Exhibit 10.5


 


PRIVATE PLACEMENT WARRANTS SUBSCRIPTION
AGREEMENT


 


THIS PRIVATE PLACEMENT WARRANTS SUBSCRIPTION
AGREEMENT, dated as of January 19, 2021 (as it may be amended from time to time, this “Agreement”), is
entered into by and between Oyster Enterprises Acquisition Corp., a Delaware corporation (the “Company”), and
Imperial Capital, LLC (the “Purchaser”).


 


WHEREAS, the Company intends to consummate
an initial public offering of the Company’s units (the “Public Offering”), each unit consisting of one
share of the Company’s Class A common stock (“Class A Common Stock”), par value $0.0001 per
share (each, a “Share”) and one-half of one redeemable warrant, each whole warrant entitling the holder to purchase
one Share at an exercise price of $11.50 per Share (subject to adjustment), as set forth in the Company’s registration statement
on Form S-1 related to the Public Offering (the “Registration Statement”) filed with the Securities and
Exchange Commission; and


 


WHEREAS, the Purchaser has agreed to purchase
an aggregate of 1,200,000 warrants (or 1,380,000 warrants if the over-allotment option in connection with the Public Offering is
exercised in full) (the “Private Placement Warrants”), each Private Placement Warrant entitling the holder to
purchase one Share at an exercise price of $11.50 per Share (subject to adjustment), during the period commencing on the later
of (i) twelve (12) months from the date of the closing of the Public Offering and (ii) 30 days following the consummation
of the Company’s initial business combination (the “Business Combination”), as such term is defined in
the Registration Statement, and expiring on the fifth anniversary of the consummation of the Business Combination (provided that
so long as the Private Placement Warrants are held by Imperial Capital, LLC or I-Bankers Securities, Inc. or their respective
designees or affiliates, Imperial Capital, LLC or I-Bankers Securities, Inc. or their respective designees or affiliates
will not be permitted to exercise such Private Placement Warrants after the fifth anniversary of the effective date of the Registration
Statement in accordance with Rule 5110(g)(8)(A) of the Financial Industry Regulatory Authority (“FINRA”).


 


NOW THEREFORE, in consideration of the mutual
promises contained in this Agreement and other good and valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the parties to this Agreement hereby, intending legally to be bound, agree as follows:


 


AGREEMENT


 


Section 1. Authorization, Purchase
and Sale; Terms of the Private Placement Warrants.


 


A. Authorization of the Private
Placement Warrants. The Company has duly authorized the issuance and sale of the Private Placement Warrants to the Purchaser.


 


B. Purchase and Sale of the Private
Placement Warrants. On the date of the consummation of the Public Offering, and concurrently with the consummation thereof,
or on such earlier time and date as may be mutually agreed by the Purchaser and the Company (the “Initial Closing Date”),
the Company shall issue and sell to the Purchaser, and the Purchaser shall purchase from the Company 1,200,000 Private Placement
Warrants at a price of $1.00 per warrant for an aggregate purchase price of $1,200,000 (the “Purchase Price”),
which shall be paid by wire transfer of immediately available funds in accordance with the Company’s wiring instructions.
On the Initial Closing Date, upon payment by the Purchaser of the Purchase Price, the Company, shall either, at its option, deliver
a certificate evidencing the Private Placement Warrants purchased by the Purchaser on such date duly registered in the Purchaser’s
name to the Purchaser, or effect such delivery in book-entry form. On the date of the consummation of the closing of the over-allotment
option in connection with the Public Offering, and concurrently with the consummation thereof, or on such earlier time and date
as may be mutually agreed by the Purchaser and the Company (each such date, an “Over-allotment Closing Date”;
together with the Initial Closing Date, the “Closing Dates” and each, a “Closing Date”),
the Company shall issue and sell to the Purchaser, and the Purchaser shall purchase from the Company, up to an aggregate of 180,000
Private Placement Warrants, in the same proportion as the amount of the over-allotment option that is exercised, at a price of
$1.00 per warrant for an aggregate purchase price of up to $180,000 (if the over-allotment option in connection with the Public
Offering is exercised in full) (the “Over-allotment Purchase Price”), which shall be paid by wire transfer of
immediately available funds in accordance with the Company’s wiring instructions. On the Over-allotment Closing Date, upon
the payment by the Purchaser of the Over-allotment Purchase Price payable by it, the Company shall either, at its option, deliver
a certificate evidencing the Private Placement Warrants purchased by the Purchaser on such date duly registered in the Purchaser’s
name to the Purchaser, or effect such delivery in book-entry form.


 






     


     


    

 


C. Terms of the Private Placement
Warrants.


 


(i) The Private Placement Warrants
shall have the terms set forth in a warrant agreement to be entered into by the Company and a warrant agent, in connection with
the Public Offering (the “Warrant Agreement”).


 


(ii) At or prior to the time of the
Initial Closing Date, the Company and the Purchaser shall enter into a registration rights agreement (the “Registration
Rights Agreement”) pursuant to which the Company will grant certain registration rights to the Purchaser relating to
the Private Placement Warrants and the Shares underlying the Private Placement Warrants.


 


Section 2. Representations and Warranties
of the Company. As a material inducement to the Purchaser to enter into this Agreement and purchase the Private Placement
Warrants, the Company hereby represents and warrants to the Purchaser (which representations and warranties shall survive each
Closing Date) that:


 


A. Organization and Corporate Power.
The Company is a corporation duly incorporated, validly existing and in good standing under the laws of the State of Delaware and
is qualified to do business in every jurisdiction in which the failure to so qualify would reasonably be expected to have a material
adverse effect on the financial condition, operating results or assets of the Company. The Company possesses all requisite corporate
power and authority necessary to carry out the transactions contemplated by this Agreement and the Warrant Agreement.


 


B. Authorization; No Breach.


 


(i) The execution, delivery and performance
of this Agreement and the Private Placement Warrants have been duly authorized and approved by the Company as of each Closing Date.
This Agreement constitutes a valid and binding obligation of the Company, enforceable against the Company in accordance with its
terms, subject to bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium and other laws of general applicability
relating to or affecting creditors’ rights and to general equitable principles (whether considered in a proceeding in equity
or law) (the “Enforceability Exceptions”). Upon issuance in accordance with, and payment pursuant to, the terms
of the Warrant Agreement and this Agreement, the Private Placement Warrants will constitute valid and binding obligations of the
Company, enforceable against the Company in accordance with their terms, subject to the Enforceability Exceptions.


 


(ii) The execution and delivery by
the Company of this Agreement and the Private Placement Warrants, the issuance and sale of the Private Placement Warrants, the
issuance of the Shares upon exercise of the Private Placement Warrants and the fulfillment of, and compliance with, the respective
terms hereof and thereof by the Company, do not and will not as of each Closing Date (a) (A) conflict with or result
in a breach of the terms, conditions or provisions of, (B) constitute a default under, (C) result in the creation of
any lien, security interest, charge or encumbrance upon the Company’s capital stock or assets under, or (D) result in
a violation of, the certificate of incorporation or the bylaws of the Company (in effect on the date hereof or as may be amended
prior to completion of the Public Offering), or any material law, statute, rule or regulation to which the Company is subject,
or any agreement, order, judgment or decree to which the Company is subject, or (b) require any authorization, consent, approval,
exemption, action, notice, declaration or filing, in each case, by or to any court or administrative or governmental body or agency,
except for any filings required after the date hereof under federal or state securities laws.


 


C. Title to Securities. Upon
issuance in accordance with, and payment pursuant to, the terms hereof and the Warrant Agreement, the Placement Warrants will be
duly and validly issued and the Shares issuable upon exercise of the Private Placement Warrants will be duly and validly issued,
fully paid and nonassessable. On the date of issuance of the Private Placement Warrants, the Shares issuable upon exercise of the
Private Placement Warrants shall have been reserved for issuance. Upon issuance in accordance with, and payment pursuant to, the
terms hereof and the Warrant Agreement, the Purchaser will have good title to the Private Placement Warrants and the Shares issuable
upon exercise of such Private Placement Warrants, free and clear of all liens, claims and encumbrances of any kind, other than
(i) transfer restrictions hereunder and under the other agreements contemplated hereby, (ii) transfer restrictions under
federal and state securities laws, and (iii) liens, claims or encumbrances imposed due to the actions of the Purchaser.


 






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D. Valid Issuance. The total
number of shares of all classes of capital stock which the Company has authority to issue is 111,000,000 shares of common stock
(which consist of 100,000,000 shares of Class A Common Stock and 10,000,000 shares of the Company’s Class B common
stock, par value $0.0001 per share (the “Class B Common Stock”)) and 1,000,000 shares of the Company’s
preferred stock, par value $0.0001, per share (the “Preferred Stock”). As of the date hereof, the Company has
issued and outstanding no shares of Class A Common Stock, 5,750,000 shares of Class B Common Stock (of which up to 750,000
shares are subject to forfeiture as described in the Registration Statement) and no shares of Preferred Stock. All of the issued
shares of capital stock of the Company have been duly authorized, validly issued, and are fully paid and non-assessable.


 


Section 3. Representations and Warranties
of the Purchaser. As a material inducement to the Company to enter into this Agreement and issue and sell the Private
Placement Warrants to the Purchaser, the Purchaser hereby represents and warrants to the Company (which representations and warranties
shall survive each Closing Date) that:


 


A. Organization and Requisite Authority.
The Purchaser is duly organized, validly existing and in good standing under the laws of the State of Delaware and possesses all
requisite power and authority necessary to carry out the transactions contemplated by this Agreement.


 


B. Authorization; No Breach.


 


(i) This Agreement constitutes a valid
and binding obligation of the Purchaser, enforceable against the Purchaser in accordance with its terms, except subject to the
Enforceability Exceptions.


 


(ii) The execution and delivery by
the Purchaser of this Agreement and the fulfillment of and compliance with the terms hereof by the Purchaser does not and shall
not as of each Closing Date conflict with, violate, or result in a breach by the Purchaser of the terms, conditions or provisions
of, or constitute a default under the charter or bylaws or other organizational documents of the Purchaser, or any agreement, instrument,
order, judgment or decree to which the Purchaser is subject.


 


C. Investment Representations.


 


(i) The Purchaser is acquiring the
Private Placement Warrants and, upon exercise of the Private Placement Warrants, the Shares issuable upon such exercise (the Private
Placement Warrants and such Shares, the “Securities”), for the Purchaser’s own account, for investment
purposes only and not with a view towards, or for resale in connection with, any public sale or distribution thereof.


 


(ii) The Purchaser is an “accredited
investor” as such term is defined in Rule 501(a)(3) of Regulation D under the Securities Act of 1933, as amended
(the “Securities Act”).


 


(iii) The Purchaser understands that
the Securities are being offered and will be sold to it in reliance on specific exemptions from the registration requirements of
the United States federal and state securities laws and that the Company is relying upon the truth and accuracy of, and the Purchaser’s
compliance with, the representations and warranties of the Purchaser set forth herein in order to determine the availability of
such exemptions and the eligibility of the Purchaser to acquire such Securities.


 


(iv) The Purchaser did not enter into
this Agreement as a result of any general solicitation or general advertising within the meaning of Rule 502(c) under
the Securities Act.


 


(v) The Purchaser has been furnished
with all materials relating to the business, finances and operations of the Company and materials relating to the offer and sale
of the Securities which have been requested by the Purchaser. The Purchaser has been afforded the opportunity to ask questions
of the executive officers and directors of the Company. The Purchaser understands that its investment in the Securities involves
a high degree of risk and it has sought such accounting, legal and tax advice as it has considered necessary to make an informed
investment decision with respect to the acquisition of the Securities.


 






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(vi) The Purchaser understands that
no United States federal or state agency or any other government or governmental agency has passed on or made any recommendation
or endorsement of the Securities or the fairness or suitability of the investment in the Securities by the Purchaser nor have such
authorities passed upon or endorsed the merits of the offering of the Securities.


 


(vii) The Purchaser understands that:
(a) the Securities have not been and are not being registered under the Securities Act or any state securities laws, and may
not be offered for sale, sold, assigned or transferred unless (1) subsequently registered thereunder or (2) sold in reliance
on an exemption therefrom; and (b) except as specifically set forth in the Registration Rights Agreement, neither the Company
nor any other person is under any obligation to register the Securities under the Securities Act or any state securities laws or
to comply with the terms and conditions of any exemption thereunder. While such Purchaser understands that Rule 144 under
the Securities Act is not available for the resale of securities initially issued by shell companies (other than business combination
related shell companies) or issuers that have been at any time previously a shell company, such Purchaser understands that Rule 144
includes an exception to this prohibition if the following conditions are met: (i) the issuer of the securities that was formerly
a shell company has ceased to be a shell company; (ii) the issuer of the securities is subject to the reporting requirements
of Section 13 or 15(d) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”); (iii) the
issuer of the securities has filed all Exchange Act reports and material required to be filed, as applicable, during the preceding
12 months (or such shorter period that the issuer was required to file such reports and materials), other than Form 8-K reports;
and (iv) at least one year has elapsed from the time that the issuer filed current Form 10 type information with the
SEC reflecting its status as an entity that is not a shell company.


 


(viii) The Purchaser understands the
high degree of risk associated with investments in the securities of companies in the development stage such as the Company, has
such knowledge and experience in financial and business matters to be able to evaluate the merits and risks of an investment in
the Securities and is able to bear the economic risk of an investment in the Securities in the amount contemplated hereunder for
an indefinite period of time. The Purchaser has adequate means of providing for its current financial needs and contingencies and
will have no current or anticipated future needs for liquidity which would be jeopardized by the investment in the Securities.
The Purchaser can afford a complete loss of its investment in the Securities.


 


Section 4. Conditions of the Purchaser’s
Obligations. The obligations of the Purchaser to purchase and pay for the Private Placement Warrants are subject to the
fulfillment, on or before each Closing Date, of each of the following conditions:


 


A. Representations and Warranties.
The representations and warranties of the Company contained in Section 2 shall be true and correct at and as of such Closing
Date as though then made.


 


B. Performance. The Company
shall have performed and complied with all agreements, obligations and conditions contained in this Agreement that are required
to be performed or complied with by it on or before such Closing Date.


 


C. No Injunction. No litigation,
statute, rule, regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed
by or in any court or governmental authority of competent jurisdiction or any self-regulatory organization having authority over
the matters contemplated hereby, which prohibits the consummation of any of the transactions contemplated by this Agreement or
the Warrant Agreement.


 


D. Warrant Agreement and Registration
Rights Agreement. The Company shall have entered into the Warrant Agreement and the Registration Rights Agreement, each on
terms satisfactory to the Purchaser.


 


E. Corporate Consents. The Company
shall have obtained the consent of its Board of Directors authorizing the execution, delivery and performance of this Agreement
and the Warrant Agreement and the issuance and sale of the Private Placement Warrants hereunder.


 






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Section 5. Conditions of the Company’s
Obligations. The obligations of the Company to the Purchaser under this Agreement are subject to the fulfillment, on or
before each Closing Date, of each of the following conditions:


 


A. Representations and Warranties.
The representations and warranties of the Purchaser contained in Section 3 shall be true and correct at and as of such Closing
Date as though then made.


 


B. Performance. The Purchaser
shall have performed and complied with all agreements, obligations and conditions contained in this Agreement that are required
to be performed or complied with by the Purchaser on or before such Closing Date.


 


C. Corporate Consents. The Company
shall have obtained the consent of its Board of Directors authorizing the execution, delivery and performance of this Agreement
and the Warrant Agreement and the issuance and sale of the Private Placement Warrants hereunder.


 


D. No Injunction. No litigation,
statute, rule, regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed
by or in any court or governmental authority of competent jurisdiction or any self-regulatory organization having authority over
the matters contemplated hereby, which prohibits the consummation of any of the transactions contemplated by this Agreement or
the Warrant Agreement.


 


E. Warrant Agreement. The Company
shall have entered into the Warrant Agreement on terms satisfactory to the Company.


 


Section 6. Transfer Restrictions.


 


A. Lock-Up. The Purchaser agrees
that it shall not Transfer any Private Placement Warrants and their underlying Shares until 30 days following the consummation
of the Business Combination; provided, however, that Transfers of Private Placement Warrants and their underlying Shares are permitted
(i) to the Company’s officers or directors, any affiliates or family members of any of the Company’s officers
or directors, any members of Oyster Enterprises LLC, a Delaware limited liability company (the “Sponsor”), or
any affiliates of the Sponsor, including to funds affiliated with Alden Global Capital LLC, and to limited partners of funds affiliated
with Alden Global Capital LLC, provided that any such transfers to limited partners are made on a pro rata basis pursuant
to the organizational documents of such funds and internal allocation policy; (ii) in the case of an individual, 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 individual, or to a charitable organization; (iii) in the case of an individual,
by virtue of the laws of descent and distribution upon death of the individual; (iv) in the case of an individual, pursuant
to a qualified domestic relations order; (v) by private sales or transfers made in connection with the consummation of the
Business Combination at prices no greater than the price at which the Private Placement Warrants or their underlying Shares, as
the case may be, were originally purchased; (vi) in the event of the Company’s liquidation prior to the completion of
the Business Combination; (vii) by virtue of the laws of the State of Delaware or the Sponsor’s limited liability company
agreement upon dissolution of the Sponsor; (viii) in the event of the Company’s completion of a 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 Company’s completion
of the Business Combination; (ix) to the Purchaser’s affiliates or any entity controlled by the Purchaser or (x) to
a nominee or custodian of a person or entity to whom a disposition or transfer would be permissible under clauses (i) through
(ix) above; provided, however, that in the case of clauses (i) through (v) and (ix) and
(x), these permitted transferees must enter into a written agreement with the Company agreeing to be bound by the Transfer restrictions
herein.


 


For purposes of this Section, the term “Transfer”
shall mean the (i) 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 Exchange
Act and the rules and regulations promulgated thereunder with respect to the Private Placement Warrants or their underlying
Shares, (ii) entry into any swap or other arrangement that transfers to another, in whole or in part, any of the economic
consequences of ownership of the Private Placement Warrants or their underlying Shares, whether any such transaction is to be settled
by delivery of the Private Placement Warrants or their underlying Shares, as the case may be, in cash or otherwise, or (iii) public
announcement of any intention to effect any transaction specified in clause (i) or (ii).


 






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B. FINRA Lock-Up. In addition to
the restrictions on transfer described in Section 6.A, the Purchaser acknowledges and agrees that the Private Placement Warrants
will be deemed compensation by FINRA and will therefore, pursuant to FINRA Rule 5110(g), be subject to lock-up for a period
of 180 days immediately following the date of effectiveness or commencement of sales in the Public Offering, subject to FINRA Rule 5110(e)(1).
Additionally, the Private Placement Warrants may not be sold, transferred, assigned, pledged or hypothecated during the 180-day
period following the effective date of the Registration Statement except to any underwriter or selected dealer participating in
the Public Offering and the bona fide officers or partners of the Purchaser and any such participating underwriter or selected
dealer. Additionally, the Private Placement Warrants will not be the subject of any hedging, short sale, derivative, put or call
transaction that would result in the economic disposition of such securities by any person for a period of 180 days immediately
following the date of effectiveness or commencement of sales in the Public Offering.


 


Section 7. Survival of Representations
and Warranties. All of the representations and warranties contained herein shall survive each Closing Date.


 


Section 8. Definitions. Terms
used but not otherwise defined in this Agreement shall have the meaning assigned to such terms in the Registration Statement.


 


Section 9. Miscellaneous.


 


A. Successors and Assigns. Except
as otherwise expressly provided herein, all covenants and agreements contained in this Agreement by or on behalf of any of the
parties hereto shall bind and inure to the benefit of the respective successors of the parties hereto whether so expressed or not.
Notwithstanding the foregoing or anything to the contrary herein, the parties may not assign this Agreement without the prior written
consent of the other party hereto, other than assignments by the Purchaser to affiliates thereof (including, without limitation,
one or more of its members).


 


B. Severability. Whenever possible,
each provision of this Agreement shall be interpreted in such manner as to be effective and valid under applicable law, but if
any provision of this Agreement is held to be prohibited by or invalid under applicable law, such provision shall be ineffective
only to the extent of such prohibition or invalidity, without invalidating the remainder of this Agreement.


 


C. Counterparts. This Agreement
may be executed in counterparts, each of which when so executed shall be deemed to be an original and all of which when taken together
shall constitute one and the same instrument. The words “execution,” “signed,” “signature,”
and words of like import in this Agreement or in any other certificate, agreement or document related to this Agreement shall include
images of manually executed signatures transmitted by facsimile or other electronic format (including, without limitation, “pdf,”
 “tif” or “jpg”) and other electronic signatures (including, without limitation, DocuSign and AdobeSign).
The use of electronic signatures and electronic records (including, without limitation, any contract or other record created, generated,
sent, communicated, received, or stored by electronic means) shall be of the same legal effect, validity and enforceability as
a manually executed signature or use of a paper-based record-keeping system to the fullest extent permitted by applicable law,
including the Federal Electronic Signatures in Global and National Commerce Act, the New York State Electronic Signatures and Records
Act and any other applicable law, including, without limitation, any state law based on the Uniform Electronic Transactions Act
or the Uniform Commercial Code.


 


D. Descriptive Headings; Interpretation.
The descriptive headings of this Agreement are inserted for convenience only and do not constitute a substantive part of this Agreement.
The use of the word “including” in this Agreement shall be by way of example rather than by limitation.


 


E. Governing Law. This Agreement
shall be deemed to be a contract made under the laws of the State of New York and for all purposes shall be construed in accordance
with the internal laws of the State of New York without regard to the conflicts of laws principles thereof.


 


F. Amendments. This Agreement
may not be amended, modified or waived as to any particular provision, except by a written instrument executed by all parties hereto.


 


[Signature Page Follows]


 






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IN WITNESS WHEREOF, the parties hereto
have executed this Agreement to be effective as of the date first set forth above.


 


	 	COMPANY:
	 	 
	 	OYSTER ENTERPRISES ACQUISITION CORP.
	 	 
	 	By:	/s/ Heath B. Freeman
	 	 	Name: Heath B. Freeman 

Title: Chief Executive Officer
	 	 	 
	 	PURCHASER:
	 	 
	 	IMPERIAL CAPITAL, LLC    
	 	 	 
	 	By:	/s/ Chris Shepard
	 	 	Name: Chris Shepard 

Title: Executive Vice President



 


[Signature
Page to Private Placement Warrants Subscription Agreement]