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Held for Sale and Discontinued Operations - Financial Statement Disclosures (Details) - USD ($)
$ in Millions
 3 Months Ended 9 Months Ended
Sep. 28, 2017
Sep. 30, 2018
Sep. 30, 2017
Sep. 30, 2018
Sep. 30, 2017
Sep. 28, 2017
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Earned insurance premiums   $ 3.3 $ 2.4 $ 9.7 $ 6.6  
Net investment income   13.4 12.2 44.9 39.7  
Net realized and unrealized investment (losses) gains   66.1 32.5 22.9 102.5  
Total revenues   198.7 87.5 363.1 259.8  
Insurance acquisition expenses   1.2 0.9 3.9 3.0  
Other underwriting expenses   0.1 0.1 0.3 0.3  
General and administrative and other expenses   68.5 41.7 174.6 156.1  
Interest expense   3.4 0.9 6.0 1.8  
Total expenses   154.4 79.1 397.2 257.2  
Net (loss) income from discontinued operations, net of tax   0.0 (15.2) 0.0 20.5  
Net (loss) gain from sale of discontinued operations, net of tax     554.3 (17.2) 552.7  
Total income (loss) from discontinued operations   (17.3) 539.1 (17.2) 573.2  
Total comprehensive income (loss)   40.0 565.1 (5.4) 608.1  
OneBeacon            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Net (loss) income from discontinued operations, net of tax     (15.2)     $ 20.5
Net (loss) gain from sale of discontinued operations, net of tax $ 554.6          
Other Discontinued Operations            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Total comprehensive income (loss)         (1.0)  
Discontinued Operations            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Total income (loss) from discontinued operations   (17.3) 539.1 (17.2) 573.2  
Discontinued Operations | Net gain (loss) from sale of discontinued operations            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Net (loss) gain from sale of discontinued operations, net of tax     554.5   554.5  
Discontinued Operations | OneBeacon            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Earned insurance premiums     268.4   807.6  
Net investment income     13.0   39.7  
Net realized and unrealized investment (losses) gains     11.5   38.8  
Other revenue     2.2   7.7  
Total revenues     295.1   893.8  
Loss and loss adjustment expenses     206.8   546.0  
Insurance acquisition expenses     51.9   145.6  
Other underwriting expenses     44.9   156.2  
General and administrative and other expenses     7.4   21.2  
Interest expense     3.4   10.0  
Total expenses     314.4   879.0  
Pre-tax (loss) income     (19.3)   14.8  
Income tax benefit     4.1   5.7  
Net (loss) income from discontinued operations, net of tax     (15.2)   20.5  
Total income (loss) from discontinued operations     539.3   575.0  
Net change in foreign currency translation and other     0.1   0.3  
Recognition of benefit plan assets and obligations from the sale of OneBeacon, net of tax     2.9   2.9  
Total comprehensive income (loss)     542.3   578.2  
Discontinued Operations | Sirius Group            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Earned insurance premiums     0.0   0.0  
Net investment income     0.0   0.0  
Net realized and unrealized investment (losses) gains     0.0   0.0  
Other revenue     0.0   0.0  
Total revenues     0.0   0.0  
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 and other expenses     0.0   0.0  
Interest expense     0.0   0.0  
Total expenses     0.0   0.0  
Pre-tax (loss) income     0.0   0.0  
Income tax benefit     0.0   0.0  
Net (loss) income from discontinued operations, net of tax     0.0   0.0  
Net (loss) gain from sale of discontinued operations, net of tax   $ (17.3) (0.2) $ 0.1 (0.8)  
Total income (loss) from discontinued operations     (0.2)   (0.8)  
Total comprehensive income (loss)     (0.2)   (0.8)  
Discontinued Operations | Sirius Group | Net gain (loss) from sale of discontinued operations            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Net (loss) gain from sale of discontinued operations, net of tax     (0.2)   (0.8)  
Discontinued Operations | Other Discontinued Operations            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Earned insurance premiums         0.0  
Net investment income         0.0  
Net realized and unrealized investment (losses) gains         0.0  
Other revenue         0.0  
Total revenues         0.0  
Loss and loss adjustment expenses         0.0  
Insurance acquisition expenses         0.0  
Other underwriting expenses         0.0  
General and administrative and other expenses         0.0  
Interest expense         0.0  
Total expenses         0.0  
Pre-tax (loss) income         0.0  
Income tax benefit         0.0  
Net (loss) income from discontinued operations, net of tax         0.0  
Total income (loss) from discontinued operations         (1.0)  
Discontinued Operations | Other Discontinued Operations | Net gain (loss) from sale of discontinued operations            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Net (loss) gain from sale of discontinued operations, net of tax         (1.0)  
Discontinued Operations | Total            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Earned insurance premiums     268.4   807.6  
Net investment income     13.0   39.7  
Net realized and unrealized investment (losses) gains     11.5   38.8  
Other revenue     2.2   7.7  
Total revenues     295.1   893.8  
Loss and loss adjustment expenses     206.8   546.0  
Insurance acquisition expenses     51.9   145.6  
Other underwriting expenses     44.9   156.2  
General and administrative and other expenses     7.4   21.2  
Interest expense     3.4   10.0  
Total expenses     314.4   879.0  
Pre-tax (loss) income     (19.3)   14.8  
Income tax benefit     4.1   5.7  
Net (loss) income from discontinued operations, net of tax     (15.2)   20.5  
Total income (loss) from discontinued operations     539.1   573.2  
Net change in foreign currency translation and other     0.1   0.3  
Recognition of benefit plan assets and obligations from the sale of OneBeacon, net of tax     2.9   2.9  
Total comprehensive income (loss)     542.1   576.4  
Discontinued Operations | Total | Net gain (loss) from sale of discontinued operations            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Net (loss) gain from sale of discontinued operations, net of tax     $ 554.3   $ 552.7