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Reserves for Unpaid Losses and Loss Adjustment Expenses (Narrative) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Dec. 31, 2010
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses $ (48.4) $ (41.9) $ (76.7)  
Increase (decrease) in reserves 1,040.5 1,193.9 1,174.3  
Accretion of fair value adjustment to net loss and LAE reserves 1.7 10.6 8.3  
Un-accreted fair value, adjustment to loss and loss adjustment expense reserves, before tax 4.7      
Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses (23.9) (34.5) (46.9)  
Liability for asbestos and environmental claims, gross 227.8 228.6 207.2 214.3
Liability for asbestos and environmental claims 193.9 189.4 162.7 169.6
Asbestos and Environmental Loss Three Year Survival Ratio Period 8 years 9 years    
Liability for asbestos claims, net, period increase (decrease) 11.8 46.4 10.3  
Liabilty for environmental claims, net, period increase (decrease) 0.8 (0.5) 2.0  
OneBeacon
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses   (7.4) (29.8)  
Liability for asbestos and environmental claims, gross 1.0      
Chile Earthquake Loss Cover | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Increase (decrease) in reserves     (13.1)  
Asbestos | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Liability for asbestos and environmental claims, gross 207.4 208.2 185.1 191.9
Liability for asbestos and environmental claims 178.7 174.2 146.2 151.5
Environmental | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Liability for asbestos and environmental claims, gross 20.4 20.4 22.1 22.4
Liability for asbestos and environmental claims 15.2 15.2 16.5 18.1
WM Solutions | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Liability for asbestos claims, net, period increase (decrease) 13.0 11.0    
Liabilty for environmental claims, net, period increase (decrease) 1.0 0.7    
Accident and Health Insurance Product Line [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses (9.2)      
Asbestos [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses 11.8 46.4    
Casualty Runoff [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses   (31.5)    
Aviation Space [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses (10.1) (5.3)    
Property [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses (16.6) (28.4)    
Property Insurance Product Line [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Increase (decrease) in reserves     (41.2)  
asbestos and environmental [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Increase (decrease) in reserves     12.3  
Marine Energy [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses   (11.6)    
Trade Credit [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses   (6.8)    
Accident and Health | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Loss and LAE incurred relating prior year losses   4.3    
Professional Liability | OneBeacon
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Increase (decrease) in reserves     (11.5)  
Property and Casualty, Commercial Insurance Product Line [Member] | OneBeacon
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Increase (decrease) in reserves     (14.0)  
Other Lines of Business [Member] | OneBeacon
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Increase (decrease) in reserves     (4.3)  
Quarterly Monitoring [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Liability for asbestos claims, net, period increase (decrease)   14.0    
In-depth Analysis [Member] | Sirius Group
       
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity        
Liability for asbestos claims, net, period increase (decrease)   $ 33.0