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Discontinued Operations (Details) - USD ($)
$ in Millions
3 Months Ended 6 Months Ended
Apr. 18, 2016
Sep. 30, 2016
Jun. 30, 2016
Sep. 30, 2015
Jun. 30, 2015
Jun. 30, 2016
Jun. 30, 2015
Dec. 31, 2015
Discontinued Operations [Line Items}                
Sales of consolidated and unconsolidated subsidiaries, net of cash sold           $ 2,248.5 $ 24.0  
Payments to Acquire Other Investments           13.3 28.6  
Investments     $ 5,521.3     5,521.3   $ 4,271.1
Net realized and unrealized investment gains (losses)     28.1   $ (15.0) 57.6 10.0  
Net gain on sale of discontinued operations     366.6   (0.1) 366.6 7.9  
Net (loss) income from discontinued operations, net of tax     (8.0)   (0.4) (6.9) 62.9  
Net Realized and Unrealized Gain (Loss) on Trading Securities     28.1   (15.0) 57.6 10.0  
Sirius Group                
Discontinued Operations [Line Items}                
Sales of consolidated and unconsolidated 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)     0.4   2.4 3.7 2.7  
Net gain on sale of discontinued operations           366.6    
Accumulated Other Comprehensive Income Loss Net Of Tax Other Period Increase Decrease     (5.2)   44.0 32.0 (43.6)  
Increase of Book Value           479.9    
Sale of Sirius Group [Member]                
Discontinued Operations [Line Items}                
Accumulated Other Comprehensive Income Loss Net Of Tax Other Period Increase Decrease     113.3   0.0 113.3 0.0  
Symetra | Sirius Group                
Discontinued Operations [Line Items}                
Investments               $ 528.6
Discontinued Operations [Member]                
Discontinued Operations [Line Items}                
Net realized and unrealized investment gains (losses)     7.3   (46.1) (1.5) 32.3  
Net gain on sale of discontinued operations     (8.0)   (0.4) (6.9) 62.9  
Discontinued Operations [Member] | Sirius Group                
Discontinued Operations [Line Items}                
Net realized and unrealized investment gains (losses)     7.3   (46.1) (1.5) 32.3  
Net gain on sale of discontinued operations     (3.4)   3.8 (4.3) 69.7  
Net (loss) income from discontinued operations, net of tax     (3.4)     (4.3)    
Discontinued Operations [Member] | Tranzact [Member]                
Discontinued Operations [Line Items}                
Net (loss) income from discontinued operations, net of tax     $ (0.5)   (6.5) (2.5) (4.0)  
Discontinued Operations [Member] | OneBeacon Runoff [Member]                
Discontinued Operations [Line Items}                
Net gain on sale of discontinued operations         0.3   0.3  
Discontinued Operations [Member] | Esurance                
Discontinued Operations [Line Items}                
Net gain on sale of discontinued operations       $ 10.3 $ (0.3) $ 28.3 $ 7.6  
Sale of Tranzact [Member]                
Discontinued Operations [Line Items}                
Sales of consolidated and unconsolidated subsidiaries, net of cash sold   $ 221.3            
Sale of Tranzact [Member] | Tranzact [Member]                
Discontinued Operations [Line Items}                
Sales of consolidated and unconsolidated subsidiaries, net of cash sold   $ 221.3