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Insurance Contract Liabilities - Additional Information (Details) - USD ($)
$ in Millions
12 Months Ended
Jan. 31, 2020
Jan. 01, 2020
Jan. 01, 2019
Oct. 01, 2018
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Dec. 31, 2010
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Consideration paid (received)     $ (561.5) $ (670.5)                    
Provision for losses and loss adjustment expenses         $ 28,500.2 $ 29,081.7 $ 28,610.8 $ 19,481.8 $ 19,816.4 $ 17,749.1 $ 19,212.8 $ 19,648.8 $ 17,232.2 $ 16,049.3
Net loss reserves, case reserves         9,061.1 9,409.3                
Net loss reserves, IBNR         12,504.3 13,213.3                
Net earned premium         13,229.7 12,066.0                
Loss reserve development         166.0 (166.0) $ (608.2) $ (907.0) $ (1,549.3) $ (1,429.0) $ (1,383.7) $ (1,136.9) $ (432.1) $ (336.9)
Net                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Provision for losses and loss adjustment expenses         21,565.4 22,622.6                
RiverStone (UK)                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Insurance contract liabilities, net           529.3                
Consideration paid (received)           (633.0)                
Gain related to Part VII transfer           103.7                
Insurance contract payables           553.2                
Net earned premium           37.5                
European Run-off                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Insurance contract liabilities, net     $ 556.8                      
Net loss reserves, case reserves         793.4                  
Net loss reserves, IBNR         796.8                  
European Run-off | Net                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Provision for losses and loss adjustment expenses         $ 1,590.2                  
RiverStone (UK)                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Insurance contract liabilities, net       $ 566.8                    
UK Insurer | RiverStone (UK)                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Profit commission payable           $ (18.8)                
Subsequent event                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Consideration paid (received) $ (143.4) $ (155.6)                        
Subsequent event | European Run-off                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Insurance contract liabilities, net   $ 154.6                        
Subsequent event | RiverStone (UK)                            
Disclosure of net, gross and reinsurer's share for amounts arising from insurance contracts [line items]                            
Insurance contract liabilities, net $ 134.2