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Other Investments (Other Investments and Share of Earnings (Loss) (Details)
$ in Thousands
12 Months Ended
Dec. 31, 2016
USD ($)
Dec. 31, 2015
USD ($)
Dec. 31, 2014
USD ($)
Investee
Schedule of Equity Method Investments [Line Items]      
Carrying value $ 214,406 $ 254,172  
Earnings (loss) from equity method investments 77,349 32,153 $ 94,905
Net proceeds from sale of other investments 43,936 0 0
Other real estate equity investments      
Schedule of Equity Method Investments [Line Items]      
Earnings (loss) from equity method investments 11,600   32,900
Net proceeds from sale of other investments 39,800    
Recognized earnings 31,500    
Other Strategic Investments      
Schedule of Equity Method Investments [Line Items]      
Carrying value 33,350 73,525  
Earnings (loss) from equity method investments 9,907 8,586 41,477
Equity Method Investee Two      
Schedule of Equity Method Investments [Line Items]      
Earnings (loss) from equity method investments 11,600   $ 23,400
Equity method Investee Three      
Schedule of Equity Method Investments [Line Items]      
Equity method investee | Investee     1
Oak Hill Funds Group      
Schedule of Equity Method Investments [Line Items]      
Earnings (loss) from equity method investments 4,300 2,200 $ 9,000
Real Estate Investment      
Schedule of Equity Method Investments [Line Items]      
Carrying value 181,056 180,647  
Earnings (loss) from equity method investments 67,442 23,567 53,428
Real Estate Investment | iStar Net Lease I LLC      
Schedule of Equity Method Investments [Line Items]      
Carrying value 92,669 69,096  
Earnings (loss) from equity method investments 3,567 5,221 1,915
Real Estate Investment | Marina Palms      
Schedule of Equity Method Investments [Line Items]      
Carrying value 35,185 30,099  
Earnings (loss) from equity method investments 22,053 23,626 14,671
Real Estate Investment | Other real estate equity investments      
Schedule of Equity Method Investments [Line Items]      
Carrying value 53,202 81,452  
Earnings (loss) from equity method investments 41,822 $ (5,280) $ 36,842
Noncontrolling Interests      
Schedule of Equity Method Investments [Line Items]      
Recognized earnings $ 10,100