Istar : Form of prospectus reflecting facts events constituting substantive change from last form

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Filed Pursuant to Rule 424(b)(3)

Registration No. 333-220353

The information in this prospectus supplement and the accompanying prospectus is not complete and may be changed. This prospectus supplement and the accompanying prospectus are not an offer to sell these securities and are not soliciting an offer to buy these securities in any state where an offer or sale is not permitted.

Subject to Completion, dated September 11, 2019

PRELIMINARY PROSPECTUS SUPPLEMENT (TO PROSPECTUS DATED SEPTEMBER 5, 2017)

$675,000,000

• % Senior Notes Due 2024

We are offering $675 million aggregate principal amount of our	% Senior Notes due 2024, or the "Notes." The Notes will mature on	,
2024. We will pay interest on the Notes on each	and	, commencing on	, 2020.
Prior to	, 2024 (three months prior to the maturity date), we may redeem some or all of the Notes at any time and from time to time at a

price equal to 100% of the principal amount thereof, plus the applicable "make whole" premium and accrued but unpaid interest, if any, to, but excluding, the

date of redemption. On or after	, 2024 (three months prior to the maturity date), we may redeem some or all of the Notes at any time and from time
to time at 100% of the principal amount thereof, plus accrued but unpaid interest, if any, to, but excluding, the date of redemption. In addition, prior
to	, 2021, we may redeem up to 35% of the Notes using the proceeds of certain equity offerings.

The Notes are our unsecured senior obligations and rank equally with all of our other unsecured, unsubordinated indebtedness from time to time outstanding. The Notes are effectively subordinated to any of our existing and future secured indebtedness to the extent of the value of the assets securing such indebtedness. In addition, the Notes are structurally subordinated to all indebtedness and other liabilities of our subsidiaries.

The Notes will not be listed on any securities exchange or included in any automated quotation system.

This prospectus supplement and the accompanying prospectus include additional information about the terms of the Notes, including covenants.

See "Risk Factors," beginning on page S-4 of this prospectus supplement and on page 5 of our Annual Report on Form 10-K for the fiscal year ended December 31, 2018, for a discussion of certain risks you should consider before investing in the Notes.

Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of these securities or determined that this prospectus supplement or the accompanying prospectus is accurate or complete. Any representation to the contrary is a criminal offense.

Public offering		Underwriting		Proceeds, before
price(1)		discount		expenses, to us(1)

Per Note	$	%
Total			$
(1)	Plus accrued interest from September	, 2019, if settlement occurs after that date.

%%

$

The public offering price set forth above does not include accrued interest, if any. Interest on the Notes will accrue from September , 2019 and must be paid if the Notes are delivered after September , 2019.

The Notes will be ready for delivery in book entry form only through the facilities of The Depository Trust Company against payment in New York, New York on or about September , 2019.

Joint Bookrunners

BofA Merrill Lynch	J.P. Morgan	Barclays
Morgan Stanley		Goldman Sachs & Co. LLC
	The date of this prospectus supplement is	, 2019.

Table of Contents

TABLE OF CONTENTS
Prospectus Supplement	Page
SUMMARY	S-1
RISK FACTORS	S-4
USE OF PROCEEDS	S-7
CAPITALIZATION	S-8
DESCRIPTION OF CERTAIN OTHER INDEBTEDNESS	S-9
DESCRIPTION OF THE NOTES	S-12
BOOK-ENTRY; SETTLEMENT AND CLEARANCE	S-34
CERTAIN U.S. FEDERAL INCOME TAX CONSEQUENCES	S-37
UNDERWRITING	S-41
LEGAL MATTERS	S-46
EXPERTS	S-46
WHERE YOU CAN FIND MORE INFORMATION AND INCORPORATION BY REFERENCE	S-46
Prospectus
ABOUT THIS PROSPECTUS	1
FORWARD-LOOKING STATEMENTS	2
iSTAR INC.	3
RATIO OF EARNINGS TO FIXED CHARGES	4
USE OF PROCEEDS	5
DESCRIPTION OF THE DEBT SECURITIES	6
DESCRIPTION OF WARRANTS	9
DESCRIPTION OF COMMON STOCK AND PREFERRED STOCK	10
DESCRIPTION OF DEPOSITARY SHARES	14
CERTAIN U.S. FEDERAL INCOME TAX CONSEQUENCES	16
PLAN OF DISTRIBUTION	47
LEGAL MATTERS	49
EXPERTS	50
INCORPORATION OF CERTAIN DOCUMENTATION BY REFERENCE	51
INFORMATION WE FILE	52

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Table of Contents

This document is in two parts. The first part is the prospectus supplement, which describes the terms of this offering and adds to and updates information contained in the accompanying prospectus. The second part, the accompanying prospectus, provides more general information, some of which may not apply to this offering. Generally, when we refer to "this prospectus," we are referring to both parts of this document combined. To the extent there is a conflict between the information contained in this prospectus supplement, on the one hand, and the information contained in the accompanying prospectus, on the other hand, you should rely on the information contained in this prospectus supplement. In addition, any statement in a filing we make with the Securities and Exchange Commission, or the "SEC," that is incorporated by reference herein and that adds to, updates or changes information contained in an earlier filing we made with the SEC and that was incorporated by reference herein shall be deemed to modify and supersede such information in such earlier filing.

We have not, and the underwriters have not, authorized any other person to provide you with any information other than that contained or incorporated by reference in this prospectus supplement, the accompanying prospectus, any amendment or supplement to this prospectus supplement or the accompanying prospectus or in any free writing prospectus prepared by or on behalf of us or to which we have referred you. We and the underwriters take no responsibility for, and can provide no assurance as to the reliability of, any other information. We are not, and the underwriters are not, making an offer to sell these securities in any jurisdiction where the offer or sale is not permitted. You should assume that the information appearing in this prospectus supplement, the accompanying prospectus and the documents incorporated by reference is accurate only as of their respective dates. Our business, financial condition, results of operations and prospects may have changed since those dates.

Unless otherwise stated or the context requires otherwise, references to "iStar," "the Company," "we," "us" and "our" are to iStar Inc. and its consolidated subsidiaries.

FORWARD-LOOKING STATEMENTS

We make statements in this prospectus supplement, the accompanying prospectus and the documents we incorporate by reference, other than purely historical information, including estimates, projections, statements relating to our business plans, objectives and expected operating results, and the assumptions upon which those statements are based, are "forward-looking statements" within the meaning of the Private Securities Litigation Reform Act of 1995, Section 27A of the Securities Act of 1933, as amended, or the "Securities Act," and Section 21E of the Securities Exchange Act of 1934, as amended, or the "Exchange Act." Forward-looking statements are included with respect to, among other things, our current business plan, business strategy, portfolio management, prospects and liquidity. These forward-looking statements generally are identified by the words "believe," "project," "expect," "anticipate," "estimate," "intend," "strategy," "plan," "may," "should," "will," "would," "will be," "will continue," "will likely result" and similar expressions. Forward- looking statements are based on current expectations and assumptions that are subject to risks and uncertainties which may cause actual results or outcomes to differ materially from those contained in the forward-looking statements. Certain important factors that we believe might cause such differences are discussed in the section entitled "Risk Factors," beginning on page S-4 of this prospectus supplement and on page 5 of our Annual Report on Form 10-K for the fiscal year ended December 31, 2018. We undertake no obligation to update or revise any forward-looking statements, whether as a result of new information, future events or otherwise. In assessing all forward looking statements, readers are urged to read carefully all cautionary statements contained in this prospectus and the documents we incorporate by reference.

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SUMMARY

iStar Inc.

We finance, invest in and develop real estate and real estate-related projects as part of our fully integrated investment platform. We also manage entities focused on ground lease, or "Ground Lease", and net lease investments. We have invested more than $40 billion over the past two decades and are structured so as to qualify as a real estate investment trust for U.S. federal income tax purposes, or a "REIT," with a diversified portfolio focused on larger assets located in major U.S. metropolitan markets. Our primary reportable business segments are real estate finance, net lease, operating properties and land and development.

Our real estate finance portfolio is primarily comprised of senior and mezzanine real estate loans that may be either fixed-rate or variable-rate and are structured to meet the specific financing needs of borrowers. Our portfolio also includes leasehold loans, preferred equity investments and senior and subordinated loans to business entities, particularly entities engaged in real estate or real estate-related businesses, and may be either secured or unsecured. Our loan portfolio includes whole loans and loan participations.

Our net lease portfolio includes our net lease and Ground Lease investment strategies, both of which offer stable long-term cash flows. We own net lease properties directly and through ventures that we manage. We operate our Ground Lease investment strategy primarily through Safehold Inc., or "SAFE", a publicly traded REIT focused exclusively on Ground Leases that we launched in 2017 and manage pursuant to a management agreement. As of September 10, 2019, we owned approximately 66.6% of SAFE's outstanding common stock, which we account for as an equity investment. We also directly participate in Ground Leases by offering leasehold loans to SAFE's tenants.

Our operating properties portfolio is comprised of commercial and residential properties, which represent a pool of assets across a broad range of geographies and property types. We generally seek to reposition or redevelop our transitional properties with the objective of maximizing their value through the infusion of capital and/or intensive asset management efforts. The commercial properties within this portfolio include office, retail, hotel and other property types. The residential properties within this portfolio are generally luxury condominium projects located in major U.S. cities where our strategy is to sell individual units through retail distribution channels.

Our land and development portfolio is primarily comprised of land entitled for master planned communities as well as waterfront and urban infill land parcels located throughout the United States. Master planned communities represent large-scale residential projects that we will entitle, plan and/or develop and may sell through retail channels to home builders or in bulk. The communities also typically have a smaller portion of their land reserved for future commercial development. Waterfront parcels are generally entitled for residential projects and urban infill parcels are generally entitled for mixed-use projects. We may develop these properties ourselves, or in partnership with commercial real estate developers, or may sell the properties.

Our primary sources of revenues are operating lease income, which is comprised of the rent and reimbursements that tenants pay to lease our properties, interest income, which is the interest that borrowers pay on loans, and land development revenue from lot and parcel sales. We primarily generate income through a "spread" or "margin," which is the difference between the revenues net of property-related expenses generated from leases and loans and interest expense. In addition, we generate income from sales of our real estate and income from equity in earnings of our unconsolidated ventures.

Our principal executive and administrative offices are located at 1114 Avenue of the Americas, New York, New York 10036. Our telephone number and web address are [phone] and www.istar.com, respectively. The information on our website, other than the reports filed with the SEC that are incorporated by reference herein, is not considered part of this prospectus supplement or the accompanying prospectus.

Recent Developments

We are seeking commitments from lenders to amend the 2015 Revolving Credit Agreement. The proposed amendment would, among other things, extend the expiration date of the revolving commitment period to at or about September 2022 with the option to convert outstanding borrowings at the end of the revolver commitment period to a one year term loan. There can be no assurance that we will receive commitments for the amendment of the 2015 Revolving Credit Agreement or that the amendment will be completed if we receive the commitments. Certain of the underwriters and/or their affiliates act as lenders, agents, arrangers and/or bookrunners under the 2015 Revolving Credit Agreement. See "Description of Certain Other Indebtedness" and "Underwriting."

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