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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, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2017
Sep. 30, 2017
Jun. 30, 2017
Mar. 31, 2017
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Numerator for basic earnings per share:                      
Income (loss) from continuing operations attributable to iStar Inc. and allocable to common shareholders $ (115,455) $ (18,984) $ 42,873 $ 26,809 $ (4,910) $ (34,530)     $ (64,757) $ (17,433) $ 25,708
Income from discontinued operations                 0 4,939 18,264
Gain from discontinued operations                 0 123,418 0
Net income (loss) allocable to common shareholders             $ 177,467 $ (27,102) (64,757) 110,924 43,972
Numerator for diluted earnings per share:                      
Income (loss) from continuing operations attributable to iStar Inc. and allocable to common shareholders $ (115,455) $ (18,984) $ 45,123 $ 29,059         (64,757) (17,433) 25,715
Income from discontinued operations                 0 4,939 18,264
Gain from discontinued operations                 0 123,418 0
Net income (loss) attributable to iStar Inc. and allocable to common shareholders             $ 179,722 $ (27,102) $ (64,757) $ 110,924 $ 43,979
Denominator for basic and diluted earnings per share:                      
Weighted average number of shares, Basic (in shares) 68,012 67,975 67,932 67,913 68,200 71,713 72,142 72,065 67,958 71,021 73,453
Add: Effect of assumed shares issued under treasury stock method or restricted stock units (in shares)                 0 0 84
Add: Effect of joint venture shares (in shares)                 0 0 298
Weighted average common shares outstanding for diluted earnings per common share (in shares) 68,012 67,975 83,694 83,670 68,200 71,713 88,195 72,065 67,958 71,021 73,835
Basic earnings per common share:                      
Income (loss) from continuing operations attributable to iStar Inc. and allocable to common shareholders (in dollars per share)                 $ (0.95) $ (0.25) $ 0.35
Income from discontinued operations (in dollars per share)                 0.00 0.07 0.25
Gain from discontinued operations (in dollars per share)                 0.00 1.74 0.00
Earnings per share, basic (in dollars per share) $ (1.70) $ (0.28) $ 0.63 $ 0.39 $ (0.07) $ (0.48) $ 2.46 $ (0.38) (0.95) 1.56 0.60
Diluted earnings per common share:                      
Income (loss) from continuing operations attributable to iStar Inc. and allocable to common shareholders (in dollars per share)                 (0.95) (0.25) 0.35
Income from discontinued operations (in dollars per share)                 0.00 0.07 0.25
Gain from discontinued operations (in dollars per share)                 0.00 1.74 0.00
Net income (loss) attributable to iStar Inc. and allocable to common shareholders (in dollars per share) $ (1.70) $ (0.28) $ 0.54 $ 0.35 $ (0.07) $ (0.48) $ 2.04 $ (0.38) $ (0.95) $ 1.56 $ 0.60