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Contingencies (Details) - USD ($)
$ in Millions
1 Months Ended 3 Months Ended 6 Months Ended
Jun. 30, 2007
Jun. 30, 2016
Sep. 30, 2015
Jun. 30, 2015
Jun. 30, 2016
Jun. 30, 2015
Oct. 07, 2011
Loss Contingencies [Line Items]              
Net gain on sale of discontinued operations   $ 366.6   $ (0.1) $ 366.6 $ 7.9  
Esurance              
Loss Contingencies [Line Items]              
Percentage of fluctuation in loss reserves of transferred subsidiaries retained             90.00%
Tribune Company Litigation | Pending Litigation | OneBeacon [Member]              
Loss Contingencies [Line Items]              
Proceeds from Sale, Maturity and Collection of Investments $ 32.0            
Discontinued Operations [Member]              
Loss Contingencies [Line Items]              
Net gain on sale of discontinued operations   (8.0)   (0.4) (6.9) 62.9  
Esurance | Discontinued Operations [Member]              
Loss Contingencies [Line Items]              
Net gain on sale of discontinued operations     $ 10.3 (0.3) 28.3 7.6  
OneBeacon Runoff [Member] | Discontinued Operations [Member]              
Loss Contingencies [Line Items]              
Net gain on sale of discontinued operations       0.3   0.3  
Sirius Group              
Loss Contingencies [Line Items]              
Net gain on sale of discontinued operations         366.6    
Sirius Group | Discontinued Operations [Member]              
Loss Contingencies [Line Items]              
Net gain on sale of discontinued operations   $ (3.4)   $ 3.8 $ (4.3) $ 69.7