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UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): November 3, 2022

iStar Inc.

(Exact name of registrant as specified in its charter)

Maryland

1-15371

95-6881527

(State or other jurisdiction of incorporation)

(Commission File Number)

(IRS Employer Identification No.)

1114 Avenue of the Americas, 39th Floor

New York, New York 10036

(Address of principal executive offices, including zip code)

Registrant’s telephone number, including area code: (212) 930-9400

N/A

(Former name or former address, if changed since last report.)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instruction A.2. below):

 Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

 Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

 Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

 Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class

    

Trading Symbol(s)

    

Name of each exchange on which registered

Common Stock, $0.001 par value

 

STAR

 

New York Stock Exchange

8.00% Series D Cumulative Redeemable Preferred Stock, $0.001 par value

STAR-PD

New York Stock Exchange

7.65% Series G Cumulative Redeemable Preferred Stock, $0.001 par value

STAR-PG

New York Stock Exchange

7.50% Series I Cumulative Redeemable Preferred Stock, $0.001 par value

STAR-PI

New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.

Item 2.02Results of Operations and Financial Condition.

On November 3, 2022, iStar Inc. issued an earnings release and made available on its website an earnings presentation for the quarter ended September 30, 2022. A copy of the earnings release and earnings presentation are attached as Exhibit 99.1 and Exhibit 99.2, respectively, hereto and incorporated herein by reference.

The information in this Current Report, including the exhibits hereto, is being furnished and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended, unless it is specifically incorporated by reference therein.

Item 7.01Regulation FD Disclosure.

On November 3, 2022, iStar Inc. made available on its website an earnings presentation for the quarter ended September 30, 2022. A copy of the earnings presentation is attached as Exhibit 99.2 hereto and incorporated by reference.

The earnings presentation, including Exhibit 99.2 hereto, is being furnished and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended, unless it is specifically incorporated by reference therein.

Item 9.01Financial Statements and Exhibits.

Exhibit 99.1Earnings Release

Exhibit 99.2Earnings Presentation

Exhibit 104Inline XBRL for the cover page of this Current Report on Form 8-K.

SIGNATURE

Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the Registrant has duly caused this Report to be signed on its behalf by the undersigned, thereunto duly authorized.

iStar Inc.

Date:

       November 3, 2022

By:

/s/ BRETT ASNAS

Brett Asnas

Chief Financial Officer

(principal financial officer)

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Exhibit 99.1

Press Release

iStar Reports Third Quarter 2022 Results

NEW YORK, November 3, 2022

iStar Inc. (NYSE: STAR) today reported results for the third quarter ended September 30, 2022.

Highlights for the quarter include:

oNet income of $12.1 million or $0.14 per diluted common share
oAdjusted earnings of $28.5 million or $0.33 per diluted common share
oDuring the quarter, extinguished $155 million of debt including $93 million of convertible notes and $62 million of open market bond repurchases
o$105 million of proceeds from legacy asset sales and loan repayments
oSafehold closed $284 million1 of new originations, bringing Safehold’s total aggregate portfolio to $6.1 billion and total UCA to approximately $10.5 billion

“iStar continues to focus on streamlining its balance sheet, monetizing its legacy assets and expanding the ground lease ecosystem,” said Jay Sugarman, Chairman and Chief Executive Officer. “Together with Safehold, we look forward to unlocking the full value of the ground lease platform we have built.”

The Company published a presentation detailing its results and a reconciliation of non-GAAP financial metrics, which can be found on its website, in the "Investors" section.

1 Investments in Q3 ‘22 include $29m of new forward commitments that have not yet been funded. Such funding commitments are subject to certain conditions. There can be no assurance that Safehold will complete these transactions.

1114 Avenue of the Americas

New York, NY 10036
T 212.930.9400
E investors@istar.com


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The Company will host an earnings conference call reviewing this presentation beginning at 10:00 a.m. ET. This conference call will be broadcast live and can be accessed by all interested parties through iStar's website and by using the dial-in information listed below:

Dial-In:

877.545.0523

International:

973.528.0016

Access Code:

923085

A replay of the call will be archived on the Company’s website. Alternatively, the replay can be accessed via dial-in from 2:00 p.m. ET on November 3, 2022 through 12:00 a.m. ET on November 17, 2022 by calling:

Replay:

877.481.4010

International:

919.882.2331

Access Code:

46958

iStar Inc. (NYSE: STAR) is focused on reinventing the ground lease sector, unlocking value for real estate owners throughout the country by providing modern, more efficient ground leases on institutional quality properties. As the founder, investment manager and largest shareholder of Safehold Inc. (NYSE: SAFE), the creator of the modern ground lease industry, iStar is using its national investment platform and its historic strengths in finance and net lease to expand the use of modern ground leases within the $7 trillion institutional commercial real estate market. Recognized as a consistent innovator in the real estate markets, iStar specializes in identifying and scaling newly discovered opportunities and has completed more than $40 billion of transactions over the past two decades. Additional information on iStar is available on its website at www.istar.com.

1114 Avenue of the Americas

New York, NY 10036
T 212.930.9400

E investors@istar.com


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Company Contact:

Jason Fooks

Senior Vice President

Investor Relations & Marketing

T 212.930.9400

E investors@istar.com

1114 Avenue of the Americas

New York, NY 10036
T 212.930.9400

E investors@istar.com


Exhibit 99.2

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Q3 ‘22Earnings Results (NYSE: STAR)

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Statementsinthispresentationwhicharenothistoricalfactmaybedeemedforward-lookingstatementswithinthemeaningofSection27AoftheSecuritiesActof1933andSection21EoftheSecuritiesExchangeActof1934.AlthoughiStarbelievestheexpectationsreflectedinanyforward-lookingstatementsarebasedonreasonableassumptions,theCompanycangivenoassurancethatitsexpectationswillbeattained.TheCompanyundertakesnoobligationtoupdateorpubliclyreviseanyforward-lookingstatement,whetherasaresultofnewinformation,futureeventsorotherwise.ThispresentationshouldbereadinconjunctionwithourconsolidatedfinancialstatementsandrelatednotesinourQuarterlyReportonForm10-QforthequarterendedSeptember30,2022andourAnnualReportonForm10-K,asamendedbyForm10K/A(“Form10-K”),fortheyearendedDecember31,2021.Inassessingallforward-lookingstatementsherein,readersareurgedtoreadcarefullytheRiskFactorssectionandothercautionarystatementsinourForm10-K. FactorsthatcouldcauseactualresultstodiffermateriallyfromiStar’sexpectationsinclude(1)thewarinUkraineandescalatinggeopoliticaltensionsasaresultofRussia’sinvasionofUkraine;(2)theabilitytoconsummatetheannouncedtransactionsontheexpectedtermsandwithintheanticipatedtimeperiods,oratall,whichisdependentontheparties’abilitytosatisfycertainclosingconditions,includingtheapprovalofSAFE’sandSTAR’sstockholders,completionoftheSpin-Off,salesofassetsandotherfactors;(3)anydelayorinabilityofNewSafeholdand/orSpinCotorealizetheexpectedbenefitsofthetransactions;(4)changesintaxlaws,regulations,rates,policiesorinterpretations;(5)thevalueofNewSafeholdsharestobeissuedinthetransaction;(6)thevalueofSpinCo'ssharesandliquidityinSpinCo'sshares;(7)theriskofunexpectedsignificanttransactioncostsand/orunknownliabilities;(8)potentiallitigationrelatingtotheproposedtransactions;(9)theimpactofactionstakenbysignificantstockholders;(10)thepotentialdisruptiontoSTAR’sorSAFE’srespectivebusinessesofdivertedmanagementattention,andtheunanticipatedlossofkeymembersofseniormanagementorotheremployees,ineachcaseasaresultoftheannouncedtransactions;(11)generaleconomicandbusinessconditionsthatcouldaffectNewSafeholdandSpinCofollowingthetransactions;(12)generaleconomicconditionsandconditionsinthecommercialrealestateandcreditmarketsincluding,withoutlimitation,theimpactofinflationonrisinginterestrates;(13)theeffectoftheCOVID-19pandemiconourbusinessandgrowthprospects;(14)theperformanceofSAFE;(15)theCompany’sabilitytogrowitsgroundleasebusinessdirectlyandthroughSAFE;(16)theCompany’sabilitytogenerateliquidityandtorepayindebtednessasitcomesdue;(17)additionalloanlossprovisionsandthepricingandtimingofanysuchsales;(18)assetimpairments;(19)themarketdemandforlegacyassetstheCompanyseekstosellandthepricingandtimingofsuchsales;(20)changesinNPLs;(21)repaymentlevels;(22) theCompany'sabilitytomakenewinvestments;(23)theCompany’sabilitytomaintaincompliancewithitsdebtcovenants;(24)theCompany’sabilitytogenerateincomeandgainsfromitsportfolioandotherrisksdetailedin“RiskFactors”inour2021AnnualReportonForm10-K,andanyupdatestheretomadeinoursubsequentfillingswiththeSEC. Note : Pleaserefertothe“Glossary”sectionintheAppendixforalistofdefinedtermsandmetrics. Forward-Looking Statements and Other Matters1 Investor Relations Contact Jason FooksSenior Vice President212.930.9400investors@istar.com

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I. Highlights 2

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Q3 ‘22 Highlights3 $284mNew Originations at Safehold$46mNet Gain From Sale of aGround Lease $155mDebt Extinguished withinthe Quarter$1.3bTotal Cash Asset Monetization Progress Momentum at Safehold Strengthening the Balance Sheet $105mProceeds from Asset Salesand Loan Repayments80%iStar Portfolio Focused on Ground Lease Ecosystem(1) (1) Figure is presented using the SAFE market value of iStar’sinvestment in SAFE. Q3 ‘22 SAFE market value of iStar’sinvestment in SAFE is $1,178m, calculated as iStar’sownership of 40.3m shares of SAFE at the October 31, 2022 closing stock price of $29.25 which represents a $281m discount to the carrying value. iStar owns approximately 65% of SAFE’s common stock and there can be no assurance that iStar would realize $29.25 or any other closing price on a particular day if it weretoseek to liquidate SAFE shares.

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Earnings Results4 Q3 ‘22 Q3 ’ n 4$g2 (Allocable to Common Shareholders)$12.1m$121.9m W.A. Shares (Diluted)85.9m80.5m EPS (Diluted)$0.14$1.51 Adj. Earnings (Allocable to Common Shareholders)$28.5m$141.3m W.A. Shares (Diluted)85.9m80.5m AEPS (Diluted)$0.33$1.76Note: Please refer to the “Adjusted Earnings Reconciliation” section of the Appendix for more information with regard tothe calculation of Adjusted Earnings.•Net Income for the quarter is net of $13 million of losses on early extinguishment of debt, primarily associated with various convertible exchange transactions completed during the quarter which also resulted in a $38 million increase in equity.

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iStar Overview iStar’s strategy remains focused on the growth of the Ground Lease Ecosystem 5(1) Q3 ‘22 SAFE market value of iStar’s investment in SAFE is $1,178m, calculated as iStar’s ownership of 40.3m shares of SAFE at the October 31, 2022 closing stock price of $29.25 which represents a $281m discount to the carrying value. iStar owns approximately 65% of SAFE’s common stock and there can be no assurance that iStar would realize $29.25 or any other closing price on a particular day if it were to seek to liquidate SAFE shares.(2) Represents an estimate for the value of the total potential iPIP distribution less the amounts already accrued for as of September 30, 2022, assuming SAFE is valued at a price of $29.25 per share and the Company's other assets perform in line with current underwriting expectations. Please see the “Supplemental iPIP Information” in the Appendix for additional details and sensitivity analysis. Cash $1,336 Ground Lease Ecosystem Safehold1,459Other Ground Lease Ecosystem90 Total GL Ecosystem (excl. cash) 1,550 Non - Core Assets RE Finance177Legacy and Strategic394Other assets, net66 Total Non - Core Assets 637 Total Assets $3,522 iPIP liability (accrued)$46AP and other liabilities98Debt obligations, net1,681 Total Liabilities $1,825 Total Equity $1,698 Total Liabilities & Equity $3,522 Total Equity 1,698 Less:Non controlling interests(17)Less: Preferred equity(305) Total Common Equity 1,375 Less:SAFE mark-to-market adjustment(1)(281)Less: Incremental iPIP amount(2)(25) Total Common Equity (as adjusted) $1,069 Shares Outstanding 86.7 Common Equity per share (as adjusted) $12.33 Total Assets Total Liabilities and EquitySimplified Balance SheetIn millions, except per share data Sensitivity: Common Equity (as adjusted) SAFE Share Price Per Share +$10 $16.21 - $10 $8.19

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$1.1bCarrying Value $30.96 per SAFE share)Q3 '21Q3 '22Safehold6Note: Please refer to the SAFE Earnings Presentation dated November 1, 2022, available on SAFE’s website for additional details.Q3 ‘21 share price as of September 30, 2021 and Q3 ‘22 share price as of October 31, 2022. iStar’s Investment in Safehold $284mQ3 ‘22 New Originations at Safehold $2.0bCaret Valuation Basedon Most Recent Third-Party Commitment $756mCash & Credit Facility Availability Positive OutlookMoody’s Rating Actionin Q3 ’22$1.5bUnrealizedGain Q3 ‘22 Safehold Progress ($0.3b)Unrealized Loss$2.6bMarket Value(36.0m shares / $71.89 per sh)$1.5bCarrying Value($36.23 per SAFE share)$1.2bMarket Value(40.3m shares / $29.25 per sh)

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7Note: Figures are based on carrying value, which represents iStar’s pro rata share of investment in ground lease and leasehold loan assets.Ground Lease Ecosystem (excl. SAFE) Investment opportunities that target the origination and acquisition of pre-development phase ground leases (Ground Lease Plus) and leasehold loans made in conjunction with a Safehold ground lease (SAFExSTAR) Carrying Value $90m # of Assets7Targeted Returns9 -12%Unfunded Commitments$147mGeographic Region Southwest$48m53%Northeast$32m36%West$10m11%Monetization:•One Ground Lease Plus asset sold during the quarter for $36m of proceeds at $1m gain

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RE Finance & Legacy and Other Strategic Assets8 RE Finance(1)(Non-Ground Lease Ecosystem)Legacy andStrategic Assets Property Type (1) Excludes iStar’s$24m investment in leasehold loans reported within the RE Finance segment.Carrying Value: $177m, 14% decrease vs Q2 ’22•6 loans remainingMonetization Progress:•$33m of repayments and proceeds from the sales of securities; $3m of gains associated with sales of securitiesCarrying Value: $394m, 5% decrease vs Q2 ’22• Short - Term Legacy and Strategic: 13 assets across Land & Development, Operating Properties and Corporate • Long - Term Legacy: 2 projects across Land & Development and Operating Properties Monetization Progress:•$35m of proceeds and distributions from asset sales within the quarter•$11m of gains generated Short-Term Legacy$69m17%Strategic (Operating)$33m8%Strategic (Corporate)$22m6%Long-Term Legacy$270m69%Asbury: $180mMagnolia Green: $90m Multifamily$65m37%Retail$60m34%Hotel$45m25%Condo$7m4%

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Debt Profile2024 Oct. $754m 4.75%2025 Aug. $502m 4.25%2026Feb. $347m 5.50%2035Oct. $100m L + 150 Total / W.A. $1,702m 4.79% Corporate Debt Maturity ProfileNote: $ in millions.9 3.2 yearsw.a. debtmaturity $754m$502m$347m$100m Unsecured Debt Trust Preferred$155m of debt extinguished in Q3 ‘22: Principal (Loss) / Gain ‘22 Convertible Notes$93m($12)m‘24 Unsecured Notes14m($0)m‘25 Unsecured Notes48m($1)m Total $155m($13)m

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II. Capital Structure10

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Credit Metrics11Note: Figures are presented using the SAFE market value of iStar’s investment in SAFE. Q3 ‘22 SAFE market value of iStar’s investment in SAFE is $1,178m, calculated as iStar’s ownership of 40.3m shares of SAFE at the October 31, 2022 closing stock price of $29.25 which represents a $281m discount to the carrying value. iStar owns approximately 65% of SAFE’s common stock and there can be no assurance that iStar would realize $29.25 or any other closing price on a particular day if it were to seek to liquidate SAFE shares.(1) Leverage is calculated as the ratio of debt, net of cash, to total equity gross of non-controlling interests, or “NCI”, and applying the SAFE MTM adjustment and impact of the full estimated value of the potential iPIP distributions. Please refer to the “Capital Structure Overview” section of the presentation for more information.Unencumbered Asset Base Secured Debt / Total DebtUA / UDLeverage(1) $3.2b 1.9x1.2x1.6x 0.25x 0%

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Common Equity$1.4bNoncontrolling Interest -$17m Preferred Equity - $305m (3) Senior Unsecured Debt $1.7b (4) Capital Structure Overview(1) SAFE mark-to-market calculations based on the October 31, 2022 closing stock price of $29.25 with respect to 40.3m shares held by iStar.(2) Corporate leverage is the ratio of total debt less cash and cash equivalents divided by Total Equity, gross of NCI.(3) Represents liquidation preference of preferred equity.(4) Debt is presented net of fees and discounts.(5) A portion of the profits realized on iStar’s investment portfolio, including iStar’s investment in SAFE, is allocable to iPIP, iStar’s shareholder-approved long-term incentive plan. The figures represent the full estimated value of the potential iPIP distributions. For more detail on the iPIP adjustment presented here, see the “Supplemental iPIP Information” in the Appendix to this presentation. Total Equity $1.7b12 Credit Metrics 9/30/22 SAFE MTM and iPIP Adj. (1)(5) Cash$1,336m$1,336mDebt(4)$1,681m$1,681mDebt, net of cash$345m$345mTotal Equity, gross of NCI$1,698m$1,392mLeverage(2)0.20x0.25x Shares Shares Outstanding86.7m86.7mCommon Equity$1,375m$1,069mCommon Equity per Share$15.86$12.33

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III. Appendix13

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$3.2b Diversified AssetsNote: Figures based on Carrying Value of the Company’s total investment portfolio, adjusted to present the investment in SAFEatmarket value, and includes 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’s ownership of 40.3m shares of SAFE at the October 31, 2022closing stock price of $29.25. 14 SAFE$1,178m36%Land & Development$248m8%RE Finance$201m6%Operating Properties$124m4%Net Lease (Ground Lease Plus)$66m2%Other Assets$66m2%Strategic Investments$22m1%Cash$1,336m41%Business Line(1) Ground Leases$1,244m38%Land$219m7%Multifamily$110m3%Hotel$107m3%Retail$81m3%Other$36m1%Condo$28m1%Office$14m1%Cash & Other Assets$1,402m43%PropertyType(1) Northeast$794m24%West$388m12%Mid Atlantic$249m8%Southeast$180m5%Southwest$121m4%Various$54m2%Central$53m2%Cash & Other Assets$1,402m43% Geographic Region (1)

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Consolidated Statements of OperationsNote:$inthousands.15 Three Months Nine Months Ended September 30, Ended September 30, 2022 2021 2022 2021 Revenues Operating lease income $3,424 $3,732 $9,715 $13,456 Interest income 2,093 6,972 11,262 24,846 Interest income from sales -type leases 129 526 861 683 Other income 27,024 39,033 51,545 60,950 Land development revenue 15,087 93,369 54,390 157,936 Total revenues $47,757 $143,632 $127,773 $257,871 Cost and Expenses Interest expense $22,664 $28,695 $76,056 $86,145 Real estate expense 16,204 13,369 39,337 33,404 Land development cost of sales 16,778 87,380 55,369 147,507 Depreciation and amortization 1,290 1,742 3,985 5,715 General and administrative 14,584 14,120 41,130 45,654 General and administrative –stock-based compensation (374) 3,001 (30,724) 23,300 Provision for (recovery of) loans & other lending investments (157) (1,610) 22,556 (7,411) Provision for (recovery of) net investment in leases (380) (315) - 465 Impairment of assets - 421 1,768 679 Other expense 4,171 894 6,624 1,358 Total costs and expenses $74,780 $147,697 $216,101 $336,816 Income from sales of real estate 951 25,611 1,443 26,319 Income (loss) from operations before earnings from equity method investments and other items ($26,072) $21,546 ($86,885) ($52,626) Loss on early extinguishment of debt (13,209) - (131,200) - Earnings from equity method investments 57,797 87,795 102,222 110,661 Income tax (expense) benefit (564) 39 (567) 117 Net income (loss) from continuing operations $17,952 $109,380 ($116,430) $58,152 Net income from discontinued operations - 21,614 797,688 69,415 Net income $17,952 $130,994 $681,258 $127,567 Net (income) loss from continuing operations attributable to noncontrolling interests 53 (10) (46) 55 Net (income) from discontinued operations attributable to noncontrolling interests - (3,254) (179,089) (8,092) Net income attributable to iStar $18,005 $127,730 $502,123 $119,530 Preferred dividends (5,874) (5,874) (17,622) (17,622) Net income allocable to common shareholders $12,131 $121,856 $484,501 $101,908

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Earnings per ShareNote:Inthousands,exceptpersharedata.(1)Allocabletocommonshareholdersaftertheeffectofpreferreddividends,non-controllinginterestsandincomefromsalesofrealestate.16 Three Months Nine Months Ended September 30, Ended September 30, Earnings Information for Common Shares 2022 2021 2022 2021 Net income (loss) from continuing operations and allocable to common shareholders (1) Basic $0.14 $1.45 ($1.70) $0.56 Diluted $0.14 $1.28 ($1.70) $0.52 Net income from discontinued operations and allocable to common shareholders Basic $0.00 $0.26 $7.86 $0.84 Diluted $0.00 $0.23 $7.86 $0.78 Net income allocable to common shareholders Basic $0.14 $1.71 $6.16 $1.40 Diluted $0.14 $1.51 $6.16 $1.30 Adjusted earnings Basic $0.33 $1.98 $7.65 $2.42 Diluted $0.33 $1.76 $7.30 $2.24 Weighted average shares outstanding Basic 85,458 71,299 78,706 72,675 Diluted (for net income) 85,867 80,487 78,706 78,402 Diluted (for adjusted earnings) 85,867 80,487 82,460 78,402 Common shares outstanding at the end of period 86,695 70,031 86,695 70,031

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Adjusted Earnings Reconciliation17Note: $ 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 and deployed a substantial portion of the proceeds into additionalinvestments in SAFE and new loan and net lease originations relating to the Ground Lease business. 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. Three Months Nine Months Ended September 30, Ended September 30, 2022 2021 2022 2021 Net income allocable to Common Shareholders $12,131 $121,856 $484,501 $101,908 Add: Depreciation and amortization 3,705 16,449 11,606 50,790 Add: Stock-based compensation expense (374) 3,001 (30,724) 23,300 Add: Loss on early extinguishment of debt 13,051 - 136,464 - Adjusted earnings allocable to common shareholders $28,513 $141,306 $601,847 $175,998

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Consolidated Balance SheetsNote:$inthousands.18 As of As of September 30, 2022 December 31, 2021 Assets Real Estate Real estate, at cost $111,719 $113,510 Less: accumulated depreciation (22,575) (21,360) Real estate, net 89,144 92,150 Real estate available and held for sale 1,283 301 Total real estate 90,427 92,451 Real estate and other assets available and held for sale and classified as discontinued operations 11,925 2,299,711 Net investment in leases - 43,215 Land and development, net 248,246 286,810 Loans receivable and other lending investments, net 176,623 332,844 Loans receivable held for sale - 43,215 Other investments 1,605,268 1,297,281 Cash and cash equivalents 1,335,722 339,601 Accrued interest and operating lease income receivable, net 1,035 1,813 Deferred operating lease income receivable, net 2,842 3,159 Deferred expenses and other assets, net 50,044 100,434 Total Assets $3,522,132 $4,840,534 Liabilities and Equity Accounts payable, accrued expenses, and other liabilities $140,876 $236,732 Liabilities associated with real estate held for sale and classified as discontinued operations 2,918 968,419 Liabilities associated with properties held for sale - 3 Debt obligations, net 1,680,708 2,572,174 Total Liabilities $1,824,502 $3,777,328 Total iStar shareholders’ equity cmitliomu ctminur 4$$$$ miom nmmium cmiusiol cmilroil 2$ coiqnnimon cpipliqop

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Q3 ‘22 Portfolio ReconciliationNote: $ in millions. Figures in this table may not foot due to rounding.(1) Market value of iStar’s investment in Safehold is $1,178m, calculated as iStar’s ownership of 40.3m shares of SAFE at theOctober 31, 2022 closing stock price of $29.25.19 Real Estate Finance Net Lease Operating Properties Land & Development Corporate / Other Total Real estate, net-- $89 --$89Real estate available and held for sale--1--1Real estate and other assets available and held for sale and classified as discontinued operations----$1212Net investment in leases------Land and development, net---$248-248Loans receivable and other lending investments, net$177----177Other investments24$1,52534-221,605 Carrying Value $201 $1,525 $124 $248 $34 $2,133 Add: Cash and other assets----1,3901,390Add: SAFE MTM(1)-(281)---(281) Portfolio Carrying Value $201 $1,244 $124 $248 $1,423 $3,241

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Supplemental iPIP InformationNote: $ in thousands. Figures in this table may not foot due to rounding.(1) Market value of iStar’s investment in Safehold is $1,178m, calculated as iStar’s ownership of 40.3m shares of SAFE at theOctober 31, 2022 closing stock price of $29.25.(2) Represents an estimate for the value of the total potential iPIP distribution less the amounts already accrued for as of September 30, 2022, assuming SAFE is valued at a price of $29.25 per share and the Company's other assets perform in line with current underwriting expectations.20 As of September 30, 2022 Total Equity $1,697,630 Less: Non controlling interests (17,311) Less: Preferred equity (305,000) Total Common Equity 1,375,319 Less: SAFE mark -to-market adjustment(1) (281,313) Less: Incremental iPIP amount (2) (24,645) Total Common Equity (as adjusted) $1,069,361 Shares Outstanding 86,695 Common Equity per share (as adjusted) $12.33 Sensitivity analysis Change in price of SAFE common stock +$10 - $10 Change in incremental iPIP amount ($67,073) $43,526 Change in SAFE mark -to-market adj. 402,791 (402,791) Change in total common equity (as adjusted) $335,717 ($359,265) Common Equity Per Share Impact $3.87 ($4.14) Thepresentationaboveincludesnon-GAAPfinancialmeasures.ItshouldbereadinconjunctionwiththeCompany'sauditedfinancialstatementsandotherinformationincludedintheCompany'sAnnualReportonForm10-KfortheyearendedDecember31,2021anditsunauditedfinancialstatementsinitsQuarterlyReportonForm10-QforthequarterendedSeptember30,2022.ThesupplementalpresentationisnotintendedtoreplacetheGAAPfinancialstatements.ItisintendedtobesupplementalinformationtoprovideinvestorsintheCompany'ssecuritieswithadditionalinformationabouttheCompany'sfinancialposition.UndertheiPIPprogram,participantswhoholdvestedinterestsareentitledtoreceive20%ofthedisposition(ordeemeddisposition)proceedsofCompanyassets,iftheCompanyhasreceivedaspecifiedminimumreturnandonlyiftheCompanyhasachievedaminimumtotalstockholderreturn.IftheCompany'ssharesofSAFEcommonstockarethelastmaterialassetinaniPIPpool,theCompanymayelectnottosellthesharesandinlieuthereoftodistributeaportionofthesharestoiPIPparticipantshavingavaluebasedonthecashproceedsthatwouldhavebeenreceivedbytheCompanyfromanactualsaleoftheSAFEshares,providedthattherelevantperformanceandtotalstockholderreturnhurdlesaresatisfied.TherecanbenoassurancethattheactualmarketpricesofSAFEcommonstockorotherCompanyassetsinthefuturewillalignwiththeassumptionsusedtopreparethesupplementalpresentation.TheCompanyowns40.3msharesofSAFE,representing64.8%ofSAFE’ssharesoutstanding.Giventhesubstantialinterest,theCompanymaynotbeabletoliquidateitsinvestmentattheclosingpriceof$29.25fromOctober31,2022oronanyotherday.ThesensitivityanalysisshownaboveisintendedtogivereadersasenseofhowthepotentialiPIPdistributionsmaychangeasthemarketpriceofSAFEcommonstockchangesbecausethesharesofSAFEcommonstockownedbyiStararethelargestassetintheiPIPplans.ItisnotintendedtobeapredictionofwhattheactualiPIPdistributionsmaybe.TherearefactorsinadditiontothemarketpriceofSAFEcommonstockthatwillaffectthepotentialiPIPdistributionsthatarenottakenintoaccountinthesensitivityanalysis,including,withoutlimitation,changesinthemarketpriceofiStarcommonstockandtheperformanceoftheotherassetsintheiPIPplans.ForadditionalinformationabouttheiPIPprogram,pleasereadthecompany'sdefinitiveProxyStatementforits2021annualmeetingfiledwiththeSEConApril2,2021,andthedefinitiveProxyStatementforthe2022annualmeetingfiledwiththeSEConApril1,2022.

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Glossary 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.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.Carrying ValueNet Real Estate Value for Net Lease, Operating Properties, Land & Development; Net Book Value for Real Estate FinanceNet Real Estate Value (Net Lease, 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, net of accumulated depreciation and amortization, plus our basisin equity method investments.Net Book Value(Real Estate Finance)Real Estate Finance Gross Book Value reduced for CECL allowances.21 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.