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Held for Sale and Discontinued Operations (Loss from Discontinued Operations) (Details) - USD ($)
$ in Millions
 3 Months Ended 9 Months Ended 12 Months Ended
Sep. 28, 2017
Dec. 31, 2019
Sep. 30, 2019
Jun. 30, 2019
Mar. 31, 2019
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Sep. 28, 2017
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Revenues                          
Earned insurance premiums                     $ 16.3 $ 13.9 $ 10.4
Net investment income                     79.7 59.0 56.0
Other revenue                     47.6 15.3 7.1
Net realized and unrealized investment gains (losses)                     433.2 (108.3) 133.3
Revenues   $ 175.3 $ 155.5 $ 129.0 $ 433.6 $ 6.0 $ 198.7 $ 122.3 $ 42.1   893.4 369.1 373.8
Expenses                          
Loss and loss adjustment expenses                         1.1
Other underwriting expenses                     0.4 0.4 0.4
General and administrative expenses                     327.8 233.5 208.0
Interest expense on debt                     17.6 9.5 2.3
Total expenses   118.8 104.4 113.2 151.9 150.1 154.4 134.7 108.1   488.3 547.3 366.0
Net income from discontinued operations, net of tax   $ (0.8) $ 0.9 $ 0.0 $ 0.7 $ 0.0 $ (17.3) $ 0.0 $ 0.1   0.0 0.0 20.5
Gain (loss) on sale of other discontinued operations, net of tax                     0.8 (17.2) 557.0
Total income (loss) from discontinued operations                     0.8 (17.2) 577.5
Comprehensive income from discontinued operations                     413.1 (146.0) 630.7
Discontinued Operations                          
Expenses                          
Total income (loss) from discontinued operations                     0.8 (17.2) 577.5
Recognition of foreign currency translation from sale of OneBeacon, net of tax                         0.0
OneBeacon                          
Expenses                          
Net income from discontinued operations, net of tax                   $ 20.5      
Gain (loss) on sale of other discontinued operations, net of tax $ 554.6                        
OneBeacon | Discontinued Operations                          
Revenues                          
Earned insurance premiums                         807.6
Net investment income                         39.7
Other revenue                         7.7
Net realized and unrealized investment gains (losses)                         38.8
Revenues                         893.8
Expenses                          
Loss and loss adjustment expenses                         546.0
Insurance and reinsurance acquisition expenses                         145.6
Other underwriting expenses                         156.2
General and administrative expenses                         21.2
Interest expense on debt                         10.0
Total expenses                         879.0
Net income from discontinued operations                         14.8
Income tax benefit                         5.7
Net income from discontinued operations, net of tax                         20.5
Gain (loss) on sale of other discontinued operations, net of tax                         554.5
Total income (loss) from discontinued operations                         575.0
Change in foreign currency translation and other comprehensive income from discontinued operations, net of tax                         0.3
Recognition of foreign currency translation from sale of OneBeacon, net of tax                         2.9
Comprehensive income from discontinued operations                         578.2
Sirius Group                          
Expenses                          
Gain (loss) on sale of other discontinued operations, net of tax                       (17.3)  
Sirius Group | Discontinued Operations                          
Revenues                          
Earned insurance premiums                         0.0
Net investment income                         0.0
Other revenue                         0.0
Net realized and unrealized investment gains (losses)                         0.0
Revenues                         0.0
Expenses                          
Loss and loss adjustment expenses                         0.0
Insurance and reinsurance acquisition expenses                         0.0
Other underwriting expenses                         0.0
General and administrative expenses                         0.0
Interest expense on debt                         0.0
Total expenses                         0.0
Net income from discontinued operations                         0.0
Income tax benefit                         0.0
Net income from discontinued operations, net of tax                         0.0
Gain (loss) on sale of other discontinued operations, net of tax                     $ 0.8 (17.2) (0.7)
Total income (loss) from discontinued operations                         (0.7)
Change in foreign currency translation and other comprehensive income from discontinued operations, net of tax                         0.0
Comprehensive income from discontinued operations                         (0.7)
Tranzact                          
Expenses                          
Gain (loss) on sale of other discontinued operations, net of tax                       $ 3.2 3.2
Tranzact | Discontinued Operations                          
Revenues                          
Earned insurance premiums                         0.0
Net investment income                         0.0
Other revenue                         0.0
Net realized and unrealized investment gains (losses)                         0.0
Revenues                         0.0
Expenses                          
Loss and loss adjustment expenses                         0.0
Insurance and reinsurance acquisition expenses                         0.0
Other underwriting expenses                         0.0
General and administrative expenses                         0.0
Interest expense on debt                         0.0
Total expenses                         0.0
Net income from discontinued operations                         0.0
Income tax benefit                         0.0
Net income from discontinued operations, net of tax                         0.0
Gain (loss) on sale of other discontinued operations, net of tax                         3.2
Total income (loss) from discontinued operations                         3.2
Change in foreign currency translation and other comprehensive income from discontinued operations, net of tax                         0.0
Comprehensive income from discontinued operations                         3.2
Total | Discontinued Operations                          
Revenues                          
Earned insurance premiums                         807.6
Net investment income                         39.7
Other revenue                         7.7
Net realized and unrealized investment gains (losses)                         38.8
Revenues                         893.8
Expenses                          
Loss and loss adjustment expenses                         546.0
Insurance and reinsurance acquisition expenses                         145.6
Other underwriting expenses                         156.2
General and administrative expenses                         21.2
Interest expense on debt                         10.0
Total expenses                         879.0
Net income from discontinued operations                         14.8
Income tax benefit                         5.7
Net income from discontinued operations, net of tax                         20.5
Gain (loss) on sale of other discontinued operations, net of tax                         557.0
Change in foreign currency translation and other comprehensive income from discontinued operations, net of tax                         0.3
Recognition of foreign currency translation from sale of OneBeacon, net of tax                         2.9
Comprehensive income from discontinued operations                         $ 580.7