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Discontinued Operations (Details) (USD $)
In Millions, unless otherwise specified
 3 Months Ended 12 Months Ended 12 Months Ended 1 Months Ended 12 Months Ended 3 Months Ended 12 Months Ended 12 Months Ended 12 Months Ended 12 Months Ended 3 Months Ended
Dec. 31, 2013
Sep. 30, 2013
Jun. 30, 2013
Mar. 31, 2013
Dec. 31, 2012
Sep. 30, 2012
Jun. 30, 2012
Mar. 31, 2012
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Dec. 31, 2010
Dec. 31, 2013
Discontinued Operations
Dec. 31, 2012
Discontinued Operations
Dec. 31, 2011
Discontinued Operations
Oct. 31, 2011
Esurance
Dec. 31, 2012
AutoOne
Discontinued Operations
Dec. 31, 2011
AutoOne
Discontinued Operations
Feb. 22, 2012
AutoOne
Discontinued Operations
Entity
Dec. 31, 2013
OneBeacon Runoff
Contract
Dec. 31, 2012
OneBeacon Runoff
Dec. 31, 2013
OneBeacon Runoff
Discontinued Operations
Rating
Jun. 30, 2013
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2013
OneBeacon Runoff
Discontinued Operations
Rating
Dec. 31, 2012
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2011
OneBeacon Runoff
Discontinued Operations
Mar. 31, 2013
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2012
Minimum
OneBeacon Runoff
Discontinued Operations
Mar. 31, 2013
Minimum
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2012
Maximum
OneBeacon Runoff
Discontinued Operations
Mar. 31, 2013
Maximum
OneBeacon Runoff
Discontinued Operations
Mar. 31, 2013
Causes of Increase (Decrease) in Liability for Unpaid Claims and Claims Adjustment Expense, Cause [Domain]
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2013
N I C O Cover [Member]
OneBeacon Runoff
Dec. 31, 2013
G R C Cover [Member]
OneBeacon Runoff
May 31, 2001
General Reinsurance Corporation
G R C Cover [Member]
OneBeacon Runoff
Dec. 31, 2013
Workers compensation
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2013
Personal Auto Liability [Member]
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2013
Property and Casualty, Personal Insurance Product Line [Member]
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2012
Workers compensation loss reserves [Member]
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2013
Insurance Claims [Member]
OneBeacon Runoff
Discontinued Operations
Dec. 31, 2013
Change in Assumption of Liability [Member]
OneBeacon Runoff
Discontinued Operations
Jun. 30, 2013
Safeco v. American International Group, Inc. [Member]
OneBeacon Runoff
Discontinued Operations
Reinsurance Retention Policy [Line Items]                                                                                    
Gain (loss) on sale of discontinued operations, net of tax                 $ 46.6 $ (91.0) $ 658.3   $ 46.6 $ (91.0) $ 658.3 $ 677.5 $ 0.5 $ (19.2)           $ 44.9 $ 91.5                                  
Number of insurance companies sold                                     2                                              
Loss and loss adjustment expense reserves 3,079.3       3,168.9       3,079.3 3,168.9 5,702.3 5,736.8 1,793.1 2,052.6               188.4   188.4     166.0   215.0   668.0 78.9                    
Net income (loss) from discontinued operations                         4.5 (115.0) 621.6                                                      
Loss and LAE incurred relating prior year losses                 48.4 41.9 76.7                     71.5   (6.5) (40.0) (26.7)                     (16.9) (78.9)   (5.4) (12.6)  
Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims                                                                       36.6            
Loss and loss adjustment expenses                 1,040.5 1,193.9 1,174.3   78.9 48.4 574.9               7.4 78.9                                    
Other revenue                 57.5 100.3 (10.0)   10.8 0 55.1                                                     7.8
liability for unpaid claims and claims adjustment expenses, incurred claims, prior years, after-tax                                           46.5                                        
Net loss from discontinued operations, net of tax (0.3) 0.4 3.9 0.5 0.5 (106.8) 0.5 (9.2) (42.1) (24.0) (36.7)   (42.1) (24.0) (36.7)             46.6     24.0                           9.0      
Maximum Number of Days to Extend the Termination Date                                               90 days                                    
Discontinued Operation, Income (Loss) from Discontinued Operation, before Income Tax                                               69.0                                    
Number of contracts seller caused One Beacon to purchase prior to acquisition                                       2                                            
Reinsurance recoverables, gross 453.5       447.0       453.5 447.0                                             2,500.0 570.0                
Workers compensation discount percent                 3.50% 3.50%                                   3.50%   4.50%                        
Workers compensation discount amount 3.0       4.6       3.0 4.6                   61.7 77.9       15.2                                  
Adverse loss reserve development                                                                     400.0              
Loss reserves ceded at acquisition                                                                     170.0              
Reinsurance recoverable on paid and unpaid losses                                           1,243.7   1,243.7                                    
AM Best Rating System Number Of Ratings                                           16   16                                    
Reinsurance recoverable on paid losses 25.4       17.9       25.4 17.9       15.6               10.7   10.7                                    
Reinsurance recoverables                                           1,741.6   1,741.6                                    
Purchase accounting adjustments                                           $ 136.9   $ 136.9