Exhibit 5
EXECUTION VERSION
July 21, 2020
CWA LLC
150 N. Riverside Plaza
Suite 4200
Chicago, IL 60606
Attn: Michael G. Medzigian
Email: medzigian@watermarklodging.com
Dear Sirs:
Reference is made to that certain Securities Purchase Agreement, dated July 21, 2020 (the “Purchase Agreement”), by and among Watermark Lodging Trust, Inc., a Maryland corporation (the “Company”), CWI 2 OP, LP, a Delaware limited partnership (the “Operating Partnership”), ACP Watermark Investment LLC, a Delaware limited liability company, as the purchaser (the “Purchaser”), and certain guarantors party thereto, providing for the purchase and sale of the Company’s 12% Series B Cumulative Redeemable Preferred Stock (the “Series B Preferred Stock”) and a series of warrants (the “Warrants”) to purchase 16,778,446 of the Operating Partnership’s operating partnership units (“OP Units”). Each capitalized term used but not defined herein shall have the meaning ascribed thereto in the Purchase Agreement.
In recognition of the benefit that such a sale will confer upon the Purchaser, and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Purchaser agrees that, without the prior written consent of CWA LLC, not to be unreasonably withheld, conditioned or delayed, neither the Purchaser nor any of its Affiliates shall, and the Purchaser shall cause each of its Affiliates not to, directly or indirectly, transfer any shares of Series B Preferred Stock or Warrants prior to December 31, 2022. Without the prior written consent of CWA LLC, not to be unreasonably withheld, conditioned or delayed, neither the Purchaser nor any of its Affiliates shall, and the Purchaser shall cause each of its Affiliates not to, directly or indirectly, transfer any OP Units acquired upon the exercise of the Warrants or shares of Common Stock acquired upon exchange of OP Units until after the earlier of (x) April 24, 2023; (y) the date on which the Company shall no longer have the right to repurchase the Warrants, OP Units and Common Stock in accordance with Section 3 of the Warrants, and (z) the completion of the Company’s initial underwritten public offering of its Common Stock, subject to standard lock-up conditions, in each case, except to a Permitted Transferee. “Permitted Transferee” means any controlled Affiliate of the Purchaser who agrees to be bound by the Purchaser’s obligations under Sections 3.05 and 3.06 of the Purchase Agreement and this Lockup Letter.
Notwithstanding anything to the contrary in this Lockup Letter, the Purchaser and its Affiliates shall be permitted to transfer any shares of Series B Preferred Stock, Warrants, OP Units or Common Stock, at any time (unless otherwise indicated herein), under the following circumstances: (i) transfers pursuant to a merger, consolidation or other business combination involving the Company or the Operating Partnership, and (ii) transfers that have been approved by the Board or, transfers pursuant to a tender offer or exchange offer for equity securities of the Company that have been recommended by the Board as of the fifth Business Day prior to the expiration date of such offer, in each case, subject to such conditions as the Board determines.
Notwithstanding anything to the contrary in this Lockup Letter, the Purchaser shall not (whether before or after the expiration of the restrictions contained in this Lockup Letter) transfer any Series B