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Discontinued Operations (Details) - USD ($)
$ in Millions
 3 Months Ended 9 Months Ended 60 Months Ended
Apr. 18, 2016
Sep. 30, 2016
Jun. 30, 2016
Sep. 30, 2015
Sep. 30, 2016
Sep. 30, 2015
Sep. 30, 2016
Dec. 31, 2015
Discontinued Operations [Line Items}                
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold         $ 2,657.2 $ 24.0    
Payments to Acquire Other Investments         37.3 30.5    
Investments   $ 5,213.5     5,213.5   $ 5,213.5 $ 4,271.1
Net realized and unrealized investment gains (losses)   26.4   $ (43.9) 84.0 (33.9)    
Net gain on sale of discontinued operations         414.5 18.2    
Net (loss) income from discontinued operations, net of tax   14.0   (3.8) 7.1 59.1    
Other liabilities   210.9     210.9   210.9 220.9
Income Tax Expense (Benefit)   (6.7)   (1.6) (22.4) 0.8    
Net Realized and Unrealized Gain (Loss) on Trading Securities   26.4   (43.9) 84.0 (33.9)    
Sirius Group                
Discontinued Operations [Line Items}                
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold $ 2,600.0   $ 2,600.0          
Payments to Acquire Other Investments $ 161.8   161.8          
Investments               686.2
Net realized and unrealized investment gains (losses)       0.8 3.7 3.5    
Net gain on sale of discontinued operations   (4.0) 366.6 0.0 362.6 0.0    
Accumulated Other Comprehensive Income Loss Net Of Tax Other Period Increase Decrease   0.0 113.3 (18.5) 32.0 (62.1)    
Tranzact [Member]                
Discontinued Operations [Line Items}                
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold   221.3            
Net gain on sale of discontinued operations   51.9            
Discontinued Operation, Tax Effect of Discontinued Operation   30.2            
Esurance                
Discontinued Operations [Line Items}                
Net gain on sale of discontinued operations       10.3   18.2    
Symetra | Sirius Group                
Discontinued Operations [Line Items}                
Investments               $ 528.6
Discontinued Operations [Member]                
Discontinued Operations [Line Items}                
Net realized and unrealized investment gains (losses)   0.0   (0.9) (1.5) 31.4    
Net gain on sale of discontinued operations   14.0   (3.8) 7.1 59.1    
Discontinued Operation, Tax Effect of Discontinued Operation   15.9   (2.3) 16.9 (22.2)    
Discontinued Operations [Member] | Sirius Group                
Discontinued Operations [Line Items}                
Net realized and unrealized investment gains (losses)     0.0 (0.9) (1.5) 31.4    
Net gain on sale of discontinued operations     0.0 4.0 (6.4) 73.7    
Net (loss) income from discontinued operations, net of tax         (4.3)      
Discontinued Operation, Tax Effect of Discontinued Operation     $ 0.0 (2.3) 3.1 (22.2)    
Discontinued Operations [Member] | Tranzact [Member]                
Discontinued Operations [Line Items}                
Net (loss) income from discontinued operations, net of tax   (2.1)   (7.7) (2.6) (14.2)    
Other liabilities   2.8     2.8   2.8  
Income Tax Expense (Benefit)   (14.0)     $ (14.0)      
Tax Effect of Extraordinary Item, Gain (Loss)   30.2            
Discontinued Operation, Tax Effect of Discontinued Operation   (16.1)            
Discontinued Operations [Member] | OneBeacon Runoff [Member]                
Discontinued Operations [Line Items}                
Net gain on sale of discontinued operations           0.3    
Discontinued Operations [Member] | Esurance                
Discontinued Operations [Line Items}                
Net gain on sale of discontinued operations   $ 10.3   $ 10.3   $ 17.9 $ 28.3