 $ 56.4    
Purchases   0.0   0.0    
Realized and unrealized gains (losses) (0.3) (2.3) (2.0) (7.8)    
Transfers in 0.0 0.0 0.0 0.0    
Sales/settlements (12.8) (9.0) (18.1) (12.9)    
End of period 0.0 35.7 0.0 35.7    
Change in fair value of variable annuity death benefit liabilities, included in other general and administrative expenses 0.0 0.0 0.0 0.0    
Collective account values of underlying variable annuities as a percentage of the guarantee value         109.00% 109.00%
White Mountains Life Re | Level 2 Inputs            
Variable Annuity Reinsurance [Line Items]            
Fair Value Derivatives Measured on Recurring Basis, Asset Purchases 0.0   0.0      
Changes in derivative instruments            
Beginning of period 10.3 31.2 16.5 33.8    
Purchases   0.0   0.0    
Realized and unrealized gains (losses) (1.8) 0.6 (0.7) (5.9)    
Transfers in 0.0 0.0 0.0 0.0    
Sales/settlements (8.5) 0.7 (15.8) 4.6    
End of period 0.0 32.5 0.0 32.5    
White Mountains Life Re | Level 1 Inputs            
Variable Annuity Reinsurance [Line Items]            
Fair Value Derivatives Measured on Recurring Basis, Asset Purchases 0.0   0.0      
Changes in derivative instruments            
Beginning of period 0.2 (1.2) 0.9 3.7    
Purchases   0.0   0.0    
Realized and unrealized gains (losses) (0.2) 5.4 (4.2) 7.1    
Transfers in 0.0 0.0 0.0 0.0    
Sales/settlements   (9.3) 3.3 (15.9)    
End of period 0.0 (5.1) 0.0 (5.1)    
Variable Annuity | White Mountains Life Re | Level 3 Inputs            
Variable Annuity Reinsurance [Line Items]            
Fair Value Derivatives Measured on Recurring Basis, Asset Purchases 0.0   0.0      
Changes in derivative instruments            
Beginning balance (0.1) (1.1) (0.3) (0.7)    
Realized and unrealized gains (losses) 0.1 0.7 (0.3) 1.1    
Transfers in 0.0 0.0 0.0 0.0    
Sales/settlements 0.0 0.0 0.0 0.0    
Ending balance 0.0 (1.8) 0.0 (1.8)    
Purchases   0.0   0.0    
Derivative [Member] | White Mountains Life Re | Level 3 Inputs            
Variable Annuity Reinsurance [Line Items]            
Fair Value Derivatives Measured on Recurring Basis, Asset Purchases 0.0   0.0      
Changes in derivative instruments            
Beginning of period 2.6 17.0 2.7 18.9    
Purchases   0.0   0.0    
Realized and unrealized gains (losses) 1.7 (8.3) 2.9 (9.0)    
Transfers in 0.0 0.0 0.0 0.0    
Sales/settlements (4.3) (0.4) (5.6) (1.6)    
End of period $ 0.0 $ 8.3 $ 0.0 $ 8.3