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Derivatives (Variable Annuity Reinsurance Liabilities and Derivative Instruments) (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Changes in derivative instruments      
Purchases $ 1,394.3 $ 3,332.5  
Level 2      
Changes in derivative instruments      
Purchases 783.8 2,007.9  
Level 1      
Changes in derivative instruments      
Purchases $ 514.7 1,209.3  
White Mountains Life Re      
Changes in derivative instruments      
Realized and unrealized gains (losses)     $ (2.0)
Variable Annuity Liabilities | White Mountains Life Re | Level 3      
Changes in variable annuity (liabilities)      
Beginning balance   0.0 0.3
Purchases     0.0
Realized and unrealized (losses) gains     (0.3)
Transfers in     0.0
Sales/settlements     0.0
Ending balance     0.0
Derivative Instruments | White Mountains Life Re      
Changes in derivative instruments      
Beginning of period   0.0 20.1
Purchases     0.0
Realized and unrealized gains (losses)     2.0
Transfers in     0.0
Sales/settlements     (18.1)
Ending balance     0.0
Derivative Instruments | White Mountains Life Re | Level 3      
Changes in derivative instruments      
Beginning of period   0.0 2.7
Purchases     0.0
Realized and unrealized gains (losses)     (2.9)
Transfers in     0.0
Sales/settlements     (5.6)
Ending balance     0.0
Derivative Instruments | White Mountains Life Re | Level 2      
Changes in derivative instruments      
Beginning of period   0.0 16.5
Purchases     0.0
Realized and unrealized gains (losses)     0.7
Transfers in     0.0
Sales/settlements     (15.8)
Ending balance     0.0
Derivative Instruments | White Mountains Life Re | Level 1      
Changes in derivative instruments      
Beginning of period   $ 0.0 0.9
Purchases     0.0
Realized and unrealized gains (losses)     4.2
Transfers in     0.0
Sales/settlements     3.3
Ending balance     $ 0.0