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Discontinued Operations - Financial Statement Disclosures (Details) - USD ($)
$ in Millions
3 Months Ended 9 Months Ended
Sep. 30, 2015
Sep. 30, 2014
Jun. 30, 2014
Sep. 30, 2015
Sep. 30, 2014
Jun. 30, 2015
Dec. 31, 2014
Dec. 31, 2013
Disposal Group, Including Discontinued Operation, Assets [Abstract]                
Fixed maturity investments $ 2,602.2     $ 2,602.2     $ 2,422.0  
Short-term investments 325.0     325.0     376.8  
Common equity securities 482.1     482.1     611.7  
Convertible fixed maturity and preferred investments 5.6     5.6     13.9  
Other long-term investments 294.6     294.6     318.0  
Total investments 3,709.5     3,709.5     3,742.4  
Cash 200.0     200.0     261.7  
Reinsurance recoverable on unpaid losses 214.6     214.6     161.7  
Reinsurance recoverable on paid losses 22.6     22.6     12.2  
Insurance premiums receivable 273.3     273.3     241.1  
Funds held by ceding entities 4.6     4.6     37.1  
Deferred acquisition costs 110.8     110.8     107.2  
Deferred tax asset 133.9     133.9     114.6  
Ceded unearned insurance premiums 41.4     41.4     17.8  
Goodwill and intangible assets 381.7     381.7     351.2  
Other assets 307.7     307.7     311.6  
Assets held for sale 4,528.1     4,528.1     4,630.6  
Loss and loss adjustment expense reserves 1,433.3 $ 1,169.5 $ 1,137.8 1,433.3 $ 1,169.5 $ 1,357.0 1,350.0 $ 1,054.3
Unearned insurance premiums 671.3     671.3     616.7  
Debt 383.3     383.3     343.1  
Accrued incentive compensation 121.0     121.0     108.1  
Ceded reinsurance payable 46.8     46.8     34.2  
Funds held under insurance contracts 100.3     100.3     81.0  
Other liabilities 304.9     304.9     278.4  
Total liabilities held for sale 3,032.8     3,032.8     3,105.3  
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Earned insurance premiums 284.9 307.2   896.0 879.1      
Net investment income 16.8 13.8   42.6 44.7      
Net realized and unrealized investment (losses) gains (43.9) (27.5)   (33.9) 64.4      
Other revenue 76.9 29.7   225.4 60.3      
Total revenues 334.7 323.2   1,130.1 1,048.5      
Loss and loss adjustment expenses 170.0 185.5   534.1 527.3      
Insurance and Reinsurance Acquisition Expenses 55.3 55.2   166.1 153.0      
Other Underwriting Expense 56.5 51.3   165.5 152.6      
General and administrative expenses 142.6 63.0   354.1 168.3      
Interest expense 4.9 3.7   13.5 10.6      
Total expenses 429.3 358.7   1,233.3 1,011.8      
Discontinued Operation, Income (Loss) from Discontinued Operation, before Income Tax       73.3 166.8      
Net gain on sale of discontinued operations 10.3 7.0   18.2 9.7      
Other Comprehensive Income (Loss), Foreign Currency Transaction and Translation Adjustment, Net of Tax 0.0 (0.2)   0.3 (0.1)      
Comprehensive (loss) income (73.8) (22.9)   (61.5) 201.8      
Net Cash Provided by (Used in) Discontinued Operations [Abstract]                
Net change in cash during the period       17.5 (27.6)      
Cash balances at beginning of period       238.0 233.5      
Cash balances at end of period 183.2 395.4   183.2 395.4      
Net income tax refund from national governments       (8.0) (0.3)      
Sirius Group                
Disposal Group, Including Discontinued Operation, Assets [Abstract]                
Total investments 510.8     510.8        
Fireman's Fund Insurance Company [Member]                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Net gain on sale of discontinued operations   14.0            
OneBeacon Runoff [Member]                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Net gain on sale of discontinued operations   6.7 5.3          
Esurance                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Net gain on sale of discontinued operations         3.2      
Discontinued Operations [Member]                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Earned insurance premiums 202.8 231.7   623.3 656.6      
Net investment income 10.5 9.7   28.6 30.0      
Net realized and unrealized investment (losses) gains (0.9) 48.3   31.4 134.1      
Other revenue 1.7 0.0   (20.6) (47.3)      
Total revenues 214.2 266.9   662.7 773.4      
Loss and loss adjustment expenses 121.7 103.6   311.3 273.1      
Insurance and Reinsurance Acquisition Expenses 45.4 50.2   135.5 146.4      
Other Underwriting Expense 24.8 30.5   78.0 93.9      
General and administrative expenses 9.4 6.3   22.4 21.6      
Interest expense 6.6 6.6   20.0 19.8      
Total expenses 207.9 197.2   567.2 554.8      
Discontinued Operation, Income (Loss) from Discontinued Operation, before Income Tax 6.2 69.7   95.5 218.6      
Discontinued Operation, Tax Effect of Discontinued Operation (2.3) (12.8)   (22.2) (51.8)      
Net gain on sale of discontinued operations 3.9 56.9 $ 2.7 73.3 166.8      
Net loss from discontinued operations, net of tax 14.2 63.9   91.5 176.5      
Other Comprehensive Income (Loss), Foreign Currency Transaction and Translation Adjustment, Net of Tax (18.4) (64.1)   (62.1) (99.9)      
Comprehensive (loss) income (4.2) (0.2)   29.4 76.6      
Net Cash Provided by (Used in) Discontinued Operations [Abstract]                
Net cash provided from operations - discontinued operations       6.7 49.8      
Net cash provided from investing activities - discontinued operations       35.7 47.5      
Net cash used for financing activities - discontinued operations       (2.4) (55.6)      
Effect of exchange rate changes on cash       (4.1) (10.6)      
Net change in cash during the period       35.9 31.1      
Cash balances at beginning of period       111.5 93.2      
Cash balances at end of period 147.4 124.3   147.4 124.3      
Interest paid       (25.5) (34.9)      
Net income tax refund from national governments       (30.3) 7.5      
Discontinued Operations [Member] | Discontinued Operations, Held-for-sale [Member]                
Disposal Group, Including Discontinued Operation, Assets [Abstract]                
Fixed maturity investments 2,394.3     2,394.3     2,362.3  
Short-term investments 360.5     360.5     494.9  
Common equity securities 164.3     164.3     189.9  
Convertible fixed maturity and preferred investments 0.0     0.0     6.6  
Other long-term investments 82.1     82.1     89.0  
Total investments 3,001.2     3,001.2     3,142.7  
Cash 147.4     147.4     111.5  
Reinsurance recoverable on unpaid losses 276.5     276.5     322.2  
Reinsurance recoverable on paid losses 11.0     11.0     11.4  
Insurance premiums receivable 416.6     416.6     306.6  
Funds held by ceding entities 81.1     81.1     91.9  
Deferred acquisition costs 82.7     82.7     69.9  
Deferred tax asset 309.6     309.6     341.5  
Ceded unearned insurance premiums 118.4     118.4     76.2  
Goodwill and intangible assets 10.2     10.2     15.2  
Other assets 73.4     73.4     83.4  
Assets held for sale 4,528.1     4,528.1     4,630.6  
Loss and loss adjustment expense reserves 1,662.9     1,662.9     1,809.8  
Unearned insurance premiums 429.4     429.4     338.6  
Debt 403.5     403.5     403.5  
Deferred tax liability 257.8     257.8     282.8  
Accrued incentive compensation 55.5     55.5     76.5  
Ceded reinsurance payable 131.4     131.4     71.5  
Funds held under insurance contracts 45.1     45.1     57.9  
Other liabilities 47.2     47.2     64.7  
Total liabilities held for sale 3,032.8     3,032.8     3,105.3  
Discontinued Operations [Member] | Sirius Group                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Earned insurance premiums 202.8 231.4   623.3 656.5      
Net investment income 10.5 9.7   28.6 30.0      
Net realized and unrealized investment (losses) gains (0.9) 48.3   31.4 134.1      
Other revenue 1.8 (22.8)   (20.2) (47.3)      
Total revenues 214.2 266.6   663.1 773.3      
Loss and loss adjustment expenses 121.7 103.6   311.3 273.8      
Insurance and Reinsurance Acquisition Expenses 45.4 50.1   135.5 146.3      
Other Underwriting Expense 24.8 29.7   78.0 91.7      
General and administrative expenses 9.4 6.3   22.4 21.6      
Interest expense 6.6 6.6   20.0 19.8      
Total expenses 207.9 196.3   567.2 553.2      
Discontinued Operation, Income (Loss) from Discontinued Operation, before Income Tax 6.3 70.3   95.9 220.1      
Discontinued Operation, Tax Effect of Discontinued Operation (2.3) (13.1)   (22.2) (52.4)      
Net gain on sale of discontinued operations 4.0 57.2   73.7 167.7      
Net loss from discontinued operations, net of tax 4.0 57.2   73.7 167.7      
Other Comprehensive Income (Loss), Foreign Currency Transaction and Translation Adjustment, Net of Tax (18.4) (64.1)   (62.1) (99.9)      
Comprehensive (loss) income (14.4) (6.9)   11.6 67.8      
Discontinued Operations [Member] | Other Discontinued Operations [Member]                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Earned insurance premiums 0.0 0.3   0.0 0.1      
Net investment income 0.0 0.0   0.0 0.0      
Net realized and unrealized investment (losses) gains 0.0 0.0   0.0 0.0      
Other revenue (0.1) 0.0   (0.4) 0.0      
Total revenues (0.1) 0.3   (0.4) 0.1      
Loss and loss adjustment expenses 0.0 0.0   0.0 (0.7)      
Insurance and Reinsurance Acquisition Expenses 0.0 0.1   0.0 0.1      
Other Underwriting Expense 0.0 0.8   0.0 2.2      
General and administrative expenses 0.0 0.0   0.0 0.0      
Interest expense 0.0 0.0   0.0 0.0      
Total expenses 0.0 0.9   0.0 1.6      
Discontinued Operation, Income (Loss) from Discontinued Operation, before Income Tax (0.1) (0.6)   (0.4) (1.5)      
Discontinued Operation, Tax Effect of Discontinued Operation 0.0 0.3   0.0 0.6      
Net gain on sale of discontinued operations (0.1) (0.3)   (0.4) (0.9)      
Net loss from discontinued operations, net of tax 10.2 6.7   17.8 8.8      
Other Comprehensive Income (Loss), Foreign Currency Transaction and Translation Adjustment, Net of Tax 0.0 0.0   0.0 0.0      
Comprehensive (loss) income 10.2 6.7   17.8 8.8      
Discontinued Operations [Member] | OneBeacon | Discontinued Operations, Held-for-sale [Member]                
Disposal Group, Including Discontinued Operation, Assets [Abstract]                
Other assets 0.0     0.0     $ 58.1  
Discontinued Operations [Member] | Fireman's Fund Insurance Company [Member]                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Net gain on sale of discontinued operations 0.0 14.0   0.0 14.0      
Discontinued Operations [Member] | OneBeacon Runoff [Member]                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Net gain on sale of discontinued operations 0.0 (7.0)   0.3 (7.5)      
Discontinued Operations [Member] | Esurance                
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]                
Net gain on sale of discontinued operations $ 10.3 $ 0.0   $ 17.9 $ 3.2