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Contingencies (Details) - USD ($)
$ in Millions
1 Months Ended 3 Months Ended 9 Months Ended 60 Months Ended
Jun. 30, 2007
Sep. 30, 2016
Jun. 30, 2016
Sep. 30, 2015
Sep. 30, 2016
Sep. 30, 2015
Sep. 30, 2016
Oct. 07, 2011
Loss Contingencies [Line Items]                
Net gain on sale of discontinued operations         $ 414.5 $ 18.2    
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   $ 14.0   $ (3.8) 7.1 59.1    
Esurance                
Loss Contingencies [Line Items]                
Net gain on sale of discontinued operations       10.3   18.2    
Esurance | Discontinued Operations [Member]                
Loss Contingencies [Line Items]                
Net gain on sale of discontinued operations   10.3   10.3   17.9 $ 28.3  
OneBeacon Runoff [Member] | Discontinued Operations [Member]                
Loss Contingencies [Line Items]                
Net gain on sale of discontinued operations           0.3    
Sirius Group                
Loss Contingencies [Line Items]                
Net gain on sale of discontinued operations   $ (4.0) $ 366.6 0.0 362.6 0.0    
Sirius Group | Discontinued Operations [Member]                
Loss Contingencies [Line Items]                
Net gain on sale of discontinued operations     $ 0.0 $ 4.0 $ (6.4) $ 73.7