Exhibit 10.5


 


Gordon Pointe Acquisition Corp.


780 Fifth Avenue South


Naples, FL 34102


 


Re: Initial Public Offering


 


Gentlemen:


 


This letter (this “Letter Agreement”)
is being delivered to you in accordance with the Underwriting Agreement (the “Underwriting Agreement”) to be entered
into by and between Gordon Pointe Acquisition Corp., a Delaware corporation (the “Company”), and B. Riley FBR,
Inc. (the “Underwriter”), relating to an underwritten initial public offering (the “Public Offering”),
of 14,375,000 of the Company’s units (including up to 1,875,000 units that may be purchased to cover over-allotments, if
any) (the “Units”), each comprised of one share of the Company’s Class A common stock, par value $0.0001 per
share (the “Common Stock”), and one warrant. Each Warrant (each, a “Warrant”) entitles the holder thereof
to purchase one share of Common Stock at a price of $11.50 per share, subject to adjustment. The Units shall be sold in the Public
Offering pursuant to a registration statement on Form S-1 and prospectus (the “Prospectus”) filed by the Company with
the Securities and Exchange Commission (the “Commission”) and the Company shall apply to have the Units listed on the
Nasdaq Capital Market. Certain capitalized terms used herein are defined in paragraph 11 hereof.


 


In order to induce the Company and the Underwriter
to enter into the Underwriting Agreement and to proceed with the Public Offering and for other good and valuable consideration,
the receipt and sufficiency of which are hereby acknowledged, Gordon Pointe Management, LLC (the “Sponsor”) and the
undersigned individuals, each of whom is a member of the Company’s board of directors and/or management team (each, an “Insider”
and collectively, the “Insiders”), hereby agrees with the Company as follows:


 


1. The
Sponsor and each Insider agrees that if the Company seeks stockholder approval of a proposed Business Combination, then in connection
with such proposed Business Combination, it or he shall (i) vote any shares of Capital Stock owned by it or him in favor of any
proposed Business Combination and (ii) not redeem any shares of Common Stock owned by it or him in connection with such stockholder
approval.


 






    	 		 



     


    

 


2. The
Sponsor and each Insider hereby agrees that in the event that the Company fails to consummate a Business Combination within 18
months from the closing of the Public Offering, or such later period approved by the Company’s stockholders in accordance
with the Company’s amended and restated certificate of incorporation, the Sponsor and each Insider shall take all reasonable
steps to cause the Company to (i) cease all operations except for the purpose of winding up, (ii) as promptly as reasonably possible
but not more than 10 business days thereafter, subject to lawfully available funds therefor, redeem 100% of the Common Stock sold
as part of the Units in the Public Offering (the “Offering Shares”), at a per-share price, payable in cash, equal to
the aggregate amount then on deposit in the Trust Account, including interest earned on the funds held in the Trust Account and
not previously released to the Company to pay its franchise and income taxes (less up to $100,000 of interest to pay dissolution
expenses), divided by the number of then outstanding Offering Shares, which redemption will completely extinguish all Public Stockholders’
rights as stockholders (including the right to receive further liquidation distributions, if any), subject to applicable law, and
(iii) as promptly as reasonably possible following such redemption, subject to the approval of the Company’s remaining stockholders
and the Company’s board of directors, dissolve and liquidate, subject in each case to the Company’s obligations under
Delaware law to provide for claims of creditors and other requirements of applicable law. The Sponsor and each Insider agrees to
not propose any amendment to the Company’s amended and restated certificate of incorporation that would affect the substance
or timing of the Company’s obligation to redeem 100% of the Offering Shares if the Company does not complete a Business Combination
within 18 months from the closing of the Public Offering, unless the Company provides its public stockholders with the opportunity
to redeem their shares of Common Stock upon approval of any such amendment at a per-share price, payable in cash, equal to the
aggregate amount then on deposit in the Trust Account, including interest earned on the funds held in the Trust Account and not
previously released to the Company to pay its franchise and income taxes, divided by the number of then outstanding Offering Shares.


 


The Sponsor and each Insider acknowledges
that it or he has no right, title, interest or claim of any kind in or to any monies held in the Trust Account or any other asset
of the Company as a result of any liquidation of the Company with respect to the Founder Shares held by it. The Sponsor and each
Insider hereby further waives, with respect to any shares of Common Stock held by it or him, if any, any redemption rights it or
he may have in connection with the consummation of a Business Combination, including, without limitation, any such rights available
in the context of a stockholder vote to approve such Business Combination or in the context of a tender offer made by the Company
to purchase shares of Common Stock (although the Sponsor, the Insiders and their respective affiliates shall be entitled to redemption
and liquidation rights with respect to any Offering Shares it or they hold if the Company fails to consummate a Business Combination
within 18 months from the date of the closing of the Public Offering).


 


3. Subject
to the provisions set forth in paragraphs 7(a) and (b) below, during the period commencing on the effective date of the Underwriting
Agreement and ending 180 days after such date, the Sponsor and each Insider shall not, without the prior written consent of the
Representative, (i) sell, offer to sell, contract or agree to sell, hypothecate, pledge, grant any option to purchase or otherwise
dispose of or agree to dispose of, directly or indirectly, or establish or increase a put equivalent position or liquidate or decrease
a call equivalent position within the meaning of Section 16 of the Securities Exchange Act of 1934, as amended, and the rules and
regulations of the Commission promulgated thereunder, with respect to any Units, shares of Common Stock, Founder Shares, Warrants
or any securities convertible into, or exercisable, or exchangeable for, shares of Common Stock owned by it or him, (ii) enter
into any swap or other arrangement that transfers to another, in whole or in part, any of the economic consequences of ownership
of any Units, shares of Common Stock, Founder Shares, Warrants or any securities convertible into, or exercisable, or exchangeable
for, shares of Common Stock owned by it or him, whether any such transaction is to be settled by delivery of such securities, in
cash or otherwise, or (iii) publicly announce any intention to effect any transaction specified in clause (i) or (ii). Each of
the Insiders and the Sponsor acknowledges and agrees that, prior to the effective date of any release or waiver, of the restrictions
set forth in this paragraph 3 or paragraph 7 below, the Company shall announce the impending release or waiver by press release
through a major news service at least two business days before the effective date of the release or waiver. Any release or waiver
granted shall only be effective two business days after the publication date of such press release. The provisions of this paragraph
will not apply if the release or waiver is effected solely to permit a transfer not for consideration and the transferee has agreed
in writing to be bound by the same terms described in this Letter Agreement to the extent and for the duration that such terms
remain in effect at the time of the transfer.


 






    	 	2	 



     


    

 


4. In
the event of the liquidation of the Trust Account, the Sponsor (which for purposes of clarification shall not extend to any other
shareholders, members or managers of the Sponsor) agrees to indemnify and hold harmless the Company against any and all loss, liability,
claim, damage and expense whatsoever (including, but not limited to, any and all legal or other expenses reasonably incurred in
investigating, preparing or defending against any litigation, whether pending or threatened, or any claim whatsoever) to which
the Company may become subject as a result of any claim by (i) any third party for services rendered or products sold to the Company
or (ii) a prospective target business with which the Company has entered into an acquisition agreement (a “Target”);
provided, however, that such indemnification of the Company by the Sponsor shall apply only to the extent necessary to ensure that
such claims by a third party for services rendered (other than the Company’s independent public accountants) or products
sold to the Company or a Target do not reduce the amount of funds in the Trust Account to below (i) $10.10 per share of the Offering
Shares or (ii) such lesser amount per share of the Offering Shares held in the Trust Account due to reductions in the value of
the trust assets as of the date of the liquidation of the Trust Account, in each case, net of the amount of interest earned on
the property in the Trust Account which may be withdrawn to pay taxes, except as to any claims by a third party (including a Target)
who executed a waiver of any and all rights to seek access to the Trust Account and except as to any claims under the Company’s
indemnity of the Underwriter against certain liabilities, including liabilities under the Securities Act of 1933, as amended. In
the event that any such executed waiver is deemed to be unenforceable against such third party, the Sponsor shall not be responsible
to the extent of any liability for such third party claims. The Sponsor shall have the right to defend against any such claim with
counsel of its choice reasonably satisfactory to the Company if, within 15 days following written receipt of notice of the claim
to the Sponsor, the Sponsor notifies the Company in writing that it shall undertake such defense.


 


5. To
the extent that the Underwriter does not exercise its over-allotment option to purchase up to an additional 1,875,000 Units within
45 days from the date of the Prospectus (and as further described in the Prospectus), the Sponsor agrees to forfeit, at no cost,
a number of Founder Shares in the aggregate equal to 468,750 multiplied by a fraction, (i) the numerator of which is 1,875,000
minus the number of Units purchased by the Underwriter upon the exercise of its over-allotment option, and (ii) the denominator
of which is 1,875,000. The forfeiture will be adjusted to the extent that the over-allotment option is not exercised in full by
the Underwriter so that the Initial Stockholders will own an aggregate of 20.0% of the Company’s issued and outstanding shares
of Capital Stock after the Public Offering.


 






    	 	3	 



     


    

 


6. The
Sponsor and each Insider hereby agrees and acknowledges that: (i) the Underwriter and the Company would be irreparably injured
in the event of a breach by such Sponsor or an Insider of its or his obligations under paragraphs 1, 2, 3, 4, 5, 7(a), 7(b), and
9 of this Letter Agreement (ii) monetary damages may not be an adequate remedy for such breach and (iii) the non-breaching party
shall be entitled to injunctive relief, in addition to any other remedy that such party may have in law or in equity, in the event
of such breach.


 


7. (a) The Sponsor and each
Insider agrees that it, he or she shall not Transfer any Founder Shares (or shares of Common Stock issuable upon conversion
thereof) until the earlier of (i) one year after the completion of a Business Combination or earlier if, subsequent to a
Business Combination, (x) the last sale price of the Common Stock equals or exceeds $12.00 per share (as adjusted for stock
splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day
period commencing at least 150 days after a Business Combination or (y) the date following the completion of a Business
Combination on which the Company completes a liquidation, merger, capital stock exchange, reorganization or other similar
transaction that results in all of the Company’s stockholders having the right to exchange their shares of Common Stock
for cash, securities or other property (the “Founder Shares Lock-up Period”).


 


    (b) The Sponsor
and each Insider agrees that it or he shall not Transfer any Private Placement Warrants (or shares of Common Stock issued or issuable
upon the conversion of the Private Placement Warrants), until 30 days after the completion of a Business Combination (the “Private
Placement Warrants Lock-up Period”, together with the Founder Shares Lock-up Period, the “Lock-up Periods”).


 


    (c) Notwithstanding
the provisions set forth in paragraphs 7(a) and (b), Transfers of the Founder Shares, Private Placement Warrants and shares of
Common Stock issued or issuable upon the exercise or conversion of the Private Placement Warrants or the Founder Shares and that
are held by the Sponsor, any Insider or any of their permitted transferees (that have complied with this paragraph 7(c)), are
permitted (a) to the Company’s officers or directors, any affiliates or family members of any of the Company’s officers
or directors, any members of the Sponsor, or any affiliates of the Sponsor; (b) in the case of an individual, transfers by gift
to a member of the individual’s immediate family, to a trust, the beneficiary of which is a member of the individual’s
immediate family or an affiliate of such person, or to a charitable organization; (c) in the case of an individual, transfers
by virtue of laws of descent and distribution upon death of the individual; (d) in the case of an individual, transfers pursuant
to a qualified domestic relations order; (e) transfers by private sales or transfers made in connection with the consummation
of a Business Combination at prices no greater than the price at which the securities were originally purchased; (f) transfers
in the event of the Company’s liquidation prior to the completion of an initial Business Combination; (g) transfers by virtue
of the laws of the State of Delaware or the Sponsor’s limited liability company agreement upon dissolution of the Sponsor;
and (h) in the event of the Company’s liquidation, merger, capital stock exchange, reorganization or other similar transaction
which results in all of the Company’s stockholders having the right to exchange their shares of Common Stock for cash, securities
or other property subsequent to the completion of the Company’s initial Business Combination; provided, however, that in
the case of clauses (a) through (e), these permitted transferees must enter into a written agreement agreeing to be bound by the
restrictions herein.


 






    	 	4	 



     


    

 


8. The
Sponsor and each Insider represents and warrants that it or he has never been suspended or expelled from membership in any securities
or commodities exchange or association or had a securities or commodities license or registration denied, suspended or revoked.
Each Insider’s biographical information furnished to the Company (including any such information included in the Prospectus)
is true and accurate in all respects and does not omit any material information with respect to the Insider’s background.
Each Insider’s questionnaire furnished to the Company is true and accurate in all respects. Each Insider represents and warrants
that: it is not subject to or a respondent in any legal action for, any injunction, cease-and-desist order or order or stipulation
to desist or refrain from any act or practice relating to the offering of securities in any jurisdiction; it has never been convicted
of, or pleaded guilty to, any crime (i) involving fraud, (ii) relating to any financial transaction or handling of funds of another
person, or (iii) pertaining to any dealings in any securities and it is not currently a defendant in any such criminal proceeding.


 


9. There
will be no restrictions on payments made to Insiders. However, prior to consummation of the Business Combination the Company shall
not make any payment to an Insider from the proceeds held in the Trust Account; payment to an affiliate of the Sponsor for office
space, utilities and secretarial and administrative support for a total of $10,000 per month; reimbursement of legal fees and expenses
incurred by the Sponsor or any Insider in connection with the Company’s formation, the initial Business Combination and their
services to the Company; payment of fees and reimbursement of out-of-pocket expenses related to identifying, investigating and
consummating an initial Business Combination; and repayment of loans, if any, and on such terms as to be determined by the Company
from time to time, made by the Sponsor or any of the Company’s officers or directors to finance transaction costs in connection
with an intended initial Business Combination, provided, that, if the Company does not consummate an initial Business Combination,
a portion of the working capital held outside the Trust Account may be used by the Company to repay such loaned amounts so long
as no proceeds from the Trust Account are used for such repayment. Up to $1,500,000 of such loans may be convertible into warrants
at a price of $1.00 per warrant at the option of the lender. Such warrants would be identical to the Private Placement Warrants,
including as to exercise price, exercisability and exercise period.


 


10. The
Sponsor and each Insider has full right and power, without violating any agreement to which it is bound (including, without limitation,
any non-competition or non-solicitation agreement with any employer or former employer), to enter into this Letter Agreement and,
as applicable, to serve as a director on the board of directors of the Company and hereby consents to being named in the Prospectus
as a director of the Company.


 






    	 	5	 



     


    

 


11. As
used herein, (i) “Business Combination” shall mean a merger, capital stock exchange, asset acquisition, stock purchase,
reorganization or similar business combination, involving the Company and one or more businesses; (ii) “Capital Stock”
shall mean, collectively, the Common Stock and the Founder Shares; (iii) “Founder Shares” shall mean the 3,593,750
shares of the Company’s Class F common stock, par value $0.0001 per share, initially issued to the Sponsor (or 3,125,000
shares if the over-allotment option is not exercised by the Underwriter) for an aggregate purchase price of $25,000, or approximately
$0.007 per share, prior to the consummation of the Public Offering; (iv) “Initial Stockholders” shall mean the Sponsor
and any Insider that holds Founder Shares; (v) “Private Placement Warrants” shall mean the Warrants to purchase up
to 4,900,000 shares of Common Stock of the Company (or 5,462,500 shares of Common Stock if the over-allotment option is exercised
in full) that the Sponsor has agreed to purchase for an aggregate purchase price of $4,900,000 in the aggregate (or $5,462,500
if the over-allotment option is exercised in full), or $1.00 per Warrant, in a private placement that shall occur simultaneously
with the consummation of the Public Offering; (vi) “Public Stockholders” shall mean the holders of securities issued
in the Public Offering; (vii) “Trust Account” shall mean the trust fund into which a portion of the net proceeds of
the Public Offering shall be deposited; and (viii) “Transfer” shall mean the (a) sale of, offer to sell, contract or
agreement to sell, hypothecate, pledge, grant of any option to purchase or otherwise dispose of or agreement to dispose of, directly
or indirectly, or establishment or increase of a put equivalent position or liquidation with respect to or decrease of a call equivalent
position within the meaning of Section 16 of the Securities Exchange Act of 1934, as amended, and the rules and regulations of
the Commission promulgated thereunder with respect to, any security, (b) entry into any swap or other arrangement that transfers
to another, in whole or in part, any of the economic consequences of ownership of any security, whether any such transaction is
to be settled by delivery of such securities, in cash or otherwise, or (c) public announcement of any intention to effect any transaction
specified in clause (a) or (b).


 


12. This
Letter Agreement constitutes the entire agreement and understanding of the parties hereto in respect of the subject matter hereof
and supersedes all prior understandings, agreements, or representations by or among the parties hereto, written or oral, to the
extent they relate in any way to the subject matter hereof or the transactions contemplated hereby. This Letter Agreement may not
be changed, amended, modified or waived (other than to correct a typographical error) as to any particular provision, except by
a written instrument executed by all parties hereto.


 


13. No
party hereto may assign either this Letter Agreement or any of its rights, interests, or obligations hereunder without the prior
written consent of the other party. Any purported assignment in violation of this paragraph shall be void and ineffectual and shall
not operate to transfer or assign any interest or title to the purported assignee. This Letter Agreement shall be binding on the
Sponsor and each Insider and their respective successors, heirs and assigns and permitted transferees.


 


14. This
Letter Agreement shall be governed by and construed and enforced in accordance with the laws of the State of New York, without
giving effect to conflicts of law principles that would result in the application of the substantive laws of another jurisdiction.
The parties hereto (i) all agree that any action, proceeding, claim or dispute arising out of, or relating in any way to, this
Letter Agreement shall be brought and enforced in the courts of New York City, in the State of New York, and irrevocably submit
to such jurisdiction and venue, which jurisdiction and venue shall be exclusive and (ii) waive any objection to such exclusive
jurisdiction and venue or that such courts represent an inconvenient forum.


 


15. Any notice, consent or request
to be given in connection with any of the terms or provisions of this Letter Agreement shall be in writing and shall be sent by
express mail or similar private courier service, by certified mail (return receipt requested), by hand delivery or facsimile transmission.


 


16. This
Letter Agreement shall terminate on the earlier of (i) the expiration of the Lock-up Periods or (ii) the liquidation of the Company;
provided, however, that this Letter Agreement shall earlier terminate in the event that the Public Offering is not consummated
and closed by July 30, 2019; provided further that paragraph 4 of this Letter Agreement shall survive such liquidation.


 


[Signature Page Follows]


 



    	 	6	 



     


    

 


	 	Sincerely,
	 	 
	 	GORDON POINTE
    MANAGEMENT, LLC,
	 	a
        Florida limited liability company

	 	 
	 	By:	/s/
    James J. Dolan
	 	 	Name:
        James J. Dolan, Manager 

	 	 	 
	 	By:	/s/
    James J. Dolan
	 		Name:
        James J. Dolan

	 	 	 
	 	By:	/s/
    Douglas L. Hein
	 	 	Name: Douglas L. Hein
	 	 	 
	 	By:	/s/
    Robert B. Cross
	 	 	Name: Robert B. Cross
	 	 	 
	 	By:	/s/
    David Dennis
	 	 	Name: David Dennis
	 	 	 
	 	By:	/s/
    Joseph F. Mendel
	 	 	Name: Joseph F. Mendel
	 	 	 
	 	By:	/s/
    Neeraj Vohra
	 	 	Name: Neeraj Vohra


  


[Signature Page to Letter Agreement]


 






    	 	7	 



     


    

 


	 	By:	/s/ Brian P. Dolan
	 	 	Name: Brian P. Dolan as Custodian for Anne Elizabeth Dolan under UGMA
	 	 	 
	 	By:	/s/ Brian P. Dolan
	 	 	Name: Brian P. Dolan as Custodian for John H. Dolan under UGMA
	 	 	 
	 	By:	/s/ Brian P. Dolan
	 	 	Name: Brian P. Dolan as Custodian for Mary Grace Dolan under UGMA
	 	 	 
	 	By:	/s/ Brian P. Dolan
	 	 	Name: Brian P. Dolan as Custodian for Peter F. Dolan under UGMA
	 	 	 
	 	By:	/s/ Brian P. Dolan
	 	 	Name: Brian P. Dolan as Custodian for Katherine T. Dolan under UGMA
	 	 	 
	 	By:	/s/ Brian P. Dolan
	 	 	Name: Brian P. Dolan as Custodian for Luke P. Dolan under UGMA
	 	 	 
	 	By:	/s/ Brian P. Dolan
	 	 	Name: Brian P. Dolan as Custodian for Clara A. Dolan under UGMA
	 	 	 
	 	By:	/s/ James J. Dolan
	 	 	Name: James J. Dolan as Custodian for Olivia J. Dolan under UGMA
	 	 	 
	 	By:	/s/ James J. Dolan
	 	 	Name: James J. Dolan as Custodian for Abigail R. Dolan under UGMA
	 	 	 
	 	By:	/s/ James J. Dolan
	 	 	
        Name: James J. Dolan as Custodian for James J. Dolan
III under UGMA



 


[Signature Page to Letter Agreement]


 






    	 	8	 



     


    

 


	 	By:	/s/ Charles D. Dolan
	 	 	Name: Charles D. Dolan as Custodian for Loeffler C. Dolan under UGMA
	 	 	 
	 	By:	/s/ Gregory F. Dolan
	 	 	Name: Gregory F. Dolan as Custodian for Bridget R. Dolan under UGMA
	 	 	 
	 	By:	/s/ Gregory F. Dolan
	 	 	Name: Gregory F. Dolan, Trustee of the PPD 2012 Family Trust dated 12/31/2012
	 	 	 
	 	By:	/s/ Gregory F. Dolan
	 	 	Name: Gregory F. Dolan, Trustee of the JJD 2012 Family Trust dated 12/31/2012
	 	 	 
	 	By:	/s/ James Dolan Jr.
	 	 	Name: James Dolan Jr.
	 	 	 
	 	By:	/s/ Michael A. Dolan 
	 	 	Name: Michael A. Dolan
	 	 	 
	 	By:	/s/ Brian P. Dolan
	 	 	Name: Brian P. Dolan 
	 	 	 
	 	By:	/s/ Peter J. Dolan
	 	 	Name: Peter J. Dolan 
	 	 	 
	 	By:	/s/ Gregory F. Dolan
	 	 	Name: Gregory F. Dolan
	 	 	 
	 	By:	/s/ Charles D. Dolan
	 	 	
        Name: Charles D. Dolan



 


[Signature Page to Letter Agreement]




 


9