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Other Investments (Schedule of Other Investments) (Details) - USD ($)
$ / shares in Units, $ in Thousands, shares in Millions
12 Months Ended
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Schedule of Equity Method Investments [Line Items]      
Other investments $ 907,875 $ 304,275  
Equity in Earnings (Losses) $ 41,849 (5,007) $ 13,015
Safehold Inc.      
Schedule of Equity Method Investments [Line Items]      
Number of investor units owned (in shares) 31.2    
Investor units closing price (in dollars per share) $ 40.30    
Fair value $ 1,300,000    
Equity method investment realized gain (loss) 7,600    
Other real estate equity investments      
Schedule of Equity Method Investments [Line Items]      
Equity method investment realized gain (loss) 19,300    
Other Strategic Investments      
Schedule of Equity Method Investments [Line Items]      
Other investments 43,253 7,516  
Equity in Earnings (Losses) (6) (9,373) 1,410
Impairment on foreign equity method investment   10,000  
Real Estate Investment      
Schedule of Equity Method Investments [Line Items]      
Carrying value 864,622 296,759  
Equity in Earnings (Losses) 41,855 4,366 11,605
Real Estate Investment | Safehold Inc.      
Schedule of Equity Method Investments [Line Items]      
Carrying value 729,357 149,589  
Equity in Earnings (Losses) 29,764 4,711 551
Real Estate Investment | iStar Net Lease II LLC (Net Lease Venture II)      
Schedule of Equity Method Investments [Line Items]      
Carrying value 30,712 16,215  
Equity in Earnings (Losses) (529) (333) 0
Real Estate Investment | Net Lease Venture      
Schedule of Equity Method Investments [Line Items]      
Carrying value 0 0  
Equity in Earnings (Losses) 0 4,100 4,534
Real Estate Investment | Other real estate equity investments      
Schedule of Equity Method Investments [Line Items]      
Carrying value 104,553 130,955  
Equity in Earnings (Losses) $ 12,620 (4,112) $ 6,520
Impairment on foreign equity method investment   $ 6,100