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Significant Transactions (Dispositions) (Details) - USD ($)
$ in Millions
3 Months Ended 9 Months Ended 12 Months Ended
Sep. 28, 2017
Oct. 05, 2016
Jul. 21, 2016
Apr. 18, 2016
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2017
Sep. 30, 2017
Jun. 30, 2017
Mar. 31, 2017
Sep. 30, 2016
Sep. 28, 2017
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Significant Transactions                                  
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold                             $ 0.0 $ 1,131.0 $ 2,646.2
Gain (loss) on sale of other discontinued operations, net of tax                             (17.2) 557.0 415.1
Other comprehensive (loss) income, net of tax                             (4.8) 0.3 (0.7)
Repayments of debt, principal                             15.4 365.0 404.6
Payments to acquire other investments                             95.9 84.1 38.5
Net income from discontinued operations, net of tax         $ 0.0 $ (17.3) $ 0.0 $ 0.1 $ 4.3 $ 539.1 $ 2.8 $ 31.3     0.0 20.5 108.3
OneBeacon                                  
Significant Transactions                                  
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold $ 1,300.0                                
Gain (loss) on sale of other discontinued operations, net of tax 554.6                                
Other comprehensive (loss) income, net of tax $ 2.9                                
Net income from discontinued operations, net of tax                           $ 20.5     108.6
Tranzact                                  
Significant Transactions                                  
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold   $ 1.2 $ 221.3                            
Gain (loss) on sale of other discontinued operations, net of tax                               3.2 51.9
Repayments of debt, principal     56.3                            
Tax effect of discontinued operation                                 30.2
Increase of book value     $ 82.1                           82.1
Sirius Group                                  
Significant Transactions                                  
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold       $ 2,600.0                          
Gain (loss) on sale of other discontinued operations, net of tax                         $ (4.0)       363.2
Payments to acquire other investments       $ 161.8                          
Net change in pension liability and other accumulated comprehensive items                                 113.3
Sale of Sirius Group                                  
Significant Transactions                                  
Net change in pension liability and other accumulated comprehensive items                                 113.3
Discontinued Operations | OneBeacon                                  
Significant Transactions                                  
Gain (loss) on sale of other discontinued operations, net of tax                             0.0 554.5 0.0
Tax effect of discontinued operation                               (5.7) (12.5)
Net change in pension liability and other accumulated comprehensive items                               2.9 0.0
Net income from discontinued operations, net of tax                               20.5 108.6
Discontinued Operations | Tranzact                                  
Significant Transactions                                  
Gain (loss) on sale of other discontinued operations, net of tax                             0.0 3.2 51.9
Tax effect of discontinued operation                               0.0 (6.4)
Net change in pension liability and other accumulated comprehensive items                               0.0 0.0
Net income from discontinued operations, net of tax                               0.0 6.1
Discontinued Operations | Sirius Group                                  
Significant Transactions                                  
Gain (loss) on sale of other discontinued operations, net of tax                             (17.2) (0.7) 363.2
Tax effect of discontinued operation                               0.0 (3.1)
Net change in pension liability and other accumulated comprehensive items                               0.0 113.3
Net income from discontinued operations, net of tax                               $ 0.0 (6.4)
Discontinued Operations | Sale of Sirius Group                                  
Significant Transactions                                  
Net income from discontinued operations, net of tax                                 $ (4.3)
Swedish Tax Authority | Sirius Group | Sirius Group                                  
Significant Transactions                                  
Net income from discontinued operations, net of tax                             $ (17.3)