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Investments - Narrative (Details) - USD ($)
3 Months Ended 9 Months Ended 12 Months Ended
Dec. 18, 2017
Mar. 31, 2019
Mar. 31, 2018
Sep. 30, 2018
Dec. 31, 2018
Dec. 31, 2017
Sep. 19, 2018
Sep. 18, 2018
May 10, 2018
Dec. 20, 2017
Jan. 01, 2017
Jul. 26, 2016
Jan. 01, 2015
Investment Holdings [Line Items]                          
Catastrophe bonds   $ 38,100,000     $ 36,200,000                
Equity method investment, aggregate cost   67,000,000     67,100,000                
Restricted assets   4,564,600,000     4,419,200,000                
Other investments   104,000,000     102,500,000                
Investment funds   0     0                
OTTI charge recognized   0 $ 0                    
MVI                          
Investment Holdings [Line Items]                          
Equity method investment, aggregate cost   500,000     500,000               $ 800,000
Additional investment       $ 100,000   $ 100,000              
Bene                          
Investment Holdings [Line Items]                          
Equity method investment, aggregate cost   3,100,000     3,200,000             $ 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   900,000     900,000           $ 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                
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%