111 Monument Circle, Suite 2700 | Indianapolis, Indiana 46204 | (317) 684-5000 | (317) 684-5173 (fax) | www.boselaw.com Bose McKinney & Evans LLP is a member of Mackrell International, a network of independent law firms from more than 60 countries. April 1, 2026 MediaCo Holding Inc. 48 West 25th Street, Third Floor New York, New York 10010 Ladies and Gentlemen: We have acted as local Indiana counsel to MediaCo Holding Inc., an Indiana corporation (the “Company”), in connection with the registration by the Company of shares (the “Plan Shares”) of the Company’s Class A Common Stock, par value $0.01 per share (the “Common Stock”) to be sold by the Company pursuant to the Company’s 2025 Equity Compensation Plan (the “Plan”). The Plan Shares are the subject of a Registration Statement, as amended (the “Registration Statement”) filed by the Company on Form S-8 under the Securities Act of 1933, as amended (the “Act”) on or immediately after the date of this opinion letter. This opinion letter is being furnished at your request in accordance with the requirements of Item 601(b)(5) of Regulation S-K under the Act. In our capacity as such counsel, we are familiar with the proceedings taken and proposed to be taken by the Company in connection with the authorization, issuance and sale of the Plan Shares as contemplated by the Plan and as described in the Registration Statement. For purposes of this opinion letter, and except to the extent set forth in the opinion below, we have assumed that all such proceedings have been or will be timely completed in the manner presently provided in the Plan and the Registration Statement. For purposes of issuing this opinion letter, we have made such legal and factual examinations and inquiries, including an examination of originals or copies certified or otherwise identified to our satisfaction as being true copies of (i) the Registration Statement, (ii) the Plan, (iii) the Amended and Restated Articles of Incorporation and Amended and Restated Bylaws of the Company, as amended to date; and (iv) such agreements, instruments, resolutions of the board of directors of the Company or committees thereof, and other corporate records, and such other documents as we have deemed necessary or appropriate for the purpose of issuing this opinion letter, and we have obtained from officers and other representatives and agents of the Company and from public officials, and have relied upon, such certificates, representations and assurances, and public filings, as we have deemed necessary or appropriate. Without limiting the generality of the foregoing, in our examination, we have, with your permission, assumed without independent verification: (i) the statements of fact and all representations
MediaCo Holding Inc. April 1, 2026 Page Two and warranties set forth in the documents we have reviewed are true and correct as to factual matters, in each case as of the date or dates of such documents and as of the date hereof; (ii) each natural person executing any of the documents we have reviewed has sufficient legal capacity to do so; (iii) all documents submitted to us as originals are authentic, the signatures on all documents that we have reviewed are genuine and all documents submitted to us as certified, conformed, photostatic, facsimile or electronic copies conform to the original document; (iv) all corporate records made available to us by the Company, and all public records we have reviewed, are accurate and complete; (v) any issuance of Plan Shares pursuant to the Plan will be made in accordance with the requirements of the Plan and in accordance with resolutions of the board of directors of the Company and committees thereof; and (vi) after any issuance of Plan Shares, the total number of issued and outstanding shares of Common Stock, together with the total number of shares of Common Stock then reserved for issuance or obligated to be issued by the Company pursuant to any agreement or arrangement or otherwise, will not exceed the total number of shares of Common Stock then authorized under the Company’s Amended and Restated Articles of Incorporation, as amended to such date. We have also assumed that the Shares will not be issued (and the Company will not commit to issue Shares) in such quantities to “aliens” (as defined in Article XI of the Company’s Amended and Restated Articles of Incorporation, as amended) as would cause the Company to violate Article XI of the Company’s Amended and Restated Articles of Incorporation, as amended, or that an appropriate ruling has been first received by the Company from the Federal Communications Commission or any successor governmental agency (the “FCC”) to the effect that such issuance by the Company would be authorized under the Communications Act of 1934, as amended, and the rules, regulations, orders and policies of the FCC. We are qualified to practice law in the State of Indiana. The opinion set forth herein is expressly limited to and based exclusively on the general corporate laws of the State of Indiana, and we do not purport to be experts on, or to express any opinion with respect to the applicability or effect of, the laws of any other jurisdiction. We express no opinion concerning, and we assume no responsibility as to laws or judicial decisions related to, or any orders, consents or other authorizations or approvals as may be required by, any federal laws, rules or regulations, including, without limitation, any federal securities laws, rules or regulations, or any state securities or “blue sky” laws, rules or regulations. Based upon the foregoing and in reliance thereon, and having regard to legal considerations and other information that we deem relevant, we are of the opinion that if, when and to the extent any Plan Shares are issued and sold by the Company in accordance with the terms and conditions of, and in the manner contemplated by, the Plan, including payment in full to the Company of the consideration for such Plan Shares in an amount determined by the Company’s board of directors under Indiana law to be adequate at the time of sale, such Plan Shares will be validly issued, fully paid and nonassessable.
MediaCo Holding Inc. April 1, 2026 Page Three The opinion expressed herein is based upon the applicable laws of the State of Indiana and the facts in existence on the date hereof. In delivering this opinion letter to you, we disclaim any obligation to update or supplement the opinion set forth herein or to apprise you of any changes in any laws or facts after the later of the date hereof and the filing date of Registration Statement. No opinion is offered or implied as to any matter, and no inference may be drawn, beyond the strict scope of the specific issues expressly addressed by the opinion set forth herein. We hereby consent to the filing of this opinion letter as an exhibit to the Registration Statement relating to the Plan Shares. In giving such consent, we do not admit that we are in the category of persons whose consent is required under Section 7 of the Act or the rules and regulations of the Commission promulgated thereunder. This opinion is intended solely for use in connection with the issuance and sale of the Shares subject to the Plan and the Registration Statement and is not to be relied upon for any other purpose. Sincerely, BOSE McKINNEY & EVANS LLP