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Investments - Equity Method Investments (Details) - USD ($)
$ in Thousands
Dec. 31, 2019
Dec. 31, 2018
Schedule of Equity Method Investments [Line Items]    
Investment $ 266,823 $ 197,860
Ownership % 47.40% 47.40%
Equity method investments $ 326,277 $ 204,507
EnhanzedRe    
Schedule of Equity Method Investments [Line Items]    
Investment $ 154,050 $ 94,800
Ownership % 47.40% 47.40%
Equity method investments $ 182,856 $ 94,800
Citco    
Schedule of Equity Method Investments [Line Items]    
Investment $ 50,000 $ 50,000
Ownership % 31.90% 31.90%
Equity method investments $ 51,742 $ 50,812
Monument    
Schedule of Equity Method Investments [Line Items]    
Investment $ 26,600 $ 26,600
Ownership % 26.60% 26.60%
Equity method investments $ 60,598 $ 42,193
Clear Spring    
Schedule of Equity Method Investments [Line Items]    
Investment $ 11,210 $ 11,210
Ownership % 20.00% 20.00%
Equity method investments $ 10,645 $ 10,070
Other    
Schedule of Equity Method Investments [Line Items]    
Investment $ 24,963 $ 15,250
Ownership % 30.00% 30.00%
Equity method investments $ 20,436 $ 6,632
Equity Method Investments    
Schedule of Equity Method Investments [Line Items]    
Unfunded commitments $ 93,100