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Investments - Narrative (Details) - USD ($)
3 Months Ended 9 Months Ended 12 Months Ended
Dec. 18, 2017
Sep. 30, 2018
Sep. 30, 2017
Sep. 30, 2018
Sep. 30, 2017
Dec. 31, 2017
Sep. 19, 2018
Sep. 18, 2018
Jun. 30, 2018
May 10, 2018
Jan. 01, 2017
Jul. 26, 2016
Jan. 01, 2015
Investment Holdings [Line Items]                          
Catastrophe bonds   $ 37,400,000   $ 37,400,000   $ 32,400,000              
Equity method investment, aggregate cost   66,900,000   66,900,000   66,400,000     $ 67,100,000        
Restricted assets   4,526,400,000   4,526,400,000   4,638,800,000              
Other investments   100,500,000   100,500,000   0              
Investment funds   0   0   0              
OTTI charge recognized   0 $ 100,000 0 $ 500,000                
MVI                          
Investment Holdings [Line Items]                          
Equity method investment, aggregate cost   400,000   400,000   500,000     300,000       $ 800,000
Additional investment       100,000   100,000              
Bene                          
Investment Holdings [Line Items]                          
Equity method investment, aggregate cost   3,500,000   3,500,000   2,900,000     3,800,000     $ 3,300,000  
Additional investment           1,200,000              
Equity method investment, ownership percentage                       20.00%  
Digital Re                          
Investment Holdings [Line Items]                          
Equity method investment, aggregate cost   500,000   500,000   500,000     500,000   $ 2,300,000    
Equity method investment, ownership percentage                     49.00%    
Crop Re                          
Investment Holdings [Line Items]                          
Equity method investment, aggregate cost $ 62,500,000 62,500,000   62,500,000   62,500,000     $ 62,500,000        
Additional investment $ 5,900,000                        
Equity method investment, ownership percentage 23.20%                        
AgriLogic Consulting, LLC                          
Investment Holdings [Line Items]                          
Equity method investment, aggregate cost               $ 0          
Equity method investment, ownership percentage               40.00%          
CGB DS | Crop Re                          
Investment Holdings [Line Items]                          
Equity method investment, counterparty ownership percentage 76.80%                        
Limited Partner | Real estate funds                          
Investment Holdings [Line Items]                          
Restricted assets   $ 0   $ 0   $ 100,000,000              
Other investments             $ 13,800,000     $ 86,200,000      
Disposed of by Sale | Consulting Relationships | AgriLogic Consulting, LLC                          
Investment Holdings [Line Items]                          
Sale of interest of consulting business               60.00%