| Exhibit B
May 6, 2022
Board of Directors
Watermark Lodging Trust, Inc.
50 North Riverside Plaza, Suite 4200
Chicago, Illinois 60606
Members of the Board:
We understand that Watermark Lodging Trust, Inc. (the “Company”), Ruby I Holdings LLC (“Parent 1”), Ruby II
Holdings LLC (“Parent 2”), Ruby III Holdings LLC (“Parent 3”), Ruby IV Holdings LLC (“Parent 4”, and together with
Parent 1, Parent 2, and Parent 3, the “Parent Entities”), Ruby Merger Sub I LLC (“Merger Sub I”), Ruby Merger Sub II LP
(“Merger Sub II”), and CWI 2 OP, LP (the “Partnership”), propose to enter into an Agreement and Plan of Merger,
substantially in the form of the draft dated May 5, 2022 (the “Merger Agreement”), which provides, among other things, for
(i) the merger of Merger Sub II with and into the Partnership, with the Partnership being the surviving entity (the
“Partnership Merger”), and (ii) immediately following the consummation of the Partnership Merger, the merger of Merger
Sub I with and into the Company, with the Company being the surviving entity (the “Company Merger,” and together with
the Partnership Merger, the “Mergers”). Pursuant to the Company Merger, each issued and outstanding share of (a) Class A
Common Stock, par value $0.001 per share, of the Company (the “Class A Common Stock”), other than shares held by the
Parent Entities, Merger Sub I, or any subsidiary of the Parent Entities, the Company, or Merger Sub I (collectively, the
“Excluded Shares”), will be converted into the right to receive $6.768 per share in cash, without interest (the “Per Company
A Share Merger Consideration”), and (b) Class T Common Stock, par value $0.001 per share, of the Company (the “Class T
Common Stock,” and together with the Class A Common Stock, the “Company Common Stock”), other than the Excluded
Shares, will be converted into the right to receive $6.699 per share in cash, without interest (the “Per Company T Share
Merger Consideration”), in each case, subject to adjustment in certain circumstances. We have been advised by you that the
Company has paid distribution and servicing fees to broker dealers on behalf of the holders of Class T Common Stock in an
amount equal to approximately $4,198,641 (the “Paid Broker Dealer Fees”), and as a result of the reimbursement of such
Paid Broker Dealer Fees to the Company, the Per Company T Share Merger Consideration is less than the Per Company A
Share Merger Consideration by $0.069 per share. The terms and conditions of the Mergers are more fully set forth in the
Merger Agreement.
You have asked for our opinion as to whether, taking into account the Paid Broker Dealer Fees, both the Per Company
A Share Merger Consideration to be received by the holders of shares of the Class A Common Stock and the Per Company
T Share Merger Consideration to be received by the holders of shares of the Class T Common Stock pursuant to the Merger
Agreement (other than the holders of the Excluded Shares) are fair from a financial point of view to such holders of shares
of the Company Common Stock.
For purposes of the opinion set forth herein, we have:
1) Reviewed certain publicly available financial statements and other business and financial information of the
Company;
2) Reviewed certain internal financial statements and other business, financial and operating data concerning the
Company;
3) Reviewed certain financial projections prepared by the management of the Company;
4) Discussed the past and current operations and financial condition and the prospects of the Company with senior
executives of the Company;
5) Reviewed information relating to certain strategic, financial and operational benefits anticipated from the Mergers,
prepared by the management of the Company;
6) Discussed the past and current operations and financial condition and the prospects of the Company, including
information relating to certain strategic, financial and operational benefits anticipated from the Mergers, with
senior executives of the Company;
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