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Segment Information (Details) - USD ($)
$ in Millions
 3 Months Ended 12 Months Ended
Dec. 31, 2016
Sep. 30, 2016
Jun. 30, 2016
Mar. 31, 2016
Dec. 31, 2015
Sep. 30, 2015
Jun. 30, 2015
Mar. 31, 2015
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
Segment reporting information                      
Percentage of par value of policy reinsured 15.00%               15.00%    
Earned insurance premiums                 $ 1,114.0 $ 1,188.2 $ 1,185.0
Net investment income                 86.8 60.8 59.5
Net realized and unrealized investment gains                 10.3 225.4 78.5
Other revenue                 149.6 147.3 88.1
Total revenues $ 268.2 $ 365.0 $ 358.2 $ 369.3 $ 602.6 $ 296.1 $ 368.7 $ 354.3 1,360.7 1,621.7 1,411.1
Loss and loss adjustment expenses                 664.0 708.9 824.0
Insurance acquisition expenses                 211.6 220.1 206.2
Other underwriting expenses                 209.5 218.6 179.6
General and administrative expenses                 299.9 302.2 216.5
Amortization of Intangible Assets                 12.5 10.6 8.3
Interest expense on debt                 16.1 14.6 14.2
Total expenses 335.0 345.0 360.3 360.8 356.3 383.0 373.8 351.3 1,401.1 1,464.4 1,440.5
Pre-tax (loss) income from continuing operations $ (66.8) $ 20.0 $ (2.1) $ 8.5 $ 246.3 $ (86.9) $ (5.1) $ 3.0 (40.4) 157.3 (29.4)
Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 287.4 291.6 208.2
OneBeacon                      
Segment reporting information                      
Earned insurance premiums                 1,100.6 1,176.2 1,177.1
Net investment income                 50.6 45.9 43.4
Net realized and unrealized investment gains                 37.7 (35.1) 40.4
Other revenue                 5.5 (0.6) 5.8
Total revenues                 1,194.4 1,186.4 1,266.7
Loss and loss adjustment expenses                 656.0 700.7 815.1
Insurance acquisition expenses                 206.0 213.8 203.3
Other underwriting expenses                 209.0 218.2 179.2
Interest expense on debt                 13.1 13.0 13.0
Total expenses                 1,098.3 1,161.1 1,224.4
Pre-tax (loss) income from continuing operations                 96.1 25.3 42.3
OneBeacon | Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 13.0 14.1 12.4
BAM                      
Segment reporting information                      
Earned insurance premiums                 1.5 0.8 0.4
Net investment income                 6.8 4.2 5.7
Net realized and unrealized investment gains                 0.6 0.9 6.6
Other revenue                 1.1 0.7 0.6
Total revenues                 (7.8) (9.2) (2.4)
Loss and loss adjustment expenses                 0.0 0.0 0.0
Insurance acquisition expenses                 2.5 2.3 1.8
Other underwriting expenses                 0.4 0.4 0.4
Interest expense on debt                 0.0 0.0 0.0
Total expenses                 41.1 38.1 38.1
Pre-tax (loss) income from continuing operations                 (48.9) (47.3) (40.5)
BAM | Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 $ 38.2 35.4 35.9
HG Global                      
Segment reporting information                      
Percentage of par value of policy reinsured 15.00%               15.00%    
Earned insurance premiums                 $ 4.4 2.5 1.4
Net investment income                 2.2 1.9 1.4
Net realized and unrealized investment gains                 0.1 (0.3) 1.7
Other revenue                 0.0 0.0 0.0
Total revenues                 24.5 19.9 20.2
Loss and loss adjustment expenses                 0.0 0.0 0.0
Insurance acquisition expenses                 0.9 0.6 0.3
Other underwriting expenses                 0.0 0.0 0.0
Interest expense on debt                 0.0 0.0 0.0
Total expenses                 2.3 2.0 1.9
Pre-tax (loss) income from continuing operations                 22.2 17.9 18.3
HG Global | Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 1.4 1.4 1.6
Other Segments                      
Segment reporting information                      
Earned insurance premiums                 7.5 8.7 6.1
Net investment income                 27.2 8.8 9.0
Net realized and unrealized investment gains                 (28.1) 259.9 29.8
Other revenue                 143.0 147.2 81.7
Total revenues                 149.6 424.6 126.6
Loss and loss adjustment expenses                 8.0 8.2 8.9
Insurance acquisition expenses                 2.2 3.4 0.8
Other underwriting expenses                 0.1 0.0 0.0
Interest expense on debt                 3.0 1.6 1.2
Total expenses                 259.4 263.2 176.1
Pre-tax (loss) income from continuing operations                 (109.8) 161.4 (49.5)
Other Segments | Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 234.8 240.7 158.3
General and Administrative Expense [Member]                      
Segment reporting information                      
Amortization of Intangible Assets                 12.5 10.6 8.3
General and Administrative Expense [Member] | OneBeacon                      
Segment reporting information                      
Amortization of Intangible Assets                 1.2 1.3 1.4
General and Administrative Expense [Member] | BAM                      
Segment reporting information                      
Amortization of Intangible Assets                 0.0 0.0 0.0
General and Administrative Expense [Member] | HG Global                      
Segment reporting information                      
Amortization of Intangible Assets                 0.0 0.0 0.0
General and Administrative Expense [Member] | Other Segments                      
Segment reporting information                      
Amortization of Intangible Assets                 11.3 9.3 6.9
Symetra | Other Segments                      
Segment reporting information                      
Net realized and unrealized investment gains                   258.8  
MediaAlpha [Member] | Other Segments                      
Segment reporting information                      
Other revenue                 116.5 105.5 65.3
General and administrative expenses                 109.6 99.0 60.6
Surplus Note                      
Segment reporting information                      
Net investment income                 0.0 0.0 0.0
Surplus Note | OneBeacon                      
Segment reporting information                      
Net investment income                 0.0 0.0 0.0
Surplus Note | BAM                      
Segment reporting information                      
Net investment income                 (17.8) (15.8) (15.7)
Surplus Note | HG Global                      
Segment reporting information                      
Net investment income                 17.8 15.8 15.7
Surplus Note | Other Segments                      
Segment reporting information                      
Net investment income                 $ 0.0 $ 0.0 $ 0.0