Document:

Exhibit
10.44

 

SECURITY
AGREEMENT

 

THIS
SECURITY AGREEMENT (as amended, restated, amended and restated, modified or supplemented and in effect from time to time, this
“Agreement”) is entered into as of March 17, 2020, by GlassBridge Athlete, LLC, a Delaware limited liability
company, as grantor (“Grantor”), for the benefit of ORIX PTP Holdings, LLC, a Delaware limited liability
company, as Lender (as defined in the Note) (together with any successor Lender under the Note, “Secured Party”).

 

W
I T N E S S E T H:

 

WHEREAS,
Grantor, GlassBridge Enterprises, Inc., a Delaware corporation, and Lender have entered into that certain Secured Promissory Note
Agreement of even date herewith (as from time to time amended, restated, supplemented or otherwise modified, the “Note”);
and

 

WHEREAS,
the execution and delivery of this Agreement is a condition precedent to the obligation of Lender to extend credit to the Grantor
pursuant to the Note.

 

NOW,
THEREFORE, in consideration of the foregoing and as an inducement to Secured Party to enter into the Note and extend credit to
Grantor, and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties
hereto agree as follows:

 

Section
1. Definitions.

 

(a)
When used herein, the terms Account, Account Debtor, Cash Proceeds, Certificated Security, Chattel Paper, Commercial Tort Claim,
Deposit Account, Document, Electronic Chattel Paper, Equipment, Financial Asset, Fixtures, General Intangibles, Goods, Health-Care-Insurance
Receivable, Inventory, Instrument, Investment Property, Letter of Credit Rights, Payment Intangibles, Proceeds, Security, Security
Entitlement, Supporting Obligations and Uncertificated Security have the respective meanings assigned thereto in the UCC (as defined
below).

 

(b)
Capitalized terms used herein and not otherwise defined shall have the meanings assigned thereto in the Note.

 

(c)
The following terms have the following meanings (such definitions to be applicable to both the singular and plural forms of such
terms):

 

Collateral
means all property and rights of Grantor in which a security interest is granted hereunder. Notwithstanding anything herein
to the contrary, in no event shall “Collateral” include, and Grantor shall not be deemed to have granted a security
interest in, any contract, lease, license or other agreement which by its terms prohibits the granting of a security interest
therein (except to the extent such prohibition is unenforceable pursuant to the provisions of Article 9 of the UCC); provided,
however, that Grantor will use commercially reasonable efforts to promptly obtain consent to the collateral assignment thereof
and the granting of a security interest therein to Secured Party and, at such time such consent is obtained, the contract, lease,
license or other agreement shall constitute “Collateral” hereunder, and provided, further, that notwithstanding the
foregoing, the term “Collateral” shall include any and all proceeds arising from such excluded property to the extent
that the assignment or encumbering of such proceeds is not subject to the same or similar prohibitions or restrictions.

 

    	 	 	 

    	 

    

 

Computer
Hardware and Software means all of Grantor’s rights (including rights as licensee and lessee) with respect to: (a)
computer and other electronic data processing hardware, including all integrated computer systems, central processing units, memory
units, display terminals, printers, computer elements, card readers, disk drives, cables, electrical supply hardware, generators,
power equalizers, accessories, peripheral devices and other related computer hardware; (b) all software programs designed for
use on the computers and electronic data processing hardware described in clause (a) above, including all operating system software,
utilities and application programs in whatsoever form (source code and object code in magnetic tape, disk or hard copy format
or any other listings whatsoever); (c) any firmware associated with any of the foregoing; and (d) any documentation for hardware,
software and firmware described in clauses (a), (b) and (c) above, including flow charts, logic diagrams, manuals, specifications,
training materials, charts and pseudo codes.

 

Intellectual
Property means all: trade secrets and other proprietary information; trademarks, service marks, business names, Internet
domain names, designs, logos, trade dress, slogans, indicia and other source and/or business identifiers, and the goodwill of
the business relating thereto and all registrations or applications for registrations which have heretofore been or may hereafter
be issued thereon throughout the world; copyrights (including copyrights for computer programs and software) and copyright registrations
or applications for registrations which have heretofore been or may hereafter be issued throughout the world and all tangible
property embodying the copyrights; unpatented inventions (whether or not patentable); patent applications and patents; industrial
designs, industrial design applications and registered industrial designs; license agreements related to any of the foregoing
and income therefrom; books, records, writings, computer tapes or disks, flow diagrams, specification sheets, source codes, object
codes and other physical manifestations, embodiments or incorporations of any of the foregoing; the right to sue for all past,
present and future infringements of any of the foregoing; and all common law and other rights throughout the world in and to all
of the foregoing.

 

Non-Tangible
Collateral means, collectively, Grantor’s Accounts and General Intangibles.

 

Obligations
means all obligations (monetary or otherwise) of Grantor under the Note, any other Basic Document or any instrument executed
in connection therewith, whether direct or indirect, absolute or contingent, now or hereafter existing, or due or to become due.

 

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Obligor
means a Person that, with respect to an obligation secured by a security interest in the Collateral, (a) owes payment
or other performance on the obligation, (b) has provided property or other security or credit support other than the Collateral
to secure payment or other performance of the obligation, or (c) is otherwise accountable in whole or in part for payment or other
performance of the obligation. The term does not include issuers or nominated persons under a letter of credit.

 

Organizational
I.D. Number means the organizational identification number assigned to Grantor by the applicable governmental unit or
agency of the jurisdiction of organization for Grantor.

 

Patents
means all of the following now owned or hereafter acquired by Grantor: (a) all letters patent of the United States or
any other country, all registrations and recordings thereof, and all applications for letters patent of the United States or any
other country, including registrations, recordings and pending applications in the United States Patent and Trademark Office or
any similar offices in any other country, and (b) all reissues, continuations, divisions, continuations-in-part, renewals or extensions
thereof, and the inventions disclosed or claimed therein, including the right to make, use and/or sell the inventions disclosed
or claimed therein.

 

Receivable(s)
means all Accounts and all right, title and interest in any returned goods, together with all right, title, securities
and guarantees with respect thereto, including any rights to stoppage in transit, replevin, reclamation and re-sales, and all
related security interests, Liens, charges, encumbrances and pledges, whether voluntary or involuntary, in each ease whether now
existing or owned or hereafter arising or acquired.

 

Security
Interest is defined in Section 2.

 

Trademarks
means all of the following now owned or hereafter acquired by Grantor: (a) all trademarks, service marks, trade names,
corporate names, company names, business names, fictitious business names, trade styles, trade dress, logos, other source or business
identifiers, designs and general intangibles of like nature, now existing or hereafter adopted or acquired, all registrations
and recordings thereof, and all registration and recording applications filed in connection therewith, including registrations
and registration applications in the United States Patent and Trademark Office, any State of the United States or any similar
offices in any other country or any political subdivision thereof, and all extensions or renewals thereof, (b) all goodwill associated
therewith or symbolized thereby, and (c) all other assets, rights and interests that uniquely reflect or embody such goodwill.

 

Type
of Organization means the kind or type of entity of Grantor, such as a corporation, limited partnership or limited liability
company.

 

    	 	3	 

    	 

    

 

UCC
means the Uniform Commercial Code as in effect in the State of New York on the date of this Agreement, as it may be amended
or modified from time to time hereafter; provided, however, that, as used in Section 5 hereof, UCC shall mean the
Uniform Commercial Code as in effect from time to time in any applicable jurisdiction.

 

Section
2. Grant of Security Interest. As security for the payment and performance of all Obligations, Grantor hereby assigns to
Secured Party, and grants to Secured Party a continuing security interest (the “Security Interest”)
in, all of the following property of Grantor whether now or hereafter existing or acquired, regardless of where located, all of
Grantor’s:

 

(a)
Accounts;

 

(b)
cash and Cash Proceeds;

 

(c)
Certificated Securities;

 

(d)
Chattel Paper, including Electronic Chattel Paper;

 

(e)
Computer Hardware and Software and all rights with respect thereto, including, any and all licenses, options, warranties, service
contracts, program services, test rights, maintenance rights, support rights, improvement rights, renewal rights and indemnifications,
and any substitutions, replacements, additions or model conversions of any of the foregoing;

 

(f)
Commercial Tort Claims;

 

(g)
Deposit Accounts and all cash held in such Deposit Accounts (other than Excluded Accounts);

 

(h)
Documents;

 

(i)
Financial Assets;

 

(j)
General Intangibles, including, without limitation, Payment Intangibles;

 

(k)
Goods (including all of its Equipment, Fixtures and Inventory), and all embedded software, accessions, additions, attachments,
improvements, substitutions and replacements thereto and therefor;

 

(l)
Instruments;

 

(m)
Intellectual Property;

 

(n)
Investment Property;

 

(o)
Letter of Credit Rights;

 

(p)
Security Entitlements;

 

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(q)
Supporting Obligations;

 

(r)
Uncertificated Securities; and

 

(s)
to the extent not included in the foregoing, all other personal property of any kind or description;

 

together
with all books, records, writings, databases, information and other property relating to, used or useful in connection with, or
evidencing, embodying, incorporating or referring to any of the foregoing, and all Proceeds, products, offspring, rents, issues,
profits and returns of and from any of the foregoing.

 

Section
3. Representations and Warranties. Grantor represents and warrants to Secured Party, as of the Closing Date and as of each
other date required under any Basic Document, that:

 

(a)
No financing statement or other instrument similar in effect covering all or any part of the Collateral or listing Grantor as
debtor is on file in any recording office, except such as have been filed in favor of the Secured Party pursuant to this Agreement
or as otherwise permitted under the Basic Documents.

 

(b)
Grantor is and will be the owner of all Collateral, free of all Liens, claims, security interests and encumbrances whatsoever,
other than the Permitted Liens, with full power and authority to execute this Agreement and perform its obligations hereunder,
and to subject the Collateral to the security interest hereunder.

 

(c)
All material information required to be delivered under the Basic Documents with respect to Collateral and Account Debtors set
forth in any schedule, certificate or other writing at any time heretofore or hereafter furnished by Grantor to Secured Party
is and will be true and correct in all material respects as of the date furnished.

 

(d)
The execution and delivery of this Agreement and the performance by Grantor of its obligations hereunder are within Grantor’s
powers, have been duly authorized by all necessary action, have received all necessary governmental approval (if any shall be
required), and do not contravene or conflict, in any material respect, with any provision of law or of the articles of incorporation,
certificate of formation, by-laws, limited liability company agreement, limited partnership agreement or any similar governing
documents of Grantor or of any material agreement, indenture, instrument or other document, or any material judgment, order or
decree, which is binding upon Grantor.

 

(e)
This Agreement is a legal, valid and binding obligation of Grantor, enforceable in accordance with its terms, except that the
enforceability of this Agreement may be limited by bankruptcy, insolvency, fraudulent conveyance, fraudulent transfer, reorganization,
moratorium or other similar laws now or hereafter in effect relating to creditors’ rights generally and by general principles
of equity (regardless of whether enforcement is sought in a proceeding in equity or at law).

 

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(f)
The Security Interest in the Collateral created by this Agreement will be duly perfected once the appropriate actions required
for perfection under applicable law has been taken by the Secured Party. The creation, attachment and perfection of the Security
Interest do not require the consent of any third party. Once perfected in accordance with this clause (f), the Security Interest
will constitute a first and prior Lien on the Collateral.

 

(g)
Grantor’s chief executive office and principal place of business are as set forth on Schedule I hereto; Schedule
I also sets forth each location where Grantor maintains a place of business, maintains any Inventory, or owns or leases
any real property.

 

(h)
Grantor is duly organized, validly existing and in good standing under the laws of the state set forth on Schedule II
hereto, except where the failure to do so would not reasonably be expected to result in a Material Adverse Event; Schedule
II sets forth the Type of Organization, Organizational I.D. Number and federal taxpayer identification number of Grantor.

 

(i)
Grantor’s exact legal name is as set forth on the signature pages of this Agreement and on Schedule II; Schedule
III sets forth all of Grantor’s prior legal names and prior Types of Organizations, and lists all mergers or other
reorganizations to which Grantor has been subject, within the five (5) year period immediately preceding the Closing Date.

 

(j)
Schedule IV hereto contains a complete listing of all of Grantor’s registered Intellectual Property that is
subject to any registration statutes.

 

(k)
Schedule V hereto contains a complete listing of all of Grantor’s Instruments, Investment Property, Letter-of-Credit
Rights, Chattel Paper, Documents and Commercial Tort Claims.

 

(l)
Except as set forth on Schedule VI hereto, Grantor has no tangible Collateral located outside of the United States.

 

(m)
Schedule VIII hereto contains a complete listing of all of Grantor’s Collateral that is subject to certificate
of title statutes.

 

(n)
As of the Closing Date, Schedule IX hereto contains a complete listing of all of Grantor’s Deposit Accounts
(other than Excluded Accounts) and other bank accounts, including locations and applicable account numbers.

 

(o)
None of Grantor’s Equipment is a Fixture to real estate unless such real estate is owned by Grantor and is subject to a
mortgage in favor of Secured Party, or if such real estate is leased, is subject to a landlord's agreement in favor of Secured
Party on terms acceptable to Secured Party.

 

(p)
Any amounts due to Grantor under the Collateral are not subject to any material setoff, counterclaim, defense, allowance or adjustment
(other than discounts for prompt payment shown on the invoice) or to any material dispute, objection or complaint by any Account
Debtor or other Obligor.

 

    	 	6	 

    	 

    

 

(q)
Grantor has the right to use all of its registered Patents and Trademarks material to Grantor’s business and such Patents
and Trademarks owned, controlled, or acquired by Grantor, or which Grantor has a right to use: (i) are subsisting and have not
been adjudged or claimed to be invalid or unenforceable (either in whole or in part) and Grantor is not aware of any basis for
such a claim, (ii) are valid and enforceable, (iii) are in the name of Grantor, and (iv) are properly recorded and/or filed in
the United States Patent and Trademark Office. Grantor’s right, title and interest in such Intellectual Property is free
and clear of any Liens (other than Permitted Liens), registered user agreements, or covenants by Grantor not to sue third Persons
or licenses.

 

(r)
Grantor has properly completed all necessary filings, payments, renewals and obligations in the United States Patent and Trademark
Office to maintain the registered Patents and Trademarks material to Grantor’s business as fully valid and enforceable,
except with respect to any Patent or Trademark that Grantor shall reasonably determine is of immaterial economic value to it in
its ordinary course of business.

 

(s)
To the actual knowledge of Grantor, no claim has been made that the ownership or use of any of the registered Patents and Trademarks,
or the manufacture, use or sale of any product made in accordance therewith or service rendered thereunder, does violate the rights
of any third Person, and Grantor has no actual knowledge of any third party rights which may be infringed or otherwise violated
by the use of any of the registered Patents and Trademarks material to the operations of Grantor.

 

(t)
Grantor has reasonably maintained all trade secrets material to the operations of Grantor in accordance with applicable law and
prudent industry practices.

 

Section
4. Certificates, Schedules and Reports. Grantor will from time to time, as Secured Party may reasonably request, deliver
to Secured Party such schedules, certificates and reports respecting the Collateral at the time subject to the Security Interest
hereunder, and the items or amounts received by Grantor in full or partial payment of any of the Collateral, as Secured Party
may reasonably request. Any such schedule, certificate or report shall be executed by an authorized officer of Grantor and shall
be in such form and detail as Secured Party may specify in its reasonable discretion.

 

Section
5. Agreements of Grantor.

 

(a)
Grantor, at Secured Party’s request, at any time and from time to time, shall execute and deliver, if applicable, to Secured
Party such financing statements, amendments and any other necessary documents, including Instruments, and do such acts as Secured
Party deems reasonably necessary in order to establish and maintain valid, attached and perfected Security Interests in the Collateral
in favor of Secured Party, free and clear of all Liens and claims and rights of third parties whatsoever except Permitted Liens.
Grantor hereby irrevocably authorizes Secured Party at any time, and from time to time, to file in any appropriate jurisdiction
any initial financing statements and amendments thereto that (i) indicate the Collateral (A) as “all assets of Grantor,”
“the Collateral described in the Security Agreement” or words of similar effect, regardless of whether any particular
asset comprised in the Collateral falls within the scope of Article 9 of the UCC of the jurisdiction wherein such financing statement
or amendment is filed, or (B) as being of an equal or lesser scope or with greater detail, and (ii) contain any other information
required by Article 9 of the UCC of the jurisdiction wherein such financing statement or amendment is filed regarding the sufficiency
or filing office acceptance of any financing statement or amendment, including, without limitation, (A) whether Grantor is an
organization, the Type of Organization and the Organization ID Number issued to Grantor and (B) in the case of a financing statement
filed as a fixture filing or indicating Collateral to be extracted or timber to be cut, a sufficient description of the real property
to which the Collateral relates.

 

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(b)
During the term of this Agreement, Grantor agrees to:

 

(i)
keep all of the Collateral (other than with respect to Goods in transit between facilities, temporary warehousing for up to thirty
(30) days, or sales or leases of assets permitted by the Note) at, and will not maintain any place of business at any location
other than, its address(es) shown on Schedule I hereto or at such other addresses of which Grantor shall have given
Secured Party not less than twenty (20) days’ prior written notice;

 

(ii)
stamp on its records concerning the Collateral, and add on all Chattel Paper and Instruments, each with a face value in excess
of $100,000, constituting a portion of the Collateral, a notation, in form reasonably satisfactory to Secured Party, of the Security
Interest of Secured Party hereunder or, upon the reasonable request of Secured Party, deliver to Secured Party any such Chattel
Paper and Instruments, each with a face value in excess of $100,000, constituting a portion of the Collateral, together with transfer
powers duly executed in blank;

 

(iii)
promptly notify Secured Party in writing of any change in any material fact or circumstance represented or warranted by Grantor
with respect to any of the Collateral, and promptly notify Secured Party in writing of any material claim, action or proceeding
challenging the Security Interest or affecting title to all or any material portion of the Collateral or the Security Interest
and, at Secured Party’s request, appear in and defend any such action or proceeding at Grantor’s expense;

 

(iv)
not sell, lease, assign or create or permit to exist any Lien on any Collateral other than Permitted Liens except for the sale
or lease of its assets in accordance with Section 5(n) of the Note;

 

(v)
not (A) permit any of its Equipment to become a Fixture to real property unless such real property is owned by Grantor and is
subject to a mortgage in favor of Secured Party, or if such real property is leased, is subject to a landlord's agreement in favor
of Secured Party on terms reasonably acceptable to Secured Party, or (B) permit any of its Equipment to become an accession to
any other personal property unless such personal property is subject to a first priority Lien in favor of Secured Party.

 

    	 	8	 

    	 

    

 

(vi)
upon request of Secured Party, (A) cause to be noted on the applicable certificate, in the event any of its Equipment with a value
in excess of $100,000 individually, is covered by a certificate of title, the security interest of Secured Party in the Equipment
covered thereby, and (B) deliver all such certificates to Secured Party or its designees;

 

(vii)
take all steps reasonably necessary to protect, preserve and maintain all of its rights in the Collateral;

 

(viii)
except as listed on Schedule VI, keep all of the tangible Collateral in the United States;

 

(ix)
promptly notify Secured Party in writing upon acquiring or otherwise obtaining any Collateral after the date hereof consisting
of Investment Property, Letter-of-Credit Rights or Electronic Chattel Paper, in each case, with a value in excess of $100,000;

 

(x)
promptly notify Secured Party in writing upon acquiring or otherwise obtaining any Collateral after the date hereof consisting
of Documents or Instruments, in each case, with a value in excess of $100,000;

 

(xi)
with respect to Collateral in the possession of a third party, other than Certificated Securities and Goods covered by a Document,
use commercially reasonable efforts to obtain an acknowledgment from the third party that it is holding the Collateral for benefit
of Secured Party;

 

(xii)
promptly notify Secured Party in writing upon incurring or otherwise obtaining a Commercial Tort Claim, in excess of $250,000,
after the date hereof against any third party, and, upon the request of Secured Party, promptly enter into an amendment to this
Agreement, and do such other acts or things deemed appropriate by Secured Party to give Secured Party a security interest in such
Commercial Tort Claim;

 

(xiii)
take other action reasonably requested by Secured Party to insure the attachment, perfection and, first priority of, and the ability
of Secured Party to enforce, the security interests in any and all of the Collateral including, without limitation:

 

1)
complying, in all material respects, with any provision of any statute, regulation or treaty of the United States as to any Collateral
if compliance with such provision is a condition to attachment, perfection or priority of, or ability of Secured Party to enforce,
the security interests in such Collateral;

 

2)
use commercially reasonably efforts in obtaining governmental and other third party consents and approvals, including without
limitation any consent of any licensor, lessor or other Person obligated on Collateral with respect to any Collateral material
to the operations in Grantor’s business;

 

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3)
use commercially reasonable efforts in obtaining waivers from mortgagees and landlords in form and substance satisfactory to Secured
Party; and

 

4)
taking all reasonable and necessary actions required by the UCC in effect from time to time or by other law, as applicable in
any relevant UCC jurisdiction, or by other material laws as applicable in any foreign jurisdiction;

 

(xiv)
to the extent any of the Collateral is or becomes a “security” within the meaning of Article 8 of the UCC is governed
by Article 8 of the UCC, to (x) ensure such Collateral is certificated, (y) promptly deliver the certificates representing such
Collateral to Secured party, and (z) promptly deliver powers of equity for such Collateral, executed in blank;

 

(xv)
not change its state of formation or organization or Type of Organization without providing Secured Party with at least twenty
(20) days’ prior written notice (or such shorter period in Secured Party’s reasonable discretion); and

 

(xvi)
not change its legal name without providing Secured Party with at least ten (10) days’ prior written notice (or such shorter
period in Secured Party’s reasonable discretion).

 

(c)
Whenever an Event of Default has occurred and is continuing, Secured Party shall have the right to bring suit to enforce any or
all of the Intellectual Property or licenses thereunder, in which event Grantor shall at the request of Secured Party do any and
all lawful acts and execute any and all proper documents required by Secured Party in aid of such enforcement and Grantor shall
promptly, upon demand, reimburse and indemnify Secured Party for all costs and expenses incurred by Secured Party in the exercise
of its rights in accordance with the Note. Notwithstanding the foregoing, Secured Party shall have no obligation or liability
regarding the Collateral or any part thereof by reason of, or arising out of, this Agreement.

 

Section
6. Default; Rights and Remedies of Secured Party upon a Default

.
If an Event of Default shall have occurred and be continuing, Secured Party shall have the following rights and remedies:

 

(a)
Secured Party may exercise any or all of the remedies available to it under this Agreement, the other Basic Documents, at law,
in equity or otherwise;

 

(b)
Grantor shall hold in trust (and not commingle with its other assets) for Secured Party all Collateral that is Chattel Paper,
Instruments or Documents at any time received by it and promptly deliver same to Secured Party, unless Secured Party at its option
gives Grantor written permission to retain such Collateral; at Secured Party’s request, each contract, Chattel Paper, Instrument
or Document so retained shall be marked to state that it is assigned to Secured Party and each instrument shall be endorsed to
the order of Secured Party (but failure to so mark or endorse shall not impair the Security Interest);

 

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(c)
Grantor irrevocably appoints Secured Party its true and lawful attorney with full power of substitution, in the name of Grantor,
for the sole use and benefit of Secured Party, but at Grantor’s expense, to the extent permitted by law, to file claims
under any insurance policies of Grantor, to receive, receipt and give acquittance for any payments that may be payable thereunder,
and to execute any and all endorsements, receipts, releases, assignments, reassignments or other documents that may be necessary
to effect the collection, compromise or settlement of any claims under any such insurance policies;

 

(d)
Grantor irrevocably appoints Secured Party its true and lawful attorney with full power of substitution, in the name of Grantor,
for the sole use and benefit of Secured Party, but at Grantor’s expense, to the extent permitted by law, to exercise, all
or any of the following powers with respect to all or any of Grantor’s Collateral (to the extent necessary to pay the Obligations
in full):

 

(i)
to demand, sue for, collect, receive and give acquittance for any and all monies due or to become due upon or by virtue thereof;

 

(ii)
to settle, compromise, compound, prosecute or defend any action or proceeding with respect thereto;

 

(iii)
to take control of, sell, lease, license or otherwise dispose of the same or the Proceeds thereof, as fully and effectually as
if Secured Party were the absolute owner thereof;

 

(iv)
to extend the time of payment of any or all thereof and to make any allowance or other adjustment with reference thereto;

 

(v)
to endorse Grantor’s name on any notes, acceptances, checks, drafts, money orders or other evidences of payment on Collateral
that may come into Secured Party’s possession;

 

(vi)
to sign Grantor’s name on any invoice or bill of lading relating thereto, on any drafts against Obligors or other Persons
making payment with respect thereto, on assignments and verifications of accounts or other Collateral and on notices to Obligors
making payment with respect thereto;

 

(vii)
to send requests for verification of obligations to any Obligor; and

 

(viii)
to do all other acts and things reasonably necessary to carry out the intent of this Agreement.

 

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If,
following the occurrence of an Event of Default, any Obligor or Account Debtor fails to make payment on any Collateral when due,
Secured Party is authorized, in its sole discretion, either in its own name or in Grantor’s name, to take such action as
Secured Party reasonably shall deem appropriate for the collection of any amounts owed with respect to Collateral or upon which
a delinquency exists. Regardless of any other provision of this Agreement, however, Secured Party shall not be liable for its
failure to collect, or for its failure to exercise diligence in the collection of, any amounts owed with respect to Collateral
except for its own fraud, gross negligence, or willful misconduct, nor shall it be under any duty to anyone except Grantor to
account for funds that it shall actually receive under this Agreement. A receipt given by Secured Party to any Obligor or Account
Debtor shall be a full and complete release, discharge, and acquittance to such Obligor or Account Debtor, to the extent of any
amount so paid to Secured Party. Secured Party may apply or set off amounts paid and the deposits against any liability of Grantor
to Secured Party.

 

(e)
Secured Party’s sale of less than all the Collateral shall not exhaust Secured Party’s rights under this Agreement
and Secured Party is specifically empowered to make successive sales until all the Collateral is sold. If the proceeds of a sale
of less than all the Collateral shall be less than the Obligations, this Agreement and the Security Interest shall remain in full
force and effect as to the unsold portion of the Collateral just as though no sale had been made. In the event any sale under
this Agreement is not completed or is, in Secured Party’s opinion, defective, such sale shall not exhaust Secured Party’s
rights under this Agreement and Secured Party shall have the right to cause a subsequent sale or sales to be made. Any and all
statements of fact or other recitals made in any bill of sale or assignment or other instrument evidencing any foreclosure sale
under this Agreement as to nonpayment of the Obligations, or as to the occurrence of any Event of Default, or as to Secured Party’s
having declared all of such Obligations to be due and payable, or as to notice of time, place and terms of sale and the properties
to be sold having been duly given, or as to any other act or thing having been duly done by Secured Party, shall be taken as prima
facie evidence of the truth of the facts so stated and recited. Secured Party may appoint or delegate any one or more Persons
as agent to perform any act or acts necessary or incident to any sale held by Secured Party, including the sending of notices
and the conduct of sale, but such acts must be done in the name and on behalf of Secured Party. In connection with the sale of
Collateral that constitutes Securities, Secured Party is authorized, but not obligated, to limit prospective purchasers to the
extent deemed necessary or desirable by Secured Party to render such sale exempt from registration requirements of the Securities
Act of 1933, as amended, and any applicable state securities laws, and no sale so made in good faith by Secured Party shall be
deemed not be “commercially reasonable” because so made.

 

(f)
In addition to any and all other rights afforded to Secured Party in this Section 6, Secured Party may exercise
all the rights of a secured party under the UCC (whether or not in effect in the jurisdiction where such rights are exercised)
with respect to any Collateral and, if cash shall be insufficient to pay all the Obligations in full, sell, lease, license or
otherwise dispose of the Collateral or any part thereof in accordance with the provisions of the UCC. Notice of any such sale
or other disposition shall be given to Grantor as required under this Section 6 or as required by applicable law.

 

    	 	12	 

    	 

    

 

Section
7. Application of Proceeds.

 

(a)
If an Event of Default shall have occurred and be continuing, Secured Party may apply the proceeds of any sale or other disposition
of all or any part of the Collateral, in the following order of priorities:

 

(i)
first, to pay the expenses of such sale or other disposition, including reasonable compensation to Secured Party and counsel
for Secured Party, and all expenses, liabilities and advances incurred or made by Secured Party in connection with this Agreement,
and any other amounts then due and payable in connection with this Agreement;

 

(ii)
second, to pay all interest (including post-petition interest) and other fees payable under the Note, until payment in
full of all such interest and fees shall have been made;

 

(iii)
third, to pay the unpaid principal of the Obligations, until payment in full of the principal of all Obligations shall
have been made (or so provided for);

 

(iv)
fourth, to pay all other Obligations, until payment in full of all such other Obligations shall have been made (or so provided
for); and

 

(v)
finally, to pay to Grantor, or as a court of competent jurisdiction may direct, any surplus then remaining from the proceeds
of the Collateral owned by it.

 

Secured
Party may make such distributions hereunder in cash or in kind or, on a ratable basis, in any combination thereof.

 

(b)
All distributions made by Secured Party pursuant to this section shall be final (except in the event of manifest error).

 

Section
8. Existence of Default. Regarding the existence of any Default for purposes of this Agreement, Grantor agrees that the
Obligors or Account Debtors on any Collateral may rely upon written certification from Secured Party that such a Default exists
and Grantor expressly agrees that Secured Party shall not be liable to Grantor for any claims, damages, costs, expenses or causes
of action of any nature whatsoever in connection with, arising out of, or related to Secured Party’s exercise of any rights,
powers or remedies under any Basic Document except for its own fraud, negligence, or willful misconduct.

 

Section
9. Limitation on Duty in Respect of Collateral.

 

(a)
Beyond the exercise of reasonable care in the custody and preservation thereof, Secured Party will have no duty as to any Collateral
in its possession or control or in the possession or control of any bailee or any income therefrom or as to the preservation of
rights against prior parties or any other rights pertaining thereto. Secured Party will be deemed to have exercised reasonable
care in the custody and preservation of the Collateral in its possession or control if such Collateral is accorded treatment substantially
equal to that which it accords its own property, and will not be liable or responsible for any loss or damage to any Collateral,
or for any diminution in the value thereof, by reason of any act or omission of any bailee selected by Secured Party in good faith
or by reason of any act or omission by Secured Party pursuant to instructions from Grantor, except to the extent that such liability
arises from Secured Party’s gross negligence or willful misconduct.

 

    	 	13	 

    	 

    

 

(b)
To the extent that applicable law imposes duties on Secured Party to exercise remedies in a commercially reasonable manner, Grantor
acknowledges and agrees that it is not commercially unreasonable for Secured Party (i) to fail to incur expenses reasonably deemed
significant by Secured Party to prepare Collateral for disposition or otherwise to complete raw material or work-in-process into
finished goods or other finished products for disposition, (ii) to fail to obtain third party consents for access to Collateral
to be disposed of, or to obtain or, if not required by other law, to fail to obtain governmental or third party consents for the
collection or disposition of Collateral to be collected or disposed of, (iii) to fail to exercise collection remedies against
Account Debtors or other Persons obligated on Collateral or to remove Liens or encumbrances on or any adverse claims against Collateral,
(iv) to exercise collection remedies against Account Debtors and other Persons obligated on Collateral directly or through the
use of collection agencies and other collection specialists, (v) to advertise dispositions of Collateral through publications
or media of general circulation, whether or not the Collateral is of a specialized nature, (vi) to contact other Persons, whether
or not in the same business as Grantor, for expressions of interest in acquiring all or any portion of the Collateral, (vii) to
hire one or more professional auctioneers to assist in the disposition of Collateral, whether or not the collateral is of a specialized
nature, (viii) to dispose of Collateral by utilizing Internet sites that provide for the auction of assets of the types included
in the Collateral or that have the reasonable capability of doing so, or that match buyers and sellers of assets, (ix) to dispose
of assets in wholesale rather than retail markets, (x) to disclaim disposition warranties, including, without limitation, any
warranties of title, (xi) to purchase insurance of credit enhancements to insure Secured Party against risks of loss, collection
or disposition of Collateral, or to provide to Secured Party a guaranteed return from the collection or disposition of Collateral,
or (xii) to the extent deemed appropriate by Secured Party, to obtain the services of other brokers, investment bankers, consultants
and other professionals to assist Secured Party in the collection or disposition of any of the Collateral. Grantor acknowledges
that the purpose of this section is to provide non-exhaustive indications of what actions or omissions by Secured Party would
not be commercially unreasonable in Secured Party’s exercise of remedies against the Collateral and that other actions or
omissions by Secured Party shall not be deemed commercially unreasonable solely on account of not being indicated in this section.
Without limitation upon the foregoing, nothing contained in this section shall be construed to grant any right to Grantor or to
impose any duties on Secured Party that would not have been granted or imposed by this Agreement or by applicable law in the absence
of this section.

 

(c)
The Security Interest is given to secure the prompt, unconditional and complete payment and performance of the Obligations when
due, and is given as security only. Secured Party does not assume, and shall not be liable for, any of Grantor’s liabilities,
duties or obligations under, or in connection with, the Collateral. Secured Party’s acceptance of this Agreement, or its
taking any action in carrying out this Agreement, does not constitute Secured Party’s approval of the Collateral or Secured
Party’s assumption of any obligation under or in connection with the Collateral. This Agreement does not affect or modify
Grantor’s obligations with respect to the Collateral.

 

    	 	14	 

    	 

    

 

Section
10. Fraudulent Conveyance. Notwithstanding anything contained in this Agreement to the contrary, Grantor agrees that if,
but for the application of this Section 10, the Obligations or any Security Interest would constitute a preferential
transfer under 11 U.S.C. § 547, a fraudulent conveyance under 11 U.S.C. § 548 (or any successor section of that statute)
or a fraudulent conveyance or transfer under any state fraudulent conveyance or fraudulent transfer law or similar Law in effect
from time to time (each a “Fraudulent Conveyance”), then the Obligations and each affected Security
Interest will be enforceable to the maximum extent possible without causing the Obligations or any Security Interest to be a Fraudulent
Conveyance, and shall be deemed to have been automatically amended to carry out the intent of this Section 10.

 

Section
11. General.

 

(a)
Unless otherwise provided hereunder, any consent, notice, or other communication under or in connection with this Agreement must
be given as prescribed in the Note.

 

(b)
No delay on the part of Secured Party in the exercise of any right or remedy shall operate as a waiver thereof, and no single
or partial exercise by Secured Party of any right or remedy shall preclude other or further exercise thereof or the exercise of
any other right or remedy.

 

(c)
This Agreement shall remain in full force and effect until all Obligations have been paid in full and no commitment under the
Note or any other Basic Document remains outstanding. If at any time all or any part of any payment theretofore applied by Secured
Party to any of the Obligations is or must be rescinded or returned by Secured Party for any reason whatsoever (including the
insolvency, bankruptcy or reorganization of Grantor), such Obligations shall, for the purposes of this Agreement, to the extent
that such payment is or must be rescinded or returned, be deemed to have continued in existence, notwithstanding such application
by Secured Party, and this Agreement shall continue to be effective or be reinstated, as the case may be, as to such Obligations,
all as though such application by Secured Party had not been made.

 

(d)
Section 9 of the Note is hereby incorporated into this Agreement by reference, shall apply herein mutatis mutandis and
shall have the same force and effect as if expressly set forth herein.

 

(e)
THIS AGREEMENT, THE NOTE AND THE OTHER BASIC DOCUMENTS, INCLUDING BUT NOT LIMITED TO, THE PROVISIONS RELATING TO GOVERNING
LAW, JURY WAIVER, VENUE, SERVICE OF PROCESS AND ARBITRATION, CONSTITUTE THE ENTIRE UNDERSTANDINGS BETWEEN THE PARTIES AND SUPERSEDE
ALL PRIOR WRITTEN OR ORAL AGREEMENTS AND ANY CONTEMPORANEOUS ORAL AGREEMENTS WITH RESPECT TO THE SUBJECT MATTER HEREOF.

 

(f)
The rights and privileges of Secured Party hereunder shall inure to the benefit of its successors and assigns. Grantor may not
assign or transfer its rights hereunder or any interest herein or delegate its duties hereunder without the prior written consent
of Secured Party. No amendment of this Agreement shall be effective unless such amendment shall be in writing signed by Grantor
and Secured Party.

 

(g)
This Agreement may be executed and delivered (including by facsimile or Portable Document Format (pdf) transmission) in any number
of counterparts with the same effect as if all signatories had signed the same document. Facsimile and other electronic copies
of manually-signed originals shall have the same effect as manually-signed originals and shall be binding on Grantor and Secured
Party. All counterparts must be construed together to constitute one and the same instrument.

 

[Signatures
Appear on Following Page]

 

    	 	15	 

    	 

    

 

IN
WITNESS WHEREOF, this Security Agreement has been duly executed as of the day and year first above written.

 

	 	GRANTOR:
	 	 
	 	GLASSBRIDGE ATHLETE, LLC,
	 	a Delaware limited liability company
	 	 	 
	 	By:	/s/
    Daniel Strauss       
	 	Name:	Daniel
    Strauss 
	 	Title:	President
    

 

[Signature
Page to Security Agreement]

 

    	 	 	 

    	 

    

 

	 	SECURED PARTY:
	 	 	 
	 	ORIX PTP HOLDINGS, LLC
	 	a Delaware limited liability company
	 	 	 
	 	By:	/s/
    Paul Wilson
	 	Name:	Paul
    Wilson
	 	Title:	President
    of ORIX Corporate Capital, Inc. (sole member of ORIX PTP Holdings)

 

[Signature
Page to Security Agreement]

 

    	 	 	 

    	 

    

 

SCHEDULE
I

 

TO
SECURITY AGREEMENT

 

CHIEF
EXECUTIVE OFFICE AND OTHER ADDRESSES OF GRANTOR

 

	1.	GlassBridge
    Athlete, LLC
	 	411
    E 57th Street Suite 1-A New York NY 10022

 

    	 	 	 

    	 

    

 

SCHEDULE
II

 

TO
SECURITY AGREEMENT

 

STATE
OF FORMATION OR ORGANIZATION

 

	Information
    Required	 	Grantor
	 	 	 
	Exact
    Legal Name:	 	GLASSBRIDGE
    ATHLETE, LLC
	 	 	 
	State
    of Organization: 	 	Delaware
	 	 	 
	Type
    of Organization:	 	Limited
    liability company
	 	 	 
	Organizational
    I.D. Number:	 	7781937
	 	 	 
	Federal
    Taxpayer I.D. Number	 	84-4832519
	 	 	 
	Place
    of Business (or, if more than one, the	 	411
    E 57th Street Suite 1-A NY NY 10022
	Chief
    Executive Office):	 	 

 

    	 	 	 

    	 

    

 

SCHEDULE
III

 

TO
SECURITY AGREEMENT

 

TRADE
NAMES, PRIOR LEGAL NAMES AND TYPES OF ORGANIZATION, ETC.

 

Grantor’s
prior legal names and Types of Organizations were:

 

GlassBridge
Athlete, LLC

 

    	 	 	 

    	 

    

 

SCHEDULE
IV

 

TO
SECURITY AGREEMENT

 

INTELLECTUAL
PROPERTY

 

Patents:
none

 

Copyrights:
none

 

    	 	 	 

    	 

    

 

SCHEDULE
V

 

TO
SECURITY AGREEMENT

 

INSTRUMENTS,
ETC.

 

	Instruments:	-	none
	 	 	 
	Investment
    Property:	-	none
	 	 	 
	Letter-of-Credit
    Rights:	-	none
	 	 	 
	Chattel
    Paper:	-	none
	 	 	 
	Documents:	-	none
	 	 	 
	Commercial
    Tort Claims:	-	none

 

    	 	 	 

    	 

    

 

SCHEDULE
VI

 

TO
SECURITY AGREEMENT

 

COLLATERAL
NOT LOCATED IN THE UNITED STATES

 

None

 

    	 	 	 

    	 

    

 

SCHEDULE
VIII

 

TO
SECURITY AGREEMENT

 

COLLATERAL
SUBJECT TO CERTIFICATE OF TITLE STATUTE

 

None

 

    	 	 	 

    	 

    

 

SCHEDULE
IX

 

TO
SECURITY AGREEMENT

 

LIST
OF DEPOSIT ACCOUNTS AND OTHER BANK ACCOUNTS

 

The
following information has been omitted:

 

Signature
Bank

ABA
[***]

Account
Name: GlassBridge Athlete, LLC

Acct#
[***]Exhibit
10.45

 

PLEDGE
AGREEMENT

 

(PARENT)

 

THIS
PLEDGE AGREEMENT (as amended, restated, amended and restated, supplemented or otherwise modified from time to time, this “Agreement”)
is entered into as of March 17, 2020 (the “Closing Date”), by GlassBridge Enterprises, Inc.,
a Delaware corporation (“Pledgor”), for the benefit of ORIX PTP Holdings, LLC, a Delaware limited
liability company, as lender (“Lender”).

 

 RECITALS

 

A.
Pledgor owns membership interests in GlassBridge Athlete, LLC, a Delaware limited liability company (“Borrower”),
representing one hundred percent (100%) of the issued and outstanding membership interests of Borrower.

 

B.
Pledgor, Borrower and Lender have entered into that certain Secured Promissory Note Agreement of even date herewith (as amended,
restated, amended and restated, supplemented or otherwise modified from time to time, the “Note”).

 

C.
As the owner of 100% of the outstanding membership interests of the Borrower, Pledgor will receive the benefits of the transactions
contemplated by the Note.

 

D.
The board of directors of Pledgor has determined that Pledgor’s execution, delivery and performance of this Agreement may
reasonably be expected to benefit Pledgor, directly or indirectly, and are in the best interests of Pledgor.

 

E.
Pledgor has agreed to grant to Lender a security interest in, and pledge and assign to Lender the Collateral described herein,
to secure the payment and performance of the Obligations when due.

 

F.
It is expressly understood between Pledgor, Borrower and Lender that the execution and delivery of this Agreement is a condition
precedent to the obligation of the Lender to extend credit under the Note.

 

NOW,
THEREFORE, in consideration of the foregoing and as an inducement to Lender to enter into the Note and extend credit to Borrower,
and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties hereto
agree as follows:

 

    	 

     

    

 

1.
Certain Definitions. CAPITALIZED TERMS USED BUT NOT DEFINED IN THIS AGREEMENT HAVE THE MEANINGS GIVEN THEM IN THE NOTE
OR IN THE UCC. If the definition given a term in the Note conflicts with the definition given that term in the UCC, the Note definition
shall control to the extent allowed by applicable law. Terms used in this Agreement which are not capitalized but which are defined
in the UCC, shall have the meaning given them in the UCC. If the definition given a term in Chapter 9 of the UCC conflicts with
the definition given that term in any other chapter of the UCC, the Chapter 9 definition shall control. As used in this Agreement:

 

“Agreement”
means this Agreement together with all schedules and annexes attached hereto, and all amendments, restatements, and supplements
to this Agreement, the schedules and exhibits.

 

“Borrower”
is defined in the recitals hereto.

 

“Closing
Date” is defined in the introductory paragraph hereto.

 

“Collateral”
is defined in Section 3 of this Agreement.

 

“Equity
Power” means an equity power, substantially in the form of Annex A to this Agreement, executed and
delivered by Pledgor to Lender in connection with this Agreement.

 

“Equity
Securities” means, with respect to any Person (other than an individual), all of such Person’s issued and
outstanding:

 

(i)
capital stock (including but not limited to common stock and preferred stock), partnership interests, membership interests, equity
interests, profits interests, warrants, options or other rights for the purchase or acquisition from such Person of shares of
capital stock or other equity or profits interests of such Person;

 

(ii)
all of the securities convertible into or exchangeable for shares of capital stock, equity or profits interests, warrants, rights
or options for the purchase or acquisition from such Person of such shares or interests; and

 

(iii)
all of the other equity or profit interests in such Person, whether voting or nonvoting, and whether or not such shares, warrants,
options, rights or other interests are outstanding on any date of determination.

 

“Fraudulent
Conveyance” is defined in Section 5 of this Agreement.

 

“Initial
Pledged Interests” is defined Section 3 of this Agreement.

 

“Note”
is defined in the Recitals.

 

“Obligor”
is defined in Section 12(b) of this Agreement.

 

“Pledged
Interests” is defined Section 3 of this Agreement.

 

“Pledgor”
is defined in the introductory paragraph hereto and includes, without limitation, Pledgor as a debtor-in-possession, and any receiver,
trustee, liquidator, conservator, custodian, or similar party hereafter appointed for Pledgor or all or substantially all of Pledgor’s
assets pursuant to any liquidation, conservatorship, bankruptcy, moratorium, rearrangement, receivership, insolvency, reorganization,
or similar Law from time to time in effect affecting the rights of creditors generally.

 

    	2

     

    

 

“Security
Interest” means the security interests granted, and the transfers, pledges and collateral assignments made, under
Section 3 of this Agreement.

 

“UCC”
means (a) generally, and with respect to the definitions above, the Uniform Commercial Code, as adopted in the State of New York,
as amended from time to time, and (b) with respect to rights in states other than the State of New York, the Uniform Commercial
Code as enacted in the applicable state, as amended from time to time.

 

“Voting
Interests” means, of any Person, the capital stock, membership interests or other equity interests issued by such
Person which has voting power for the election of directors, managers or individuals performing similar functions.

 

2.
Secured Promissory Note. This Agreement is being executed and delivered pursuant to the terms and conditions of the Note
and the other Basic Documents. Each Security Interest is a “Lien” referred to in the Note.

 

3.
Security Interest. In order to secure the full and complete payment and performance of the Obligations when due, Pledgor
hereby grants to Lender a continuing security interest in, and pledges and assigns to Lender all of its rights, title and interest
in and to the following (collectively, the “Collateral”):

 

(a)
the Equity Securities described in attached Schedule 1 (the “Initial Pledged Interests”),
whether or not evidenced or represented by any certificated security or other instrument, the certificates representing the Initial
Pledged Interests, all options and other rights, contractual or otherwise, in respect thereof and all dividends, distributions,
cash, instruments, investment property and other property (including, but not limited to, any membership or other equity dividend
and any distribution in connection with a membership or other equity split) from time to time received, receivable or otherwise
distributed in respect of or in exchange for any or all of the Pledged Interests;

 

(b)
any other Equity Securities of the Borrower at any time and from time to time acquired by Pledgor (together with the Initial Pledged
Interests, the “Pledged Interests”), the certificates representing such Equity Securities, all options
and other rights, contractual or otherwise, in respect thereof and all dividends, distributions, cash, instruments, investment
property and other property (including, but not limited to, any membership or other equity dividend and any distribution in connection
with a stock or other equity split) from time to time received, receivable or otherwise distributed in respect of or in exchange
for any or all of the foregoing;

 

(c)
all security entitlements of Pledgor in any and all of the foregoing; and

 

(d)
all proceeds (including proceeds of proceeds) of any and all of the foregoing;

 

in
each case, whether now owned or hereafter acquired by Pledgor and howsoever its interest therein may arise or appear (whether
by ownership, security interest, Lien, claim or otherwise).

 

    	3

     

    

 

4.
No Assumption or Modification. The Security Interest is given to secure the prompt, unconditional and complete payment
and performance of the Obligations when due, and is given as security only. Lender neither assumes nor shall be liable for Pledgor’s
liabilities, duties, or obligations under or in connection with the Collateral. Neither Lender’s acceptance of this Agreement
nor its taking any action in carrying out this Agreement shall constitute Lender’s approval of the Collateral or Lender’s
assumption of any obligation under or in connection with the Collateral. This Agreement does not affect or modify Pledgor’s
obligations with respect to the Collateral.

 

5.
Fraudulent Conveyance. Notwithstanding anything contained in this Agreement to the contrary, Pledgor agrees that if, but
for the application of this Section 5, the Obligations or any Security Interest would constitute a preferential
transfer under 11 U.S.C. § 547, a fraudulent conveyance under 11 U.S.C. § 548 (or any successor section), or a fraudulent
conveyance or transfer under any state’s fraudulent conveyance or fraudulent transfer Law or similar Law in effect from
time to time (each a “Fraudulent Conveyance”), then the Obligations and each affected Security Interest
will be enforceable against Pledgor to the maximum extent possible without causing the Obligations or any Security Interest to
be a Fraudulent Conveyance, and shall be deemed to have been automatically amended to carry out the intent of this Section
5.

 

6.
Representations and Warranties. Pledgor hereby represents and warrants to Lender as of the Closing Date and each other
date required under any Basic Document as follows:

 

(a)
Pledgor has full power and capacity to execute and deliver this Agreement and to perform fully his obligations hereunder. The
execution, delivery and performance by Pledgor of this Agreement are within Pledgor’s lawful powers and have been duly authorized
by the board of directors, board of managers, general partner, managing member or other applicable governing body of Pledgor,
and no other corporate or equivalent action on the part of Pledgor is necessary to authorize this Agreement.

 

(b)
The execution and delivery by Pledgor of this Agreement and Pledgor’s performance of its obligations under this Agreement
(i) do not require action by, or filing with, any Governmental Authority or any action by any other Person (other than
any action taken or filing made on or before the Closing Date), (ii) do not violate any provision of Pledgor’s organizational
documents, (iii) do not violate, in any material respect, any provision of Law or any order of any Governmental Authority, in
each case applicable to Pledgor, (iv) do not violate, in any material respect, or constitute a material breach of, any material
agreements to which it is a party (and no default exists on the part of Pledgor under any material agreement to which it is a
party), and (v) will not result in the creation or imposition of any Lien on any asset of Pledgor other than Permitted Liens.

 

(c)
This Agreement has been duly executed by Pledgor and constitutes the legal, valid, and binding obligation of Pledgor, enforceable
against Pledgor in accordance with its terms, except as such enforceability may be limited by applicable bankruptcy, insolvency,
and similar laws affecting creditors’ rights generally and by general principles of equity (whether considered in a proceeding
in equity or at law), and except to the extent the indemnification provisions contained herein may be limited by applicable federal
or state securities laws.

 

    	4

     

    

 

(d)
Pledgor has received and will receive the benefits of the transactions contemplated by the Note, and such benefits constitute
good and valuable consideration for the Security Interest.

 

(e)
The Pledged Interests are duly authorized, validly issued, fully paid and non-assessable, and the transfer of the Pledged Interests
is not subject to any restrictions other than restrictions imposed by applicable securities and corporate laws.

 

(f)
Pledgor owns the Collateral free and clear of all Liens except for the Permitted Liens.

 

(g)
The information contained in Schedule 1 attached to this Agreement is true and accurate and sufficiently describes
all of the Collateral.

 

(h)
Pledgor has reviewed this Agreement and the other Basic Documents and has had the opportunity to review their respective rights
and responsibilities thereunder with counsel. Pledgor understands these rights and responsibilities and shall comply therewith.

 

7.
Covenants. Pledgor shall:

 

(a)
Promptly notify Lender of any material change in any fact represented or warranted by Pledgor with respect to any of the Collateral.

 

(b)
Promptly notify Lender upon its acquisition of any Equity Securities of the Borrower subsequent to the execution of this Agreement
and, if applicable, deliver to Lender any certificates (together with Equity Powers executed in blank) representing such Equity
Securities.

 

(c)
Promptly notify Lender of any claim, action or proceeding materially and adversely affecting the security interest granted and
the pledge and assignment made under Section 3 or title to any of the Collateral, and, if an Event of Default has
occurred and is continuing, at the request of Lender, appear in and defend, at Pledgor’s expense, any such action or proceeding.

 

(d)
Except as may be permitted under the Note, not sell, assign or otherwise dispose of any Collateral.

 

(e)
Not create, incur or suffer to exist any Lien upon any of the Collateral (other than Permitted Liens).

 

(f)
At Pledgor’s expense and Lender’s reasonable request, file or cause to be filed such applications and take such other
actions to obtain the consent or approval of any Governmental Authority to Lender’s rights hereunder, including, without
limitation, the right to sell all the Collateral upon the occurrence and during the continuance of an Event of Default without
additional consent or approval from such Governmental Authority (and, because Pledgor agrees that Lender’s remedies at law
for failure of Pledgor to comply with this provision would be inadequate and that such failure would not be adequately compensable
in damages, Pledgor agrees that its covenants in this provision may be specifically enforced).

 

    	5

     

    

 

(g)
To the extent any of the Pledged Interests is or becomes a “security” within the meaning of Article 8 of the UCC and
is governed by Article 8 of the UCC, such interest shall be certificated, and the certificates representing such Pledged Interests
shall be promptly delivered to Lender together with Equity Powers executed in blank.

 

(h)
From time to time promptly execute and deliver to Lender all such other assignments, certificates, supplemental documents, and
financing statements (if appropriate) and amendments thereto, and do all other acts or things as Lender may reasonably request
in order to more fully create, evidence, perfect, continue and preserve the priority of the Security Interest.

 

8.
Default; Remedies. Should an Event of Default occur and be continuing, Lender may, at its election, exercise any and all
rights available to a secured party under the UCC, in addition to any and all other rights afforded by the Note, at law, in equity,
or otherwise, including, without limitation applying by appropriate judicial proceedings for appointment of a receiver for all
or part of the Collateral (and Pledgor hereby consents to any such appointment).

 

9.
Notice. Reasonable notification of the time and place of any public sale of the Collateral, or reasonable notification
of the time after which any private sale or other intended disposition of the Collateral is to be made, shall be sent to Pledgor
and to any other person entitled to notice under the UCC. It is agreed that notice sent or given not less than ten (10) calendar
days prior to the taking of the action to which the notice relates is reasonable for the purposes of this Section 9.

 

10.
Sales of Securities. Pledgor recognizes that the Lender may deem it impracticable to effect a public sale of all or any
part of the Pledged Interests or any other securities constituting Collateral. Lender is authorized, but not obligated, to limit
prospective purchasers to the extent deemed necessary or desirable by Lender to render such sale exempt from the registration
requirements of the Securities Act, and any applicable state securities laws, and no sale so made in good faith by Lender shall
be deemed not to be “commercially reasonable” because so made. Lender may make one or more private sales of any such
securities to a restricted group of purchasers who will be obligated to agree, among other things, to acquire such securities
for their own account, for investment and not with a view to the distribution or resale thereof. Pledgor acknowledges that any
such private sale may be at prices and on terms less favorable to the seller than the prices and other terms which might have
been obtained at a public sale and, notwithstanding the foregoing, agrees that such private sales shall be deemed to have been
made in a commercially reasonable manner and that the Lender shall have no obligation to delay the sale of any such securities
for the period of time necessary to permit the issuer of such securities to register such securities for public sale under the
Securities Act. Pledgor further acknowledges and agrees that any offer to sell such securities which has been (i) publicly advertised
on a bona fide basis in a newspaper or other publication of general circulation in the financial community of New York, New York
(to the extent that such an offer may be so advertised without prior registration under the Securities Act) or (ii) made privately
in the manner described above to not less than fifteen (15) bona fide offerees shall be deemed to involve a “public
disposition” for the purposes of Section 9-610(c) of the UCC, notwithstanding that such sale may not constitute a “public
offering” under the Securities Act, and that the Lender may, in such event, bid for the purchase of such securities.

 

    	6

     

    

 

11.
Application of Proceeds. Lender shall apply the proceeds of any sale or other disposition of the Collateral in accordance
with Section 2.5(b) of the Note. Any surplus remaining shall be delivered to Pledgor or as a court of competent jurisdiction may
direct. If the proceeds of the Collateral are insufficient to pay the Obligations in full, Pledgor shall remain liable for any
deficiency.

 

12.
Other Rights of Lender.

 

(a)
Performance. In the event Pledgor shall fail to perform any of its obligations hereunder with respect to the Collateral,
then Lender may, at its option, but without being required to do so, take such action which Pledgor is required, but has failed
or refused, to take. Any sum which may be expended or paid by Lender under this Section 12(a) (including, without
limitation, court costs and reasonable attorneys’ fees) shall bear interest from the dates of expenditure or payment at
the Default Rate until paid and, together with such interest, shall be payable by Pledgor within 30 days after receipt by Pledgor
of written notice of such documented costs and expenses, and shall be part of the Obligations.

 

(b)
Collection. Upon notice from Lender, each Person obligated with respect to any of the Collateral, whether as an issuer,
account debtor or otherwise (an “Obligor”) is hereby authorized and directed by Pledgor to make payments
on any of the Collateral (including, without limitation, dividends and other distributions) directly to Lender, regardless of
whether Pledgor was previously making collections thereon. Subject to Section 12(e) hereof, until such notice is
given, Pledgor is authorized to retain and expend all payments made on Collateral. Lender shall have the right in its own name
or in the name of any Pledgor to compromise or extend time of payment with respect to all or any portion of the Collateral for
such amounts and upon such terms as Lender may determine; to demand, collect, receive, receipt for, sue for, compound and give
acquittances for any and all amounts due or to become due with respect to Collateral; to take control of cash and other proceeds
of any Collateral; to endorse the name of any Pledgor on any notes, acceptances, checks, drafts, money orders or other evidences
of payment on Collateral that may come into the possession of Lender; to send requests for verification of obligations to any
Obligor; and to do all other acts and things necessary to carry out the intent of this Agreement. If any Obligor fails or refuses
to make payment on any Collateral when due, Lender is authorized, in its sole reasonable discretion, either in its own name or
in the name of Pledgor, to take such action as Lender shall deem appropriate for the collection of any such amounts. The foregoing
rights granted to Lender under this Section 12(b) may only be exercised when an Event of Default has occurred and
is continuing. Regardless of any other provision hereof, Lender shall not be liable for its failure to collect, or for its failure
to exercise diligence in the collection of, any amounts owed with respect to Collateral, nor shall they be under any duty whatsoever
to anyone except Pledgor to account for funds that Lender shall actually receive hereunder. Without limiting the generality of
the foregoing, Lender shall have no responsibility for ascertaining any maturities, calls, conversions, exchanges, offers, tenders
or similar matters relating to any Collateral, or for informing Pledgor with respect to any of such matters (irrespective of whether
Lender actually has, or may be deemed to have, knowledge thereof). The receipt by Lender of any such payment from any Obligor
shall be a full and complete release, discharge and acquittance to such Obligor, to the extent of any amount so paid to Lender.

 

    	7

     

    

 

(c)
Record Ownership of Securities. When an Event of Default has occurred and is continuing, Lender at any time may have the
Collateral registered in its name, or in the name of its nominee or nominees, as pledgee; and Pledgor shall execute and deliver
to Lender all such proxies, powers of attorney, dividend coupons or orders and other documents as Lender may reasonably request
for the purpose of enabling Lender to exercise the voting rights and powers which it is entitled to exercise hereunder and to
receive the dividends and other payments which it is authorized to receive and retain hereunder. Nothing in this Agreement shall
prohibit the issuance of cash dividends by Borrower if such distribution is permitted under the Note.

 

(d)
Voting of Securities. So long as no Event of Default has occurred and is continuing, Pledgor shall be entitled to exercise
all voting rights pertaining to the Collateral. After the occurrence and during the continuance of an Event of Default, the right
to vote the Collateral shall be vested exclusively in Lender. To this end, and only so long as no Event of Default has occurred
and is continuing Pledgor irrevocably appoints Lender the proxy and attorney-in-fact of Pledgor, with full power of substitution,
to vote and to act with respect to the Collateral, subject to the understanding that such proxy may not be exercised unless an
Event of Default has occurred and is continuing. The proxy herein granted is coupled with an interest, is irrevocable, and shall
continue until the Obligations have been paid and performed in full.

 

(e)
Certain Proceeds. Any and all dividends or distributions in property made on or in respect of the Collateral, and any proceeds
of the Collateral, whether such dividends, distributions, or proceeds result from a subdivision, combination or reclassification
of the Equity Securities of any Person or as a result of any merger, consolidation, acquisition or other exchange of assets to
which Pledgor may be a party, or otherwise, shall be part of the Collateral hereunder, shall, if received by Pledgor, be held
in trust for the benefit of Lender, and shall forthwith be delivered to Lender (accompanied by proper instruments of assignment
and/or stock and/or bond powers executed by the Pledgor in accordance with Lender’s instructions) to be held subject to
the terms hereof. Prior to the occurrence and continuation of an Event of Default, any cash proceeds of Collateral which come
into the possession of Lender may, at the Pledgor’s option, be applied in whole or in part to the Obligations, or be released
in whole or in part to or on the written instructions of the Pledgor(s) for any general or specific purpose not in violation of
the Note, or be retained in whole or in part by Lender as additional Collateral. Upon the occurrence and continuation of an Event
of Default, any cash proceeds of Collateral may, at Lender’s option, be applied to the Obligations. Any dividends, distributions
or other payments received in respect of the Collateral that are received by Pledgor contrary to the provisions of this clause
(e) shall be received in trust for the benefit of Lender, shall be segregated from the other funds of Pledgor and shall immediately
be paid over to Lender as Collateral in the same form as so received.

 

    	8

     

    

 

(f)
Financing Statements. Pledgor hereby irrevocably authorizes Lender at any time, and from time to time, to file in any jurisdiction
any initial financing statements and amendments thereto that (i) (A) indicate the Collateral as “the Collateral described
in the Pledge Agreement,” (B) describe the Collateral in terms similar to those used in Section 3, or (B)
otherwise describe the Collateral as being of an equal or lesser scope or with greater detail, regardless of whether any particular
asset comprised in the Collateral falls within the scope of Article 9 of the UCC of the jurisdiction wherein such financing statement
or amendment is filed, and (ii) contain any other information required by Article 9 of the UCC of the jurisdiction wherein such
financing statement or amendment is filed regarding the sufficiency or filing office acceptance of any financing statement or
amendment.

 

13.
Miscellaneous.

 

(a)
Term. Upon payment in full of the Obligations and termination of Lender’s commitment to lend under the Note without
Lender having exercised its rights under this Agreement, this Agreement shall terminate; provided that no Obligor on any
of the Collateral shall be obligated to inquire as to the termination of this Agreement, but shall be fully protected in making
payment directly to Lender, which payment shall be promptly paid over to Pledgor after termination of this Agreement.

 

(b)
Notice. Any notice or communication required or permitted under this Agreement must be given as prescribed in the Note.

 

(c)
Note. In the event of any conflict or inconsistency between the terms hereof and the Note, the terms of the Note shall
be controlling and this Agreement shall be deemed to be amended to conform to the terms of the Note. The provisions of Section
9 of the Note are hereby incorporated mutatis mutandis and shall have the same force and effect as if expressly set forth
herein.

 

(d)
Multiple Counterparts and Facsimile Signatures. This Agreement may be executed in any number of counterparts with the same
effect as if all signatories had signed the same document. All counterparts must be construed together to constitute one and the
same instrument. This Agreement may be transmitted and signed by facsimile or PDF, and facsimile or PDF copies of manually-signed
originals shall have the same effect as manually-signed originals and shall be binding on Pledgor and Lender.

 

(e)
Binding Effect; Survival. This Agreement is binding upon, and inures to the benefit of, the parties hereto and their respective
successors and permitted assigns. Unless otherwise provided, all covenants, agreements, indemnities, representations and warranties
made in any of the Basic Documents survive and continue in effect as long as the Obligations are outstanding or the Lender’s
commitment to lend under the Note is in effect.

 

(f)
Amendments. This Agreement may be amended, modified, supplemented or be the subject of a waiver only by a writing executed
by Lender and Pledgor.

 

(g)
Entirety. THIS AGREEMENT REPRESENTS THE FINAL AGREEMENT BETWEEN THE PARTIES ON THE SUBJECT MATTER HEREOF AND MAY NOT BE
CONTRADICTED BY EVIDENCE OF PRIOR, CONTEMPORANEOUS OR SUBSEQUENT ORAL AGREEMENTS BETWEEN THE PARTIES. THERE ARE NO UNWRITTEN ORAL
AGREEMENTS AMONG THE PARTIES.

 

[Signatures
appear on the next page.]

 

    	9

     

    

 

IN
WITNESS WHEREOF, the parties have executed and delivered this Agreement as of the date first above written.

 

	 	PLEDGOR:
	 	 	 
	 	GLASSBRIDGE
    ENTERPRISES, INC.,
	 	a Delaware corporation
	 	 	 
	 	By:	/s/
    Daniel Strauss               
	 	Name:	Daniel
    Strauss 
	 	Title:	CEO
    

 

[Signature
Page to Pledge Agreement (Parent)]

 

    	 

     

    

 

	 	LENDER:
	 	 	 
	 	ORIX PTP HOLDINGS, LLC
	 	a Delaware limited liability company
	 	 	 
	 	By:
    	/s/
    Paul Wilson           
	 	Name:
    	Paul
    Wilson
	 	Title:	President
    of ORIX Corporate Capital, Inc. (sole member of ORIX PTP Holdings)

 

[Signature
Page to Pledge Agreement (Parent)]

 

    	 

     

    

 

SCHEDULE
1

Pledged Interests

 

	Pledgor	 	Issuer	 	Pledged

 Interests	 	Percentage 

Interest
	GlassBridge Enterprises, Inc.	 	GlassBridge Athlete, LLC	 	 	 	100%
	TOTAL:	 	 	 	 	 	100%

 

Schedule 1 to Pledge Agreement

 

    	 

     

    

 

ANNEX
A

TO

PLEDGE AGREEMENT

 

FORM
OF EQUITY POWER

 

FOR
VALUE RECEIVED, the undersigned does hereby sell, assign and transfer unto ____________________ (_____) Units of Membership Interest
of _________________, a _________________ (the “Company”), registered in its name on the books of the
Company [represented by Certificate No. ____ herewith], and does hereby irrevocably constitute and appoint __________________
as its attorney to transfer said units on the books of the Company with full power of substitution in the premises.

 

Dated:
_______________,_____

 

__________________________________________ 

 

	 	By:	 
	 	Name:    	 
	 	Title:	 

 

	 		[or,
    for an individual Pledgor]

 

__________________________________________ 

 

________________

 

Annex A to Pledge Agreement

 

    	 

     

    

 

INSTRUCTIONS
TO PLEDGOR: Please do not fill in any blanks other than the signature line. The purposes of this Equity Power is to enable
Lender and/or its assignee(s) to acquire the pledged interests upon an Event of Default without requiring additional signatures
on the part of Pledgor.

 

IN
THE PRESENCE OF

 

______________________________________

[WITNESS]

 

Annex A to Pledge Agreement

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