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Discontinued Operations (Loss from Discontinued Operations) (Details) - USD ($)
$ in Millions
3 Months Ended 12 Months Ended 51 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
Dec. 31, 2015
Dec. 31, 2012
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                          
Net cash provided from (used for) discontinued operations                 $ 14.7 $ 60.0 $ (61.5)    
Net cash provided from investing activities — discontinued operations                 31.3 35.8 148.7    
Revenues                          
Earned insurance premiums                 1,188.2 1,185.0 1,120.9    
Net investment income                 60.8 59.5 59.8    
Other revenue                 334.2 131.1 47.0    
Net realized and unrealized investment gains                 225.4 78.5 133.9    
Revenues (including realized gains and losses) $ 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    
Expenses                          
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    
Interest expense on debt                 18.6 15.6 16.2    
General and administrative expenses                 487.5 257.7 149.1    
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    
Net income from discontinued operations, net of tax 7.3 $ 14.2 $ 3.5 $ 73.8 82.1 $ 63.9 $ 61.1 $ 51.5 80.6 260.2 99.9    
Gain (loss) on sale of discontinued operations, net of tax                 18.2 (1.6) 46.6    
Change in foreign currency translation, net of tax                 (65.8) (168.5) 2.7    
Comprehensive Income (Loss), Net of Tax, Including Portion Attributable to Noncontrolling Interest                 197.2 207.3 247.0    
Net cash (used for) provided from financing activities — discontinued operations                 (9.1) (63.2) (87.5)    
Cash and Cash Equivalents, at Carrying Value 173.5       238.0       173.5 238.0 233.5 $ 173.5 $ 118.9
Discontinued Operations                          
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                          
Net cash provided from (used for) discontinued operations                 14.7 60.0 (61.5)    
Net cash provided from investing activities — discontinued operations                 31.3 35.8 148.7    
Revenues                          
Earned insurance premiums                 847.0 874.0 867.2    
Net investment income                 40.7 40.9 46.7    
Other revenue                 (21.3) (62.4) 27.6    
Net realized and unrealized investment gains                 15.1 205.4 27.8    
Revenues (including realized gains and losses)                 881.5 1,057.9 969.3    
Expenses                          
Loss and loss adjustment expenses                 422.7 344.6 497.3    
Insurance and reinsurance acquisition expenses                 189.8 193.7 166.5    
Other underwriting expenses                 107.9 133.2 125.9    
Interest expense on debt                 26.6 26.3 26.3    
General and administrative expenses                 27.0 30.5 32.2    
Total expenses                 774.0 728.3 848.2    
Net income (loss) from discontinued operations                 107.5 329.6 121.1    
Income tax expense                 (26.9) (69.4) (21.2)    
Net income from discontinued operations, net of tax                 80.6 260.2 99.9    
Gain (loss) on sale of discontinued operations, net of tax                     46.6    
Total income from discontinued operations                 98.8 258.6 146.5    
Change in foreign currency translation, net of tax                   (169.5) 6.1    
Comprehensive Income (Loss), Net of Tax, Including Portion Attributable to Noncontrolling Interest                 33.8 89.1 152.6    
Net cash (used for) provided from financing activities — discontinued operations                 (9.1) (63.2) (87.5)    
Effect of Exchange Rate on Cash                 (4.5) (14.3) (0.2)    
Net Cash Provided by (Used in) Discontinued Operations                 32.4 18.3 (0.5)    
Cash and Cash Equivalents, at Carrying Value $ 143.9       $ 111.5       143.9 111.5 93.2 143.9 $ 93.7
Sirius Group                          
Revenues                          
Net investment income                 225.0 4.0 1.0    
Net realized and unrealized investment gains                 225.0 4.0 1.0    
Sirius Group | Discontinued Operations                          
Revenues                          
Earned insurance premiums                 847.0 873.9 866.4    
Net investment income                 40.7 40.9 46.7    
Other revenue                 (20.6) (62.4) 16.8    
Net realized and unrealized investment gains                 15.1 205.4 27.8    
Revenues (including realized gains and losses)                 882.2 1,057.8 957.7    
Expenses                          
Loss and loss adjustment expenses                 422.7 345.3 418.4    
Insurance and reinsurance acquisition expenses                 189.8 193.6 166.5    
Other underwriting expenses                 107.9 129.7 126.1    
Interest expense on debt                 26.6 26.3 26.3    
General and administrative expenses                 27.0 30.5 32.2    
Total expenses                 774.0 725.4 769.5    
Net income (loss) from discontinued operations                 108.2 332.4 188.2    
Income tax expense                 27.1 70.4 46.2    
Net income from discontinued operations, net of tax                 81.1 262.0 142.0    
Gain (loss) on sale of discontinued operations, net of tax                     0.0    
Total income from discontinued operations                 81.1 262.0 142.0    
Change in foreign currency translation, net of tax                 (65.0) (169.5) 6.1    
Comprehensive Income (Loss), Net of Tax, Including Portion Attributable to Noncontrolling Interest                 16.1 92.5 148.1    
Other Operations | Discontinued Operations                          
Revenues                          
Earned insurance premiums                 0.0 0.1 0.8    
Net investment income                 0.0 0.0 0.0    
Other revenue                 (0.7) 0.0 10.8    
Net realized and unrealized investment gains                 0.0 0.0 0.0    
Revenues (including realized gains and losses)                 (0.7) 0.1 11.6    
Expenses                          
Loss and loss adjustment expenses                 0.0 (0.7) 78.9    
Insurance and reinsurance acquisition expenses                 0.0 0.1 0.0    
Other underwriting expenses                 0.0 3.5 (0.2)    
Interest expense on debt                 0.0 0.0 0.0    
General and administrative expenses                 0.0 0.0 0.0    
Total expenses                 0.0 2.9 78.7    
Net income (loss) from discontinued operations                 (0.7) (2.8) (67.1)    
Income tax expense                 (0.2) (1.0) (25.0)    
Net income from discontinued operations, net of tax                 (0.5) (1.8) (42.1)    
Total income from discontinued operations                 17.7 (3.4) 4.5    
Change in foreign currency translation, net of tax                 (65.0) 0.0 0.0    
Comprehensive Income (Loss), Net of Tax, Including Portion Attributable to Noncontrolling Interest                 17.7 (3.4) 4.5    
Fireman's Fund Insurance Company [Member] | Discontinued Operations                          
Expenses                          
Gain (loss) on sale of discontinued operations, net of tax                   14.0      
OneBeacon Runoff | Discontinued Operations                          
Expenses                          
Gain (loss) on sale of discontinued operations, net of tax                 0.3 (18.8) 46.6    
Esurance [Member] | Discontinued Operations                          
Expenses                          
Net income from discontinued operations, net of tax                     4.5    
Gain (loss) on sale of discontinued operations, net of tax                 17.9 3.2   $ 28.3  
Other Segments                          
Revenues                          
Earned insurance premiums                 8.7 6.1 0.0    
Net investment income                 8.8 9.0 11.1    
Other revenue                 334.1 124.7 15.4    
Net realized and unrealized investment gains                 259.9 29.8 95.8    
Revenues (including realized gains and losses)                 611.5 169.6 122.3    
Expenses                          
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    
Symetra | Sirius Group                          
Revenues                          
Net realized and unrealized investment gains                 218.5        
Symetra | Other Segments                          
Revenues                          
Net realized and unrealized investment gains                 258.8        
Tranzact [Member] | Other Segments                          
Revenues                          
Other revenue                 186.9 43.2      
Expenses                          
General and administrative expenses                 167.3 37.4      
MediaAlpha [Member] | Other Segments                          
Revenues                          
Other revenue                 105.5 65.3      
Expenses                          
General and administrative expenses                 $ 99.0 $ 60.6