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TABLE OF CONTENTS

TABLE OF CONTENTS

Table of Contents

CALCULATION OF REGISTRATION FEES

Proposed Maximum

Title of Each Class of Securities

Aggregate Offering

Amount of

to be Registered

Price

Registration Fee(1)

4.75% Senior Notes Due 2024

$675,000,000

$81,810.00

  1. Calculated in accordance with Rules 457(o) and 457(r) of the Securities Act of 1933, as amended, or the Act. In accordance with Rule 457(r) of the Act, the registrant initially deferred payment of all of the registration fees for the Registration Statement filed by the registrant on September 6, 2017.

Table of Contents

Filed Pursuant to Rule 424(b)(5)

Registration No. 333-220353

PROSPECTUS SUPPLEMENT

(TO PROSPECTUS DATED SEPTEMBER 5, 2017)

$675,000,000

4.75% Senior Notes Due 2024

We are offering $675 million aggregate principal amount of our 4.75% Senior Notes due 2024, or the "Notes." The Notes will mature on October 1, 2024. We will pay interest on the Notes on each April 1 and October 1, commencing on April 1, 2020.

Prior to July 1, 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 July 1, 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 October 1, 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

100%

1.250%

98.750%

Total

$675,000,000

$8,437,500

$666,562,500

  1. Plus accrued interest from September 16, 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 16, 2019 and must be paid if the Notes are delivered after September 16, 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 16, 2019.

Joint Bookrunners

BofA Merrill Lynch

J.P. Morgan

Barclays

Morgan Stanley

Goldman Sachs & Co. LLC

Co-Managers

Raymond James

Citigroup

Mizuho Securities

The date of this prospectus supplement is September 12, 2019.

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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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iStar Inc. published this content on 13 September 2019 and is solely responsible for the information contained therein. Distributed by Public, unedited and unaltered, on 13 September 2019 20:01:03 UTC