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Earnings Per Share (Earnings Allocable to Common Shares) (Details) - USD ($)
$ / shares in Units, shares in Thousands, $ 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
Numerator for basic earnings per share:                      
Income (loss) from continuing operations attributable to iStar Inc. and allocable to common shareholders                 $ 291,547 $ (64,757) $ (17,433)
Income from discontinued operations                 0 0 4,939
Gain from discontinued operations                 0 0 123,418
Net income (loss) allocable to common shareholders $ (46,260) $ (7,343) $ 362,715 $ (17,565) $ (115,455) $ (18,984) $ 42,873 $ 26,809 291,547 (64,757) 110,924
Numerator for diluted earnings per share:                      
Income (loss) from continuing operations attributable to iStar Inc. and allocable to common shareholders                 300,547 (64,757) (17,433)
Income from discontinued operations                 0 0 4,939
Gain from discontinued operations                 0 0 123,418
Net income (loss) attributable to iStar Inc. and allocable to common shareholders $ (46,260) $ (7,343) $ 364,965 $ (17,565) $ (115,455) $ (18,984) $ 45,123 $ 29,059 $ 300,547 $ (64,757) $ 110,924
Denominator for basic and diluted earnings per share:                      
Weighted average number of shares, Basic (in shares) 64,910 62,168 64,019 67,747 68,012 67,975 67,932 67,913 64,696 67,958 71,021
Add: Effect of assumed shares issued under treasury stock method or restricted stock units (in shares)                 146 0 0
Add: Effect of series J convertible perpetual preferred stock (in shares)                 15,824 0 0
Weighted average common shares outstanding for diluted earnings per common share (in shares) 64,910 62,168 80,259 67,747 68,012 67,975 83,694 83,670 80,666 67,958 71,021
Basic earnings per common share:                      
Income (loss) from continuing operations attributable to iStar Inc. and allocable to common shareholders (in dollars per share)                 $ 4.51 $ (0.95) $ (0.25)
Income from discontinued operations (in dollars per share)                 0 0 0.07
Gain from discontinued operations (in dollars per share)                 0 0 1.74
Earnings per share, basic (in dollars per share) $ (0.71) $ (0.12) $ 5.67 $ (0.26) $ (1.70) $ (0.28) $ 0.63 $ 0.39 4.51 (0.95) 1.56
Diluted earnings per common share:                      
Income (loss) from continuing operations attributable to iStar Inc. and allocable to common shareholders (in dollars per share)                 3.73 (0.95) (0.25)
Income from discontinued operations (in dollars per share)                 0 0 0.07
Gain from discontinued operations (in dollars per share)                 0 0 1.74
Net income (loss) attributable to iStar Inc. and allocable to common shareholders (in dollars per share) $ (0.71) $ (0.12) $ 4.55 $ (0.26) $ (1.70) $ (0.28) $ 0.54 $ 0.35 $ 3.73 $ (0.95) $ 1.56