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Other Investments - Schedule of Other Investments (Details) - USD ($)
$ / shares in Units, $ in Thousands, shares in Millions
3 Months Ended 9 Months Ended
Sep. 30, 2020
Sep. 30, 2019
Sep. 30, 2020
Sep. 30, 2019
Dec. 31, 2019
Schedule of Equity Method Investments [Line Items]          
Other investments $ 1,123,093   $ 1,123,093   $ 907,875
Earnings (losses) from equity method investments 6,805 $ 7,617 26,003 $ 16,566  
Interest expense 42,407 46,522 127,748 136,851  
Dilution gain   8,200   8,200  
Mark-to-market gain 14,000   23,900    
Equity in earnings   8,200   8,200  
Equity Method Investment, Nonconsolidated Investee or Group of Investees          
Schedule of Equity Method Investments [Line Items]          
Depreciation expense 4,600 3,500 13,400 10,700  
Interest expense $ 14,600 8,200 $ 44,000 21,600  
SAFE          
Schedule of Equity Method Investments [Line Items]          
Number of shares owned (in shares) 33.7   33.7    
Closing price (in dollars per share) $ 62.10   $ 62.10    
Market value $ 2,100,000   $ 2,100,000    
Dilution gain     7,900    
Equity in earnings     7,900    
Other strategic investments          
Schedule of Equity Method Investments [Line Items]          
Other investments 72,220   72,220   43,253
Earnings (losses) from equity method investments 205 195 (1,953) 162  
Real estate equity investments          
Schedule of Equity Method Investments [Line Items]          
Carrying value 1,050,873   1,050,873   864,622
Earnings (losses) from equity method investments 6,600 7,422 27,956 16,404  
Real estate equity investments | SAFE          
Schedule of Equity Method Investments [Line Items]          
Carrying value 855,925   855,925   729,357
Earnings (losses) from equity method investments 9,331 2,946 36,905 14,076  
Real estate equity investments | iStar Net Lease II LLC (Net Lease Venture II)          
Schedule of Equity Method Investments [Line Items]          
Carrying value 103,276   103,276   30,712
Earnings (losses) from equity method investments 811 (98) 1,568 (416)  
Real estate equity investments | Other real estate equity investments          
Schedule of Equity Method Investments [Line Items]          
Carrying value 91,672   91,672   $ 104,553
Earnings (losses) from equity method investments $ (3,542) $ 4,574 $ (10,517) $ 2,744