UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 13D

Under the Securities Exchange Act of 1934

If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box. ☐

Note: Schedules filed in paper format shall include a signed original and five copies of the schedule, including all exhibits. See Rule 13d-7 for other parties to whom copies are to be sent.

The information required on the remainder of this cover page shall not be deemed to be “filed” for the purpose of section 18 of the Securities Exchange Act of 1934 (“Act”) or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).

(1) Represents 9,300,650 shares of Class A common stock, par value $0.01 per share (“Class A Common Stock”), of MediaCo Holding Inc. (the “Company”) issuable upon the exercise of the Class A Common Stock Purchase Warrant (the “Warrant”) issued by the Company to SLF LBI Aggregator, LLC (“Aggregator”) on April 17, 2024.

(2) Based on (i) 41,323,741 shares of Class A Common Stock that were issued and outstanding, as reported in Exhibit 2.1 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission (the “SEC”) on April 17, 2024 and (ii) 9,300,650 shares of Class A Common Stock issuable upon exercise of the Warrant.

(1) Represents 9,300,650 shares of Class A Common Stock issuable upon exercise of the Warrant issued by the Company to Aggregator on April 17, 2024.

(2) Based on (i) 41,323,741 shares of Class A Common Stock that were issued and outstanding, as reported in Exhibit 2.1 of the Company’s Current Report on Form 8-K filed with the SEC on April 17, 2024 and (ii) 9,300,650 shares of Class A Common Stock issuable upon exercise of the Warrant.

(1) Represents 9,300,650 shares of Class A Common Stock issuable upon exercise of the Warrant issued by the Company to Aggregator on April 17, 2024.

(2) Based on (i) 41,323,741 shares of Class A Common Stock that were issued and outstanding, as reported in Exhibit 2.1 of the Company’s Current Report on Form 8-K filed with the SEC on April 17, 2024 and (ii) 9,300,650 shares of Class A Common Stock issuable upon exercise of the Warrant.

Item 1. Security and Issuer.

This Schedule 13D relates to the Class A Common Stock Purchase Warrant (the “Warrant”) to purchase up to 28,206,152 shares of Class A common stock, par value $0.01 per share (the “Class A Common Stock”), of MediaCo Holding Inc. (the “Company”), an Indiana corporation. The address of the principal executive offices of the Company is 395 Hudson Street, Floor 7, New York, New York 10014.

Item 2. Identity and Background.

(a), (f) This Schedule 13D is being filed jointly by (i) Scott Kapnick, a United States citizen, (ii) HPS Group GP, LLC, a Delaware limited liability company (“HPS Group”) and (iii) SLF LBI Aggregator, LLC, a Delaware limited liability company (“Aggregator” and, together with Scott Kapnick and HPS Group, the “Reporting Persons”).

(b) The principal business address of each Reporting Person is 40 West 57th Street, 33rd Floor, New York, New York 10019.

(c) Scott Kapnick is chief executive officer of HPS Investment Partners, LLC, which is a registered investment adviser and is affiliated with HPS Group (collectively with HPS Group, “HPS”). The principal business of HPS and Aggregator is to engage in making investments in public and private companies through various strategies across the capital structuring including privately negotiated senior debt; privately negotiated junior capital solutions in debt, preferred and equity formats; liquid credit including syndicated leveraged loans, collateralized loan obligations and high yield bonds; asset-based finance and real estate.

(d), (e) During the last five years, none of the Reporting Persons have (i) been convicted in a criminal proceeding (excluding traffic violations or similar misdemeanors) or (ii) been a party to a civil proceeding of a judicial or administrative body of competent jurisdiction and as a result of such proceeding was or is subject to a judgment, decree or final order enjoining future violations of, or prohibiting or mandating activities subject to, federal or state securities laws or finding any violation with respect to such laws.

Item 3. Source and Amount of Funds or Other Consideration.

On April 17, 2024, the Company and its wholly-owned subsidiary MediaCo Operations LLC, a Delaware limited liability company (“Purchaser”), entered into an asset purchase agreement (the “Asset Purchase Agreement”) with Estrella Broadcasting, Inc. (“Estrella”), a Delaware corporation and subsidiary of Aggregator, and Aggregator, an affiliate of HPS Investment Partners, LLC, pursuant to which Purchaser purchased substantially all of the assets of Estrella and its subsidiaries (other than certain broadcast assets owned by Estrella and its subsidiaries (the “Estrella Broadcast Assets”)), and assumed substantially all of the liabilities of Estrella and its subsidiaries. As consideration in the transaction, Aggregator received the Warrant; $60.0 million of newly issued shares of Series B Preferred Stock of the Company; a $30 million second lien term loan; and approximately $30 million in cash for the repayment of certain indebtedness of Estrella and payment of certain Estrella transaction expenses.

Item 4. Purpose of Transaction.

The Reporting Persons have acquired the Warrant for investment purposes. The Reporting Persons intend to review their holdings in the Company on a continuing basis and, depending upon the price and availability of the Company’s securities, subsequent developments affecting the Company, the business prospects of the Company, general stock market and economic conditions, tax considerations, investment considerations and/or other factors deemed relevant, may consider increasing or decreasing their investments in the Company.

Except as set forth in this Schedule 13D, none of the Reporting Persons have any plan or proposals that relate to or would result in any of the transactions described in subparagraphs (a) through (j) of Item 4 of Schedule 13D. However, each of the Reporting Persons reserves the right to change its plans at any time, as it deems appropriate, in light of its ongoing evaluation of (i) its business and liquidity objectives, (ii) the Company’s financial condition, business, operations, competitive position, prospects and/or share price, (iii) industry, economic and/or securities markets conditions, (iv) alternative investment opportunities and (v) other relevant factors.

Without limiting the generality of the preceding sentence, each of the Reporting Persons reserves the right (subject to any applicable restrictions under law or contracts by which it is bound) to at any time or from time to time (A) purchase or otherwise acquire additional shares of Class A Common Stock or other securities of the Company, or instruments convertible into or exercisable for any such securities (collectively, “Company Securities”), in the open market, in privately negotiated transactions or otherwise, (B) sell, transfer or otherwise dispose of Company Securities in public or private transactions, (C) acquire or write options contracts, or enter into derivatives or hedging transactions, relating to Company Securities, (D) pledge Company Securities to secure obligations of the Reporting Persons and/or (E) encourage (including, without limitation, through any designated or nominated member of the Company’s board of directors (the “Board of Directors”) and/or communications with directors, management and existing or prospective security holders, investors or lenders of the Company, existing or potential strategic partners, industry analysts and other investment and financing professionals) the Company to consider or explore the following: (i) sales or acquisitions of assets or businesses or extraordinary corporate transactions, such as a merger (including transactions in which affiliates of Reporting Persons may be proposed as acquirers or as a source of financing), (ii) changes to the Company’s capitalization or dividend policy, (iii) changes to the present Board of Directors, including changes to the number or term of members of the Board of Directors or filling existing vacancies on the Board of Directors, (iv) changes to the Company’s by-laws and (v) other changes to the Company’s business or structure.

For avoidance of doubt, the Reporting Persons further reserve the right to act in concert with shareholders of the Company, or other persons, for a common purpose should it determine to do so, and/or to recommend courses of action to management and the shareholders of the Company.

Item 5. Interest in Securities of the Issuer.

(a) Scott Kapnick is the sole member of HPS Group. HPS Group is the non-member manager of Aggregator.

The responses of each Reporting Person to Items 7 through 11 of the cover pages of this Schedule 13D relating to beneficial ownership of the shares of Class A Common Stock are incorporated herein by reference.

Each of the Reporting Persons disclaims beneficial ownership of the shares of Class A Common Stock, except to the extent of such Reporting Person’s pecuniary interest therein.

(b) See Item 5(a) above.

(c) Except for the transactions described herein, there have been no other transactions in the securities of the Company effected by any Reporting Person within the last 60 days.

(d) No person (other than the Reporting Persons) is known to have the right to receive or the power to direct the receipt of dividends from, or the proceeds from the sale of, the shares of Class A Common Stock reported herein. Estrella has the right to receive the shares of Class A Common Stock subject to the terms of the Option Agreement (as discussed in further detail below); however, such option is not exercisable until October 17, 2024.

(e) Not applicable.

Item 6. Contracts, Arrangements, Understandings or Relationships with Respect to Securities of the Issuer.

Asset Purchase Agreement

The description of the Asset Purchase Agreement under Item 3 above is incorporated by reference herein.

Warrant

On April 17, 2024, in connection with the transactions contemplated by the Asset Purchase Agreement (the “Transactions”), the Company issued the Warrant, which provides for the purchase of up to 28,206,152 shares of Class A Common Stock (the “Warrant Shares”), subject to customary adjustments as set forth in the Warrant, at an exercise price per share of $0.00001. Subject to certain limitations, the Warrant also provides that the Warrant holder has the right to participate in distributions on Class A Common Stock on an as-exercised basis.  The Warrant further provides that in no event shall the aggregate number of Warrant Shares issuable to the Warrant holder upon exercise of the Warrant exceed 19.9% of the aggregate number of shares of common stock of the Company outstanding, or the voting power of such outstanding shares of common stock, on the business day immediately preceding the issue date for such Warrant Shares, calculated in accordance with the applicable rules of the Nasdaq Capital Market, unless and until the stockholder approval of the Proposal (as defined below).

Option Agreement

On April 17, 2024, in connection with the Transactions, the Company and Purchaser entered into an Option Agreement (the “Option Agreement”) with Estrella, a subsidiary of Aggregator, and certain subsidiaries of Estrella pursuant to which (i) Purchaser was granted the option to purchase 100% of the equity interests of certain subsidiaries of Estrella holding the Estrella Broadcast Assets (the “Option Subsidiaries Equity”) in exchange for 7,051,538 shares of Class A Common Stock, and (ii) Estrella was granted the right to put the Option Subsidiaries Equity to Purchaser for the same consideration beginning six months after the date of the closing of the Transactions (the “Closing Date”).

Stockholders Agreement

On April 17, 2024, in connection with the Transactions, the Company entered into a stockholders’ agreement with SG Broadcasting LLC (“SG Broadcasting”) and Aggregator (the “Stockholders Agreement”). The Stockholders Agreement provides Aggregator (i) the right to designate up to three individuals for election to the Board of Directors, subject to reduction and termination based on certain stock ownership requirements of the Company (including that such designation right falls away upon Aggregator ceasing to beneficially own at least 10% of the fully diluted common stock of the Company for ten consecutive days), and (ii) certain consent rights over material actions taken by the Company. Under the Stockholder Agreement, (i) SG Broadcasting agreed, solely with the Company and not with any party to the Stockholders Agreement, to vote all shares of Company common stock, including Class A Common Stock, held by such party in favor of such designees and (ii) Aggregator agreed, solely with the Company and not with any party to the Stockholders Agreement, to vote all shares of Company common stock, including Class A Common Stock, beneficially owned by such party in favor of nominees nominated by the Company for election at such meeting and otherwise in accordance with the recommendation of the Board of Directors on any other proposal relating to the appointment, election or removal of directors.

Registration Rights Agreement

On April 17, 2024, in connection with the Transactions, the Company entered into a registration rights agreement with SG Broadcasting and Aggregator (the “Registration Rights Agreement”), pursuant to which the Company has granted each of SG Broadcasting and Aggregator customary underwritten shelf takedown and piggyback rights with respect to the registration of shares of Class A Common Stock with the SEC under the Securities Act of 1933, as amended (the “Securities Act”).  In addition, the Company has agreed to prepare and file within three months of the Closing Date a registration statement covering the sale or distribution of shares of Class A Common Stock held by SG Broadcasting and Aggregator.

Voting and Support Agreement

On April 17, 2024, in connection with the Transactions, SG Broadcasting, the holder of shares of Class A Common Stock and Class B Common Stock, par value $0.01 per share (“Class B Common Stock”), representing a majority of the voting power of the shares of the Company, entered into a Voting and Support Agreement with the Company and Estrella (the “Voting and Support Agreement”), pursuant to which SG Broadcasting agreed to, among other things, and subject to the terms and conditions set forth therein, at any meeting of the Company stockholders, or at any adjournment or postponement thereof, vote in favor of a proposal to consider approval of the issuance of shares of Class A Common Stock upon exercise of the Warrant and the issuance of shares of Class A Common Stock pursuant to the Option Agreement (the “Proposal”) and against any action or proposal that would reasonably be expected to prevent or materially delay consummation of the Proposal. The Voting and Support Agreement also includes certain customary restrictions on SG Broadcasting’s ability to transfer its shares of Company stock. The Voting and Support Agreement will automatically terminate upon the date on which the Proposal is approved.

The foregoing descriptions of the Asset Purchase Agreement, Warrant, Option Agreement, Stockholders Agreement, Registration Rights Agreement and Voting and Support Agreement are only summaries, do not purport to be complete and are qualified in their entirety by reference to the full text of such agreements, which are attached as Exhibits 2, 3, 4, 5, 6 and 7, respectively, and incorporated by reference herein.

Item 7. Material to Be Filed as Exhibits.

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, the undersigned certifies that the information set forth in this statement is true, complete and correct.

Dated: April 24, 2024

EXHIBIT 1

JOINT FILING AGREEMENT

Pursuant to Rule 13d-1(k)(1) promulgated under the Securities Exchange Act of 1934, as amended, each of the undersigned acknowledges and agrees that the foregoing statement on this Schedule 13D is filed on behalf of the undersigned and that all subsequent amendments to this statement on Schedule 13D shall be filed on behalf of the undersigned without the necessity of filing additional joint acquisition statements. Each of the undersigned acknowledges that it shall be responsible for the timely filing of such amendments, and for the completeness and accuracy of the information concerning it contained therein, but shall not be responsible for the completeness and accuracy of the information concerning the others, except to the extent that he or it knows or has reason to believe that such information is inaccurate.

Dated: April 24, 2024

EXHIBIT 4

Execution Version

OPTION AGREEMENT

THIS OPTION AGREEMENT (this “Agreement”) is made and entered into as of April 17, 2024 by and among (i) MediaCo Operations LLC, a Delaware limited liability company (together with its successors and assigns, “Option Holder”), (ii) solely for purposes of Section 5(a) and Section 32(b) hereof, MediaCo Holding Inc., an Indiana corporation (“Parent”), (iii) Estrella Broadcasting, Inc., a Delaware corporation (“Estrella Broadcasting”), (iv) Estrella Media, Inc., a Delaware corporation (the “Company”), (v) each of Estrella Radio Broadcasting of California LLC, a California limited liability company, Estrella Radio Broadcasting of Houston LLC, a Delaware limited liability company, Estrella Television of Houston LLC, a Delaware limited liability company, Estrella Television LLC, a California limited liability company, Estrella Television of Dallas LLC, a Delaware limited liability company, and Estrella Radio Broadcasting of Dallas LLC, a Delaware limited liability company (each, together with its successors and permitted assigns, a “Company Subsidiary”), (vi) Estrella KRCA Television LLC, a California limited liability company (“KRCA”), and (vii) each of Estrella Radio License of California LLC, a California limited liability company, Estrella Radio License of Houston LLC, a Delaware limited liability company, Estrella Television License of Houston LLC, a Delaware limited liability company, Estrella Television License LLC, a California limited liability company, and Estrella Radio License of Dallas LLC, a Delaware limited liability company, and Estrella Television License of Dallas LLC, a Delaware limited liability company (each, together with its successors and permitted assigns, a “LicenseCo Subsidiary”; the Company, together with each Company Subsidiary, KRCA, and each LicenseCo Subsidiary, collectively, the “Grantor Parties”).

W I T N E S S E T H

WHEREAS, simultaneously with the execution hereof, Parent, Option Holder, Estrella Broadcasting, the Company and certain other parties hereto have entered into that certain Asset Purchase Agreement (the “Purchase Agreement”), with respect to the acquisition of certain assets, including the program network assets, of the Company by Option Holder, but excluding the Excluded Assets (as such term is defined in the Purchase Agreement) (terms not otherwise defined herein shall have the meaning given them in the Purchase Agreement or in Schedule A hereto);

WHEREAS, each LicenseCo Subsidiary holds the FCC Licenses (hereinafter defined) for the television and radio stations listed on Schedule I hereto (the “Stations”) opposite the name of such LicenseCo Subsidiary on such Schedule I;

WHEREAS, the Company directly owns 100% of the issued and outstanding equity interests of each Company Subsidiary (the “Equity Interests”) as described on Schedule 2 hereto, and a Company Subsidiary (directly or indirectly through KRCA) owns 100% of the issued and outstanding equity interests of each LicenseCo Subsidiary as described on Schedule 2 hereto;

WHEREAS, for U.S. federal income tax purposes, each of the Company Subsidiaries, each of the LicenseCo Subsidiaries, and KRCA is disregarded as an entity separate from the Company within the meaning of Treasury Regulations Section 301.7701-3;

WHEREAS, the Grantor Parties desire to grant to Option Holder, and Option Holder desires to acquire from the Grantor Parties, an option to purchase all (but not less than all) of the Equity Interests in each Company Subsidiary on the terms and conditions set forth herein; and

WHEREAS, Option Holder desires to grant to the Grantor Parties, and the Grantor Parties desire to acquire from Option Holder, the right to sell to Option Holder all (but not less than all) of the Equity Interests in each Company Subsidiary on the terms and conditions set forth herein.

NOW, THEREFORE, in consideration of the mutual covenants and agreements hereinafter set forth, the parties, intending to be legally bound, agree as follows:

1.         Option Grant. The Grantor Parties hereby give, grant, transfer and convey to Option Holder the sole and exclusive right, privilege and option to purchase (the “Option”), on the terms and conditions hereinafter set forth and effective as of the date hereof (the “Effective Date”) all (but not less than all) of issued and outstanding Equity Interests of each and every Company Subsidiary, now held or hereinafter acquired by the Company.

2.         Consideration for Option. This Option is granted by the Grantor Parties to Option Holder of as a component of, and as part of the consideration for, the transactions taking place at Closing as set forth in the Purchase Agreement.

3.         Option Period. This Agreement shall be effective commencing on the Effective Date and ending on the seventh (7^th) anniversary of the Effective Date (this period, as it may be extended in accordance with the language below, the “Option Period”); provided, however, that this Agreement and the Option Period will be automatically extended for a renewal term of seven (7) years unless the parties mutually agree otherwise in writing at least ninety (90) days prior to expiration of the initial Option Period, in which case this Agreement will terminate effective upon expiration of the initial Option Period. The consummation of the purchase of the Equity Interests of each Company Subsidiary, following exercise of the Option or the Put Right during the Option Period in accordance with the terms and conditions hereof, is hereinafter referred to as the “Option Closing.” There will only be one (1) Option Closing and the Option Closing may take place after the expiration of the Option Period so long as the Option Holder has delivered an Exercise Notice or the Company, on behalf of each Grantor Party, has delivered a Put Exercise Notice (as such terms are defined below) prior to the expiration of the Option Period.

4.         Exercise of Option; Exercise of Put.

(a)         Option Holder may exercise the Option with respect one hundred percent (100%) of the Equity Interests of each and every Company Subsidiary at any time during the Option Period by delivery of written notice thereof (the “Exercise Notice”) to the Company. Upon exercise of the Option, Option Holder and the applicable Grantor Parties shall be obligated to enter into the transactions to be consummated hereunder at the Option Closing, subject to the provisions of Sections 9 and 10 hereof.

(b)         Notwithstanding the foregoing, Option Holder may withdraw any Exercise Notice at any time prior to the Option Closing by written notice to the Company of such

withdrawal. No such withdrawal will affect Option Holder’s right subsequently to exercise the Option by delivering to the Company during the Option Period one or more other Exercise Notices.

(c)         If Option Holder has not exercised the Option in accordance with Section 4(a) of this Agreement within six (6) months of the Effective Date (“Put Trigger”), the Company, for itself and on behalf of the other applicable Grantor Parties, may put the Option to Option Holder (“Put Right”), and thereby require Option Holder to acquire one hundred percent (100%) of the Equity Interests of each and every Company Subsidiary by giving written notice (the “Put Exercise Notice”) to Option Holder of the Company’s exercise of the Put Right at any time after the Put Trigger date and the Put Right becoming effective hereunder. Notwithstanding the foregoing, Company may withdraw any Put Exercise Notice at any time prior to the Option Closing by written notice to the Option Holder of such withdrawal. No withdrawal of a Put Exercise Notice or any subsequent Put Exercise Notice will affect Company’s right subsequently to exercise the Put Right by delivering to the Option Holder during the Option Period after the Put Trigger one or more other Put Exercise Notices.

(d)         Upon delivery of the Put Exercise Notice, Option Holder and the applicable Grantor Parties shall be obligated to enter into the transactions to be consummated hereunder at the Option Closing, subject to the provisions of Sections 9 and 10 hereof.

5.         Purchase Price and Contemplated Transactions.

(a)         Purchase Price. At the Option Closing, and pursuant to the terms and subject to the conditions set forth in this Agreement (including the terms of Schedule 5(a)), Option Holder shall pay to the Company or its assignee, on behalf of itself and the other Grantor Parties, the applicable Purchase Price (defined on Schedule 5(a) hereto) set forth on Schedule 5(a). Parent shall comply with the terms and conditions of this Section 5(a) (including the applicable provisions of Schedule 5(a)) that are applicable to Parent, including by, in connection with the Option Closing, contributing to Option Holder the applicable Purchase Price payable at the Option Closing (if and to the extent applicable pursuant to Schedule 5(a)).

(b)         Purchase of Equity Interests.

(i)         The Company shall, on the Option Closing Date, deliver any and all documentation required to effect the transfer of such Equity Interests to Option Holder, including, the deliveries set forth in Section 11(a)(i) hereof, free and clear of all liens, claims and encumbrances of any character (“Liens”), except for liens for taxes not yet due and payable or contested in good faith by appropriate proceedings, transfer restrictions under applicable securities Laws and Permitted Liens (as defined in the Purchase Agreement).

(ii)         In connection with the Option Closing:

(A)         Estrella Broadcasting and the Company, as applicable, shall assign to the Option Holder all of their respective rights and benefits arising under the Excluded Contracts, and Option Holder shall assume all Liabilities of Estrella Broadcasting and the Company, as applicable, under such Excluded Contracts;

(B)         Each Grantor Party (other than the Company) shall assign to the Company all Liabilities of such Grantor Party with respect to the Excluded Liabilities set forth in Sections 2.4(b), 2.4(c), 2.4(d), 2.4(e), 2.4(g), 2.4(h), and 2.4(i) of the Purchase Agreement, and the Company shall assume and be responsible for all such Liabilities; and

(C)         Estrella Broadcasting and the Company, as applicable, shall contribute all cash or cash equivalents (including any marketable securities or certificates of deposit) to any Company Subsidiary mutually-agreed to by Option Holder and the Company.

(c)         Option Closing. Upon an exercise of the Option or the Put Right but subject to Section 4 above, the Option Closing shall take place no later than ten (10) Business Days after the satisfaction or, to the extent permissible by law, the waiver (by the party for whose benefit the closing condition is imposed) of, the conditions specified in Sections 9 and 10 hereof. Alternatively, the Option Closing may take place at such other place, time or date as the parties may mutually agree upon in writing. The date that the Option Closing occurs shall be referred to herein as the “Option Closing Date”.

6.         Representations and Warranties of Grantor. The Grantor Parties represent and warrant to Option Holder as follows:

(a)         Each Grantor Party has the power and authority and full legal capacity to enter into and to perform its obligations under this Agreement. The execution, delivery and performance of this Agreement by each Grantor Party has been duly authorized and this Agreement constitutes a valid and binding obligation of each Grantor Party enforceable against such Grantor Party in accordance with it terms, subject to the Remedies Exceptions.

(b)         The Company owns 100% of the Equity Interests of each Company Subsidiary, and the Company has good and valid title to such Equity Interests free and clear of all Liens, other than transfer restrictions under applicable securities Laws. Estrella Broadcasting indirectly owns 100% of the equity interests of the Company and beneficially owns 100% of the Equity Interests of each Company Subsidiary free and clear of all Liens.

(c)         No Company Subsidiary has issued or guaranteed any outstanding obligation in respect of indebtedness for borrowed money.

(d)         Each Grantor Party is duly organized, validly existing and in good standing under the laws of the jurisdiction of its organization.

(e)         With respect to each Company Subsidiary, the Equity Interests of such Company Subsidiary constitute all of the outstanding equity interests of such Company Subsidiary and all such Equity Interests are duly authorized, validly issued, fully paid and nonassessable. Other than the Equity Interests, there are no issued, reserved for issuance or outstanding (A) equity interests in, or other voting securities of or other ownership interests in, any Company Subsidiary, (B) securities of any Company Subsidiary convertible into or exchangeable for equity interests in, or other voting securities of or other ownership interests in, any Company Subsidiary, (C) warrants, calls, options or other rights to acquire from a Company Subsidiary, or other obligations of a

Company Subsidiary to issue, any equity interests in, or other voting securities of or other ownership interests in, a Company Subsidiary or securities directly or indirectly convertible into or exercisable or exchangeable for equity interests in, or other voting securities of or other ownership interests in, any Company Subsidiary or (D) restricted shares, stock appreciation rights, performance units, contingent value rights, “phantom” stock or similar securities or rights that are derivative of, or provide economic benefits based, directly or indirectly, on the value or price of any equity interests in, other voting securities of or other ownership interests in any Company Subsidiary. Neither Estrella Broadcasting nor the Company holds any equity, securities or other ownership interest of any kind, including warrants or other rights or options to acquire equity, securities or other ownership interests, in any third party other than the Company’s ownership of the Equity Interests and the issued and outstanding equity interests in the other direct or indirect subsidiaries of Estrella Broadcasting set forth on Schedule 6(e).

(f)         The LicenseCo Subsidiaries are the holders of the FCC Licenses and such FCC Licenses are valid and in full force and effect.

(g)         To the knowledge of the Company, the Grantor Parties are not aware of any reason why those of the FCC Licenses subject to expiration might not be renewed by the FCC in the ordinary course or of any reason why any of the FCC Licenses might be revoked.

(h)         All information contained in any pending applications for modification, extension or renewal of the FCC Licenses or other applications filed with the FCC by any of the Grantor Parties is true, complete and accurate in all material respects.

(i)         The applicable Grantor Party has filed all material returns, reports, and statements that such Grantor Party is required to file with the FCC, the Federal Aviation Administration, or the Securities and Exchange Commission. There is no action, suit or proceeding pending or, to Grantor Party’s knowledge, threatened in writing (or otherwise) against the Grantor Party in respect of the Stations seeking to enjoin the transactions contemplated by this Agreement and, to Grantor Party’s knowledge, there are no governmental claims or investigations pending or threatened against any Grantor Party in respect of any Station (except those affecting the broadcasting industry generally).

(j)         There is no litigation, proceeding, suit, claim, charge, grievance, or action by or before any Governmental Authority pending or, to the knowledge of the Company, threatened against any Grantor Party, or any Station Assets, or any employee, officer or director of any Grantor Party (in their capacity as such) that would, individually or in the aggregate, reasonably be expected to be material to the operation of any Station or would otherwise reasonably be expected to materially impair or delay the consummation of the transactions contemplated by this Agreement.

(k)         No broker, finder or other person is entitled to a commission, brokerage fee or other similar payment in connection with this Agreement or the transactions contemplated hereby as a result of any agreement or action of any Grantor Party or any other party acting on the behalf of any Grantor Party.

(l)         Each of the Company Subsidiaries, each of the LicenseCo Subsidiaries, and KRCA is disregarded as an entity separate from the Company within the meaning of Treasury Regulations Section 301.7701-3

7.         Representations and Warranties of Option Holder. Option Holder represents and warrants to the Grantor Parties as follows:

(a)         Option Holder is duly formed, validly existing and in good standing under the laws of its jurisdiction of incorporation or formation (as applicable).

(b)         Option Holder has the organizational power and authority to enter into and perform its obligations under this Agreement.

(c)         The execution, delivery and performance of this Agreement by Option Holder has been duly authorized and this Agreement constitutes a valid and binding obligation of Option Holder enforceable against it in accordance with its terms, subject to the Remedies Exceptions.

(d)         Option Holder has, and will have at the Option Closing occurring prior to a Collateral Event, the ability to deliver the Purchase Price free and clear of all Liens, other than transfer restrictions under applicable securities Laws. The equity securities comprising the Purchase Price at the Option Closing prior to a Collateral Event (i) will be duly authorized and validly issued and are fully paid and non-assessable, (ii) will have been offered, sold and issued in compliance in all material respects with applicable securities Laws and other applicable Law, (iii) will not be issued in violation of the Company Organizational Documents and (iv) will not be issued in violation of any preemptive rights, call option, right of first refusal or first offer, subscription rights, transfer restrictions or similar rights of any Person. Option Holder has, and will have at the Option Closing following a Collateral Event, sufficient funds to consummate the transactions contemplated by this Agreement (including the payment of the applicable Purchase Price).

(e)         There is no litigation, proceeding, suit, claim, charge, grievance, or action by or before any Governmental Authority pending or, to the knowledge of the Option Holder, threatened against the Option Holder, or any employee, officer or director of the Option Holder (in their capacity as such) that would, individually or in the aggregate, reasonably be expected to materially impair or delay the consummation of the transactions contemplated by this Agreement.

(f)         No broker, finder or other person is entitled to a commission, fee or other similar payment in connection with this Agreement or the transactions contemplated hereby as a result of any agreement or action of Option Holder or any party acting on Option Holder’s behalf.

8.         Covenants of Grantor Parties. During the Option Period until the expiration thereof or the earlier termination of this Agreement in accordance with its terms, Estrella Broadcasting and each Grantor Party, jointly and severally, covenant to (in each case, other than with respect to KEYH):

(a)         Subject to the TV and Radio Affiliation Agreements, operate the Stations in the ordinary course of business, consistent with past practice, including maintaining insurance policies of all Station Assets with respect to the operation of the Stations in amounts customary in the broadcast industry;

(b)         Operate the Stations in all material respects in accordance with the terms of the FCC Licenses, the Communications Act of 1934, as amended (the “Communications Act”), the rules and published policies of the FCC (“FCC Rules”) and all other statutes, ordinances, rules and regulations of governmental authorities;

(c)         Promptly notify Option Holder of any reason an FCC License subject to expiration might not reasonably be expected to be renewed in the ordinary course or of any reason why an FCC License might be revoked;

(d)         Cause any application for modification, extension or renewal of the FCC Licenses or other application filed with the FCC by any of the Grantor Parties to be true, complete and accurate in all material respects;

(e)         Use commercially reasonable efforts to maintain the goodwill associated with the operation of each Station;

(f)         Refrain from intentionally taking any action that would cause the FCC Licenses not to be in full force and effect or to be revoked, suspended, cancelled, rescinded, terminated or expired;

(g)         File all material returns, reports, and statements that are required to be filed with the FCC and any other Governmental Authority by or on behalf of such Grantor Party;

(h)         Subject to the TV and Radio Affiliation Agreements, maintain, preserve, and keep all Station Assets in reasonable working order and condition (ordinary wear, tear and casualty expected), and from time to time as reasonably necessary make all needful and proper repairs, renewals, replacement, and additions thereto;

(i)         (x) pay all material taxes when due and payable and (y) file all material tax returns when due (taking into account all available extensions), in each case of clauses (x) and (y), in respect of each Company Subsidiary, each LicenseCo Subsidiary, KRCA, and the Station Assets;

(j)         Not make any election, or take or permit to be taken any other action, the result of which is any Company Subsidiary, any LicenseCo Subsidiary or KRCA ceasing to be disregarded as an entity separate from the Company within the meaning of Treasury Regulations Section 301.7701-3;

(k)         Not voluntarily adopt a plan or agreement of complete or partial liquidation, dissolution, merger, consolidation, restructuring, recapitalization, or other material reorganization, or otherwise voluntarily liquidate, dissolve or wind-down any Grantor Party;

(l)         Not mortgage, pledge, subject to any Lien (other than Permitted Liens) or otherwise encumber (or cause any of the foregoing to occur) any of the Station Assets, the Equity Interests of any Company Subsidiary or any other outstanding equity interests or assets of the Company or any of its Subsidiaries;

(m)         Not issue any note, bond or other debt security (including any security or instrument convertible, exchangeable or exercisable for any equity interests) of the Company or any of its Subsidiaries, or otherwise assume or incur or guarantee any indebtedness for borrowed money or make any payment in respect of the foregoing;

(n)         Not issue any equity securities or rights to acquire equity securities (including any security or instrument that is convertible, exchangeable or exercisable for any equity securities) of any Grantor Party;

(o)         Not (1) authorize, declare, undertake or pay any dividend on or make any other distribution in respect of (whether in cash or property) any Equity Interests of a Company Subsidiary or the equity interests of any LicenseCo Subsidiary (other than dividends or distributions solely to KRCA or a Company Subsidiary) or (2) purchase, redeem or otherwise acquire or retire any Equity Interests of a Company Subsidiary or any equity interests of any LicenseCo Subsidiary;

(p)         Not make any investment (whether through cash, purchase of stock or obligations or otherwise) in, or loan or advance to, any other Person, or acquire all or any substantial part of the assets or business of any Person or division thereof, other than acquisitions of inventory and supplies in the ordinary course of business;

(q)         Except in connection with the Option Closing, not undertake, initiate, support, and/or vote for any action that would cause the Station Assets, the Equity Interests, or the equity interests or any other assets of KRCA or any Grantor Party to be directly or indirectly sold, leased, transferred, conveyed or encumbered, or otherwise be party to any merger, consolidation or amalgamation, or otherwise in connection with a transaction which would result in a change in control or a transfer of control of KRCA or any Grantor Party;

(r)         Not (A) enter into any contract or agreement, except for contracts or agreements in the ordinary course of business (taking into account the TV and Radio Affiliation Agreements) or (B) sell, lease or otherwise dispose of (i) any of the Excluded Station Equipment or FCC Licenses, or (ii) any of the other Station Assets, except, with respect to the foregoing clause (ii) fixtures, equipment and supplies (excluding fixtures, equipment and supplies that constitute Excluded Station Equipment) sold or disposed of in the ordinary course of business; and

(s)         Authorize, approve or commit to any of the foregoing.

9.         Grantor Party Closing Conditions. Upon an exercise of the Option pursuant to the terms and subject to the conditions of this Agreement, the obligations of the Grantor Parties hereunder are subject to satisfaction by Option Holder or, to the extent permissible by law, the waiver by Grantor Parties at or prior to the Option Closing, of each of the following conditions:

(a)         Representations, Warranties and Covenants. Prior to a Collateral Event, the representations and warranties of Option Holder made in this Agreement shall be true and correct in all material respects at and as of the Option Closing Date except for changes permitted or contemplated by the terms of this Agreement, and the covenants and agreements to be complied with and performed by Option Holder at or prior to the Option Closing shall have been complied with or performed in all material respects. The Company shall have received a certificate dated as of the Option Closing Date from Option Holder, executed by an authorized officer of Option Holder, to the effect that the conditions set forth in this Section 9(a) have been satisfied.

(b)         FCC Consent. With respect to any exercise of the Option, the FCC Consent (as defined below) shall have been obtained and be in effect and no court or governmental order prohibiting the Option Closing shall be in effect.

(c)         No Prohibitions. No injunction, restraining order or decree of any nature of any governmental authority of competent jurisdiction shall be in effect that restrains or prohibits any party from consummating the transactions contemplated by this Agreement.

10.         Option Holder Closing Conditions. Upon the exercise of the Option pursuant the terms and subject to the conditions of this Agreement, the obligations of Option Holder hereunder are subject to satisfaction by the Grantor Parties or, to the extent permissible by law, the waiver by Option Holder at or prior to the Option Closing, of each of the following conditions:

(a)         Representations, Warranties and Covenants. The (i) representations and warranties of the Grantor Parties (A) made in this Agreement (other than the representations and warranties of the Grantor Parties set forth in Section 6(f) and Section 6(g)) shall be true and correct in all material respects at and as of the Option Closing Date except for changes permitted or contemplated by the terms of this Agreement, and (B) made in Section 6(f) and Section 6(g) with respect to Equity Interests shall be true and correct at and as of the Option Closing Date except for changes permitted or contemplated by the terms of this Agreement or except where the failure of such representation and warranty to be true and correct would not reasonably be expected to materially and adversely affect a Grantor Party’s ownership and use of any applicable Station Assets, and the (ii) covenants and agreements to be complied with and performed by the Grantor Parties at or prior to the Option Closing shall have been complied with or performed in all material respects (except for Section 8(j), which shall have been complied with and performed in all respects). Option Holder shall have received certificates dated as of the Option Closing Date from each of Estrella Broadcasting and the Company, executed by an authorized officer of each of the foregoing, to the effect that the conditions set forth in this Section 10(a) have been satisfied.

(b)         FCC Consent. With respect to any exercise of the Option for the Equity Interests of any Company Subsidiary or the Station Assets in respect of any Station, the FCC Consent shall have been obtained and no court or governmental order prohibiting the Option Closing shall be in effect.

(c)         No Prohibitions. No injunction, restraining order or decree of any nature of any governmental authority of competent jurisdiction shall be in effect that restrains or prohibits any party from consummating the transactions contemplated by this Agreement.

11.         Option Closing Deliveries.

(a)         Purchase of Equity Interests.

(i)         Grantor Documents. Upon an exercise of the Option or the Put Right at the Option Closing, the Company shall deliver or cause to be delivered to Option Holder:

(A)         Copies of resolutions authorizing the execution, delivery and performance of this Agreement, including the consummation of the transactions contemplated hereby, by each of the Grantor Parties;

(B)         the certificates described in Section 10(a) hereof;

(C)         all certificates, if any, evidencing the Equity Interests of the each Company Subsidiary, duly endorsed for transfer to Option Holder accompanied by appropriate powers duly endorsed for transfer to Option Holder;

(D)         a duly executed IRS Form W-9 from each Grantor Party setting forth an exemption from backup withholding;

(E)         a certificate of good standing (or equivalent) from the jurisdiction of incorporation (or formation) of the Company and each Company Subsidiary;

(F)         with respect to each Company Subsidiary, all issued and outstanding stock certificates with respect to the Equity Interests, and appropriate instruments of transfer, endorsed in blank, with respect to the foregoing; and

(G)         such other documents, certificates, payments, assignments, transfers and other deliveries as Option Holder may reasonably request and as are customary to effect a closing of the matters herein contemplated.

(ii)         Option Holder Documents. Subject to the exercise of the Option with respect to the Equity Interests of any Company Subsidiary pursuant to the terms and subject to the conditions of this Agreement, at the Option Closing, Option Holder shall deliver or cause to be delivered to the Company:

(A)         the certificate described in Section 9(a) hereof;

(B)         the applicable Purchase Price set forth on Schedule 5(a); and

(C)         such other documents, certificates, payments, assignments, transfers and other deliveries as the Company may reasonably request and as are customary to effect a closing of the matters herein contemplated.

12.         Survival. Neither the representations and warranties in this Agreement nor the covenants set forth in Section 8 of this Agreement shall survive the Option Closing Date or the payment of full Purchase Price, whereupon they shall expire and be of no further force or effect.

13.         Specific Performance. The parties hereto agree that irreparable damage, for which monetary damages (even if available) would not be an adequate remedy, shall occur in the event that the parties do not perform the provisions of this Agreement (including failing to take such actions as are required of them hereunder to consummate the transactions contemplated by this Agreement) in accordance with its specified terms or otherwise breach such provisions. Accordingly, the parties acknowledge and agree that (i) the parties shall be entitled to an injunction, specific performance or other equitable relief to prevent breaches of this Agreement and to enforce specifically the terms and provisions hereof (which, for the avoidance of doubt, includes the parties’ obligation to consummate the transactions contemplated by this Agreement), in addition to any other remedy to which they are entitled at law or in equity, and (ii) the right to seek specific enforcement is an integral part of the transactions contemplated by this Agreement and without that right, none of the parties would have entered into this Agreement. Each of the parties agrees that it shall not oppose the granting of an injunction, specific performance and/or other equitable relief on the basis that any other party has an adequate remedy at law or that any award of an injunction, specific performance and/or other equitable relief is not an appropriate remedy for any reason at law or in equity. Each of the parties further agrees that the only permitted objection that it may raise in response to any action for an injunction, specific performance, or other equitable relief is that it contests the existence of a breach or threatened breach of this Agreement. Any party seeking: (A) an injunction or injunctions to prevent breaches of this Agreement; (B) to enforce specifically the terms and provisions of this Agreement; and/or (C) other equitable relief, shall not be required to show proof of actual damages or to provide any bond or other security in connection with any such remedy.

14.         Expenses. Except with respect to the FCC filing fees for the FCC Applications (defined below) which will be split equally between the Grantor Parties, on the one hand, and Option Holder, on the other, as set forth in Section 24(b) of this Agreement, and Transfer Taxes, as set forth in Section 32(b) of this Agreement, each party is responsible for its own expenses in connection with the transactions contemplated by this Agreement.

15.         Further Assurances. Subject to the terms and conditions of this Agreement, each of the parties hereto will use all commercially reasonable efforts to take, or cause to be taken, all actions, and to do, or cause to be done, all things necessary, proper or advisable under applicable laws and regulations to consummate and make effective the transactions contemplated by this Agreement.

16.         Amendment and Modification. This Agreement may be amended, modified or supplemented only by written agreement of all parties.

17.         Waiver of Compliance; Consents. The failure of any of the parties to comply with any obligation, representation, warranty, covenant, agreement or condition herein may be waived by the party entitled to the benefits thereof only by a written instrument signed by the party granting such waiver, but such waiver or failure to insist upon strict compliance with such obligation, representation, warranty, covenant, agreement or condition shall not operate as a waiver of, or estoppel with respect to, any subsequent or other failure. Whenever this Agreement requires or permits consent by or on behalf of any party hereto, such consent shall be given in

writing in a manner consistent with the requirements for a waiver of compliances as set forth in this Section 17.

18.         Notices. All notices (including notices for consent under this Agreement), requests, claims, demands and other communications hereunder shall be: (a) in writing; (b) sent by messenger, certified or registered mail, a reliable overnight delivery service, charges prepaid as applicable, to the appropriate address(es) set forth below; and (c) deemed to have been given on the date of delivery to the addressee (or, if the date of delivery is not a Business Day, on the first (1st) Business Day after the date of delivery), as evidenced by a receipt executed by the addressee (or a responsible person in his or her office), the records of the person delivering such communication or a notice to the effect that such addressee refused to claim or accept such communication, if sent by messenger, mail or express delivery service. All such communications shall be sent to the following addresses, or to such other addresses as any party may inform the others by giving five (5) Business Days’ prior written notice pursuant to this Section 18:

If to Option Holder:

MediaCo Operations LLC

c/o MediaCo Holding Inc.

48 West 25th Street, Floor 3

New York, NY 10010

Attention: Chief Financial Officer and Vice President of Legal

Email: [***]

with a copy (which shall not constitute notice) to:

Fried, Frank, Harris, Shriver & Jacobson LLP

One New York Plaza

New York, New York 10004

Attention: Philip Richter; Colum J .Weiden

If to Estrella Broadcasting:

Estrella Broadcasting, Inc

1 Estrella Way

Burbank, CA 91504

Attention: Peter Markham
Email: [***]

with a copy (which shall not constitute notice) to:

Paul, Weiss, Rifkind, Wharton & Garrison LLP

1285 Avenue of the Americas

New York, New York 10019

Attention: Brian Scrivani; Jeffrey Marell

Email: bscrivani@paulweiss.com; jmarell@paulweiss.com

If to any Grantor Party:

c/o Estrella Broadcasting, Inc

1 Estrella Way

Burbank, CA 91504

Attention: Peter Markham
Email: [***]

with a copy (which shall not constitute notice) to:

Paul, Weiss, Rifkind, Wharton & Garrison LLP

1285 Avenue of the Americas

New York, New York 10019

Attention: Brian Scrivani; Jeffrey Marell

19.         Assignment.

19.1         This Agreement and all of the provisions hereof shall be binding upon and inure to the benefit of the parties hereto and their respective successors and permitted assigns, but, except as provided for herein, neither this Agreement nor any of the rights, interests or obligations hereunder shall be assigned by any Grantor Party without the prior written consent of the Option Holder in its sole discretion; provided, however, that any Grantor Party may assign its direct or indirect rights in respect of the Purchase Price (including in respect of any Station Assets owned or to be transferred by or with respect to such Grantor Party) to the HPS Lenders, the Company Aggregator, or any Affiliate of the foregoing.

19.2         Without the consent of Estrella Broadcasting or any Grantor Party, Option Holder may assign any or all of its rights and obligations under this Agreement, in whole or in part, including, its right and/or its obligation to purchase (whether pursuant to the exercise of the Option by Option Holder or by the Company) the Equity Interests or all of the Station Assets in respect of each Station (including the right to receive the Equity Interests or all of the Station Assets of each Station), to any other party or parties; provided, however, that Option Holder, as assignor, shall not thereby be released of its obligations hereunder.

20.         No Third Party Beneficiaries. Except as otherwise specified herein, nothing expressed or implied in this Agreement is intended or shall be construed to confer upon or give

any person, other than the parties to this Agreement, any right or remedies under or by reason of this Agreement; provided, that the Nonparty Affiliates are intended third party beneficiaries of the provisions of Section 28 hereof and the Term Agent is an intended third party beneficiary in accordance with Section 31 hereof. The representations and warranties in this Agreement are the product of negotiations among the parties and, except as expressly set forth in the immediately preceding sentence, such representations and warranties are for the sole benefit of the parties and may represent an allocation of risk among the parties associated with particular matters regardless of the knowledge of any of the parties.

21.         Governing Law; Consent to Jurisdiction.

(a)         This Agreement, and any and all claims arising directly or indirectly out of or otherwise concerning this Agreement (whether based in contract, tort or otherwise) shall be governed by, and construed and enforced in accordance with, the laws of the State of Delaware (without regard to any choice or conflicts of laws principles, whether of the State of Delaware or any other jurisdiction, that might direct the application of another substantive law to govern this Agreement). With respect to any and all proceedings arising directly or indirectly out of or otherwise relating to this Agreement or the transactions contemplated hereby, each of the parties: (i) irrevocably and unconditionally submits and consents to the exclusive jurisdiction of: (A) the Court of Chancery of the State of Delaware or, if such Court of Chancery lacks subject matter jurisdiction, the Complex Commercial Division of the Superior Court of the State of Delaware or (B) in the event that a proceeding involves claims exclusively within the jurisdiction of the federal courts, in the United States District Court for the District of Delaware (all such courts, collectively, the “Chosen Courts” and, individually, each a “Chosen Court”), for itself and with respect to its property; (ii) agrees that all claims in respect of such proceeding shall be heard and determined only in a Chosen Court (and the appropriate respective appellate courts therefrom); (iii) agrees that it shall not attempt to deny or defeat such personal jurisdiction by motion or other request for leave from any Chosen Court; (iv) agrees that, except in connection with any proceeding brought against a party in another jurisdiction by an independent third person, it shall not bring any proceeding directly or indirectly relating to this Agreement or any of the transactions contemplated hereby in any forum other than a Chosen Court, except for the purpose of enforcing any award or judgment; and (v) agrees that it shall not assert and waives any objection it may have based on inconvenient forum to the maintenance of any action or proceeding so brought. Each party may make service on another party by sending or delivering a copy of the process to the party to be served at the address and in the manner provided for the giving of notices in Section 18. Nothing in this Section 21, however, shall affect the right of any person to serve legal process in any other manner permitted by law. NEITHER PARTY HERETO (OR THEIR SUCCESSORS AND ASSIGNS) SHALL BE LIABLE TO ANY OTHER PARTY TO THIS AGREEMENT FOR INDIRECT, INCIDENTAL, CONSEQUENTIAL, SPECIAL OR EXEMPLARY DAMAGES (EVEN IF SUCH PARTY HAS BEEN ADVISED OF THE POSSIBILITY OF SUCH DAMAGES).

(b)         EACH OF THE PARTIES HEREBY WAIVES TO THE FULLEST EXTENT PERMITTED BY APPLICABLE LAW ANY RIGHT IT MAY HAVE TO A TRIAL BY JURY (A) ARISING UNDER THIS AGREEMENT OR (B) IN ANY WAY CONNECTED WITH OR RELATED OR INCIDENTAL TO THE DEALINGS OF THE PARTIES IN RESPECT OF THIS AGREEMENT OR ANY OF THE TRANSACTIONS RELATED HERETO,

IN EACH CASE, WHETHER NOW EXISTING OR HEREAFTER ARISING, AND WHETHER IN CONTRACT, TORT, EQUITY, OR OTHERWISE. EACH OF THE PARTIES (I) CERTIFIES THAT NO REPRESENTATIVE, AGENT OR ATTORNEY OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF LITIGATION, SEEK TO ENFORCE THAT FOREGOING WAIVER, (II) EACH SUCH PARTY UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (III) EACH SUCH PARTY MAKES THIS WAIVER VOLUNTARILY, AND (IV) ACKNOWLEDGES THAT IT AND THE OTHER PARTIES HERETO HAVE BEEN INDUCED TO ENTER INTO THIS AGREEMENT AND THE TRANSACTIONS, AS APPLICABLE, BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS SECTION 21.

22.         Severability. If any term or other provision of this Agreement is invalid, illegal or incapable of being enforced by any rule of law, or public policy, all other conditions and provisions of this Agreement shall nevertheless remain in full force and effect so long as the economic or legal substance of the transactions contemplated hereby is not affected in any manner materially adverse to any party. Upon such determination that any term or other provision is invalid, illegal or incapable of being enforced, the parties shall negotiate in good faith to modify this Agreement so as to effect the original intent of the parties as closely as possible in a mutually acceptable manner in order that the transactions be consummated as originally contemplated to the fullest extent possible.

23.         Publicity. No party hereto shall make or issue or cause to be made or issued, any announcement (written or oral) concerning this Agreement or the transactions contemplated hereby for dissemination to the general public without the prior consent of the other party. This provision shall not apply, however, to any announcement or written statement required to be made by law or the regulations of any federal or state governmental agency (including the FCC) or any stock exchange, except that the party required to make such announcement shall provide a draft copy thereof to the other party hereto, and consult with such other party concerning the timing and content of such announcement, before such announcement is made.

24.         FCC Approval; Compliance with Laws.

(a)         Notwithstanding any provision to the contrary herein, Option Holder’s rights under this Agreement, including the exercise of the Option, are subject to applicable law, including the Communications Act and the FCC Rules.

(b)         As soon as reasonably practicable, but in no event later than fifteen (15) days after Option Holder’s delivery of an Exercise Notice (or the Company’s delivery of a Put Exercise Notice in accordance with Section 4 hereof), Option Holder, Estrella Broadcasting, the Company and the applicable Grantor Parties and LicenseCo Subsidiaries shall file an application or applications (the “FCC Application(s)”) with the FCC requesting the FCC’s written consent to (A) the assignment of the applicable FCC Licenses to Option Holder or (B) the transfer of control of the applicable Company Subsidiary from Grantor Party to Option Holder, as the case may be. In addition, in connection with the foregoing, each applicable party hereto covenants and agrees to (i) prepare, file and prosecute any alternative application, petition, motion, request or

other filing (together with the FCC Application(s), the “FCC Filings”); (ii) file any appropriate amendment or modification to the FCC Filings; (iii) provide to Option Holder or Grantor Party any information, documents or other materials reasonably requested by it in connection with the preparation of any such FCC Filings; (iv) absent a Dismissal Filing (defined below), prosecute the FCC Applications with commercially reasonable diligence and otherwise use their commercially reasonable efforts to obtain the written consent of the FCC requested in the FCC Applications (the “FCC Consent”); (v) otherwise take any other action with respect to the FCC as may be reasonably necessary or reasonably requested by Option Holder or Grantor Party in connection with the transactions contemplated hereby (including, upon the request of Option Holder with regard to an Exercise Notice, the preparation, filing, and prosecution of any motion or other filing seeking to withdraw or dismiss any FCC Filings made by the parties in connection with the transactions contemplated by this Agreement (a “Dismissal Filing”)); and (vi) cooperate in good faith with the other applicable parties with respect to the foregoing covenants, all as may be determined by Option Holder or Grantor Party to be reasonably necessary or appropriate or advisable in order to consummate the transactions contemplated hereby. Each applicable party shall promptly provide the other with a copy of any pleading, order or other document served on it relating to the FCC Filings or any Dismissal Filing, shall furnish all information required by the FCC and shall be represented at all meetings or hearings scheduled to consider the FCC Filings. The parties each agree to comply with any condition imposed on them by any FCC Consent, except that no party shall be required to comply with any materially adverse condition, including, any condition that requires such party to divest any of its direct or indirect assets in a manner not contemplated in the FCC Filings. The parties shall oppose any petitions to deny or other objections filed with respect to the FCC Filings, as well as any requests for reconsideration or review of any FCC Consent or Dismissal Filing. Option Holder and Grantor Parties shall each pay their own costs and expenses in connection with the preparation and prosecution of the FCC Filings or any Dismissal Filing, and shall each pay one-half (1/2) of all filing fees relating to the transactions contemplated hereby irrespective of whether the transactions contemplated by this Agreement are consummated.

25.         Headings. The section headings contained in this Agreement are solely for the purpose of reference, are not part of the agreement of the parties and shall not in any way affect the meaning or interpretation of this Agreement.

26.         Counterparts. This Agreement may be executed in one or more counterparts, each of which shall be deemed an original, but all of which together shall constitute one and the same instrument. The delivery of an executed counterpart of the Agreement by facsimile or electronic transmission will be deemed to be an original counterpart of the Agreement so transmitted.

27.         Entire Agreement. This Agreement, including the documents delivered pursuant to this Agreement or other written agreements referenced in this Agreement, including the Purchase Agreement, embody the entire agreement and understanding of the parties hereto in respect of the subject matter hereof. The Schedule(s) hereto are an integral part of this Agreement and are incorporated by reference herein. This Agreement and the Purchase Agreement supersede all prior negotiations and understandings between the parties with respect to the subject matter hereof, including any other writings executed prior to the date hereof relating to such negotiations, agreements and understandings.

28.         No Recourse. All claims, obligations, liabilities or causes of action (whether in contract or in tort, in law or in equity or otherwise, or granted by statute or otherwise, whether by or through attempted piercing of the corporate, limited partnership or limited liability company veil or any other theory or doctrine, including alter ego or otherwise) that may be based upon, in respect of, arise under, out of or by reason of, be connected with, or relate in any manner to this Agreement, or the negotiation, execution or performance or non-performance of this Agreement (including any representation or warranty made in, in connection with, or as an inducement to, this Agreement), may be made only against (and such representations and warranties are those solely of) the persons that are expressly identified as parties to this Agreement. In no event shall any party to this Agreement have any shared or vicarious liability for the actions or omissions of any other person. Except as otherwise expressly set forth in this Agreement, no person who is not a party to this Agreement, including any current, former or future director, officer, employee, incorporator, member, partner, manager, stockholder, Affiliate, agent, financing source, attorney or representative or assignee of any party to this Agreement, or any current, former or future director, officer, employee, incorporator, member, partner, manager, stockholder, Affiliate, agent, financing source, attorney or representative or assignee of any of the foregoing (collectively, the “Nonparty Affiliates”), shall have any liability (whether in contract or in tort, in law or in equity or otherwise, or granted by statute or otherwise, whether by or through attempted piercing of the corporate, limited partnership or limited liability company veil or any other theory or doctrine, including alter ego or otherwise) for any obligations or liabilities arising under, out of, in connection with, or related in any manner to this Agreement or for any claim based on, in respect of, or by reason of this Agreement or its negotiation, execution, performance or breach and, to the maximum extent permitted by applicable law; and each party hereto waives and releases all such liabilities, claims, causes of action and obligations against any such Nonparty Affiliates. Notwithstanding anything to the contrary herein, none of the parties to this Agreement or any Nonparty Affiliate shall be responsible or liable for any multiple, consequential, indirect, special, statutory, exemplary or punitive damages which may be alleged as a result of this Agreement or any other agreement referenced herein or the transactions contemplated hereunder, or the termination or abandonment of any of the foregoing.

29.         Certain Acknowledgements. Notwithstanding anything set forth in this Agreement to the contrary: (a) the condition set forth in Section 9(a) shall be deemed satisfied after the occurrence of a Collateral Event; and (b) the deliverables described in each of Section 11(a)(ii)(A) and Section 11(b)(ii)(A) shall not be required to be delivered by Option Holder following the occurrence of a Collateral Event.

30.         Interpretation. Unless the context of this Agreement otherwise requires, (i) words using the singular or plural number also include the plural or singular number, respectively, (ii) the definitions contained in this Agreement are applicable to the other grammatical forms of such terms, (iii) the terms “hereof,” “herein,” “hereby,” “hereto” and derivative or similar words refer to this entire Agreement, including the Schedules, and not to any particular section, subsection, paragraph, subparagraph or clause set forth in this Agreement, (iv) the terms “Section,” “this Agreement,” and “Schedule” and similar expressions refer to the specified Article, Section, or Schedule of or to this Agreement, (v) the words “include,” “includes,” or “including” shall be deemed to be followed by the words “including, without limitation,” unless otherwise specified, (vi) the word “or” shall be disjunctive but not necessarily exclusive, (vii) references to agreements

and other documents shall be deemed to include all subsequent amendments and other modifications thereto, (viii) references to any law shall include all rules and regulations promulgated thereunder and references to any law shall be construed as including all statutory, legal and regulatory provisions consolidating, amending or replacing such law, any reference to any law will be to such law (and all rules and regulations promulgated thereunder) as amended from time to time, (ix) words importing the singular shall also include the plural, and vice versa, (x) all references to “$” or “dollar” shall be references to United States dollars, (xi) the words “writing,” “written” and comparable terms refer to printing, typing and other means of reproducing words (including electronic media) in a visible form, and (xii) all references to any contract are to that contract as amended or modified from time to time in accordance with the terms thereof (subject to any restrictions on amendments or modifications set forth in this Agreement).

31.         Debt Financing Sources. Notwithstanding anything in this Agreement to the contrary, each party, on behalf of itself and each of its Affiliates hereby agrees: (a) (i) no amendment shall be made which would adversely affect Term Agent’s (or it’s successors or assigns) rights hereunder or its ability to foreclose on this Agreement or to exercise the Option after a Collateral Event, and (ii) for the avoidance of doubt, Sections 5, 6, 7, 8, 16, 17, 19, 20, 21, and 22 may not be amended without the prior written consent of the Term Agent, (b) this Agreement and all of the provisions hereof shall be binding upon and inure to the benefit of the parties hereto and their respective successors and permitted assigns, but, except as provided for herein, neither this Agreement nor any of the rights, interests or obligations hereunder shall be assigned by (i) any Grantor Party, prior to the occurrence of a Collateral Event, without the prior written consent of the Term Agent, (ii) any Grantor Party, following the occurrence of a Collateral Event, without the prior written consent of the Term Agent, and (iii) by the Option Holder, prior to the occurrence of a Collateral Event, without the prior written consent of the Term Agent (other than any such assignment to another borrow or guarantor under the Term Loan Agreement, which shall be permitted hereunder), (c) notwithstanding anything to the contrary herein, upon the occurrence of a Bankruptcy Event immediately, automatically and without further action or after written notice from the Term Agent upon the occurrence of any other Collateral Event, Option Holder shall be deemed to assign to Term Agent all of Option Holder’s rights and obligations under this Agreement (such assignment the “Assignment”) and the Term Agent shall become the Option Holder for all purposes hereunder and, in order to effectuate the Assignment, the Option Holder and each Grantor Party shall, at its own cost and expense, execute and deliver any documentation requested by the Term Agent necessary or advisable to document such Assignment, (d) the Term Agent (and its successors and assigns) is an intended third party beneficiary of this Agreement, (e) the representations and warranties are for the benefit of the Term Agent (and its Affiliates), (f) the parties further agree that (x) any suit, action, or proceeding whether at law or in equity, whether in contract or in tort or otherwise, against any of the Lender Related Parties shall be subject to the exclusive jurisdiction of any state or federal court sitting in the Borough of Manhattan in the City and State of New York (whether a state or Federal court), and any appellate court from any thereof, (y) that any proceeding, whether at law or in equity, whether in contract or in tort or otherwise, against any of the Lender Related Parties shall be governed by, and construed in accordance with, the laws of the State of New York without giving effect to its principles or rules of conflict of laws to the extent such principles or rules are not mandatorily applicable by statute and would require or permit the application of the laws of another jurisdiction and (z) that

the Lender Related Parties are express third-party beneficiaries of Section 21, (g) any action, proceeding or suit involving the Lender Related parties shall be subject to Section 22, (h) the parties to this Agreement agree on their own behalf and on behalf of their respective subsidiaries and Affiliates that none of the Lender Related Parties and their successors and assigns shall have any liability relating to this Agreement or any of the transactions contemplated herein, and (i) the provisions of Section 29 are intended to be for the benefit of, and enforceable by, the Lender Related Parties, and each such Person shall be a third party beneficiary of Section 29.

32.         Tax Matters.

(a)         Solely for U.S. federal, and applicable state and local, income tax purposes, it is intended that the rights of the parties in respect of the Option and Put Right will be deemed exercised on the Effective Date and that such deemed exercise shall be treated as a transaction described in Section 1001 of the Code in respect of the Station Assets in exchange for the Purchase Price (the “Intended Tax Treatment”). Consistent with the foregoing, the Purchase Price shall be allocated among the Station Assets in connection with the Purchase Price Allocation, which Purchase Price Allocation shall govern for all purposes under this Agreement. Each of Parent, Option Holder (excluding, for these purposes, any Lender Related Party in its capacity as Option Holder), the Grantor Parties, and the respective Affiliates of each of the foregoing shall file all of its Tax Returns consistent with the Intended Tax Treatment and the Purchase Price Allocation, and shall not take a position on any Tax Return (including IRS Form 8594), before any Tax Authority or in any Proceeding inconsistent with the Intended Tax Treatment or the Purchase Price Allocation without the written consent of the other parties to this Agreement or unless specifically required pursuant to a “determination” within the meaning of Section 1313(a) of the Code.

(b)         Parent shall be responsible for and shall pay any and all Transfer Taxes when due and shall, at its own expense, file all necessary Tax Returns and other documentation with respect to such Transfer Taxes; provided, however, that, if required by law, the applicable Grantor Parties will join in the execution of any such Tax Returns.

33.         Termination. This agreement shall terminate automatically upon consummation of the Option Closing.

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IN WITNESS WHEREOF, the undersigned have executed this Option Agreement as of the day and year first written above.

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Schedule A – Defined Terms

“Bankruptcy Event” shall mean the occurrence of any of the following:

(a)         Parent or any of its subsidiaries becomes insolvent within the meaning of 11 U.S.C. §101(32) or any other Debtor Relief Law applicable to such entities;

(b)         Parent or any of its subsidiaries generally does not or becomes unable to pay its debts or meet its liabilities as the same become due, or admits in writing its inability to pay its debts generally, or declares any general moratorium on its indebtedness, or proposes a compromise or arrangement or deed of company between it and any class of its creditors;

(c)         Parent or any of its subsidiaries commits an act of bankruptcy or makes an assignment of its property for the general benefit of its creditors or makes a proposal of such an assignment (or files a notice of its intention to do so);

(d)         Parent or any of its subsidiaries institutes a proceeding seeking to adjudicate it as insolvent, or seeking liquidation, dissolution, winding-up, reorganization, restructuring, compromise, arrangement, adjustment, protection, moratorium, relief, stay of proceedings of creditors generally (or any class of creditors), or composition of it or its debts or any other relief, under any applicable Debtor Relief Law or at common law or in equity, or files an answer admitting the material allegations of a petition filed against it in any such proceeding;

(e)         Parent or any of its subsidiaries applies for the appointment of, or the taking of possession by, a receiver, interim receiver, receiver/manager, sequestrator, conservator, custodian, administrator, trustee, liquidator, voluntary administrator, receiver and manager or other similar official for it or any substantial part of its property;

(f)         Any petition is filed, application made or other proceeding instituted against or in respect of Parent or any of its subsidiaries pursuant to or under Debtor Relief Laws (or otherwise in furtherance of support of any creditor of Parent or any of its subsidiaries):

(i)         seeking to adjudicate it as insolvent;

(ii)         seeking a receiving order against it;

(iii)         seeking liquidation, dissolution, winding-up, reorganization, restructuring, compromise, arrangement, adjustment, protection, moratorium, relief, stay of proceedings of creditors generally (or any class of creditors), deed of company arrangement or composition of it or its debts or any other relief under any law, now or hereafter in effect relating to bankruptcy, winding-up, insolvency, reorganization, receivership, plans of arrangement or relief or protection of debtors or at common law or in equity; or

(iv)         seeking the entry of an order for relief or the appointment of, or the taking of possession by, a receiver, interim receiver, receiver/manager, sequestrator, conservator, custodian, administrator, trustee, liquidator, voluntary administrator, receiver and manager or other similar official for it or any substantial part of its property, and

and, in each case under this clause (f), such petition, application or proceeding continues undismissed, or unstayed and in effect, for a period of sixty (60) days after the institution thereof; provided that if an order, decree or judgment is granted or entered (whether or not entered or subject to appeal) against Parent or any of its subsidiaries thereunder in the interim, such grace period will cease to apply; provided, further, that if Parent or any of its subsidiaries files an answer admitting the material allegations of a petition filed against it in any such proceeding prior to such date, the grace period will cease to apply;

(g)         Parent or any of its subsidiaries takes any action, corporate or otherwise, including, an affirmative vote by the Board or the board of directors (or equivalent management or oversight body) of any other subsidiary, to commence any Insolvency Proceeding or to approve, effect, consent to or authorize any of the actions described in the clauses (a)-(f) above; or

(h)         Any other event or circumstance occurs which, under applicable Debtor Relief Laws, has an effect equivalent to any of the events or circumstance referred to in the other clauses of this definition.

“Board” means Parent’s board of directors (or equivalent management or oversight body) as elected from time to time in accordance with the organizational documents of Parent in effect from time to time.

“Collateral Event” means (i) the occurrence of any Event of Default (as defined in the Term Loan Documents) under the Term Loan Agreement or other Term Loan Documents, resulting in the right of the Term Agent to exercise any or all of remedies the remedies available to Term Agent under the terms of the Term Loan Documents (or any successor agreement thereto) or (ii) a Bankruptcy Event.

“Debtor Relief Laws” means the Bankruptcy Code of the United States and all other liquidation, conservatorship, bankruptcy, assignment for the benefit of creditors, moratorium, rearrangement, arrangement, compromise, receivership, insolvency, reorganization, or similar debtor relief laws (including applicable provisions of any corporate laws) of the United States or any state thereof or other applicable jurisdictions from time to time in effect.

“Governmental Authority” means (a) any United States federal, state, county, municipal or foreign government, or political subdivision thereof, (b) any governmental or quasi-governmental agency, authority, board, bureau, commission, department, instrumentality or public body, (c) any court or administrative tribunal or (d) with respect to any Person, any arbitration tribunal or other similar non-governmental authority to whose jurisdiction that Person has consented.

“Insolvency Proceeding” means any proceeding commenced by or against any Person or entity under any provision of the United States Bankruptcy Code, as amended, or under any other Debtor Relief Law (domestic or foreign), including assignments for the benefit of creditors, formal or informal moratoria, compositions, extensions generally with its creditors, or proceedings seeking reorganization, restructuring, receivership, insolvency, arrangement, or other relief.

“Lender Related Parties” means the Persons (including each lender and the Term Agent) that have agreed to arrange or have otherwise entered into agreements in connection with financing the

transactions contemplated under this Agreement and other related transactions, together with their respective Affiliates, and the respective officers, directors, employees, partners, trustees, shareholders, controlling persons, agents and Representatives of the foregoing, and their respective successors and assigns.

“Letter Agreement” means that certain letter agreement, dated the date hereof, by and among the Company, the Option Holder as of the date hereof, and Parent, attached hereto as Annex B to Schedule 5(a).

“Specified Provisions” means the terms set forth on Annex A to Schedule 5(a).

“Station Assets” means all of the assets of each Station, including tangible and intangible personal property, licenses, authorizations and leases, contracts and agreements, owned or held by the Grantor Parties or in which a controlled Affiliate of a Grantor Party holds an interest, relating to the operation of any such Station, including (i) all of the licenses, permits and other authorizations issued by the FCC to the Grantor Parties (including, all licenses, permits and other authorizations of LicenseCo Subsidiaries) in respect of each Station, including any renewals, extensions or modifications thereof and additions thereto between the date hereof and the Option Closing (collectively, the “FCC Licenses”) and (ii) all other assignable licenses, permits, construction permits, approvals, concessions, franchises, certificates, consents, qualifications, registrations, privileges and other authorizations and other rights, from any Governmental Authority, to any Grantor Party used in connection with such Station, including any renewals, extensions or modifications thereof and additions thereto between the Effective Date and the Option Closing (collectively, the “Permits”).

“Term Agent” means the “Term Agent” under and as defined in the Term Loan Agreement or any successor or assign thereof.

“Term Loan Agreement” means that certain Term Loan Agreement, dated the date hereof, by and among Parent, the other persons party thereto as “Borrowers”, the financial institutions party thereto as “Lenders”, and Whitehawk Capital Partners LP in its capacity as Term Agent thereunder, as amended and in effect from time to time or any refinancing thereof.

“Term Loan Documents” shall have the meaning ascribed to “Loan Documents” in the Term Loan Agreement or any similar term in any refinancing thereof.

“Warrants” means warrants to purchase shares of Parent Class A Common Stock, each exercisable at an exercise price of $0.01 per share of Parent Class A Common Stock.

Schedule 1 - Stations

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Schedule 2 - Equity Interests

Schedule 5(a)

The purchase price payable by Option Holder (the “Purchase Price”) with respect to the exercise of the Option is listed in the table below, subject to the Specified Provisions; provided, that, in the event that Required Parent Stockholder Approval has been obtained prior to the Option Closing, the Purchase Price shall be payable in the number of shares of Parent Class A Common Stock listed in the table below under the column entitled “Purchase Price (Parent Class A Common Stock)”, subject to the Specified Provisions. Parent, on behalf of Option Holder, shall issue and deliver the Warrants or shares of Parent Class A Common Stock that are payable by Option Holder hereunder. To the extent applicable pursuant to an Option Closing, the terms and conditions of the Letter Agreement shall also apply.

Each Grantor Party acknowledges and agrees that any Warrants or shares of Class A Common Stock issued by Parent in satisfaction of the Purchase Price in respect of the sale of any Station Assets or the Equity Interests of any Company Subsidiary hereunder, and any securities issued or issuable with respect to such securities by way of stock dividend or stock split or in connection with a combination of shares, conversion of such securities, recapitalization, merger, consolidation, going private, tender offer, amalgamation, change of control, other reorganization or otherwise, shall bear restrictive legends in substantially the following form:

THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND MAY NOT UNDER ANY CIRCUMSTANCES BE SOLD, TRANSFERRED, OR OTHERWISE DISPOSED OF WITHOUT AN EFFECTIVE REGISTRATION STATEMENT FOR SUCH SECURITIES UNDER THE SECURITIES ACT AND ANY OTHER APPLICABLE SECURITIES LAWS OR DOCUMENTATION REASONABLY SATISFACTORY TO THE COMPANY THAT REGISTRATION IS NOT REQUIRED UNDER THE SECURITIES ACT OR APPLICABLE SECURITIES LAWS.

The legend set forth above shall be removed and Option Holder shall issue a certificate without such legend to the holder of any such securities upon which it is stamped, if (i) such securities are registered for sale under an effective registration statement filed under the Securities Act, (ii) such securities are eligible for resale pursuant to Rule 144 promulgated under the Securities Act, or (iii) if such securities are proposed to be sold pursuant to an exemption from registration and Option Holder receives an opinion of counsel reasonably satisfactory to Option Holder and any other documentation reasonably requested by Option Holder with respect to compliance with such exemption.

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ANNEX A

Specified Provisions

Notwithstanding anything set forth in Schedule 5(a) to the contrary, solely in the event that a Collateral Event has occurred, the Purchase Price payable by Option Holder in respect of an exercise of the Option shall be payable, in cash, securities, property or other assets (as determined by Option Holder in its sole discretion), in an aggregate amount equal to the product of (i) the applicable number of shares of Parent Class A Common Stock listed in the table above under the column entitled “Purchase Price (Parent Class A Common Stock)”, and (ii) the Current Market Value (as defined below) of a share of Parent Class A Common Stock as of the date of the applicable Exercise Notice or Put Exercise Notice.

For purposes hereof:

“30-Day VWAP” per share of Parent Class A Common Stock, measured as of any date of determination, means the arithmetic average of the VWAP per share of Parent Class A Common Stock for each of the thirty (30) consecutive Trading Days ending on, and including, the Trading Day immediately preceding such date of determination; provided, that if (i) there is no Trading Market for shares of Parent Class A Common Stock, and (ii) shares of Parent Class A Common Stock are not quoted for bid prices or asking prices by market makers for such security as reported in the OTCQX, OTCQB, Pink or Grey markets operated by OTC Markets (such that the “VWAP” of a share of Parent Class A Common Stock cannot be calculated for a period of thirty (30) consecutive Trading Days in accordance with this definition and clauses (i) and (ii) of the definition of “VWAP” hereunder), then the “30-Day VWAP” shall be calculated in accordance with the most recent thirty (30) consecutive Trading Days for which the “VWAP” of a share of Parent Class A Common Stock can be calculated for a period of thirty (30) consecutive Trading Days.

“Current Market Value” means an amount, determined by Option Holder in good faith, equal to the value of a share of Parent Class A Common Stock as of the applicable date of determination (taking into account all factors deemed relevant by Option Holder), which such determination (A) shall be final, conclusive, and binding on the parties to this Agreement, and (B) may (but is not required to) be calculated taking into account the applicable 30-Day VWAP as of such date of determination, upon the recommendation of a nationally recognized investment bank, accounting or valuation firm selected by Option Holder, or such other method of calculation as the Option Holder (in its sole discretion) may determine.

“Trading Day” means a day on which trading of shares of Parent Class A Common Stock generally occurs on the principal Trading Market for shares of Parent Class A Common Stock. If shares of Parent Class A Common Stock are not so listed or traded, then “Trading Day” means a Business Day.

“Trading Market” means the following market(s) or exchange(s) on which the Parent Class A Stock is primarily listed or quoted for trading on the date in question (as applicable): the Nasdaq Capital Market, the Nasdaq Global Market, the Nasdaq Global Select Market, the NYSE American or the New York Stock Exchange (or any successors to any of the foregoing).

“VWAP” means, for any Trading Day, (i) the per share volume-weighted average price of a share of Parent Class A Common Stock as reported by Bloomberg, L.P. in respect of the period from the scheduled open of trading until the scheduled close of trading of the primary trading session on such Trading Day, or (ii) if there is no Trading Market for any such Trading Day, then the price used for such day shall be the average of the highest closing bid price and the lowest closing ask price of any of the market makers for such security as reported in the OTCQX, OTCQB, Pink or Grey markets (in that order) operated by OTC Markets.

ANNEX B

Letter Agreement

[Attached]

Schedule 6(e) - Other Subsidiaries

EXHIBIT 5

Corrected Execution Version

MEDIACO HOLDINGS INC.

STOCKHOLDERS AGREEMENT

Dated as of April 17, 2024

Table of Contents

Page

STOCKHOLDERS AGREEMENT

This STOCKHOLDERS AGREEMENT is made as of April 17, 2024, by and among MediaCo Holding Inc., an Indiana corporation (together with its successors and assigns, the “Company”), SLF LBI Aggregator, LLC, a Delaware limited liability company (together with its Permitted Transferees hereunder, the “HPS Investor”), and, solely for purposes of Section 3.3, Article IV and Article V hereof, SG Broadcasting LLC, a Delaware limited liability company (together with its Permitted Transferees hereunder, the “SG Investor” and, together with the HPS Investor, each an “Investor” and, collectively, the “Investors”).

WHEREAS, concurrently with the execution and delivery of this Agreement, the HPS Investor and the Company are entering into that certain Asset Purchase Agreement, dated the date hereof, by and among the HPS Investor, the Company and the other parties thereto (the “Purchase Agreement”);

WHEREAS, capitalized terms used but not defined herein shall have the meaning set forth in the Purchase Agreement; and

WHEREAS, the parties hereto desire to enter into this Agreement to govern certain of their rights, duties and obligations with respect to the Investors’ ownership of Warrants and shares of Company Common Stock.

NOW, THEREFORE, in consideration of the mutual covenants and agreements contained herein, the parties mutually agree as follows:

Article I

DEFINITIONS

Section 1.1         Definitions. As used in this Agreement, the following terms shall have the meanings set forth below:

“Affiliate” means, with respect to any Person, (a) any other Person that directly or indirectly, controls, is controlled by or is under common control with such Person or (b) any Person who is a general partner, partner, managing director, manager, officer, director or principal of the specified Person. The term “control” (including the terms “controlled by” and “under common control with”) as used with respect to any Person, means the power to direct or cause the direction of the management and policies of such Person, directly or indirectly, whether through the ownership of voting securities, as trustee or executor, by contract or otherwise to control such Person within the meaning of such term as used in Rule 405 under the Securities Act. “Controlled” and “controlling” have meanings correlative to the foregoing.

“Affiliated” shall have a correlative meaning to the term “Affiliate”.

“Agreement” means this Stockholders Agreement.

“Beneficial Ownership”, “Beneficial Owner”, “Beneficially Own” and similar terms have the meanings set forth in Rule 13d-3 under the Exchange Act; provided, however, that

no Investor shall be deemed to Beneficially Own any securities of the Company held by any other Investor solely by virtue of the provisions of this Agreement (other than this definition). For the avoidance of doubt, for purposes of this Agreement, at any given time, the HPS Investor will be deemed to Beneficially Own the number of shares of Class A Common Stock issuable upon exercise of all Warrants then held by the HPS Investor, or that the HPS Investor would then be entitled to receive upon the exercise of the Option Agreement in full, whether or not such Warrants and/or Option Agreement are then exercisable.

“Board” means the Board of Directors of the Company.

“Business Day” means any day, other than a Saturday, Sunday or one on which banks are authorized or required by law to be closed in New York, New York.

“Bylaws” means the Company’s Amended and Restated Code of By-Laws, as amended and in effect from time to time.

“Change of Control” means the occurrence of any of the following events:

(a)         the sale or disposition, in one or a series of related transactions, of all or substantially all of the assets of the Company to any “person” or “group” (as such terms are defined in Section 13(d)(3) of the Exchange Act), other than to any of the Investors or any of their respective Affiliates that are not portfolio companies of the Investors and their respective Affiliates (collectively, the “Permitted Holders”);

(b)         any person or group, other than the Permitted Holders, is or becomes the Beneficial Owner, directly or indirectly, of more than fifty percent (50%) of the total voting power of the voting stock of the Company (or any entity which controls the Company, or which is a successor to all or substantially all of the assets of the Company), including by way of merger, recapitalization, reorganization, redemption, issuance of capital stock, consolidation, tender or exchange offer or otherwise; or

(c)         a merger of the Company with or into another Person (other than the Permitted Holders) in which the voting stockholders of the Company immediately prior to such merger cease to hold at least fifty percent (50%) of the voting securities of the surviving entity or ultimate parent entity (in each case, including the Company) immediately following such merger; provided that, in each case under clause (a), (b) or (c), no Change in Control shall occur unless the Permitted Holders in such transaction cease to have the ability, without the approval of any Person who is not a Permitted Holder, to elect more directors of the Company (or any resulting entity) than any other stockholder or group of Affiliated stockholders of the Company.

“Charter” means the Amended and Restated Articles of Incorporation of the Company, as amended and in effect from time to time.

“Chosen Courts” has the meaning set forth in Section 5.2(b).

“Company” has the meaning set forth in the Preamble.

“Company Class A Common Stock” means the Company’s Class A Common Stock, par value $0.01 per share.

“Company Common Stock” means the Company Class A Common Stock, the Company’s Class B Common Stock, par value $0.01 per share, and the Company’s Class C Common Stock, par value $0.01 per share, and any other class or series of the Company’s common stock.

“Company Preferred Stock” means the Company’s preferred stock, par value $0.01 per share.

“Exchange Act” means the Securities Exchange Act of 1934 and the rules and regulations promulgated thereunder.

“Fully Diluted Company Common Stock” means, at any given time, the total number of shares of Company Common Stock that are issued and outstanding at such time on a fully diluted and as-converted, as-exchanged and as-exercised basis, including (without duplication): (a) the aggregate number of shares of Company Common Stock that are issued and outstanding (including each share of Company Class A Common Stock that is subject to vesting, forfeiture repurchase or other lapse restrictions), (b) the aggregate number of shares of Company Class A Common Stock that are issuable upon conversion of all issued and outstanding shares of preferred stock, par value $0.01 per share of the Company designated as “Series A Convertible Preferred Stock”, (c) the aggregate number of shares of Company Common Stock that are issuable upon conversion, exercise, exchange or other settlement of any then-outstanding equity or equity-linked award of the Company (in each case, whether or not then vested or exercisable) or other equity interests of the Company convertible into or exchangeable or exercisable for Parent Common Stock and (d) the aggregate number of shares of Company Common Stock issuable upon conversion, exchange or exercise of any then-outstanding options, warrants or similar rights or instruments (including all such shares issuable upon exercise of the Warrants then held by the HPS Investor, or that the HPS Investor would then be entitled to receive upon the exercise of the Option Agreement in full, whether or not such Warrants and/or Option Agreement are then exercisable).

“Governmental Authority” means any United States or foreign government, any state or other political subdivision thereof, any entity exercising executive, legislative, judicial, regulatory or administrative functions of or pertaining to government, including the SEC, or any other authority, agency, department, board, commission or instrumentality of the United States, any State of the United States or any political subdivision thereof or any foreign jurisdiction, and any court, tribunal or arbitrator(s) of competent jurisdiction, and any United States or foreign governmental or non-governmental self-regulatory organization, agency or authority.

“HPS Investor” has the meaning set forth in the Preamble.

“Independent” means “independent” as set forth in NASDAQ Rule 5605(a)(2), otherwise in the NASDAQ Rules (or in any applicable rules of an exchange on which the securities of the Company are listed) and also “independent” as set forth in Rule 10A-3 under the Exchange Act.

“Investor” has the meaning set forth in the Preamble.

“Investor Director Designee” means any individual designated to the Board by the HPS Investor pursuant to the terms and conditions of this Agreement.

“Law” with respect to any Person, means (a) all provisions of all laws, statutes, ordinances, rules, regulations, permits, certificates or orders of any Governmental Authority applicable to such Person or any of its assets or property or to which such Person or any of its assets or property is subject, and (b) all judgments, injunctions, orders and decrees of any Governmental Authority in proceedings or actions in which such Person is a party or by which it or any of its assets or properties is or may be bound or subject.

“NASDAQ” means the Nasdaq Stock Market.

“NASDAQ Rules” means the rules and regulations of the Nasdaq Stock Market.

“Necessary Action” means, with respect to any party and a specified result, all actions (to the extent such actions are not prohibited by applicable Law or the NASDAQ Rules (or the applicable rules of an exchange on which the securities of the Company are listed) and within such party’s control, and in the case of any action that requires a vote or other action on the part of the Board to the extent such action is consistent with fiduciary duties that the Company’s directors may have in such capacity) necessary to cause such result, including (a) calling special meetings of stockholders, (b) voting or providing a written consent or proxy, if applicable in each case, with respect to shares of Company Common Stock, (c) causing the adoption of stockholders’ resolutions, (d) executing agreements and instruments, (e) making, or causing to be made, with Governmental Authorities, all filings, registrations or similar actions that are required to achieve such result, and (f) nominating and promoting certain Persons for election to the Board (including by soliciting proxies therefor) in connection with the annual or special meeting of stockholders of the Company.

“Permitted Holders” has the meaning set forth in the definition of “Change of Control.”

“Permitted Transferee” means, with respect to any Investor and as of any date of determination, any Affiliate of such Investor.

“Person” means an individual, partnership, corporation, business trust, joint stock company, trust, unincorporated association, joint venture, limited liability company, Governmental Authority or any other entity or organization of whatever nature, and shall include any successor (by merger or otherwise) of such entity or organization.

“SEC” means the United States Securities and Exchange Commission.

“Securities Act” means the Securities Act of 1933 and the rules and regulations promulgated thereunder.

“SG Investor” has the meaning set forth in the Preamble.

“Subsidiary” means, with respect to any Person, any corporation, partnership, trust, limited liability company or other non-corporate business enterprise in which such Person (or

another Subsidiary of such Person) holds shares, stock or other ownership interests representing (a) more than fifty percent (50%) of the voting power of all outstanding shares, stock or ownership interests of such entity, (b) the right to receive more than fifty percent (50%) of the net assets of such entity available for distribution to the holders of outstanding shares, stock or ownership interests upon a liquidation or dissolution of such entity, or (c) a general or managing partnership interest in such entity.

“Sunset Date” means the tenth (10^th) consecutive day on which the HPS Investor ceases to Beneficially Own a number of shares of Company Common Stock equal to at least twenty-five percent (25.0%) of the then-outstanding Fully Diluted Company Common Stock.

“Threshold Date” means the tenth (10^th) consecutive day on which the HPS Investor ceases to Beneficially Own a number of shares of Company Common Stock equal to at least ten percent (10%) of the then-outstanding Fully Diluted Company Common Stock.

“Voting Agreement” means that certain Voting and Support Agreement, dated as of the date hereof, by and among Estrella Broadcasting, Inc., the Company, and the SG Investor.

“Warrants” means all warrants to purchase shares of Company Class A Common Stock issued to the HPS Investor pursuant to the Purchase Agreement or the Option Agreement.

Section 1.2         General Interpretive Principles. The name assigned to this Agreement and the section captions used herein are for convenience of reference only and shall not be construed to affect the meaning, construction or effect hereof. References to this Agreement shall include all Exhibits, Schedules and Annexes to this Agreement. References to any statute, rule or regulation refer to such statute, rule or regulation as amended, modified, supplemented or replaced from time to time (and, in the case of any statute, include any rules and regulations promulgated under the statute) and references to any section of any statute or regulation include any successor to such section. References to any Governmental Authority include any successor to such Governmental Authority. Unless otherwise specified, the terms “hereof,” “herein” and similar terms refer to this Agreement as a whole. For purposes of this Agreement, the words, “include,” “includes” and “including,” when used herein, shall be deemed in each case to be followed by the words “without limitation.” The terms defined in the singular have a comparable meaning when used in the plural, and vice versa. The terms “dollars” and “$” shall mean United States dollars. The parties hereto have participated jointly in the negotiation and drafting of this Agreement. If an ambiguity or question of intent or interpretation arises, this Agreement will be construed as if drafted jointly by the parties and no presumption or burden of proof will arise favoring or disfavoring any party because of the authorship of any provision of this Agreement.

Article II

REPRESENTATIONS AND WARRANTIES

Section 2.1         Representations and Warranties of the Investors. Each Investor, severally and not jointly, hereby represents and warrants to the Company and each other Investor that as of the date hereof:

(a)         This Agreement has been duly authorized, executed, and delivered by such Investor and, assuming the due execution and delivery of this Agreement by the other parties hereto, this Agreement constitutes a valid and binding obligation of such Investor, enforceable against such Investor in accordance with its terms, except as such enforceability may be limited by applicable bankruptcy, insolvency, fraudulent transfer, moratorium, reorganization or similar Laws of general applicability relating to or affecting the rights of creditors generally and subject to general principles of equity (regardless of whether enforcement is considered in a proceeding in equity or at law).

(b)         The execution, delivery, and performance by such Investor of this Agreement and the agreements contemplated hereby and the consummation by such Investor of the transactions contemplated hereby do not and will not, with or without the giving of notice or the passage of time or both: (i) violate the provisions of any Law applicable to such Investor, or (ii) result in any material breach of any terms or conditions of, or constitute a material default under, any contract, agreement or instrument to which such Investor is a party.

Section 2.2         Representations and Warranties of the Company. The Company hereby represents and warrants to each Investor that as of the date hereof:

(a)         This Agreement has been duly authorized, executed, and delivered by the Company and, assuming the due execution and delivery of this Agreement by the other parties hereto, this Agreement constitutes a valid and binding obligation of the Company, enforceable against the Company in accordance with its terms, except as enforceability may be limited by applicable bankruptcy, insolvency, fraudulent transfer, moratorium, reorganization or similar Laws of general applicability relating to or affecting the rights of creditors generally and subject to general principles of equity (regardless of whether enforcement is considered in a proceeding in equity or at law).

(b)         The execution, delivery, and performance by the Company of this Agreement and the agreements contemplated hereby and the consummation by the Company of the transactions contemplated hereby do not and will not, with or without the giving of notice or the passage of time or both: (i) violate the provisions of any Law applicable to the Company or its properties or assets, or (ii) result in any material breach of any terms or conditions of, or constitute a material default under, any contract, agreement or instrument to which the Company is a party or by which the Company or its properties or assets are bound.

Article III

HPS DESIGNEES

Section 3.1         Board Size.

(a)         Effective immediately following the consummation of the Closing on the date hereof, the Board has (i) approved an increase the size of the Board to eleven (11) members, and (ii) appointed to the Board the following three (3) individuals, each of whom shall be considered an Investor Director Designee:

(i)           Colbert Cannon, to serve as a Class III director (as defined in the Bylaws), for a term expiring at the annual meeting of the Company’s stockholders held in 2025 and until his successor is duly elected and qualified, or, if earlier, his death, resignation, retirement or removal from office;

(ii)         Jacqueline Hernandez, to serve as a Class I director (as defined in the Bylaws), for a term expiring at the annual meeting of the Company’s stockholders held in 2026 and until her successor is duly elected and qualified, or, if earlier, her death, resignation, retirement or removal from office; and

(iii)         Brett Pertuz, to serve as a Class II director (as defined in the Bylaws), for a term expiring at the annual meeting of the Company’s stockholders held in 2027 and until his successor is duly elected and qualified, or, if earlier, his death, resignation, retirement or removal from office.

(b)         From and after the date hereof, the size of the Board shall be determined in accordance with the Charter, the Bylaws, and applicable Law; provided, that the Company and the Board shall, to the fullest extent permitted by applicable Law, take all Necessary Action to ensure that any change in the size of the Board does not, in and of itself, cause the removal of any Investor Director Designee.

Section 3.2         HPS Investor Director Designees.

(a)         To the extent permitted by applicable Law and the NASDAQ Rules (or the applicable rules of an exchange on which the securities of the Company are listed), the Company agrees that, prior to the Threshold Date, the HPS Investor shall have the right (but not the obligation) to designate, with respect to each meeting of Company stockholders at which directors will be elected (and at any election by written consent), a number of individuals for election to the Board such that, if such designees are elected to the Board, then the aggregate number of Investor Director Designees serving on the Board will equal the lesser of (i) the product of the following: (x) the percentage represented by the fraction the numerator of which is the number of shares of Company Common Stock then Beneficially Owned by the HPS Investor, and the denominator of which is the Fully Diluted Company Common Stock multiplied by (y) the then size of the Board (after taking into account any increase in the size of the Board, other than as contemplated by Section 3.1), and (ii) three (3); provided, that, in the event that the HPS Investor Beneficially Owns greater than fifty percent (50%) of the combined voting power of the Company’s issued and outstanding shares of capital stock entitled to vote upon the election of directors at a meeting of the stockholders of the Company, the foregoing clause (ii) shall be disregarded and shall not apply, such that the HPS Investor’s director designation rights pursuant to this Section 3.2(a) shall be determined in accordance with the foregoing clause (i) subject to any right of the holders of shares of any class of Company Common Stock or Company Preferred Stock to, exclusive of other classes of stockholders, elect directors by class vote set forth in the Charter. Any product obtained pursuant to the calculation in the immediately foregoing sentence shall be rounded up to the nearest whole number of directors.

(b)         For so long as the HPS Investor has the right to designate any Investor Director Designee pursuant to this Section 3.2, one of the Investor Director Designees shall be

Independent (provided, that the foregoing shall not apply for so long as any Investor Director Designee is not Independent due to such Person’s service as the Chief Executive Officer of the Company). The HPS Investor shall notify the Company in writing of its proposed Investor Director Designees (a “Designation Notice”) promptly (and in any event within two (2) Business Days) of such time that such information is reasonably requested by the Company for inclusion in the Company’s proxy statement for the applicable meeting of stockholders (which request must be made no later than the date that is fifteen (15) days prior to the filing of such proxy statement), and shall provide to the Company all information regarding any such Investor Director Designee as shall be reasonably requested by the Company (including, at a minimum, such information regarding each Investor Director Designee as shall be required to be included in a proxy statement of the Company with respect to the a meeting of stockholders at which directors are to be elected pursuant to applicable securities Laws). So long as the HPS Investor has the right to designate any Investor Director Designee pursuant to this Section 3.2, the Company shall take all Necessary Action to (i) include each Investor Director Designee in the Company’s proxy statement for the applicable meeting of stockholders among the Company’s and its directors’ nominees for election to the Board at the Company’s applicable meeting of stockholders, and at any adjournment or postponement thereof, and on every action or approval by written consent of the stockholders of the Company with respect to the election of members of the Board, and (ii) use the same efforts to cause the election of such Investor Director Designees as it uses to cause other nominees recommended by the Board to be elected, including soliciting proxies or consents in favor thereof.

(c)         If at any time the total number of individuals that the HPS Investor then has the right to have included on the Board pursuant to Section 3.2(a) is less than the total number of Investor Director Designees then serving on the Board, then the HPS Investor shall cause the corresponding number of directors designated by the HPS Investor pursuant to the foregoing provisions of this Section 3.2 to immediately resign from the Board and, if such number of directors designated by the HPS Investors fails to so resign, the Company and the HPS Investor shall be immediately required to take any and all Necessary Action to cooperate in ensuring the removal of any such individual from his or her directorship. In the event that the HPS Investor has nominated less than the total number of Investor Director Designees it is entitled to nominate for election to the Board pursuant to Section 3.2(a), the HPS Investor shall have the right, at any time, to nominate for election to the Board such additional nominees to which it is entitled, in which case, the Company shall take all Necessary Action to (i) enable the HPS Investor to nominate for election to the Board and effect the election or appointment of such Investor Director Designees, whether by increasing the size of the Board or otherwise and (ii) effect the election or appointment of such additional Investor Director Designees to fill such newly-created directorships or to fill any other existing vacancies.

(d)         In the event of any vacancy on the Board that is created by reason of the death, removal or resignation of an Investor Director Designee (other than as a result of the HPS Investor ceasing to have the right to designate any directors pursuant to Section 3.2(a) or any resignation or removal pursuant to the terms and conditions of Section 3.2(c)), the HPS Investor shall have the right, pursuant to written notice to the Company (a “Replacement Notice”), to designate another designee to fill the vacancy resulting therefrom, and the Company shall promptly take all Necessary Action to fill such vacancy pursuant to the appointment of the substitute Investor Director Designee specified by the HPS Investor in such Replacement Notice.

(e)         For the avoidance of doubt, from and after the Threshold Date, the HPS Investor shall have no right to designate any Investor Director Designees hereunder.

(f)          For so long as Section 9.2 of the Charter remains in effect, no Investor Director Designee (including, for the avoidance of doubt, the individuals named in Section 3.2 hereof) shall be classified as a Class A Director or a Class B Director (each as defined in Section 7.4 of the Company’s Charter). From and after the first date that Section 9.2 of the Charter ceases to be of any further force or effect, the Company and the HPS Investor each agree to take all Necessary Action to cause each Investor Director Designee then serving as a director of the Company or subsequently designated by the HPS Investor hereunder to be designated as a Class A Director.

(g)         For so long as an Investor Director Designee is a member of the Board in accordance with and subject to the terms of this Agreement, subject to applicable Law and NASDAQ Rules (or the applicable rules of an exchange on which the securities of the Company are listed), and taking into account any “controlled company” exemption thereunder on which the Company is not relying upon, the Company will take all Necessary Action to offer one (1) Investor Director Designee selected by the HPS Investor an opportunity to, at the HPS Investor’s election, either (i) be a member of all committees of the Board that currently exist and any special, executive, or other committees of the Board authorized by the Board after the date hereof, or (ii) attend (but not vote) at the meetings of each such committee as an observer (the foregoing clause (i) or clause (ii), either, at the election of the HPS Investor, the “Committees Opportunity”); provided, that, in the event that the HPS Investor Beneficially Owns greater than fifty percent (50%) of the combined voting power of the Company’s issued and outstanding shares of capital stock entitled to vote upon the election of directors at a meeting of the stockholders of the Company, the Company will take all Necessary Action to offer such Committees Opportunity to the number of Investor Director Designees (rounded up to the nearest whole number) equal to the product of (x) such percentage, and (y) the size of such committee.

Section 3.3         Support. Each Investor, severally and not jointly, agrees and commits solely with the Company (and not any other party hereto) that such party will appear in person or by proxy at any meeting of Company stockholders at which directors are to be elected, and at every adjournment thereof, and on every action or approval by written consent of the stockholders of the Company, and vote all shares Beneficially Owned by such party in favor of (i) in the case of the HPS Investor, each of the nominees on the slate of director nominees nominated by the Company for election at such meeting and otherwise in accordance with the Board’s recommendation on any other proposal relating to the appointment, election or removal of directors, and (ii) in the case of the SG Investor, each of the Investor Director Designees on the slate of director nominees nominated by the Company for election at such meeting. The obligation of each Investor to comply with the terms and conditions of this Section 3.3 shall automatically terminate without any further action at such time as the earliest of (A) the HPS Investor ceasing to have the right to designate any directors pursuant to Section 3.2(a), (B) the first date that the HPS Investor Beneficially Owns greater than fifty percent (50%) of the combined voting power of the Company’s issued and outstanding shares of Capital Stock entitled to vote upon the election of directors at a meeting of the stockholders of the Company, and (C) such Investor ceasing to Beneficially Own any shares of Company Common Stock. Except as set forth in this Section 3.3, the HPS Investor shall not be restricted from voting in favor of, against or abstaining with respect to any other matter presented

to the stockholders of the Company. In the event that, at any time during the period from and after the Closing and the date that the Required Parent Stockholder Approval is obtained, the SG Investor Transfers (as defined in that Voting Agreement) any Subject Shares (as defined in the Voting Agreement) to a third party, at the election of the HPS Investor, each of the Company, the SG Investor and the HPS Investor agree to take such actions as are necessary so that the HPS Investor, substantially concurrently with the consummation of such Transfers (as defined in the Voting Agreement), is afforded a direct or indirect opportunity for liquidity in respect of its Parent Shares that is commensurate with the HPS Investor’s Beneficial Ownership of the Fully Diluted Company Common Stock as of the date of such Transfer (as defined in the Voting Agreement).

Section 3.4         Expenses; D&O Insurance. For so long as any Investor Director Designee serves as a director, such director shall be entitled to (i) the same reimbursement for travel and other expenses paid to other non-employee directors incurred in connection with his or her duties as a director, including any service on any committee of the Board; and (ii) the same indemnification, exculpation and advancement of expenses rights provided to other non-employee directors, and the Company shall maintain in full force and effect directors’ and officers’ liability insurance coverage with respect to such director (subject to the limitations of such coverage, and with such coverage terms as the Company deems reasonable) to the same extent that it indemnifies and provides insurance for other non-employee directors.

Article IV

ADDITIONAL PARTIES; CONSENT RIGHTS

Section 4.1         Additional Parties. Additional parties, provided they are Permitted Transferees, may be added to and be bound by and receive the benefits afforded by this Agreement upon the signing and delivery of a counterpart of this Agreement by the Company and the acceptance thereof by such additional parties and, to the extent permitted by Section 5.5, amendments may be effected to this Agreement reflecting such rights and obligations, consistent with the terms of this Agreement, of such party as the Company, the Investors and such party may agree.

Section 4.2         Consent Rights. Prior to the Sunset Date, the Company shall not, directly or indirectly (including through any of its Subsidiaries), without the consent of the HPS Investor:

(a)         amend, alter, repeal or change any provision of the Charter or Bylaws, in each case, in a manner that would adversely change the rights of the HPS Investor hereunder;

(b)         acquire or dispose of assets (including, for the avoidance of doubt, any businesses) in one transaction, or a series of related transactions, in an amount exceeding $10.0 million (which, in the case of transactions involving partial or total consideration of property other than cash, shall be calculated based on the fair market value of the total consideration as determined in the good faith judgment of the Board);

(c)         enter into any transaction, arrangement, agreement or contract with any Affiliates of the Company or any of its Subsidiaries, unless such transaction, arrangement,

agreement or contract is on arms’ length terms approved by a majority of the disinterested directors on the Board (or a committee comprised solely of disinterested directors of the Board);

(d)         effect a Change of Control;

(e)         declare (or consent to) any voluntary or involuntary bankruptcy, dissolve, liquidate, wind up its affairs or enter into receivership; or

(f)          make any change, or enter into any transaction that would change, the classification of the Corporation as a corporation for U.S. federal income tax purposes or enter into any transaction that would otherwise result in the Holders holding equity in an entity classified for U.S. federal income tax purposes as other than a corporation.

Article V

MISCELLANEOUS

Section 5.1         Freedom to Pursue Opportunities.

(a)         The parties expressly acknowledge and agree that, to the extent permitted by applicable Law: (i) each of the Investors and their respective Affiliates shall, to the fullest extent permissible by Law, have no duty to refrain from directly or indirectly (A) engaging in the same or similar business activities or lines of business in which the Company or any of its Affiliates now engages or proposes to engage or (B) otherwise competing with the Company or any of its Affiliates; (ii) none of the Company, any of its Subsidiaries or any Investor shall have any rights in and to the business ventures of any Investor, its Affiliates, or the income or profits derived therefrom; (iii) each of the Investors and their respective Affiliates may do business with any potential or actual customer or supplier of the Company or any of its Subsidiaries or may employ or otherwise engage any officer or employee of the Company or any of its Subsidiaries; and (iv) in the event that any Investor or its respective Affiliates acquire knowledge of a potential transaction or other matter or business opportunity which may be a corporate opportunity for itself, herself or himself and the Company or any of its Affiliates, such Investor or its respective Affiliates shall, to the fullest extent permitted by applicable Law, have no fiduciary duty or other duty (contractual or otherwise) to communicate, present or offer such transaction or other business opportunity to the Company or any of its Affiliates and, to the fullest extent permitted by applicable Law, shall not be liable to the Company or its stockholders or to any Affiliate of the Company for breach of any fiduciary duty or other duty (contractual or otherwise) as a stockholder, director or officer of the Company solely by reason of the fact that such Investor or its respective Affiliates pursue or acquire such corporate opportunity for itself, herself or himself, offers or directs such corporate opportunity to another Person, or does not present such corporate opportunity to the Company or any of its Affiliates; provided, that the Company does not renounce its interest in any corporate opportunity offered to any director of the Company if such opportunity is expressly offered to such Person in his or her capacity as a director of the Company and the provisions of this Section 5.1(a) shall not apply to any such corporate opportunity.

(b)         To the extent permitted by applicable Law, each Investor (for itself and on behalf of the Company) hereby acknowledges and agrees that no Investor or any of its Affiliates

(or any designees designated to serve on the Board by such Investor or any of its Affiliates), shall be obligated to reveal to the Company or any of its Subsidiaries confidential information belonging to or relating to the business of such Investor or any of its Affiliates.

Section 5.2         Information Rights and Sharing.

(a)         So long as the HPS Investor Beneficially Owns a number of shares of Company Common Stock equal to at least five percent (5.0%) of the then-outstanding Fully Diluted Company Common Stock, the Company shall furnish to Holders (a) annual audited financial statements, quarterly unaudited financial statements and monthly unaudited financial statements, in each case, as soon as reasonably practicable after the completion of such period (and, in any event, no later than the date that such information is first required to be delivered to the Company’s security holders or lenders); (b) all notices, reports and certificates furnished by the Company or any of its Subsidiaries to the lenders or other debt holders under the agreements governing the Company’s or any of its Subsidiaries’ indebtedness; and (c) all notices delivered to the Company or any of its Subsidiaries from the lenders or other debt holders under the agreements governing the Corporation’s or any of its Subsidiaries’ indebtedness.

(b)         Individuals associated with the HPS Investor may from time to time serve on the Board or the equivalent governing body of the Company’s Subsidiaries. The Company, on its behalf and on behalf of its Subsidiaries, recognizes that such individuals (i) will from time to time receive non-public information concerning the Company and its Subsidiaries, and (ii) may (subject to the obligation to maintain the confidentiality of such information) share such information with other individuals associated with the HPS Investor. Such sharing will be for the dual purpose of facilitating support to such individuals in their capacity as members of the Board (or members of the governing body of any Subsidiary) and enabling the HPS Investor, as a stockholder, to better evaluate the Company’s performance and prospects.

Section 5.3         Entire Agreement. This Agreement constitutes the entire understanding and agreement between the parties as to the matters covered herein and supersedes and replaces any prior understanding, agreement or statement of intent, in each case, written or oral, of any and every nature with respect thereto between the parties as to the matters covered herein. In the event of any inconsistency between this Agreement and any document executed or delivered to effect the purposes of this Agreement, this Agreement shall govern as among the parties hereto.

Section 5.4         Governing Law; Submission to Jurisdiction; Waiver of Jury Trial.

(a)         This Agreement shall be construed and enforced in accordance with, and the rights and duties of the parties shall be governed by, the law of the State of Delaware, without regard to principles of conflicts of laws that would result in the application of the law of any other jurisdiction.

(b)         Each party agrees that it will bring any action or proceeding in respect of any claim arising out of this Agreement or the transactions contemplated hereby exclusively in the Court of Chancery of the State of Delaware or, if such court shall not have jurisdiction, another federal or state court of competent jurisdiction located in the State of Delaware (the “Chosen Courts”), and, solely in connection with claims arising under this Agreement or the transactions

that are the subject of this Agreement, (i) irrevocably submits to the exclusive jurisdiction of the Chosen Courts, (ii) waives any objection to laying venue in any such action or proceeding in the Chosen Courts, (iii) waives any objection that the Chosen Courts are an inconvenient forum or do not have jurisdiction over any party and (iv) agrees that service of process upon such party in any such action or proceeding will be effective if notice is given in accordance with Section 5.8.

(c)         EACH PARTY ACKNOWLEDGES AND AGREES THAT ANY CONTROVERSY WHICH MAY ARISE UNDER THIS AGREEMENT IS LIKELY TO INVOLVE COMPLICATED AND DIFFICULT ISSUES, AND THEREFORE EACH SUCH PARTY HEREBY IRREVOCABLY AND UNCONDITIONALLY WAIVES, TO THE FULLEST EXTENT PERMITTED BY APPLICABLE LAW, ANY RIGHT SUCH PARTY MAY HAVE TO A TRIAL BY JURY IN RESPECT OF ANY SUIT, ACTION OR OTHER PROCEEDING DIRECTLY OR INDIRECTLY ARISING OUT OF OR RELATING TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED BY THIS AGREEMENT. EACH PARTY CERTIFIES AND ACKNOWLEDGES THAT: (I) NO REPRESENTATIVE, AGENT OR ATTORNEY OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF ANY ACTION, SUIT OR PROCEEDING, SEEK TO ENFORCE THE FOREGOING WAIVER, (II) EACH PARTY UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (III) EACH PARTY MAKES THIS WAIVER VOLUNTARILY, AND (IV) EACH PARTY HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS Section 5.4(c).

Section 5.5         Amendment and Waiver.

(a)         The terms and provisions of this Agreement may be modified or amended at any time and from time to time only by the written consent of the parties hereto. If reasonably requested by the HPS Investor, the Company agrees to take all Necessary Action to execute and deliver any amendments to this Agreement to the extent so requested by such Investor in connection with the addition of a Permitted Transferee in accordance with Section 4.1 or a recipient of any newly-issued shares of Company Common Stock as a party hereto. Any amendment, modification or waiver effected in accordance with the foregoing shall be effective and binding on the Company and all Investors.

(b)         Any failure by any party at any time to enforce any of the provisions of this Agreement shall not be construed a waiver of such provision or any other provisions hereof.

Section 5.6         Binding Effect; Assignment. Except as otherwise expressly provided herein, the provisions hereof shall inure to the benefit of, and be binding upon, the parties’ successors and permitted assigns. No Investor may assign or transfer its rights under this Agreement except with the prior consent of the Company. Any purported assignment of rights or obligations under this Agreement in derogation of this Section 5.6 shall be null and void, ab initio. Notwithstanding the foregoing, the rights under this Agreement may be assigned (but only with all related obligations) by an Investor to a Permitted Transferee of such Investor; provided, however, that an Investor may assign any of its rights and obligations hereunder to a Permitted Transferee of such Investor without the consent of any other party hereto, but no such assignment will relieve such Investor of its obligations hereunder and provided that such Permitted Transferee

shall agree in writing to assign its rights and obligations hereunder back to such original Investor in the event that such Permitted Transferee shall cease to be an Affiliate of such original Investor.

Section 5.7         Termination. This Agreement shall automatically terminate upon the earlier of (i) the Threshold Date, (ii) a Change of Control; (iii) the written agreement of the Company and the HPS Investor; and (iv) the dissolution or liquidation of the Company. In the event of any termination of this Agreement as provided in this Section 5.7, this Agreement shall forthwith become wholly void and of no further force or effect (except for this Article V, which shall survive) and there shall be no liability on the part of any parties hereto or their respective Affiliates, except as provided in this Article V. Notwithstanding the foregoing, no party hereto shall be relieved from liability for any willful breach of this Agreement.

Section 5.8         Non-Recourse. Notwithstanding anything that may be expressed or implied in this Agreement or any document or instrument delivered in connection herewith, and notwithstanding the fact that certain of the Investors may be partnerships or limited liability companies, by its acceptance of the benefits of this Agreement, the Company and each Investor covenant, agree, and acknowledge, on behalf of themselves and each of their respective former, current or future Affiliates and any of the foregoing’s respective former, current or future, direct or indirect, officers, directors, employees, Affiliates, shareholders, equityholders, controlling persons, managers, member, partners, agents, attorneys, advisors or other representatives or any of the foregoing’s respective successors and assigns (collectively, the “Related Parties”), that no Person (including all Related Parties other than the parties hereto) has any obligations hereunder, and that no recourse under this Agreement or any documents or instruments delivered in connection with this Agreement shall be had against any Related Party (other than the parties hereto), whether by the enforcement of any assessment or by any legal or equitable proceeding, or by virtue of any statute, regulation or other applicable Law, it being expressly agreed and acknowledged that no personal liability whatsoever shall attach to, be imposed on or otherwise be incurred by any of the Related Parties (other than the parties hereto) for any obligation of any Investor under this Agreement or any documents or instruments delivered in connection with this Agreement for any claim based on, in respect of or by reason of such obligations or their creation.

Section 5.9         Notices. Any and all notices, designations, offers, acceptances or other communications provided for herein shall be deemed duly given (a) when delivered personally by hand, (b) when sent by email upon confirmation of receipt or (c) one Business Day following the day sent by overnight courier:

if to the Company, to:

MediaCo Holding Inc.

48 West 25^th Street, Floor 3

New York, New York 10010

Attention: Chief Financial Officer and Vice President of Legal

Email: [***]

with a copy (which shall not constitute notice) to:

Fried, Frank, Harris, Shriver & Jacobson LLP
One New York Plaza

New York, New York 10004

Attention: Philip Richter; Colum J. Weiden

Email: Philip.Richter@friedfrank.com; Colum.Weiden@friedfrank.com

if to the HPS Investor, to:

SLF LBI Aggregator, LLC

40 West 57th Street, 32nd Floor

New York, NY 10019

Attention: Colbert Cannon

Email: [***]

with a copy (which shall not constitute notice) to:

Paul, Weiss, Rifkind, Wharton & Garrison LLP

1285 Avenue of the Americas

New York, New York 10019

Attention: Brian Scrivani; Jeffrey Marell

Email: bscrivani@paulweiss.com; jmarell@paulweiss.com

if to the SG Investor, to:

SG Broadcasting LLC

c/o Standard General L.P.

767 5^th Avenue, 12^th Floor

New York, New York 10153

Attention: General Counsel

Email: [***]

with a copy (which shall not constitute notice) to:

Fried, Frank, Harris, Shriver & Jacobson LLP
One New York Plaza

New York, New York 10004

Attention: Philip Richter

Email: Philip.Richter@friedfrank.com;

Section 5.10        Severability. Whenever possible, each provision or portion of any provision of this Agreement shall be interpreted in such manner as to be effective and valid under applicable Law, but if any provision or portion of any provision of this Agreement is held to be invalid, illegal or unenforceable in any respect under any applicable Law in any jurisdiction, the remainder of this Agreement shall remain valid and enforceable to the fullest extent permitted by Law and such invalidity, illegality or unenforceability shall not affect any other provision or portion of any provision in such jurisdiction, and the parties hereto shall take all Necessary Action to cause this

Agreement to be reformed, construed and enforced in such jurisdiction such that the invalid, illegal or unenforceable provision or portion thereof shall be interpreted to be only so broad as is enforceable.

Section 5.11        No Third-Party Beneficiaries. This Agreement shall be binding upon and inure solely to the benefit of the parties hereto and their permitted assigns and successors, and nothing herein, express or implied, is intended to or shall confer upon any other Person or entity, any legal or equitable right, benefit or remedy of any nature whatsoever under or by reason of this Agreement.

Section 5.12        Recapitalizations; Exchanges, Etc. The provisions of this Agreement shall apply to the full extent set forth herein with respect to shares of Company Common Stock, to any and all shares of capital stock of the Company or any successor or assign of the Company (whether by merger, consolidation, sale of assets or otherwise) which may be issued in respect of, in exchange for, or in substitution of shares of Company Common Stock, by reason of a stock dividend, stock split, stock issuance, reverse stock split, combination, recapitalization, reclassification, merger, consolidation or otherwise. If, and as often as, there are any such changes in Company Common Stock (or any successor securities), appropriate adjustment shall be made in the provisions of this Agreement, as may be required, so that the rights, privileges, duties and obligations hereunder shall continue with respect to Company Common Stock (or any success securities) as so changed.

Section 5.13        Counterparts. This Agreement may be executed in any number of counterparts, each of which shall be deemed an original, but all of which together shall constitute a single instrument. Copies of executed counterparts transmitted by telecopy or other electronic transmission service shall be considered original executed counterparts for purposes of this Section 5.13.

Section 5.14        Aggregation of Securities. All shares of Company Common Stock Beneficially Owned by each Investor and its Permitted Transferees shall be aggregated together for purposes of determining the rights or obligations of the Investors under this Agreement.

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IN WITNESS WHEREOF, each of the undersigned has executed this Agreement or caused this Agreement to be executed on its behalf as of the date first written above.

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