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Letter to shareholders

I wanted to start this year’s letter with the above chart. Our team set out a two-year plan at the beginning of 2019 that emphasized building our innovative modern ground lease business, exiting legacy and non-core assets, and strengthening our balance sheet. The team worked very hard to execute on that plan and the results, as shared in last year’s annual report and above, were very good.

Coming into 2021, we wanted to push even further, and set new two-year goals for not only achieving additional progress on the three pillars of our strategy, but also to close what we believed was a material undervaluation in our stock price. Looking back now on 2021, the halfway point in our 2021–2022 plan, I am pleased to report continued progress and tangible success in key areas.

Let’s start with the most important achievement and then detail what enabled it to happen.

What happened in 2021?

Most importantly, the market began to recognize the impact and value of iStar’s rapidly growing investment in the modern ground lease business and the significant progress we made in simplifying the iStar portfolio. Total returns to shareholders during 2021 were 78% and helped shrink the gap to fair value, which we committed to work towards in last year’s annual report.

Why that happened is mostly tied to our team delivering on many of the goals we set out to achieve.


We wanted to make it simpler to understand the inherent value in iStar’s portfolio. During 2021, we sold over $400 million in legacy and non-core assets, generating over $115 million in gains and reducing legacy assets below 10% of the portfolio.

We also sold a large portfolio of net leased assets in Q1 2022 for over $3 billion, a value significantly above our carrying balance. Importantly, these transactions advance our goal of transitioning more fully to our growing ground lease business and further simplify our balance sheet.


We wanted to create a strong balance sheet and strong liquidity profile. Several achievements helped us make significant progress on this goal over the past year:

  • We generated strong earnings, with GAAP earnings of $109 million and adjusted earnings of $245 million in 2021.
  • We strengthened the balance sheet, completing several capital market transactions to extend our lease maturities and give us a clear runway to continue growing our ground lease business.
  • Our net lease transaction will enable us to meaningfully de-lever and pay off nearly all of our secured debt.

This progress was recognized by a Fitch credit rating upgrade and Moody’s putting our credit rating on positive outlook.


Lastly, and most critically, we continued to drive forward the modern ground lease business, with accelerating deal activity as markets reopened after the Covid impacts in 2020. Safehold closed a record number of deals in 2021, growing its portfolio to almost $5 billion and increasing its estimated Unrealized Capital Appreciation (UCA) to over $8 billion. This represents very sizable growth since Safehold’s IPO, and that growth has delivered significant value to iStar shareholders as the majority owner of Safehold. Total imbedded gain in our Safehold holdings was approximately $1.5 billion at year end.

What’s ahead in 2022?

We want to continue to deliver on our 2021–2022 plan and continue to unlock value in our major areas of focus. The net lease transaction was a good start, which should generate over $500 million in GAAP earnings and add over $1 billion of net cash to the balance sheet. And while the overall market in early 2022 has been hit from difficult geopolitical and financial conditions, we are confident the principal safety, locked-in growth and significant value of Safehold’s portfolio will prove to be a compelling story for investors.

As you will see in Safehold’s 2021 annual report, one of the keys to unlocking that value is to help the market properly value the rapidly growing UCA at Safehold. Forming a separate security called Caret, structured to track and capture UCA to the extent it is realized upon certain specified events, and a recently announced transaction involving the sale of Caret units represent the first steps towards realizing that value. We are encouraged by the quality of investors who are now part of the Caret investor base and the interest in this valuable asset.

In addition, there may be ways to simplify the relationship between iStar and Safehold that will enable more investors to participate as we grow the Safehold platform. Many investors have told us an externally managed structure at Safehold is an impediment to them investing in Safehold’s debt and equity, clearly a constraint that makes sense to look at as the platform grows.

We came into 2022 quite excited by our progress so far on our plans, and despite an uncertain world, we remain confident in our ability to deliver on those goals for our shareholders.

Thank you for your interest and support,

Jay Sugarman
Chairman & Chief Executive Officer

setting the pace
  1. Simplify iStar’s business to focus resources and drive shareholder value

A multi-year commitment to simplifying the business positions iStar to continue investing in a market-leading modern ground lease ecosystem while simultaneously returning capital to shareholders.



(1) Estimates are subject to increase or decrease based upon the final purchase price allocations and customary prorations, and are net of estimated distributions to its venture partner, debt prepayment fees, closing costs, promote fees, and distributions under iStar’s long-term incentive plan, iPIP.
locking in
  1. Strengthen the balance sheet to enhance liquidity and flexibility

iStar has taken a proactive approach to strengthening its balance sheet by refinancing debt maturities early and using the $3.1 billion sale of a net lease portfolio in Q1 2022 to repay indebtedness and remove almost all secured debt.

Stretch- ing the Lead
  1. Scale market-leading modern ground lease ecosystem

As Safehold’s founder, manager and largest shareholder, iStar helped Safehold generate $1.5 billion of originations in 2021, culminating in a record 17 ground leases closed in Q4 2021. Safehold’s portfolio has grown 14x since IPO in 2017. Safehold was awarded investment grade credit ratings in February 2021 of Baa1 from Moody’s and BBB+ from Fitch.

Chang- ing the Game


A better solution

We invite you to join us as we transform commercial real estate with a fundamentally more efficient capital solution for building owners and a new engine of wealth creation for shareholders.

Built for sustainability

In 2021, we solidified our commitment to a culture rooted in principles of diversity, equity and inclusion, while intensifying our efforts across a wide range of ESG initiatives.

Read our 2021 ESG report

Directors and Officers


Jay Sugarman
Chairman & Chief Executive Officer

Robin Josephs(2)(4)
Lead Director
Nominating and Governance
Committee Chair

Clifford De Souza(1)(4)
Audit Committee Chair

Richard Lieb(1)(3)
Investment Committee Chair

Barry W. Ridings(1)(2)
Compensation Committee Chair

David Eisenberg(2)(3)

(1)  Audit Committee
(2) Compensation Committee
(3) Investment Committee
(4) Nominating and Governance Committee

Executive Officers

Jay Sugarman
Chairman & Chief Executive Officer

Marcos Alvarado
President & Chief Investment Officer

Douglas Heitner
Chief Legal Officer

Brett Asnas
Chief Financial Officer

Executive Management

Elisha J. Blechner
Head of Portfolio Management

Kyle Curtin
Chief Administrative Officer

Timothy Doherty
Head of Investments

Theresa Ulyatt
Head of People, Talent & Inclusion

Steve Wylder

More about iStar’s leadership

Corporate information


New York

1114 Avenue of the Americas
New York, NY 10036
Tel: 212.930.9400
Fax: 212.930.9494

View all regional offices

Annual Meeting of Shareholders

May 12, 2022 9:00 AM ET

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Investor Information Services

iStar Inc. is a listed company on the New York Stock Exchange and is traded under the ticker “STAR.” The Company has filed all required Annual Chief Executive Officer Certifications with the NYSE. In addition, the Company has filed with the SEC, the certifications of the Chief Executive Officer and Chief Financial Officer required under Section 302 and Section 906 of the Sarbanes-Oxley Act of 2002 as exhibits to our most recently filed Annual Report on Form 10-K.

For help with questions about the Company, or to receive additional corporate information, please contact:

Investor Relations

Jason Fooks
Senior Vice President
Investor Relations & Marketing
Tel: 212.930.9400

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