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Discontinued Operations (Net Income (Loss) from Discontinued Operations) (Details) - USD ($)
$ in Millions
3 Months Ended 12 Months Ended
Sep. 28, 2017
Oct. 05, 2016
Dec. 31, 2017
Sep. 30, 2017
Jun. 30, 2017
Mar. 31, 2017
Dec. 31, 2016
Sep. 30, 2016
Jun. 30, 2016
Mar. 31, 2016
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Revenues                          
Earned insurance premiums                     $ 10.4 $ 13.4 $ 12.0
Net investment income                     56.0 32.1 10.9
Net realized and unrealized investment gains                     133.3 (27.4) 260.5
Other revenues                     7.1 21.3 49.2
Revenues       $ 87.5 $ 83.5 $ 88.8 $ (5.5) $ 56.8 $ 48.4 $ 58.0 373.8 157.7 440.0
Expenses                          
Loss and loss adjustment expenses                     1.1 8.0 8.2
Insurance acquisition expenses                     4.1 5.6 6.3
Other underwriting expenses                     0.4 0.4 0.4
General and administrative expenses                     218.7 186.0 200.7
Interest expense                     2.3 3.0 1.6
Total expenses       79.1 85.7 92.4 69.0 70.6 74.1 91.3 366.0 305.0 310.8
Net (loss) income from discontinued operations, net of tax     $ 4.3 $ 539.1 $ 2.8 $ 31.3 $ 8.0 84.4 $ 383.6 $ 47.4 20.5 108.3 116.9
Gain (loss) from sale of other discontinued operations, net of tax                     557.0 415.1 18.2
Total income (loss) from discontinued operations                     577.5 523.4 135.1
Comprehensive income (loss) from discontinued operations                     630.7 547.4 187.4
Discontinued Operations                          
Expenses                          
Total income (loss) from discontinued operations                     577.5 523.4 135.1
OneBeacon                          
Expenses                          
Net (loss) income from discontinued operations, net of tax                     20.5 108.6 38.2
Gain (loss) from sale of other discontinued operations, net of tax $ 554.6                   554.5 0.0 0.0
OneBeacon | Discontinued Operations                          
Revenues                          
Earned insurance premiums                     807.6 1,100.6 1,176.2
Net investment income                     39.7 50.6 45.9
Net realized and unrealized investment gains                     38.8 37.7 (35.1)
Other revenues                     7.7 5.5 (0.6)
Revenues                     893.8 1,194.4 1,186.4
Expenses                          
Loss and loss adjustment expenses                     546.0 656.0 700.7
Insurance acquisition expenses                     145.6 206.0 213.8
Other underwriting expenses                     156.2 209.0 218.2
General and administrative expenses                     21.2 14.2 13.0
Interest expense                     10.0 13.1 15.4
Total expenses                     879.0 1,098.3 1,161.1
Pre-tax income                     14.8 96.1 25.3
Income tax benefit                     5.7 12.5 12.9
Net (loss) income from discontinued operations, net of tax                     20.5 108.6 38.2
Gain (loss) from sale of other discontinued operations, net of tax                     554.5 0.0  
Total income (loss) from discontinued operations                     575.0 108.6 38.5
Net change in pension liability and other accumulated comprehensive items                     0.3 1.0 0.0
Recognition of other comprehensive income from sale of subsidiary                     2.9 0.0  
Comprehensive income (loss) from discontinued operations                     578.2 109.6 38.5
Sale of Sirius Group                          
Expenses                          
Gain (loss) from sale of other discontinued operations, net of tax                     (0.7) 363.2 0.0
Recognition of other comprehensive income from sale of subsidiary                       113.3  
Sale of Sirius Group | Discontinued Operations                          
Expenses                          
Net (loss) income from discontinued operations, net of tax                       (4.3) 81.1
Net change in pension liability and other accumulated comprehensive items                       32.0  
Sirius Group                          
Revenues                          
Net realized and unrealized investment gains                       3.7 205.0
Expenses                          
Gain (loss) from sale of other discontinued operations, net of tax               $ (4.0)       363.2  
Sirius Group | Discontinued Operations                          
Revenues                          
Earned insurance premiums                     0.0 240.1 847.0
Net investment income                     0.0 14.4 40.7
Net realized and unrealized investment gains                     0.0 (1.5) 15.1
Other revenues                     0.0 0.6 (20.6)
Revenues                     0.0 253.6 882.2
Expenses                          
Loss and loss adjustment expenses                     0.0 154.9 422.7
Insurance acquisition expenses                     0.0 59.0 189.8
Other underwriting expenses                     0.0 30.9 107.9
General and administrative expenses                     0.0 10.4 27.0
Interest expense                       7.9 26.6
Total expenses                     0.0 263.1 774.0
Pre-tax income                     0.0 (9.5) 108.2
Income tax benefit                     0.0 3.1 (27.1)
Net (loss) income from discontinued operations, net of tax                     0.0 (6.4)  
Gain (loss) from sale of other discontinued operations, net of tax                     (0.7) 363.2  
Total income (loss) from discontinued operations                     (0.7) 356.8 81.1
Net change in pension liability and other accumulated comprehensive items                     0.0 32.0 (65.0)
Recognition of other comprehensive income from sale of subsidiary                     0.0 113.3  
Comprehensive income (loss) from discontinued operations                     (0.7) 502.1 16.1
Tranzact                          
Expenses                          
Income tax benefit   $ (30.2)                      
Gain (loss) from sale of other discontinued operations, net of tax   $ 51.9                 3.2 51.9 0.0
Tranzact | Discontinued Operations                          
Revenues                          
Earned insurance premiums                     0.0 0.0  
Net investment income                     0.0 0.0  
Net realized and unrealized investment gains                     0.0 0.0  
Other revenues                     0.0 119.6  
Revenues                     0.0 119.6  
Expenses                          
Loss and loss adjustment expenses                     0.0 0.0  
Insurance acquisition expenses                     0.0 0.0  
Other underwriting expenses                     0.0 0.0  
General and administrative expenses                     0.0 116.7  
Interest expense                       3.2  
Total expenses                     0.0 119.9  
Pre-tax income                     0.0 (0.3)  
Income tax benefit                     0.0 6.4  
Net (loss) income from discontinued operations, net of tax                     0.0 6.1 (1.9)
Gain (loss) from sale of other discontinued operations, net of tax                     3.2 51.9  
Total income (loss) from discontinued operations                     3.2 58.0  
Net change in pension liability and other accumulated comprehensive items                     0.0 0.0  
Recognition of other comprehensive income from sale of subsidiary                     0.0 0.0  
Comprehensive income (loss) from discontinued operations                     3.2 58.0  
Other Operations | Discontinued Operations                          
Revenues                          
Earned insurance premiums                         0.0
Net investment income                         0.0
Net realized and unrealized investment gains                         0.0
Other revenues                         186.2
Revenues                         186.2
Expenses                          
Loss and loss adjustment expenses                         0.0
Insurance acquisition expenses                         0.0
Other underwriting expenses                         0.0
General and administrative expenses                         185.3
Interest expense                         4.0
Total expenses                         189.3
Pre-tax income                         (3.1)
Income tax benefit                         0.7
Net (loss) income from discontinued operations, net of tax                         (2.4)
Total income (loss) from discontinued operations                         15.5
Net change in pension liability and other accumulated comprehensive items                         0.0
Comprehensive income (loss) from discontinued operations                         15.5
Total | Discontinued Operations                          
Revenues                          
Earned insurance premiums                     807.6 1,340.7 2,023.2
Net investment income                     39.7 65.0 86.6
Net realized and unrealized investment gains                     38.8 36.2 (20.0)
Other revenues                     7.7 125.7 165.0
Revenues                     893.8 1,567.6 2,254.8
Expenses                          
Loss and loss adjustment expenses                     546.0 810.9 1,123.4
Insurance acquisition expenses                     145.6 265.0 403.6
Other underwriting expenses                     156.2 239.9 326.1
General and administrative expenses                     21.2 141.3 225.3
Interest expense                     10.0 24.2 46.0
Total expenses                     879.0 1,481.3 2,124.4
Pre-tax income                     14.8 86.3 130.4
Income tax benefit                     5.7 22.0 (13.5)
Net (loss) income from discontinued operations, net of tax                     20.5 108.3 116.9
Gain (loss) from sale of other discontinued operations, net of tax                     557.0 415.1  
Total income (loss) from discontinued operations                     577.5 523.4 135.1
Net change in pension liability and other accumulated comprehensive items                     0.3 33.0 (65.0)
Recognition of other comprehensive income from sale of subsidiary                     2.9 113.3  
Comprehensive income (loss) from discontinued operations                     $ 580.7 $ 669.7 70.1
OneBeacon Runoff | Discontinued Operations                          
Expenses                          
Gain (loss) from sale of other discontinued operations, net of tax                         0.3
Esurance & AFI | Discontinued Operations                          
Expenses                          
Gain (loss) from sale of other discontinued operations, net of tax                         $ 17.9