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Earnings Per Share (Schedule of Earnings Per Share) (Details) (USD $)
In Thousands, except Per Share data, unless otherwise specified
 3 Months Ended 12 Months Ended
Dec. 31, 2013
Sep. 30, 2013
Jun. 30, 2013
Mar. 31, 2013
Dec. 31, 2012
Sep. 30, 2012
Jun. 30, 2012
Mar. 31, 2012
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Reconciliation of income (loss) from continuing operations used in the basic and diluted EPS calculations                      
Income (loss) from continuing operations                 $ (220,768) [1] $ (314,678) [1] $ (51,010) [1]
Net (income) loss attributable to noncontrolling interests                 (718) 1,500 3,629
Income from sales of residential property               27,900 86,658 63,472 5,721
Preferred dividends                 (49,020) (42,320) (42,320)
Income (loss) from continuing operations attributable to iStar Financial Inc. and allocable to common shareholders, HPU holders and Participating Security Holders                 (183,848) (292,026) (83,980)
Numerator for basic and diluted earnings per share:                      
Gain from discontinued operations                 22,233 27,257 25,110
Net income (loss) allocable to common shareholders                 (155,769) (272,997) (62,387)
Denominator for basic and diluted earnings per share:                      
Weighted average number of common shares—basic and diluted 84,617 85,392 85,125 84,824 83,674 [2] 83,629 [2] 84,113 [2] 83,556 [2] 84,990 [1] 83,742 [1] 88,688 [1]
Weighted average number of HPU shares—basic and diluted 15 15 15 15 15 [2] 15 [2] 15 [2] 15 [2] 15 [1],[3] 15 [1],[3] 15 [1],[3]
Basic and diluted earnings per common share:                      
Income (loss) from continuing operations attributable to iStar Financial Inc. and allocable to common shareholders (in dollars per share)                 $ (2.09) [1] $ (3.37) [1] $ (0.91) [1]
Net income (loss) attributable to iStar Financial Inc. and allocable to common shareholders/HPU holders (in dollars per share) $ (0.68) $ (0.36) $ (0.31) $ (0.49) $ (1.04) [2] $ (0.86) [2] $ (0.70) [2] $ (0.66) [2] $ (1.83) [1] $ (3.26) [1] $ (0.70) [1]
Common shares
                      
Numerator for basic and diluted earnings per share:                      
Income (loss) from continuing operations attributable to iStar Financial Inc. and allocable to common shareholders                 (177,907) (282,452) (81,375)
Income (loss) from discontinued operations                 623 (16,908) (5,343)
Gain from discontinued operations                 21,515 26,363 24,331
Net income (loss) allocable to common shareholders                 (155,769) (272,997) (62,387)
Denominator for basic and diluted earnings per share:                      
Weighted average number of common shares—basic and diluted                 84,990 83,742 88,688
Basic and diluted earnings per common share:                      
Income (loss) from continuing operations attributable to iStar Financial Inc. and allocable to common shareholders (in dollars per share)                 $ (2.09) $ (3.37) $ (0.91)
Income (loss) from discontinued operations (in dollars per share)                 $ 0.01 $ (0.20) $ (0.06)
Gain from discontinued operations (in dollars per share)                 $ 0.25 $ 0.31 $ 0.27
Net income (loss) attributable to iStar Financial Inc. and allocable to common shareholders/HPU holders (in dollars per share)                 $ (1.83) $ (3.26) $ (0.70)
HPU's
                      
Numerator for basic and diluted earnings per share:                      
Income (loss) from continuing operations attributable to iStar Financial Inc. and allocable to HPU holders                 (5,941) (9,574) (2,605)
Income (loss) from discontinued operations                 21 (573) (171)
Gain from discontinued operations                 718 894 779
Net income (loss) allocable to common shareholders                 $ (5,202) $ (9,253) $ (1,997)
Denominator for basic and diluted earnings per share:                      
Weighted average number of HPU shares—basic and diluted                 15 15 15
Basic and diluted earnings per common share:                      
Income (loss) from continuing operations attributable to iStar Financial Inc. and allocable to common shareholders (in dollars per share)                 $ (396.07) $ (638.27) $ (173.66)
Income (loss) from discontinued operations (in dollars per share)                 $ 1.40 $ (38.20) $ (11.40)
Gain from discontinued operations (in dollars per share)                 $ 47.87 $ 59.60 $ 51.93
Net income (loss) attributable to iStar Financial Inc. and allocable to common shareholders/HPU holders (in dollars per share)                 $ (346.80) $ (616.87) $ (133.13)
[1] Income (loss) from continuing operations attributable to iStar Financial Inc. for the years ended December 31, 2013, 2012 and 2011 was $(221.5) million, $(313.2) million and $(47.4) million, respectively. See Note 13 for details on the calculation of earnings per share.
[2] All periods have been adjusted to reflect the impact of properties sold during 2013 and 2012 and properties classified as held for sale as of December 31, 2013, which are reflected in "Income (loss) from discontinued operations on the Consolidated Statements of Operations.(2)During the quarter ended December 31, 2012, the Company recorded a loss on early extinguishment of debt of $31.0 million primarily related to a prepayment penalty on the early repayment of 8.625% Senior Notes, as well as a loss due to the acceleration of unamortized fees and discounts related to the refinancing of the 2011 Secured Credit Facilities (see Note 8). The Company also recorded $27.9 million related to Income from sales of residential property. During the quarter ended March 31, 2012, the Madison Funds recorded a significant gain related to the sale of an investment for which the Company recorded its $13.7 million proportionate share.
[3] HPU holders are current and former Company employees who purchased high performance common stock units under the Company's High Performance Unit Program (see Note 11).