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Q4 ‘21 & FY ‘21Earnings Results (NYSE: STAR)

Statementsinthispresentationwhicharenothistoricalfactmaybedeemedforward-lookingstatementswithinthemeaningofSection27AoftheSecuritiesActof1933andSection21EoftheSecuritiesExchangeActof1934.AlthoughiStarbelievestheexpectationsreflectedinanyforward-lookingstatementsarebasedonreasonableassumptions,theCompanycangivenoassurancethatitsexpectationswillbeattained.TheCompanyundertakesnoobligationtoupdateorpubliclyreviseanyforward-lookingstatement,whetherasaresultofnewinformation,futureeventsorotherwise.ThispresentationshouldbereadinconjunctionwithourconsolidatedfinancialstatementsandrelatednotesinourAnnualReportonForm10-KfortheyearendedDecember31,2021.Inassessingallforward-lookingstatementsherein,readersareurgedtoreadcarefullytheRiskFactorssectionandothercautionarystatementsinourForm10-K.FactorsthatcouldcauseactualresultstodiffermateriallyfromiStar’sexpectationsincludegeneraleconomicconditionsandconditionsinthecommercialrealestateandcreditmarkets,theeffectoftheCOVID-19pandemiconourbusinessandgrowthprospects,theperformanceofSAFE,theCompany’sabilitytogrowitsgroundleasebusinessdirectlyandthroughSAFE,thecompletionofthependingsaleoftheCompany’snetleaseportfolio,theCompany’sabilitytogenerateliquidityandtorepayindebtednessasitcomesdue,additionalloanlossprovisionsandthepricingandtimingofanysuchsales,assetimpairments,themarketdemandforlegacyassetstheCompanyseekstosellandthepricingandtimingofsuchsales,changesinNPLs,repaymentlevels,theCompany'sabilitytomakenewinvestments,theCompany’sabilitytomaintaincompliancewithitsdebtcovenants,theCompany’sabilitytogenerateincomeandgainsfromitsportfolioandotherrisksdetailedin“RiskFactors”inour2021AnnualReportonForm10-K,andanyupdatestheretomadeinoursubsequentfillingswiththeSEC. Important Note re COVID - 19 : Readersofthispresentationarecautionedthat,duetotheuncertaintycreatedbytheCOVID-19pandemic,ourresultsforthefourthquarterand2021fiscalyearmaynotbeindicativeofourfutureresults.ReadersareurgedtoreadourAnnualReportonForm10-KfortheyearendedDecember31,2021whenitisfiledwiththeSECforamorefulsomediscussionofourfourthquarterresults,includingthe"Management'sDiscussionandAnalysisofFinancialConditionandResultsofOperations"and"RiskFactors"sectionsincludedtherein. Note : Pleaserefertothe“Glossary”sectionintheAppendixforalistofdefinedtermsandmetrics. Forward-Looking Statements and Other Matters1 Investor Relations Contact Jason FooksSenior Vice President212.930.9400investors@istar.com

I. Highlights 2

Q4 ‘21 Highlights3(1) A definitive sales agreement was signed on 2/2/22. Closing is subject to customary closing conditions and there can be noassurance that the transaction will close. For more information, please refer to the Form 8-K filed with the SEC on 2/2/22.(2) Estimates are subject to increase or decrease based upon the final purchase price allocations, customary prorations and the exact closing date, and are net of estimated distributions to its venture partner, debt prepayment fees, closing costs, promote fees, and distributions under iStar’slong-term incentive plan, iPIP. $777mNew Originations at Safehold$1.4bIncrease in UCA at Safehold $140mLegacy Asset & Strategic Asset Sales Proceeds$34mGains from Legacy Asset Sales $3.07bGross Sales Price ofNet Lease Assets(1)~$525mEstimated Net Positive Impact to Common Equity (1)(2) Signed PSA on NLA Portfolio Momentum at Safehold Simplifying the Business (Signed subsequent to the end of the quarter)

Earnings Results4 Q4 ‘21 Q4 ’ n ∆ FY ‘21 FY ‘ 20 Y/Y P Net Income (Loss) (Allocable to Common Shareholders)$7.1m($19.1m) +$26.2m $109.0m($65.9m) +$174.9m W.A. Shares (Diluted)69.3m74.1m71.8m75.7m EPS (Loss) - Continuing Operations (Diluted)($0.68)($0.55)($0.10)($1.85) EPS (Loss) - Discontinued Operations (Diluted) $0.79$0.29$1.61$0.98 EPS (Loss) (Diluted)$0.11($0.26) +$0.37 $1.51($0.87) +$2.38 Adj. Earnings (Allocable to Common Shareholders)$68.9m$11.0m +$57.9m $244.9m$40.8m +$204.1m W.A. Shares (Diluted)78.8m74.3m78.5m75.9m AEPS (Diluted)$0.87$0.15 +$0.72 $3.12$0.54 +$2.58 Note: Please refer to the “Adjusted Earnings Reconciliation” section of the Appendix for more information with regard tothe calculation of this metric.

Net Lease Transaction5 (1) iStar uses adjusted common equity, a non-GAAP financial measure, as a supplemental measure to give management a view of equity allocable to common shareholders prior to the impact of certain non-cash GAAP measures. See pages 19 and 26 for more information and a reconciliation to common equity.(2) Estimates are subject to increase or decrease based upon the final purchase price allocations, customary prorations and the exact closing date, and are net of estimated distributions to its venture partner, debt prepayment fees, closing costs, promote fees, and distributions under iStar’slong-term incentive plan, iPIP. In Q1 ‘22, iStar signed a definitive agreement to sell a portfolio of net lease assets for a gross purchase price of $3.07 billion. Transaction Overview ~$290mEstimated Impact to Adjusted Common Equity(1) Q4 ‘21 Impact Q1 ‘22 Estimated Impact(2) ~$565mEstimated Impact to Net Income / Common Equity ~$1.1bEstimated Net Cash Proceeds(After repayment of mortgage debt, full repayment of its secured term loan, debt prepayment fees, partner distributions, transaction fees, and other miscellaneous items) -$40mNet expenses associated with the net lease sale transactionIn Q4 ‘21, iStar moved all assets and liabilities related to the transaction to “held for sale” and the associated revenues and expenses for this period and historical periods were moved to discontinued operations.

iStar’sInvestment in Safehold $2.5bMarket Value(1)$2.2bMarket Value(1)$1.0bGross Book Value$1.2bGross Book ValueQ4 '20Q4 '21Safehold Results6Note: Please refer to SAFE’s Annual Report on Form 10-K for the year ended 12/31/21 and the SAFE Earnings Presentation dated February 15, 2022, each of which is available on SAFE’s website for more information and a Glossary of defined terms.(1) Q4 ‘21 market value of iStar’sinvestment in Safehold is $2,151m calculated as iStar’sownership of 36.6m shares of SAFE at the February 23, 2022 closing stock price of $58.78. Q4 ‘20 market value of iStar’sinvestment in Safehold is $2,521m, calculated as iStar’sownership of 34.8m shares of SAFE at the December 31, 2020 closing stock price of $72.49. $1.0bUnrealized Gain$1.6bUnrealizedGain o17 ground leases totaling $777m closed by Safehold in Q4 ‘21oCompleted inaugural private sale of Caret Units based on a $1.75b valuation of Caret In Q1 ‘22, Safehold sold and received commitments to sell 1.37% of the total Caret Units for $24.0 million at a valuation of $1.75b, from a group of leading private equity, sovereign wealth and high net worth investors. Safehold is obligated to seek to provide public market liquidity for the Caret Units within the next two years. If Safehold is unable to achieve a public market liquidity event at a value in excess of the New Investors’ basis, they would have the option to redeem their Caret Units at par. Path to LiquidityCaret Transaction OverviewSelected SAFE Reported Results

Asbury Park$229m68%Magnolia Green$108m32% $299m $473m$137m $252mQ4 '21Q4 '20 Land & Development Operating PropertiesLegacy Asset Progress 7$42mQ4 ‘21 Legacy Asset Sales ProceedsCount: 11 AssetsAvg. GBV: $9m$337m$99m $34mQ4 ‘21 Gains from Legacy Asset Sales $725m$436m -40%Year-over-year Legacy Asset ReductionNote: Figures are presented using Gross Book Value. Please refer to the Glossary for more details. Short-Term Legacy AssetsLong-Term Legacy Assets

Investment Activity8 $40mLoan, Net Lease, GL+, and Other Fundings $31mSTAR ShareRepurchases $8mLegacy CapEx $43mInvestmentin SAFE $122m

$5.8b Diversified PortfolioNote: Figures based on Gross Book Value of the Company’s total investment portfolio, adjusted to present the investment in SAFE at market value, and includes 100% of the assets of iStar’s consolidated joint ventures, the carrying value of iStar’s investment in non-consolidated joint ventures and affiliates (other than SAFE).(1) SAFE market value is calculated as iStar’sownership of 36.6m shares of SAFE at the February 23, 2022 closing stock price of $58.78. 9 Ground Leases$2,255m39%Entertainment / Leisure$1,042m18%Office$905m15%Industrial / Lab$450m8%Cash$340m6%Land$246m4%Hotel$192m3%Multifamily$155m3%Retail$102m2%Condo$72m1%Other$46m<1%PropertyType(1) Northeast$1,702m29%West$1,040m18%Mid Atlantic$858m15%Southeast$648m11%Southwest$583m10%Central$509m9%Cash$340m6%Various$125m2%GeographicRegion(1) SAFE$2,151m37%Net Lease$2,240m39%Net Lease (Remaining Pro Forma NLA Sale)$192m3%RE Finance$386m7%Cash$340m6%Land & Development$299m5%Operating Properties$179m3%Strategic Investments$18m<1%Business Line(1)

Equity Value per Share Adj. Common Equity per Share(1)(Gross of Depreciation, Amortization and CECL Allowance)Common Equity per Share(1)(Net of Depreciation, Amortization and CECL Allowance)(w/ SAFE MTM)(2)Note: Q4 ‘21 SAFE mark-to-market value of iStar’sinvestment in Safehold is $2,151m, calculated as iStar’sownership of 36.6m shares of SAFE at the February 23, 2022 closing stock price of $58.78. Q4 ‘20 SAFE mark-to-market value of iStar’sinvestment in Safehold is $2,521m calculated as iStar’sownership of 34.8m shares of SAFE at the December 31, 2020 closing stock price of $72.49. (1) Presented diluted for the 2022 3.125% convertible notes which were “in the money” on December 31, 2021 based on the conversion ratio of 71.9478 shares per $1,000 of principal (a conversion price of $13.90 per share) using the Q4 ’21 average closing stock price. The convertible notes were “out of the money” on December 31, 2020.(2) A portion of the profits realized on iStar’sinvestment portfolio, including the sale of the net lease portfolio and, its investment in SAFE, is allocable to iPip, iStar’sshareholder-approved long-term incentive plan. Additional information on iStar’siPipcan be found in the 2021 Annual Report on Form 10-K and its 2021 Proxy Statement, both of which are available on our website.(3) Figures are shown pro forma for the sale of the net lease asset portfolio using the currently estimated remaining $565m gainto net income and common equity and the currently estimated remaining $290m gain to adjusted common equity. The transaction is expected to close in Q1 ’22. Closing is subject to customary closing conditions and there can be no assurance that the transaction will close. Estimates are subject to increase or decrease based upon the final purchase price allocations, customaryprorations and the exact closing date, and are net of estimated distributions to its venture partner, debt prepayment fees, closing costs, promote fees, and distributions under iStar’slong-term incentive plan, iPIP. 10(w/ SAFE MTM)(2)(w/ SAFE MTM)(2)(w/ SAFE MTM)(2) (Pro Forma NLA Sale)(2)(3)(Pro Forma NLA Sale)(2)(3) $12.68$11.81$33.75$23.97$27.69Q4 '20Q4 '21 $7.65$7.00$29.05$19.58$26.82Q4 '20Q4 '21

II. PortfolioOverview11

Investment in Safehold (NYSE: SAFE)12Note: $ in millions. Please refer to SAFE’s Annual Report on Form 10-K for the year ended 12/31/21 and the SAFE Earnings Presentation dated February 15, 2022, each of which is available on SAFE’s website for more information and a Glossary of defined terms.(1) iStar’sdiscretionary voting in SAFE is capped at 41.9% and will vote remaining shares with respect to any matter in the same proportions as SAFE’s non-iStar shareholders.iStar’sinvestment in SAFE—36.6m shares (64.6% of shares outstanding)(1)—Gross Book Value of $1,201m or $32.83 per share—Market value of SAFE shares owned by iStar is $2.2b based on closing price of $58.78 per share on February 23, 2022 >60 yrs92%<20 yrs5%20-60 yrs3%Lease Term Remaining (w/ Extensions) Office$2,366m50%Multifamily$1,544m34%Hotel$668m15%Other$21m<1%Property Type Northeast$1,716m37%West$1,095m24%Mid Atlantic$757m16%Southeast$550m12%Southwest$342m7%Central$139m4%GeographicRegion Q4 ‘21FY ’21Revenue$52.0m$187.0mNet Income$21.3m$73.1mEPS$0.38$1.35SAFE Earnings

Note: $ in millions. Please refer to the “Glossary” section of the Appendix for additional details regarding definitions and calculations. The Company has entered into a definitive agreement to sell its net lease portfolio. See p. 5 of this presentation and the 8-K filed with the SEC on 2/2/22 for more information.Net Lease Consolidated Assets13 Wholly - Owned (100% Ownership) Net Lease Venture (51.9% Ownership) Total Consolidated Gross Book Value $1,3m $911m $2,299m Occupanc 9.9% 100.0% 99.3% Square Feet (000s) 9,620 5,55 15,35 ..A. Remaining Lease Term 19. rs 15.9 rs 1.0 rs ..A. ield ..% ..0% ..% 15 ears11%510 ears9% 10 ears0%.A. Remaining Lease Term Northeast$535m23%Southwest$20m1%Central$01m1%id Atlantic$3m16%est$31m1%Southeast$2m11%Various$m0%Geographic Region Entertainment / Leisure$1,025m%Office$52m3%ndustrial / Lab$336m15%Ground Lease$6m%Propert Tpe

1-5 years46%5-10 years11%> 10 years43%W.A. Remaining Lease TermNote: $ in millions. Table and pie charts presented at the venture level. Please refer to the “Glossary” section of the Appendixfor additional details regarding definitions and calculations. The Company has entered into a definitive agreement to sell its net lease portfolio. See p. 5 of this presentation and the 8-K filedwith the SEC on 2/2/22 for more information.Net Lease Venture II14 Southeast$171m60%Mid Atlantic$84m29%West$31m11%Geographic Region Net Lease Venture II (51.9% Ownership) Gross Book Value $26m Occupanc100.0%Square Feet (000s)3,220.A. Remaining Lease Term10.6 rs.A. ield9.3% Net Lease Venture is unconsolidated and 51.9% owned b iStar. Presented here at the venture level. ndustrial / Lab$26m100%Propert Tpe

Top Net Lease Assets15 Tenant (Sorted by GBV) Property Type Location Portfolio Inv. Grade Lease Term Remaining Annualized Base Rent Contractual Rent Escalator Bowlero (2 Master Leases)Entertainment147 LocationsWholly-Owned25.4 yrs$33.7m(1)Fixed BumpsBowlero(Master Lease)Entertainment58 LocationsNLJV I22.8 yrs$18.4mFixed BumpsMcCormick & Co.OfficeCockeysville, MDNLJV I*12.3 yrs$11.2mFixed BumpsCox AutomotiveOfficeNorth Hills, NYNLJV I *12.5 yrs$8.4mFixed Bumpsw/ CPI AdjustmentsIndeedOfficeAustin, TXWholly-Owned*12.0 yrs$10.6mFixed BumpsAMC Theaters (Master Lease)Entertainment3 LocationsWholly-Owned13.1 yrs$7.4mFixed Bumps + % RentNYSE-Listed Transportation Services CompanyIndustrial2 LocationsNLJV II23.8 yrs$8.1mFixed BumpsLeading Financial Services CompanyOfficeJersey City, NJWholly-Owned*11.0 yrs$10.1mFixed BumpsAT&TOfficeOakton, VANLJV I*3.9 yrs$7.2mFixed BumpsBellisioFoodsIndustrialJackson, OHNLJV I23.8 yrs$6.8mCappedCPI Adjustments Total/W.A. 18.5 yrs $121.9m Top 10 net lease assets, which represent a total of $1.6b of Gross Book Value, or 63% of the aggregate $2.6b of Gross Book Value of the combined consolidated and unconsolidated portfoliosNote: Sorted by Gross Book Value, based on the value of the asset assuming 100% ownership. Annualized Base Rent (ABR) representsannualized cash rent assuming 100% ownership. iStar’sequity interest in each of NLJV I and II is 51.9%. The Company has entered into a definitive agreement to sell its net lease portfolio. See p. 5 of this presentation and the 8-K filed with the SEC on 2/2/22 for more information.(1) iStar reached an agreement with Bowleroto defer a total of $23 million of rent owed during the period from October 2020 to June 2021. The deferred rent will accrue with interest to be repaid over two years commencing January 1, 2023. The ABR is presented as the next twelve-month rent.

Real Estate FinanceNote: $ in millions. Excludes loan receivable included in other lending investments and CECL allowances. Please refer to the “Glossary” section of the Appendix for additional details regarding definitions and calculations.(1) Includes $49m pro rata share of loans held within a joint venture.(2) Excludes nonperforming loans.16 Loans ($)W.A. W.A. YieldW.A. MaturityLast $ LTV(yrs)First mortgages / Senior debt(1)$189m62%7.6%0.6Mezzanine / Subordinated debt13m79%10.5%22.6Other lending investments125m-6.6%6.8 Total Performing Loans $327m 63% 7.5% 3.9 NPL59m Total Real Estate Finance $386m Hotel$109m28%Multifamily$108m28%Retail$62m16%Office$52m14%Other$28m7%Condo$15m4%Land$12m3%PropertyType West$145m37%Northeast$100m26%Various$97m25%Central$14m4%Southeast$30m8%GeographicRegion Floating 55%Fixed45%RateType(2)

III. Capital Structure17

Credit Metrics18Note: Figures are presented using the SAFE mark-to-market value of iStar’sinvestment in Safehold. Q4 ‘21 market value is $2,151m, calculated as iStar’sownership of 36.6m shares of SAFE at the February 23, 2022 closing stock price of $58.78. Figures to not give effect to the pending net lease sale; therefore, they are not indicative of future results if the net lease sale closes as expected.(1) Leverage is calculated as the ratio of debt, net of cash, to adjusted total equity gross of non-controlling interests, or “NCI”, and applying the SAFE MTM adjustment. Please refer to the “Capital Structure Overview” section of the presentation for more information.(2) Includes only iStar’sshare of NLJV I debt. Unencumbered Asset Base Unsecured Debt / Total Debt(2)UA / UDLeverage(1) $4.4b 2.1x1.2x1.6x 1.2x 68%

Capital Structure OverviewNote: Please refer to the “Adjusted Common Equity Reconciliation” section of the Appendix for more information.(1) SAFE mark-to-market calculations based on the February 23, 2022 closing stock price of $58.78 with respect to 36.6m shares held by iStar.(2) Corporate leverage is the ratio of total debt less cash and cash equivalents divided by Adjusted Total Equity, gross of NCI.(3) Includes accumulated depreciation, amortization, CECL allowance, and iStar’sproportionate share of accumulated depreciation and amortization relating to equity method investments. (4) Includes $48m of the proportionate share of accumulated depreciation and amortization relating to noncontrolling interests. (5) Represents liquidation preference of preferred equity. (6) Presented diluted for the 2022 3.125% convertible notes which were “in the money” on December 31, 2021 based on their current conversion ratio of 71.9478 shares per $1,000 of principal, which represents a conversion price of $13.90 per share using the Q4 ‘21 average closing stock price. (7) Includes $451m of consolidated, asset-specific non-recourse mortgage debt of NLJV I.(8) Debt is presented net of fees and discounts. (9) Figures are shown pro forma for the sale of the net lease asset portfolio using the currently estimated remaining $565m gainto net income and common equity and the currently estimated remaining $290m gain to adjusted common equity. The transaction is expected to close in Q1 ’22. Closing is subject to customary closing conditions and there can be no assurance that the transaction will close. Estimates are subject to increase or decrease based upon the final purchase price allocations, customary prorations and the exact closing date, and are net of estimated distributions to its venture partner, debt prepayment fees, closing costs, promote fees, and distributions under iStar’slong-term incentive plan, iPIP .. Preferred Equity - $305m(5) Adjusted Total Equity $1.5b Total Debt $3.3b(8) Noncontrolling Interest - $260m(4) Adjusted Common Equity $0.9b Secured Debt $1.2b(7)19 Common Equity $546m Acc. D&A/CECL Allow. - $375m(3) Credit Metrics 12/31/21 SAFE MTM (1) SAFE MTM & Pro Forma for NLA Sale (1)(9) Cash$340m$340m$1,440mDebt$3,286m$3,286m$2,082mDebt, net of cash$2,947m$2,947m$642mTotal Equity, gross of NCI$1,063m$2,046m$2,415mAdj. Total Equity, gross of NCI$1,487m$2,436m$2,483mLeverage(2)2.0x1.2x0.3x Shares Shares Outstanding(6)78.1m78.1m78.1mCommon Equity$546m$1,529m$2,094mCommon Equity per Share$7.00$19.58$26.82Adj. Common Equity$922m$1,872m$2,162mAdj. Common Equity per Share$11.81$23.97$27.69 Liquidity Cash$340mRevolving Credit Facility Availability$278mTotal Liquidity$618m Senior Unsecured Debt $2.1bAs of 12/31/21

Debt Profile2022(1)Sep.$288m3.125%2023Jun.$492mL+ 2752024 Oct.$775m4.75%2025 Aug.$550m4.25%2026Feb.$400m5.50%2035 Oct.$100mL + 150Non-Recourse MortgageFinancings(2)Various / W.A.(4)$717m4.38% Total / W.A. (3) $3,321m 4.16% Corporate Debt Maturity ProfileNote: $ in millions. Excludes extension options and revolving credit facility which was undrawn as of December 31, 2021. Amountsare not pro forma for the net lease sale.(1) The 2022 3.125% convertible notes were “in the money” on December 31, 2021 with a conversion price of $13.90 per share and aconversion of 71.9478 shares per $1,000 of principal using the Q4 ‘21 average closing stock price.(2) Represents individual non-recourse mortgages on net lease assets, including consolidated mortgage debt on assets held by NLJV I. (3) Rates presented after giving effect to interest rate hedges. (4) $654m of the debt is to be repaid in connection with the announced NLA sale.20 3.6 yearsw.a.debtmaturity $775m$550m$400m$100m$492m$288m Unsecured Debt Secured Term Loan Convertible NotesTo be repaid in connection with NLA sale

IV. Appendix21

Consolidated Statements of OperationsNote:$inthousands.22 Three Months Twelve Months Ended December 31, Ended December 31, 2021 2020 2021 2020 RevenuesOperating lease income $3,369 $5,151 $16,824 $24,276 Interest income 6,383 12,346 31,229 56,676 Interest income from sales-type leases 532 - 1,215 - Other income 9,310 26,402 70,259 78,445 Land development revenue 31,166 48,447 189,103 164,702 Total revenues $50,760 $92,346 $308,630 $324,099 Cost and ExpensesInterest expense $29,255 $30,956 $115,400 $126,828 Real estate expense 12,590 11,696 45,994 46,083 Land development cost of sales 24,454 63,023 171,961 177,727 Depreciation and amortization 1,356 1,842 7,072 7,327 General and administrative 16,788 15,063 62,442 61,525 General and administrative –stock-based compensation 45,961 12,679 69,261 39,354 Provision for (recovery of) for loan losses (675) 4,985 (8,085) 8,866 Recovery of net investment in leases (464) - - - Impairment of assets - 1,336 678 5,791 Other expense 6,756 219 8,114 569 Total costs and expenses $136,021 $141,799 $472,837 $474,070 Income from sales of real estate - 201 26,319 6,318 Loss from operations before earnings from equity method investments and other items ($85,261) ($49,252) ($137,888) ($143,653) Earnings from equity method investments 43,683 15,037 154,344 39,472 Income tax benefit (expense) - 16 118 (89) Loss on early extinguishment of debt - - - (12,038) Income from discontinued operations 52,037 24,143 121,452 85,455 Net income (loss) $10,459 ($10,056) $138,026 ($30,853) Net (income) loss from continuing operations attributable to noncontrolling interests 20 (468) 75 (337) Net (income) from discontinued operations attributable to noncontrolling interests 2,472 (2,685) (5,620) (11,251) Net income (loss) attributable to iStar $12,951 ($13,209) $132,481 ($42,441) Preferred dividends (5,874) (5,874) (23,496) (23,496) Net income (loss) allocable to common shareholders $7,077 ($19,083) $108,985 ($65,937)

Earnings per ShareNote:Inthousands,exceptpersharedata.(1)Allocabletocommonshareholdersaftertheeffectofpreferreddividends,non-controllinginterestsandincomefromsalesofrealestate.23 Three Months Twelve Months Ended December 31, Ended December 31, Earnings Information for Common Shares 2021 2020 2021 2020 Net loss from continuing operations and allocable to common shareholdersBasic& Diluted($0.68)($0.55)($0.10)($1.85)Net income from discontinued operations and allocable to common shareholdersBasic & Diluted$0.79$0.29$1.61$0.98Net income allocable to common shareholders$0.11($0.26)$1.51($0.87)Adjusted earningsBasic$0.99$0.15 $3.41 $0.54Diluted$0.87$0.15$3.12$0.54Weighted average shares outstandingBasic & Diluted (for net income)69,32874,05371,83175,684Diluted (for adjusted earnings)78,79874,33078,49475,908Common shares outstanding at the end of period68,87073,96768,87073,967

Adjusted Earnings Reconciliation24 Three Months Twelve Months Ended December 31, Ended December 31, 2021 2020 2021 2020 Net income (loss) allocable to common shareholders$7,077($19,083)$108,985($65,937)Add: Depreciation and amortization15,83817,35766,62963,882Add: Stock-based compensation expense45,96112,67969,26139,354Add: Non-cash loss on early extinguishment of debt/preferred---3,470 Adjusted earnings allocable to common shareholders $68,876 $10,953 $244,875 $40,769 Note: $ in thousands. In 2019, we announced a new business strategy that would focus our management personnel and our investment resources primarily on scaling our Ground Lease platform. As part of this strategy, we accelerated the monetization of legacy assets, reducing our legacy portfolio to approximately 9% of our overall portfolio as of December 31, 2021, and deployed a substantial portion of the proceeds into additional investments in SAFE and new loan and net lease originations relating to the Ground Leasebusiness. Adjusted earnings is a non-GAAP metric management uses to assess our execution of this strategy and the performance of our operations. Adjusted earnings is used internally as a supplemental performance measure adjusting for certain items to give management a viewof income more directly derived from operating activities in the period in which they occur. Adjusted earnings is calculated as net income (loss) allocable to common shareholders, prior to the effect of depreciation and amortization, including our proportionate share of depreciation and amortization from equity method investments and excluding depreciation and amortization allocable to noncontrolling interests, stock-based compensation expense, the non-cash portion of loss on early extinguishment of debt and the liquidation preference recorded as a premium above book value on the redemption of preferred stock (“Adjusted Earnings”). Adjusted Earnings should be examined in conjunction with net income (loss) as shown in our consolidated statements of operations. Adjusted Earnings should not be considered as an alternative to net income (loss) (determined in accordance with generally accepted accounting principles in the United StatesofAmerica (“GAAP”)), or to cash flows from operating activities (determined in accordance with GAAP), as a measure of our liquidity, nor is Adjusted Earnings indicative of funds available to fund our cash needs or available for distribution to shareholders. Rather, Adjusted Earnings is an additional measure we use to analyze our business performance because it excludes the effectsofcertain non-cash charges that we believe are not necessarily indicative of our operating performance. It should be noted that our manner of calculating Adjusted Earnings may differ from thecalculations of similarly-titled measures by other companies.

Consolidated Balance SheetsNote:$inthousands.25 As of As of December 31, 2021 December 31, 2020 Assets Real EstateReal estate, at cost $113,510 $209,952 Less: accumulated depreciation (21,360) (17,574) Real estate, net 92,150 192,378 Real estate available and held for sale 301 5,212 Total real estate 92,451 197,590 Real estate and other assets available and held for sale and classified as discontinued operations 2,299,711 2,228,570 Net investment in leases 43,215 - Land and development, net 286,810 430,663 Loans receivable and other lending investments, net 332,844 686,931 Loan receivable held for sale 43,215 - Other investments 1,297,281 1,097,562 Cash and cash equivalents 339,601 98,633 Accrued interest and operating lease income receivable, net 1,813 6,135 Deferred operating lease income receivable, net 3,159 2,905 Deferred expenses and other assets, net 100,434 112,819 Total Assets $4,840,534 $4,861,808 Liabilities and Equity Accounts payable, accrued expenses, and other liabilities $236,732 $194,961 Liabilities associated with real estate held for sale and classified as discontinued operations 968,419 990,656 Liabilities associated with properties held for sale 3 27 Loan participations payable, net - 42,501 Debt obligations, net 2,572,174 2,569,280 Total Liabilities $3,777,328 $3,797,425 Total iStar shareholders’ equity $851,296 $870,969 Noncontrolling interests 211,910 193,414 Total Equity $1,063,206 $1,064,383 Total Liabilities and Equity $4,840,534 $4,861,808

Adjusted Common Equity ReconciliationNote: Amounts in thousands, except for per share data. Q4 ‘21 SAFE mark-to-market value of iStar’sinvestment in Safehold is $2,151m, calculated as iStar’sownership of 36.6m shares of SAFE at the February 23, 2022 closing stock price of $58.78. Q4 ‘20 SAFE mark-to-market value of iStar’sinvestment in Safehold is $2,521m calculated as iStar’sownership of 34.8m shares of SAFE at the December 31, 2020 closing stock price of $72.49. We use adjusted common equity, a non-GAAP financial measure, as a supplemental measure to give management a view of equity allocable to common shareholders prior to the impact of certain non-cash GAAP measures. Management believes that adjusted common equity provides a useful measure for investors to consider in addition to total shareholders’ equity because cumulative effect of depreciation and amortization expenses and CECL allowances calculated under GAAP may not necessarily reflect an actual reduction in the value of the Company’sassets. Adjusted common equity should be examined in conjunction with total shareholders’ equity as shown on the Company’s consolidated balance sheet. Adjusted common equity should not be considered analternative to total shareholders’ equity (determined in accordance with GAAP), nor is adjusted common equity indicative of funds available for distribution to shareholders. It should be noted that our manner of calculating adjusted common equity may differ from the calculations of similarly-titled measures by other companies.(1) Net of amounts allocable to non-controlling interests and includes accumulated depreciation and amortization associated withreal estate available and held for sale.(2) Presented diluted for the 2022 3.125% convertible notes which were “in the money” on December 31, 2021 based on their current conversion ratio of 71.9478 shares per $1,000 of principal, which represents a conversion price of $13.90 per share using the Q4 ‘21 average closing stock price. The convertible notes were “out of the money”on December 31, 2020.26 As of December 31, 2021 As of December 31, 2020 Total shareholders' equity$851,296$870,969Less: Liquidation preference of preferred stock(305,000)(305,000)Common shareholders equity$546,296$565,969Add: Accumulated depreciation and amortization(1)316,817298,180Add: Proportionate share of depreciation and amortization within equity method investments54,71649,640Add: CECL allowance4,26524,326 Adjusted common equity $922,094 $938,116 Common shares outstanding –basic68,87073,967Common shares outstanding –convertible dilution(2)78,07473,967Common equity per share with convertible dilution(2)$7.00$7.65Common equity per share with SAFE MTM and convertible dilution(2)$19.58$29.05Common equity per share pro forma for net lease sale with SAFE MTM and convertible dilution(2)$26.82-Adjusted common equity per share with convertible dilution(2)$11.81$12.68Adjusted common equity per share with SAFE MTM and convertible dilution(2)$23.97$33.75Adjusted common equity per share pro forma for net lease sale with SAFE MTM and convertible dilution(2)$27.69-

Q4 ‘21 Gross Book Value ReconciliationNote: $ in millions. Figures in this table may not foot due to rounding.(1) Market value of iStar’sinvestment in Safehold is $2,151m, calculated as iStar’sownership of 36.6m shares of SAFE at the February 23, 2022 closing stock price of $58.78. Unrealized gain is calculated as the difference between the $2,151m market value and the $1,201m Gross Book Value of iStar’sinvestment in Safehold.27 Real Estate Finance Net Lease Operating Properties Land & Development Corporate / Other Total Real estate, net-- $92 --$92Real estate available and held for sale--<1--<1Net lease properties and other assets available and held for sale$1,9041,904Net investment in leases-43---43Land and development, net---$287-287Loans receivable and other lending investments, net$333----333Loan receivable held for sale-43---43Real estate-related intangibles, net-1032--105Other investments491,186431$181,297 Net Book Value $382 $3,279 $138 $288 $18 $4,104 Add: Accumulated depreciation and CECL allowance42712111-308Add: Accumulated amortization related to intangibles & leasing commission amortization - 3710--46Add: Proportionate share of joint venture accumulated depreciation and amortization - 4410--55 Gross Book Value $386 $3,633 $179 $299 $18 $4,515 Add: Cash----340340Add: SAFE MTM(1)-950---950 Portfolio Gross Book Value $386 $4,582 $179 $299 $358 $5,804

Glossary Annualized Base Rent (ABR)Contractual cash base rent for the current quarter, annualized.Dilution GainIn circumstances where Safehold issues new equity that results in iStar having a smaller percentage ownership after the issuance than before the issuance, iStar shall account for the transaction pursuant to ASC 323-10-40-1: whereby iStar shall account for a share issuance by Safehold as if iStar had sold a proportionate share of its investment. Any gain or loss to iStar resulting from Safehold’s share issuance shall be recognized in earnings.Funding / Capex (NetLease, Operating Properties, Land & Development)Acquisition price, capitalized acquisition costs, capital expenditures,contributions to equity method investments, capitalized payroll and capitalized interest.Funding / Capex(Real Estate Finance)Cash funded on loans, plus deferredinterest capitalized to the loan balance, exclusive of original issued discount, origination and arrangement fees held back at origination.Gross Book Value(NetLease, Operating Properties, Land & Development)Basis assigned to physical real estate property (net investment in leases, land & building), net of any impairments taken after acquisition date and net of basis reductions associated with unit / parcel sales, plus our basisin equity method investments, plus lease related intangibles, capitalized leasing costs and excluding accumulated depreciation and amortization, and for equity method investments, excluding the effect of our share of accumulated depreciation and amortization. Gross Book Value(RealEstate Finance)Principal funded including any deferred capitalized interest receivable, plus protective advances, exit fee receivables and any unamortized origination / modification costs,plus our basis in equity method investments, less purchase discounts and specific reserves. This amount is not reduced for CECL allowances.Net Book Value(Net Lease, OperatingProperties, Land & Development)Gross Book Value net of accumulated depreciation and amortization.Net Book Value (Real Estate Finance)Gross Book Value for Real Estate Finance less CECL allowances.Proceeds (Net Lease, OperatingProperties, Land & Development)Includes sales price for assets sold and other proceeds, less selling costs, less seller financing plus return of capital and distributed proceeds arising from sales within our equity method investments.Proceeds (Real Estate Finance)Collection of principal, deferred and capitalized interest, exit fees, origination fees previously netted against principal at inception, or original issue discount. Includes proceeds from sales of securities.Yield (Net Lease)Calculated as GAAP operating lease income and interest income from sales-type leases less operating expenses for the quarter, annualized, divided by the average Gross Book Value during the quarter.Yield (Real Estate Finance)Interest income, for the quarter, annualized, divided by the average Gross Book Value of Real Estate Finance.28 Disclaimer: Set forth in the Glossary are the current definitions of certain items that we use in this presentation. This Glossary is intended to facilitate a reader’s understanding of this presentation. There can be no assurance that we will not modify these terms in future presentations as we deem necessary or appropriate.