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Segment Information (Details) - USD ($)
$ in Millions
3 Months Ended 12 Months Ended
Dec. 31, 2015
Sep. 30, 2015
Jun. 30, 2015
Mar. 31, 2015
Dec. 31, 2014
Sep. 30, 2014
Jun. 30, 2014
Mar. 31, 2014
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Segment reporting information                      
Percentage of par value of policy reinsured 15.00%               15.00%    
Earned insurance premiums                 $ 1,188.2 $ 1,185.0 $ 1,120.9
Net investment income                 60.8 59.5 59.8
Net investment income (loss) - surplus note interest                 0.0 0.0 0.0
Net realized and unrealized investment gains                 225.4 78.5 133.9
Other revenue                 334.2 131.1 47.0
Total revenues $ 678.5 $ 334.7 $ 403.6 $ 391.8 $ 405.6 $ 323.2 $ 393.5 $ 331.8 1,808.6 1,454.1 1,361.6
Loss and loss adjustment expenses                 708.9 824.0 622.1
Insurance and reinsurance acquisition expenses                 220.1 206.2 210.4
Other underwriting expenses                 218.6 179.6 205.2
General and administrative expenses                 487.5 257.7 149.1
Amortization of Intangible Assets                 28.5 11.7 1.4
Interest expense on debt                 18.6 15.6 16.2
Total expenses 420.4 429.3 412.7 391.3 471.3 358.7 359.9 293.2 1,653.7 1,483.1 1,203.0
Pre-tax loss $ 258.1 $ (94.6) $ (9.1) $ 0.5 $ (65.7) $ (35.5) $ 33.6 $ 38.6 154.9 (29.0) 158.6
Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 458.9 246.0 147.7
OneBeacon                      
Segment reporting information                      
Earned insurance premiums                 1,176.2 1,177.1 1,120.4
Net investment income                 45.9 43.4 43.0
Net investment income (loss) - surplus note interest                 0.0 0.0 0.0
Net realized and unrealized investment gains                 (35.1) 40.4 49.4
Other revenue                 (0.6) 5.8 31.2
Total revenues                 1,186.4 1,266.7 1,244.0
Loss and loss adjustment expenses                 700.7 815.1 622.1
Insurance and reinsurance acquisition expenses                 213.8 203.3 208.9
Other underwriting expenses                 218.2 179.2 204.8
Interest expense on debt                 13.0 13.0 13.0
Total expenses                 1,161.1 1,224.4 1,060.8
Pre-tax loss                 25.3 42.3 183.2
OneBeacon | Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 14.1 12.4 10.6
BAM                      
Segment reporting information                      
Earned insurance premiums                 0.8 0.4 0.1
Net investment income                 4.2 5.7 4.7
Net investment income (loss) - surplus note interest                 (15.8) (15.7) (40.2)
Net realized and unrealized investment gains                 0.9 6.6 (9.3)
Other revenue                 0.7 0.6 0.4
Total revenues                 (9.2) (2.4) (44.3)
Loss and loss adjustment expenses                 0.0 0.0 0.0
Insurance and reinsurance acquisition expenses                 2.3 1.8 1.4
Other underwriting expenses                 0.4 0.4 0.4
Interest expense on debt                 0.0 0.0 0.0
Total expenses                 38.1 38.1 34.3
Pre-tax loss                 (47.3) (40.5) (78.6)
BAM | Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 $ 35.4 35.9 32.5
HG Global                      
Segment reporting information                      
Percentage of par value of policy reinsured 15.00%               15.00%    
Earned insurance premiums                 $ 2.5 1.4 0.4
Net investment income                 1.9 1.4 1.0
Net investment income (loss) - surplus note interest                 15.8 15.7 40.2
Net realized and unrealized investment gains                 (0.3) 1.7 (2.0)
Other revenue                 0.0 0.0 0.0
Total revenues                 19.9 20.2 39.6
Loss and loss adjustment expenses                 0.0 0.0 0.0
Insurance and reinsurance acquisition expenses                 0.6 0.3 0.1
Other underwriting expenses                 0.0 0.0 0.0
Interest expense on debt                 0.0 0.0 0.0
Total expenses                 2.0 1.9 1.5
Pre-tax loss                 17.9 18.3 38.1
HG Global | Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 1.4 1.6 1.4
Other Segments                      
Segment reporting information                      
Earned insurance premiums                 8.7 6.1 0.0
Net investment income                 8.8 9.0 11.1
Net investment income (loss) - surplus note interest                 0.0 0.0 0.0
Net realized and unrealized investment gains                 259.9 29.8 95.8
Other revenue                 334.1 124.7 15.4
Total revenues                 611.5 169.6 122.3
Loss and loss adjustment expenses                 8.2 8.9 0.0
Insurance and reinsurance acquisition expenses                 3.4 0.8 0.0
Other underwriting expenses                 0.0 0.0 0.0
Interest expense on debt                 5.6 2.6 3.2
Total expenses                 452.5 218.7 106.4
Pre-tax loss                 159.0 (49.1) 15.9
Other Segments | Segment Reconciling Items [Member]                      
Segment reporting information                      
General and administrative expenses                 408.0 196.1 103.2
General and Administrative Expense [Member]                      
Segment reporting information                      
Amortization of Intangible Assets                 28.6 11.7 1.4
General and Administrative Expense [Member] | OneBeacon                      
Segment reporting information                      
Amortization of Intangible Assets                 1.3 1.4 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                 27.3 10.3 $ 0.0
Symetra | Other Segments                      
Segment reporting information                      
Net realized and unrealized investment gains                 258.8    
Tranzact [Member] | Other Segments                      
Segment reporting information                      
Other revenue                 186.9 43.2  
General and administrative expenses                 167.3 37.4  
MediaAlpha [Member] | Other Segments                      
Segment reporting information                      
Other revenue                 105.5 65.3  
General and administrative expenses                 $ 99.0 $ 60.6