Primary Sales Agreement
On April 5, 2023, Safehold Inc. (the “Company”)
and Safehold GL Holdings LLC (“Portfolio Holdings”) entered into an ATM Equity OfferingSM Sales Agreement (the
“Primary Sales Agreement”) with BofA Securities, Inc., B. Riley Securities, Inc., Barclays Capital Inc., BNP Paribas
Securities Corp., Capital One Securities, Inc., Goldman Sachs & Co. LLC, J.P. Morgan Securities LLC, Mizuho Securities USA
LLC, Morgan Stanley & Co. LLC, Raymond James & Associates, Inc., RBC Capital Markets, LLC, SMBC Nikko Securities
America, Inc. and Truist Securities, Inc. (each, individually, a “Primary Agent” and, collectively, the “Primary
Agents”), pursuant to which the Company may sell, from time to time, shares of its common stock, $0.01 par value per share (“Common
Stock”), having an aggregate gross sales price of up to $300.0 million (the “Primary Shares”), through or to the Primary
Agents. The Company may sell the Primary Shares in amounts and at times to be determined by the Company from time to time but has no obligation
to sell any of the Primary Shares. Actual sales, if any, will depend on a variety of factors to be determined by the Company from time
to time, including, among other things, market conditions, the trading price of the Common Stock, capital needs and determinations by
the Company of the appropriate sources of its funding.
Any Primary Shares sold in the offering will be
issued pursuant to a prospectus supplement, dated April 5, 2023, filed with the Securities and Exchange Commission (the “SEC”)
on April 5, 2023, and the accompanying base prospectus, dated April 4, 2023, forming part of the Company’s shelf registration
statement on Form S-3 (Registration No. 333-271113), filed with the SEC on April 4, 2023. Sales of the Primary
Shares, if any, made pursuant to the Primary Sales Agreement may be sold in negotiated transactions, including block trades, or transactions
that are deemed to be “at the market” offerings as defined in Rule 415 under the Securities Act of 1933, as amended
(the “Securities Act”), by means of ordinary brokers’ transactions at market prices prevailing at the time of sale,
including sales made directly on the New York Stock Exchange, sales made to or through a market maker and sales made through other securities
exchanges or electronic communications networks. The Primary Sales Agreement provides that a Primary Agent will be entitled to compensation
that will not exceed, but may be lower than, 2.0% of the gross sales price of any of the Primary Shares sold through it as Primary Agent.
Under the terms of the Primary Sales Agreement, the Company may also sell Primary Shares to one or more Primary Agents, as principal,
at a price agreed upon at the time of sale. If the Company sells Primary Shares to any Primary Agent(s) as principal, it will enter
into a separate terms agreement with the Primary Agent(s), setting forth the terms of such transaction. The Company intends to contribute
any net proceeds from the sale of Primary Shares to Portfolio Holdings, which intends to use such net proceeds for general corporate
purposes, which may include repaying or repurchasing indebtedness, making additional investments in ground leases and providing for working
capital.
The Company and Portfolio Holdings made certain
customary representations, warranties and covenants concerning the Company, Portfolio Holdings and the registration statement in the Primary
Sales Agreement and also agreed to indemnify the Primary Agents against certain liabilities, including liabilities under the Securities
Act. The foregoing description of the Primary Sales Agreement does not purport to be complete and is subject to, and is qualified in its
entirety by reference to, the form of Primary Sales Agreement, which is attached hereto as Exhibit 1.1 and is incorporated herein
by reference.
On April 5, 2023, Venable LLP delivered its
legality opinion with respect to the Primary Shares that may be issued pursuant to the Primary Sales Agreement. A copy of the legality
opinion is attached hereto as Exhibit 5.1.
Selling Stockholder Sales Agreement
On
April 5, 2023, the Company, Portfolio Holdings and Star Investment Holdings SPV LLC (“Star Investment
Holdings”), a subsidiary of Star Holdings, a Maryland statutory trust (“Star Holdings”) for which the Company acts
as external manager, entered into an ATM Equity OfferingSM Sales Agreement (the “Selling Stockholder Sales
Agreement”) with BofA Securities, Inc., B. Riley Securities, Inc., Barclays Capital Inc., BNP Paribas Securities
Corp., Capital One Securities, Inc., Goldman Sachs & Co. LLC, J.P. Morgan Securities LLC, Mizuho Securities USA LLC,
Morgan Stanley & Co. LLC, Raymond James & Associates, Inc., RBC Capital Markets, LLC, SMBC Nikko Securities
America, Inc. and Truist Securities, Inc. (each, individually, a “Selling Stockholder Agent” and,
collectively, the “Selling Stockholder Agents”), pursuant to which Star Investment Holdings may sell, from time to time,
subject to receiving the Company’s consent, up to 1,000,000 shares of Common Stock (the “Selling Stockholder Shares”)
through or to the Selling Stockholder Agents. Star Investment Holdings may sell the Selling Stockholder Shares in amounts and at
times to be determined by Star Investment Holdings from time to time but has no obligation to sell any of the Selling Stockholder
Shares. Actual sales, if any, will depend on a variety of factors to be determined by Star Investment Holdings from time to time,
including, among other things, market conditions, the trading price of the Common Stock, capital needs and determinations by Star
Investment Holdings of the appropriate sources of its funding.
Any
Selling Stockholder Shares sold in the offering will be sold pursuant to a prospectus supplement, dated April 5, 2023, filed with
the SEC on April 5, 2023, and the accompanying base prospectus, dated April 4, 2023, forming part of the Company’s shelf
registration statement on Form S-3 (Registration No. 333-271113), filed with the SEC on April 4, 2023.
Sales of the Selling Stockholder Shares, if any, made pursuant to the Selling Stockholder Sales Agreement may be sold in negotiated transactions,
including block trades, or transactions that are deemed to be “at the market” offerings as defined in Rule 415 under
the Securities Act by means of ordinary brokers’ transactions at market
prices prevailing at the time of sale, including sales made directly on the New York Stock Exchange, sales made to or through a market
maker and sales made through other securities exchanges or electronic communications networks. The Selling Stockholder Sales Agreement
provides that a Selling Stockholder Agent will be entitled to compensation, payable by Star Investment Holdings, that will not exceed,
but may be lower than, 2.0% of the gross sales price of any of the Selling Stockholder Shares sold through it as Selling Stockholder Agent.
Under the terms of the Selling Stockholder Sales Agreement, Star Investment Holdings may also sell Selling Stockholder Shares to one or
more Selling Stockholder Agents, as principal, at a price agreed upon at the time of sale. If Star Investment Holdings sells Selling Stockholder
Shares to any Selling Stockholder Agent(s) as principal, it will enter into a separate terms agreement with the Selling Stockholder
Agent(s), setting forth the terms of such transaction. The Company will not directly receive any of the proceeds from any sales
of Selling Stockholder Shares by Star Investment Holdings; however, Star Investment Holdings may use the proceeds from the sale of Selling
Stockholder Shares to, among other things, repay borrowings outstanding under Star Holdings’ term loan facility, under which the
Company is a lender, or to pay a portion of the management fee payable to the Company as Star Holdings’ external manager pursuant
to the management agreement between the Company and Star Holdings. To the extent that the Company receives any such proceeds, the Company
intends to contribute any net proceeds from the sale of Selling Stockholder Shares to Portfolio Holdings, which intends to use such net
proceeds for general corporate purposes, which may include repaying or repurchasing indebtedness, making additional investments in ground
leases and providing for working capital.
The Company and Portfolio Holdings made certain
customary representations, warranties and covenants concerning the Company, Portfolio Holdings and the registration statement in the Selling
Stockholder Sales Agreement and also agreed to indemnify the Selling Stockholder Agents against certain liabilities, including liabilities
under the Securities Act. The foregoing description of the Selling Stockholder Sales Agreement does not purport to be complete and is
subject to, and is qualified in its entirety by reference to, the form of Selling Stockholder Sales Agreement, which is attached hereto
as Exhibit 1.2 and is incorporated herein by reference.
On April 5, 2023, Venable LLP delivered its
legality opinion with respect to the Selling Stockholder Shares that may be sold pursuant to the Selling Stockholder Sales Agreement.
A copy of the legality opinion is attached hereto as Exhibit 5.2.
This Current Report on Form 8-K shall not
constitute an offer to sell or a solicitation of an offer to buy any securities, nor shall there be any sale of these securities in any
state or jurisdiction in which such an offer, solicitation or sale would be unlawful prior to registration or qualification under the
securities laws of any such state or other jurisdiction.