Safehold : SAFE Corporate Presentation

Corporate Presentation

September 2020

Note: Figures in the presentation are as of 9/30/20, unless otherwise stated.

Forward-Looking Statements and Other Matters

Statements in this presentation which are not historical fact may be deemed forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Although iStar believes the expectations reflected in any forward-looking statements are based on reasonable assumptions, the Company can give no assurance that its expectations will be attained. The Company undertakes no obligation to update or publicly revise any forward-looking statement, whether as a result of new information, future events or otherwise.

This presentation should be read in conjunction with our consolidated financial statements and related notes in our Quarterly Report on Form 10-Q for the quarter ended June 30, 2020 and our Annual Report on Form 10-K for the year ended December 31, 2019. In assessing all forward-looking statements herein, readers are urged to read carefully all cautionary statements in our Form 10-K.

Factors that could cause actual results to differ materially from iStar's expectations include general economic conditions and conditions in the commercial real estate and credit markets, the effect of the COVID-19 pandemic on our business and growth prospects, the Company's ability to grow its ground lease business directly and through SAFE, the Company's ability to generate liquidity and to repay indebtedness as it comes due, additional loan loss provisions and asset impairments, the market demand for legacy assets the Company seeks to sell and the pricing and timing of such sales, changes in NPLs, repayment levels, the Company's ability to make new investments, the Company's ability to maintain compliance with its debt covenants, the Company's ability to generate income and gains from its portfolio and other risks detailed in "Risk Factors" in our 2019 Annual Report on Form 10-K, and any updates thereto made in our subsequent fillings with the SEC.

Important Note re COVID-19: Readers of this presentation are cautioned that, due to the uncertainty created by the COVID-19 pandemic, our results for the quarter may not be indicative of our results for the remainder of 2020. Readers are urged to read our Quarterly Report on Form 10-Q for the quarter ended June 30, 2020 when it is filed with the SEC for a more fulsome discussion of our quarterly results, including the "Management's Discussion and Analysis of Financial Condition and Results of Operations" and "Risk Factors" sections included therein.

Note: Please refer to the "Glossary" section in the Appendix for a list of defined terms and metrics.

Investor Relations Contact

Jason Fooks

Senior Vice President

212.930.9400

[e-mail] 1

iStar Strategy Review

We have been successfully executing on the 3-part

strategy we laid out at the beginning of 2019

1

Strengthen

Balance Sheet

1. Enhance capital structure

1. Maintain strong liquidity profile

2

Simplify

Business

1. Monetize legacy assets

1. Recycle capital into lower risk investments

3

Scale

Safehold

1. Focus management team and investment resources around new core mission

2

Strong Balance Sheet with Improving Credit Metrics

(Q2 '19 to Q2 '20)

Unencumbered

Asset Base

(SAFE MTM)

$4.5b

$3.4b

Q2 '19

Q2 '20

UA / UD		Leverage(1)
(SAFE MTM)		(SAFE MTM)

2.1x

1.9x

1.5x

1.3x

Q2 '19

Q2 '20

Q2 '19

Q2 '20

Fitch Revised to

Positive Outlook

(7/20/20)

Unsecured Debt /

Total Debt(2)

(No Repurchase Facilities)

68%

64%

Q2 '19

Q2 '20

Note: "SAFE MTM" amounts in this presentation adjust the GAAP carrying value of the SAFE shares held by iStar to reflect their market value at the dates indicated. At September 10, 2020, SAFE's closing stock price was $57.19 and
iStar owned 33.4m SAFE shares with an aggregate market value of approximately $1.9b. At June 30, 2019, SAFE's closing stock price was $30.20 and iStar owned 20.6m shares SAFE shares with an aggregate market value of
approximately $622.1m.	3
(1) Leverage is calculated using debt, net of cash and adjusted total equity are presented gross of non-controlling interests, or "NCI". Please refer to the "Adjusted Equity Reconciliation" slide in the Appendix for more details.

(2) Includes only iStar's share of Net Lease Venture I debt.