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Investments - Net Realized and Unrealized Gains (Losses) (Details) - USD ($)
$ in Thousands
3 Months Ended 12 Months Ended
Dec. 31, 2019
Sep. 30, 2019
Jun. 30, 2019
Mar. 31, 2019
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Net realized gains (losses) on sale:                      
Total net realized gains (losses) on sale                 $ 96,328 $ (27,633) $ 1,668
Net unrealized gains (losses):                      
Fixed maturity securities, trading                 349,975 (165,187)  
Total net unrealized gains (losses)                 935,023 (385,251) 188,666
Net realized gains (losses) and change in fair value of funds held- directly managed $ 152,664 $ 148,185 $ 269,711 $ 460,791 $ (158,213) $ (57,223) $ (54,418) $ (143,030) 1,031,351 (412,884) 190,334
Proceeds from sale of available from sale securities                 310,400 11,400 40,800
Fixed maturity investments                      
Net realized gains (losses) on sale:                      
Gross realized gains on fixed maturity securities, available-for-sale securities                 4,856 27 616
Gross realized losses on fixed maturity securities, available-for-sale securities                 (962) (90) (125)
Net realized gains (losses) on trading securities                 91,313 (27,646) 4,695
Net unrealized gains (losses):                      
Fixed maturity securities, trading                     35,878
Funds Held - Directly Managed                      
Net realized gains (losses) on sale:                      
Net realized gains (losses) on trading securities                 1,495 (3,940) (4,219)
Net unrealized gains (losses):                      
Fixed maturity securities, trading                 88,053 (46,257)  
Fixed maturity securities, trading                     33,902
Equity investments                      
Net realized gains (losses) on sale:                      
Net realized gains (losses) on equity investments, trading                 (374) 4,016 701
Net unrealized gains (losses):                      
Equity investments, trading                 55,359 (9,831) 16,498
Other investments                      
Net unrealized gains (losses):                      
Other investments                 $ 441,636 $ (163,976) $ 102,388