Document:

EX-10.1

 Exhibit 10.1 

EXECUTION VERSION 

AMENDMENT NO. 4 AND WAIVER TO AMENDED AND RESTATED 

TERM LOAN AGREEMENT 

AMENDMENT NO. 4 AND WAIVER TO AMENDED AND RESTATED TERM LOAN AGREEMENT, dated as of May 19, 2021, and effective March 31, 2021 (this
“Amendment No. 4”), is by and among MEDIACO HOLDING INC., an Indiana corporation (“MediaCo”), MEDIACO WQHT LICENSE LLC, an Indiana limited liability company (“MediaCo WQHT”) and
MEDIACO WBLS LICENSE LLC, an Indiana limited liability company (“MediaCo WBLS”), FMG Kentucky, LLC, a Delaware limited liability company (“FMG Kentucky”), Fairway Outdoor LLC, a Delaware limited liability company
(“Fairway”) and FMG Valdosta, LLC, a Delaware limited liability company (“FMG Valdosta”) the other Persons party hereto that are designated as “Borrowers” (collectively with MediaCo, MediaCo WQHT, MediaCo
WBLS, FMG Kentucky, Fairway and FMG Valdosta, the “Borrowers” and each a “Borrower”), GACP FINANCE CO., LLC, a Delaware limited liability company (in its individual capacity, “GACP”), as
administrative agent and collateral agent (in such capacities, the “Term Agent”) for the financial institutions from time to time party to this Agreement (collectively, the “Lenders” and individually each a
“Lender”) and for itself, and the Lenders. 
 W I T N E S S E
T H : 
 WHEREAS, Term Agent, Lenders, Borrowers and others have entered into financing arrangements pursuant to which Lenders
(or Term Agent on behalf of Lenders) have made loans and advances and provide other financial accommodations to Borrowers as set forth in the Amended and Restated Term Loan Agreement, dated as of December 13, 2019, (a) as amended by that
certain Amendment No. 1 and Waiver to Amended and Restated Term Loan Agreement (“Amendment No. 1”), dated as of February 28, 2020, (b) as supplemented by that certain Borrower Joinder Agreement, dated as
of March 13, 2020, (c) as amended by that certain Amendment No. 2 to Amended and Restated Term Loan Agreement (“Amendment No. 2”), dated as of March 27, 2020, (d) as amended by that certain
Amendment No. 3 to Amended and Restated Term Loan Agreement (“Amendment No. 3”), dated August 28, 2020 and (e) as modified by that certain Forbearance Agreement dated May 18, 2021 (the
“Forbearance Agreement”) (as may be further amended, restated and otherwise modified prior to the date hereof, the “Loan Agreement”) and the other Loan Documents; 

WHEREAS, as of the date hereof, Events of Default have occurred, or will have occurred as of May 30, 2021, as described on Exhibit
A hereto (the “Specified Events of Default”); 
 WHEREAS, Borrowers have requested that the Lenders and Term Agent make
certain amendments set forth in Section 2 below, including, inter alia, (1) modifying the amortization schedule, (2) modifying the advance rates for the Billboard Borrowing Base and Radio Borrowing Base, (3) modifying the
requirements for compliance with the Consolidated Fixed Charge Coverage Ratio in Section 5.22 and (4) modifying the definition of Consolidated Fixed Charge Coverage Ratio and the terms of compliance therewith; 

WHEREAS, Borrowers, Lenders and Term Agent have agreed to waive the Specified Events of Default and make certain additional amendments to the
Loan Agreement on the terms set forth herein; 
 WHEREAS, Section 8.1 of the Loan Agreement provides that, among other things, the
Borrowers and the Lenders may make certain amendments to the Loan Agreement and the other Loan Documents for certain purposes; and 

WHEREAS, by this Amendment No. 4, Term Agent, Lenders signatory hereto and Borrowers intend to evidence and effect such amendments; 

 

 NOW, THEREFORE, in consideration of the foregoing and the mutual agreements and covenants
contained herein, the parties hereto agree as follows: 
 1. Interpretation. For purposes of this Amendment No. 4, all terms used
herein which are not otherwise defined herein, including, but not limited to, those terms used in the recitals hereto, shall have the respective meanings assigned thereto in the Loan Agreement as amended by this Amendment No. 4. 

2. Amendments 
 (a)
Section 1.3(b) of the Loan Agreement is hereby amended and restated in its entirety to read as follows: 
 “(b) Interest on the
Term Loan (other than interest payable at the PIK Rate) shall be paid in cash in arrears on each Interest Payment Date. Interest on the Term Loan payable at the PIK Rate shall be paid in kind and added to the aggregate outstanding principal amount
of the Term Loan on each Interest Payment Date. Interest shall also be paid in cash (i) on the date of any payment or prepayment of the Term Loan (on the amount so paid or prepaid) (other than interest payable at the PIK Rate) and (ii) on
the Termination Date. Interest payable at the PIK Rate shall be paid in kind and added to the aggregate outstanding principal amount of the Term Loan on the date of any payment or prepayment of the Term Loan (on the amount so paid or prepaid).”

 (b) Clause (ii) of the proviso in the first sentence of Section 1.5(a) of the Loan Agreement is hereby amended and restated in
its entirety to read as follows: 
 “(ii) except for any such prepayment of an amount up to $3,000,000 made in respect of the Fourth
Amendment Prepayment, such prepayment shall be accompanied by interest on the amount so prepaid and any related Early Termination Fee.” 

(c) Section 1.6(a) of the Loan Agreement is hereby amended and restated in its entirety to read as follows: 

“(a) Repayment of the Term Loan. Beginning with the Fiscal Quarter ending June 30, 2022 and on the last day of each calendar
quarter thereafter (or, if such date is not a Business Day, on the immediately preceding Business Day), the Borrowers shall make quarterly payments of principal on the Term Loans in an amount equal to one and one quarter percent (1.25%) of the
initial aggregate principal amount of the Term Loans.” 
 (d) Section 5.5(k) of the Loan Agreement is hereby amended and restated
in its entirety to read as follows: 
 “(k) Indebtedness of the Borrower Representative owed to SG Broadcasting under the SG
Broadcasting Subordinated Notes, provided that the aggregate original principal amount of such Indebtedness shall not exceed $23,250,0001; provided further that following the June
2021 Contribution, the aggregate original principal amount of such Indebtedness shall not exceed $24,250,0002; provided further that if the Fourth Amendment Backstop Contributions are
contributed, the aggregate original principal amount of Indebtedness permitted to be incurred under this clause (k) shall increase by the amount so incurred up to an additional $3,000,000 such that the total aggregate original principal amount
of Indebtedness to be incurred under this clause shall not exceed $27,250,000.” 
  

	1 	 NTD – Includes $3M prepayment. 

	2 	 NTD – Includes $1M June 2021 Contribution.

  
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 (e) Section 5.22(b) of the Loan Agreement is hereby amended and restated in its
entirety to read as follows: 
 “(b) Minimum Consolidated Fixed Charge Coverage Ratio. The Borrowers shall not permit the
Consolidated Fixed Charge Coverage Ratio, measured as of the last day of any Fiscal Quarter of the Borrowers, to be less than (i) 1.10 to 1.00, through and including March 31, 2020, (ii) 1.00 to 1.00, on and after April 1, 2020 through and
including December 31, 2022, and (iii) 1.10 to 1.00, on and after January 1, 2023.” 
 (f) Section 6.1(p) of the Loan
Agreement is hereby amended and restated in its entirety to read as follows: 
 “(p) Borrowers shall fail to satisfy the requirements
set forth in (x) Sections 5 and 6 of Amendment No. 1, (y) Section 6 of Amendment No. 3 or (z) Section 6 of Amendment No. 4, in each case, on or before the date specified therein or such later date as determined by
the Term Agent in its sole discretion.” 
 (g) The following definitions set forth in Section 10.1 of the Loan Agreement are
hereby amended and restated in their entirety to read as follows:     
 “Applicable BCF
Multiple” means, with respect to Billboard Cash Flow of the Borrowers attributable to billboards, 5.0. 

“Applicable Margin” means (a) seven and one half percent (7.50%) per annum plus,
(b) commencing on the Amendment No. 4 Execution Date, if applicable, the PIK Rate. 
 “Consolidated Fixed
Charge Coverage Ratio” means, for any period, the ratio of (a) Consolidated EBITDA (including amounts that are: (x) contributed as Indebtedness of the Borrower Representative owed to SG Broadcasting to the extent permitted to be
incurred by this Agreement (including the SG Broadcasting Subordinated Notes (including any SG Broadcasting Subordinated Notes issued after the date hereof to evidence any amount of the Post-Fourth Amendment Effective Date Contributions contributed
as Subordinated Indebtedness)) or (y) contributed to the Borrower in the form of cash equity contributions from SG Broadcasting, and excluding amounts used for the repayment of Indebtedness (other than the Fourth Amendment Prepayment and the
repayment of principal under the Term Loans pursuant to Section 1.6(a) of this Agreement; for the avoidance of doubt, any amounts used to repay either the Emmis Radio Seller Note or the Emmis working capital loan that is guaranteed by SG
Broadcasting, shall not be added back to Consolidated EBITDA for purposes of this definition), plus without duplication and to the extent deducted in determining Consolidated Net Income for such period, the aggregate amount of (1) each
“Amendment Fee” paid in kind and/or paid in cash, as applicable, and (2) reasonable and documented legal fees, in the case of each of clauses (1) and (2), pursuant to the terms of and as defined in each of Amendment No. 2,
Amendment No. 3 and Amendment No. 4, to (b) the sum of (i) Consolidated Interest Expense paid or payable in cash by Borrowers during such period (excluding, for the avoidance of doubt, any interest paid in kind and added to the
aggregate outstanding principal amount of the Term Loan pursuant to Section 1.3(b)), plus (ii) all scheduled principal payments made by Borrowers during such period on account of Indebtedness

  
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(including, without limitation, obligations with respect to Capital Leases, but excluding all voluntary and mandatory prepayments and all principal payments made in connection with any revolving
credit facility which do not result in a permanent reduction of such facility), plus (iii) Restricted Payments paid in cash by MediaCo during such period, in each case determined in accordance with GAAP to the extent applicable,
plus (iv) Unfinanced Capital Expenditures paid in cash by Borrowers during such period, plus (v) the aggregate amount (but not less than $0) of federal, state, local and foreign income taxes paid in cash by Borrowers during
such period provided that, notwithstanding anything to the contrary contained herein, solely for the purpose of calculating the Consolidated Fixed Charge Coverage Ratio for any period ending prior to the first anniversary of the Original
Closing Date, the amount of the items set forth in clauses (b)(i) and (b)(ii) above shall be calculated for the period from the Original Closing Date through and including the date of determination and multiplied by a fraction, the numerator of
which is 365 and the denominator of which is the number of days in such period. 
 “Radio Borrowing Base”
means, as of any date of determination, the result of: 
 (a) 70% of the appraised value of the Emmis FCC Licenses based on the most
recently delivered Acceptable Appraisal, less 
 (b) Reserves. 

“SG Broadcasting Subordinated Note” means each of (x) Second Amended and Restated Unsecured Promissory
Note, dated as of March 27, 2020, made by MediaCo to SG Broadcasting, in the original principal amount of $20,000,000, (y) Amended and Restated Unsecured Convertible Promissory Note, dated December 8, 2020, made by MediaCo to SG
Broadcasting, in the original principal amount of $250,000 and (z) if the Post-Fourth Amendment Effective Date Contributions are contributed as Subordinated Indebtedness, any unsecured promissory note or notes issued evidencing such Post-Fourth
Amendment Effective Date Contributions in the original principal amount of up to $4,000,000 collectively. 
 “SG
Broadcasting Subordinated Note Subordination Agreement” means the Third Amended and Restated Shareholder Note Subordination Agreement, dated as of May 19, 2021, by and between SG Broadcasting and the Term Agent.” 

(h) The following definitions shall be added to Section 10.1 of the Loan Agreement in proper alphabetical order: 

“ “Amendment No. 4” means the Amendment No. 4 to Amended and Restated Term Loan Agreement, dated
as of the Amendment No. 4 Execution Date and effective as of March 31, 2021, by and among the Borrowers, the Term Agent and the lenders party thereto. 

“Amendment No. 4 Execution Date” means May 19, 2021. 

“Fourth Amendment Backstop Contributions” has the meaning set forth in Amendment No. 4. 

“June 2021 Contribution” has the meaning set forth in Amendment No. 4. 

  
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 “PIK Rate” means, at all times when (x) the advance
rate set forth in clause (a) of the definition of Radio Borrowing Base must be in excess of 60% or (y) the Applicable BCF Multiple must be in excess of 3.50, in either case, to achieve minimal compliance with the covenant set forth in
Section 5.21, one percent (1.00%). 
 “Post-Fourth Amendment Effective Date
Contributions” has the meaning set forth in Amendment No. 4.” 
 3. Waiver. Subject to the satisfaction of the
conditions set forth in Section 5 below and in reliance upon the representations and warranties set forth in Section 4 below, Term Agent and Lenders hereby waive the Specified Events of Default. For the avoidance of doubt, the foregoing
waiver shall not be deemed to be a waiver of any other existing or hereafter arising Defaults or Events of Default or any other deviation from the express terms of the Loan Agreement or any other Loan Document. This is a limited waiver and shall not
be deemed to constitute a consent or waiver of any other term, provision or condition of the Loan Agreement or any other Loan Document, as applicable, or to prejudice any right or remedy that Term Agent or any Lender may now have or may have in the
future under or in connection with the Loan Agreement or any other Loan Document. 
 4. Representations and Warranties. Each Loan
Party, jointly and severally, hereby: 
 (a) reaffirms all representations and warranties made to Term Agent and Lenders under the Loan
Agreement and all of the other Loan Documents and confirms that all are true and correct in all material respects as of the date hereof except to the extent that (i) such representations or warranties are qualified by a materiality standard, in
which case they shall be true and correct in all respects and (ii) such representations or warranties expressly relate to an earlier date (in which case such representations and warranties shall be true and correct in all material respects as
of such earlier date (or, if such representations or warranties are qualified by a materiality standard, in all respects as of such earlier date)); 

(b) reaffirms all of the covenants contained in the Loan Agreement; 

(c) represents and warrants that, after giving effect to this Agreement, no Default or Event of Default has occurred and is continuing; 

(d) represents and warrants that the execution, delivery and performance by each Loan Party of this Amendment No. 4 and the other
documents, agreements and instruments executed by any Loan Party in connection herewith (collectively, together with this Amendment No. 4, the “Amendment Documents”) and the consummation of the transactions contemplated hereby
or thereby, are within such Loan Party’s powers, have been duly authorized by all necessary organizational action, and do not contravene (i) the charter or by-laws or other organizational or
governing documents of such Loan Party or (ii) any law or any contractual restriction binding on or affecting any Loan Party, except, for purposes of this clause (ii), to the extent such contravention would not reasonably be expected to have a
Material Adverse Effect; 
 (e) represents and warrants that no authorization or approval or other action by, and no notice to or filing
with, any Governmental Authority or any other third party is required for the due execution, delivery and performance by any Loan Party of any Amendment Document to which it is a party that has not already been obtained if the failure to obtain such
authorization, approval or other action could reasonably be expected to result in a Material Adverse Effect; and 
 (f) represents and
warrants that each Amendment Document has been duly executed and delivered by each Loan Party thereto. This Amendment No. 4 constitutes, and each other Amendment Document will constitute upon execution, the legal, valid and binding obligation
of each Loan Party thereto enforceable against such Loan Party in accordance with its respective terms subject to the effect of any applicable bankruptcy, insolvency, reorganization or moratorium or similar laws affecting the rights of creditors
generally and subject to general principles of equity (regardless of whether enforcement is sought in a proceeding at law or in equity). 

  
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 5. Conditions Precedent. This Amendment No. 4 shall be effective upon the
satisfaction of each of the following conditions precedent (the “Fourth Amendment Effective Date”): 
 (a) Term Agent shall
have received counterparts of this Amendment No. 4, duly authorized, executed and delivered by Borrowers, Term Agent and the Lenders; 

(b) Term Agent shall have received counterparts of the Third Amended and Restated Shareholder Note Subordination Agreement, duly authorized,
executed and delivered by Borrowers and Term Agent in form and substance reasonably acceptable to Term Agent; 
 (c) No Default or Event of
Default shall have occurred and be continuing; 
 (d) The Borrowers shall have reimbursed the Term Agent, for all reasonable and documented
fees, costs and expenses incurred through the Fourth Amendment Effective Date (including, without limitation, Attorney Costs related to the preparation, negotiation, execution, delivery of this Amendment No. 4); 

(e) Term Agent shall have evidence that each of the Loan Parties is in good standing in its respective jurisdiction of organization; 

(f) Term Agent shall have received a certificate of an Authorized Officer of the Borrower dated as of the Fourth Amendment Effective Date
certifying the representations set forth in Section 4 hereof; 
 (g) Borrower shall have repaid an aggregate principal amount of the
Term Loans in an amount equal to at least $3,000,000 (the “Fourth Amendment Prepayment”) since the Forbearance Effective Date as defined in the Forbearance Agreement; and 

(h) Borrower shall have paid the Amendment Fee (as defined below). 

6. Post-Closing Obligations. 

(a) Standard General Controlled Funds shall invest (the “Post-Fourth Amendment Effective Date Contributions”) (i) at least an
additional $1,000,000 in MediaCo and its Subsidiaries on or before June 1, 2021 (the “June 2021 Contribution”), and (ii) solely to the extent that either (I) Liquidity falls below $3,500,000 or (II) the
Consolidated Fixed Charge Coverage Ratio, is less than 1.00 to 1.00, in each case, at any time on or before June 30, 2022, the minimum amount necessary for (I) Liquidity to be greater than or equal to $3,500,000 and (II) the
Consolidated Fixed Charge Ratio to be greater than or equal to 1.00 to 1.00 after each such investment, up to an aggregate amount equal to the lesser of (x) $3,000,000 and (y) the amount resulting from $4,000,000 minus the amount of the June
2021 Contribution, in MediaCo and its Subsidiaries (the “Fourth Amendment Backstop Contributions”), in the case of each of clauses (i) and (ii), in the form of Subordinated Indebtedness, it being understood that such
Subordinated Indebtedness shall be evidenced by a subordinated note substantially in the form of the existing SG Broadcasting Subordinated Notes or otherwise in a form satisfactory to the Term Agent. 

(b) On or prior to May 31, 2021, the Borrower shall cause Ernst & Young LLP to deliver an unqualified opinion on the audited
annual financial statements for the Fiscal Year ended December 31, 2020. For the avoidance of doubt, the parties acknowledge and agree that such opinion may be dual-dated. 

  
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 7. Amendment Fee. An amendment fee equal to 0.50% of the aggregate outstanding
principal amount of the Term Loan (the “Amendment Fee”) shall be paid in cash, which Amendment Fee shall be fully earned on the Fourth Amendment Effective Date and shall not be refundable for any reason whatsoever. 

8. General. 
 (a) Effect
of this Amendment No. 4. Except as expressly provided herein, no other consents, waivers, changes or modifications to the Loan Documents are intended or implied, and in all other respects the Loan Documents are hereby
specifically ratified, restated and confirmed by all parties hereto as of the date hereof. 
 (b) Expenses. Borrowers agree to pay on
demand all expenses of Term Agent and Lenders in connection with the administration of this Amendment No. 4 in accordance with Section 8.5 of the Loan Agreement. 

(c) Governing Law. This Amendment No. 4 shall be governed by, and construed in accordance with, the laws of the State of New York,
without regard to conflicts of laws principles thereof. 
 (d) Submission to Jurisdiction; Service of Process; Waiver of Jury Trial.
SECTIONS 8.18(a) THROUGH (d) AND SECTION 8.19 OF THE LOAN AGREEMENT ARE HEREBY INCORPORATED BY REFERENCE INTO THIS AMENDMENT NO. 4 MUTATIS MUTANDIS AND SHALL APPLY HERETO AS IF ORIGINALLY MADE A PART HEREOF. 

(e) Binding Effect. This Amendment No. 4 shall bind and inure to the benefit of the respective successors and permitted assigns of
each of the parties hereto. 
 (f) Counterparts, etc. This Amendment No. 4 may be executed in any number of counterparts and by
different parties hereto in separate counterparts, each of which when so executed shall be deemed to be an original and all of which taken together shall constitute one and the same agreement. Delivery of an executed counterpart of a signature page
to this Amendment No. 4 by telecopier or by electronic transmission of a pdf formatted counterpart shall be effective as delivery of a manually executed counterpart of this Amendment No. 4. 

(g) Financing Document. This Amendment No. 4 constitutes a Loan Document. 

(h) Reaffirmation. Each of the undersigned Loan Parties acknowledges (i) all of its Obligations under the Loan Agreement and each
other Loan Document to which it is a party are reaffirmed and remain in full force and effect on a continuous basis, (ii) its grant of security interests pursuant to the Loan Documents are reaffirmed and remain in full force and effect after
giving effect to this Amendment No. 4, (iii) the Obligations include, among other things and without limitation, the due and punctual payment of the principal of, interest on, and premium (if any) on, the Obligations and (iv) the execution
of this Amendment No. 4 shall not operate as a waiver of any right, power or remedy of Term Agent or any other Secured Party, constitute a waiver of any provision of any of the Loan Documents or serve to effect a novation of the Obligations.

 (i) Release. In consideration of the agreements of Term Agent and Lenders contained herein and for other good and valuable
consideration, the receipt and sufficiency of which is hereby acknowledged, each Borrower, on behalf of itself and its respective successors, assigns, and other legal representatives, hereby absolutely, unconditionally and irrevocably releases,
remises and forever discharges Term Agent and Lenders, and their successors and assigns, and their present and former shareholders, affiliates, subsidiaries, divisions, predecessors, directors, officers, attorneys, employees, agents and other

  
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representatives (Term Agent, each Lender and all such other Persons being hereinafter referred to collectively as the “Releasees” and individually as a
“Releasee”), of and from all demands, actions, causes of action, suits, covenants, contracts, controversies, agreements, promises, sums of money, accounts, bills, reckonings, damages and any and all other claims, counterclaims,
defenses, rights of set off, demands and liabilities whatsoever (individually, a “Claim” and collectively, “Claims”) of every name and nature, known as of the date of this Amendment No. 4, both at law and in
equity, which each Borrower, or any of its respective successors, assigns, or other legal representatives may now or hereafter own, hold, have or claim to have against the Releasees or any of them for, upon, or by reason of any circumstance, action,
cause or thing whatsoever which arises at any time on or prior to the day and date of this Amendment No. 4, in each case for or on account of, or in relation to, or in any way in connection with any of the Loan Agreement, or any of the other
Loan Documents or transactions thereunder or related thereto. 
 [Signature Pages Follow] 

  
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 IN WITNESS WHEREOF, the parties hereto have caused this Amendment No. 4 to be duly
executed and delivered by their authorized officers as of the day and year first above written. 
  

			
	BORROWERS:
	
	MEDIACO HOLDING INC., as the Borrower Representative and a Borrower
		
	By:	 	 /s/ Ryan A. Hornaday

		 	Name: Ryan A. Hornaday
		 	Title: Executive Vice President, Chief Financial Officer and Treasurer

 
			
	
	MEDIACO WQHT LICENSE LLC
	MEDIACO WBLS LICENSE LLC
	FAIRWAY OUTDOOR LLC, each as a Borrower
	Each By: MEDIACO HOLDING INC.,
		 	its sole member and manager
		
	Each By:	 	 /s/ Ryan A. Hornaday

		 	Name: Ryan A. Hornaday
		 	Title: Executive Vice President, Chief Financial Officer and Treasurer
	
	FMG KENTUCKY, LLC
	FMG VALDOSTA, LLC, each as a Borrower
	Each By: FAIRWAY OUTDOOR LLC,
		 	its sole member and manager
		
	Each By:	 	 /s/ Ryan A. Hornaday

		 	Name: Ryan A. Hornaday
		 	Title: Treasurer

  

	
	 Amendment No. 4 to Amended and Restated

Loan Agreement

 
			
	GACP FINANCE CO., LLC, as Term Agent
		
	By:	 	 /s/ Robert Louzan

	Name: Robert Louzan
	Title: Authorized Person
	
	GACP II, L.P., as a Lender
		
	By:	 	 /s/ Robert Louzan

	Name: Robert Louzan
	Title: Authorized Person

  

	
	 Amendment No. 4 to Amended and Restated

Loan Agreement

 
			
	HANMI BANK, as a Lender
		
	By:	 	 /s/ Jay Kim

	Name: Jay Kim
	Title:	 	EVP & Regional Chief Banking Officer

  

	
	 Amendment No. 4 to Amended and Restated

Loan Agreement

 EXHIBIT A 

SPECIFIED EVENTS OF DEFAULT 
  

	1.	 An Event of Default under Section 6.1(c) of the Loan Agreement due to the Borrower’s delivery and/or
filing of its audited annual financial statements for the Fiscal Year ended December 31, 2020, certified with a going concern qualification whereas Section 4.1(a) of the Loan Agreement required such audited annual financial statements to
be certified without a going concern or like qualification or exception. 

  

	2.	 An Event of Default under Section 6.1(c) of the Loan Agreement due to the Borrower’s redemption of
7,862 shares of Class A common stock held by an employee on March 31, 2021, during the continuance of an Event of Default, whereas Section 5.10(e) of the Loan Agreement required that no Event of Default have occurred and be continuing
upon any such redemption. 

  

	3.	 An Event of Default under Section 6.1(c) of the Loan Agreement due to the Borrower’s failure to
deliver its unaudited financial statements for the Fiscal Months ended February 28, 2021, March 31, 2021, and April 30, 2021, required to be delivered under Section 4.1(b) of the Loan Agreement. 

 

	4.	 An Event of Default under Section 6.1(c) of the Loan Agreement due to the Borrower’s failure to
deliver its unaudited financial statements for the Fiscal Quarter ended March 31, 2021, required to be delivered under Section 4.1(c) of the Loan Agreement. 

 

	5.	 An Event of Default under Section 6.1(c) of the Loan Agreement due to the Borrower’s failure to
deliver a Compliance Certificate for the Fiscal Year ended December 31, 2020, required to be delivered under Section 4.2(b) of the Loan Agreement. 

  

	6.	 An Event of Default under Section 6.1(c) of the Loan Agreement due to the Borrower’s failure to
deliver a Compliance Certificate for the Fiscal Months ended February 28, 2021, March 31, 2021, and April 30, 2021, required to be delivered under Section 4.2(b) of the Loan Agreement. 

 

	7.	 An Event of Default under Section 6.1(c) of the Loan Agreement due to the Borrower’s failure to
deliver a Compliance Certificate for the Fiscal Quarter ended March 31, 2021, required to be delivered under Section 4.2(b) of the Loan Agreement. 

  
 Exhibit AEX-10.2

 Exhibit 10.2 

THIS INSTRUMENT AND THE RIGHTS AND OBLIGATIONS EVIDENCED HEREBY ARE SUBORDINATE IN THE MANNER AND TO THE EXTENT SET FORTH IN THAT CERTAIN
THIRD AMENDED AND RESTATED SHAREHOLDER NOTE SUBORDINATION AGREEMENT (AS AMENDED, MODIFIED, RESTATED OR REPLACED FROM TIME TO TIME, THE “SUBORDINATION AGREEMENT”), DATED AS OF MAY 19, 2021, BETWEEN SG BROADCASTING LLC AND GACP FINANCE
CO., LLC, IN ITS CAPACITY AS AGENT. NOTWITHSTANDING ANY CONTRARY STATEMENT CONTAINED IN THE WITHIN INSTRUMENT, NO PAYMENT ON ACCOUNT OF THE PRINCIPAL THEREOF OR INTEREST THEREON SHALL BECOME DUE OR PAYABLE EXCEPT IN ACCORDANCE WITH THE EXPRESS TERMS
OF THE SUBORDINATION AGREEMENT. 
 THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY COMPARABLE
STATE SECURITIES LAW. EXCEPT AS EXPRESSLY PROVIDED HEREIN, NEITHER THIS NOTE NOR ANY PORTION HEREOF OR INTEREST HEREIN MAY BE SOLD, ASSIGNED, TRANSFERRED, PLEDGED OR OTHERWISE DISPOSED OF UNLESS THE SAME IS REGISTERED UNDER SAID ACT AND APPLICABLE
STATE SECURITIES LAWS OR UNLESS AN EXEMPTION FROM SUCH REGISTRATION IS AVAILABLE AND THE COMPANY HAS RECEIVED EVIDENCE OF SUCH EXEMPTION REASONABLY SATISFACTORY TO THE COMPANY. 

MEDIACO HOLDING INC. 

UNSECURED CONVERTIBLE PROMISSORY NOTE 
  

					
	 May 19, 2021
	  	$	7,000,000.00	 

 MediaCo Holding Inc., an Indiana corporation (the “Company”), hereby promises to pay to SG
Broadcasting LLC, a Delaware limited liability company (the “Holder”), the principal amount of up to $7,000,000.00 (the “Outstanding Principal Amount”), together with interest thereon calculated from the date hereof
in accordance with the provisions of this Unsecured Convertible Promissory Note (as amended, amended and restated, modified or supplemented, this “Note”). Except as defined in Section 6 hereof or unless
otherwise indicated herein, capitalized terms used in this Note have the same meanings set forth in the Contribution Agreement. 
 1. Interest
Accrual and Payment. Subject to Section 4(b)(ii) below, interest shall accrue on the principal sums outstanding at a rate per annum equal to the Base Rate, plus an increase of 1.00% following the second anniversary
of the Original Unsecured Note Issuance Date and additional increases of 1.00% following each anniversary of the Original Unsecured Note Issuance Date thereafter (the “Applicable Interest”). The Applicable Interest shall become due
and payable in accordance with Section 2. Any accrued interest which for any reason has not theretofore been paid shall be paid in full on the Maturity Date.

2. Payment of Principal and Interest on Note. 

(a) Scheduled Payments. The Company shall pay the Applicable Interest solely in kind annually on the date of this Note, with such
interest shall be added to the principal amount of this Note on such payment date. The Company shall pay the entire principal amount of this Note, together with all accrued interest thereon, on the Maturity Date or such earlier date as required by
the terms hereof. 
  

 (b) Optional Prepayments. The Company may, at any time and from time to time, no
later than five (5) days after providing notice thereof to the Holder, without premium or penalty, prepay all or any portion of the outstanding principal amount of, or interest on, this Note; provided that such prepayment is not prohibited by
Section 3 hereof or any applicable subordination agreement executed by the Holder. In connection with each prepayment of principal hereunder, the Company shall also pay all then accrued and unpaid interest hereunder. 

(c) Mandatory Prepayments. Upon the first to occur of (i) a Sale of the Company or (ii) a Change of Control, the Company shall
pay the outstanding principal amount of this Note, together with all accrued and unpaid interest on the principal amount being repaid. 
 (d)
Application of Payments. Payments under this Note shall be applied (i) first, to the payment of then accrued interest hereunder until all such interest is paid and (ii) second, to the repayment of the principal outstanding
hereunder.  
 3. Subordination. If at any time a Senior Lender requires this Note to be subordinated to such Senior
Lender’s Company Senior Debt, Holder hereby agrees to subordinate this Note to such Senior Lender’s Company Senior Debt upon commercially reasonable terms and conditions and execute all documents, including any amendments to this Note,
requested by such Senior Lender to evidence such subordination. Such subordination agreement shall permit payments pursuant to Section 1 hereof. 

4. Events of Default. 
 (a)
Definition. For purposes of this Note, an “Event of Default” shall be deemed to have occurred if: 
 (i) subject to any
applicable subordination agreement executed by the Holder and the Company Senior Debt, the Company fails to pay the full principal amount of this Note together with accrued and unpaid interest thereon on the date the same becomes due and payable
hereunder, and such failure to pay is not cured within fifteen (15) days after the occurrence thereof; 
 (ii) the Company fails to
comply with any other provision of this Note and such failure is not cured within thirty (30) days after the occurrence thereof; or 

(iii) an Insolvency Event occurs. 
 The foregoing
shall constitute Events of Default whatever the reason or cause for any such Event of Default and whether it is voluntary or involuntary or is effected by operation of law or pursuant to any judgment, decree or order of any court of competent
jurisdiction or any order, rule or regulation of any administrative or governmental body having jurisdiction therein. 
 (b) Consequences
of Events of Default. 
 (i) Subject to Section 3 above, any applicable subordination agreement executed by the
Holder, and the Company Senior Debt, if an Event of Default other than of the type described in Section 4(a)(ii) has occurred, the Holder may declare the aggregate principal amount of this Note (together with all accrued
interest thereon and all other amounts due and payable with respect thereto, including without limitation all interest accrued pursuant to Section 4(b)(ii), below) to be immediately due and payable and the Company shall
immediately thereafter pay to the Holder all amounts due and payable with respect to this Note. 

  
 2 

 (ii) Upon and during the continuance of an Event of Default, the Applicable Interest shall
be equal to the Base Rate plus four percentage points (4.0%). 
 (iii) Subject to Section 3 above, any applicable
subordination agreement executed by the Holder, and the Company Senior Debt, the Holder shall also have any other rights which the Holder may have pursuant to applicable law. 

5. Conversion. 
 (a)
Optional Conversion. At any time after the issuance hereof, but subject to Section 5(c), all or a portion of the outstanding principal and any accrued but unpaid interest hereunder (the “Conversion
Amount”) shall be convertible, at the option of the Holder upon notice to the Company, into shares of the Class A Common Stock, par value $0.01 per share (the “Class A Stock”), of the Company, at a
conversion price equal to the 30-Day VWAP of the Class A Stock determined as of the Conversion Date (the “Conversion Price”); provided that, in no event shall the Conversion Price be less
than $0.50 per share of Class A Stock. The “Conversion Date” shall be the fifth (5th) Business Day after the date on which the Holder gives notice of such conversion. 

(b) Conversion Procedure; Effect of Conversion. If this Note is to be converted pursuant to Section 5(a), the
Holder shall surrender this Note (or a notice to the effect that the original Note has been lost, stolen or destroyed and an agreement acceptable to the Company whereby the Holder agrees to indemnify the Company from any loss incurred by it in
connection with this Note) for cancellation. Upon conversion of this Note in part, the Company shall reissue the Holder a replacement note in an amount equal to the aggregate of the outstanding amount and accrued but unpaid interest not included in
the Conversion Amount. Upon conversion of this Note in full and the payment of the amounts specified in this section, the Company shall be forever released from all of its obligations and liabilities under this Note, and this Note shall be deemed of
no further force or effect, whether or not the original of this Note has been delivered to the Company for cancellation. 
 (c) Limitation
on Conversion. Notwithstanding anything herein to the contrary, no shares of Class A Stock may be issued in connection with the conversion of this Note unless such issuance upon conversion receives the prior approval of the shareholders of
the Company. Unless such shareholder approval is obtained, this Note shall not be convertible, and the Company shall instead either (x) repay this Note in cash or (y) obtain shareholder approval of the issuance of shares of Class A
Stock prior to the issuance thereof. For the avoidance of doubt, this Section 5(c) shall be void and have no further effect immediately following such time as shareholders of the Company approve the issuance of shares of
Class A Stock pursuant to the conversion of this Note. 
 6. Definitions. For purposes of this Note, the following capitalized
terms have the following meaning. 
 “30-Day VWAP” means the price equal to the
average of the volume-weighted average prices of the Class A Stock on the Trading Market for the last thirty (30) Trading Days prior to the date of determination; provided, that if there is no Trading Market for any such 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
OTCMarkets. 
 “Base Rate” means the interest rate on the Company Senior Debt, or if no Company Senior Debt is outstanding,
6.00%. 

  
 3 

 “Business Day” means any day other than a Saturday, Sunday or other day on
which commercial banks are authorized or required to close under the laws of, or are in fact closed in the State of New York. 

“Capital Stock” means any and all shares, interests, participations, units or other equivalents (however designated) of
capital stock of a corporation, membership interests in a limited liability company, partnership interests of a limited partnership, any and all equivalent ownership interests in a Person, and in each case any and all warrants, rights or options to
purchase, and all conversion or exchange rights, voting rights, calls or rights of any character with respect to, any of the foregoing. 

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

(a) the SG Affiliates (taken as a whole) at any time ceasing (i) to own and control, directly or indirectly, beneficially and of record,
on a fully diluted basis, at least 51.0% on a fully diluted basis of the outstanding Voting Stock of the Company or (ii) to have or exercise the power to elect a majority of the board of directors or other managing body of the Company; 

(b) any “person” or “group” (within the meaning of Sections 13(d) and 14(d) of the Exchange Act) becoming the beneficial
owner (as defined in Rule 13d-3 under the Exchange Act), directly or indirectly, of a greater amount of Voting Stock of the Company than is owned and controlled, directly or indirectly, by the SG Affiliates
(taken as a whole); 
 (c) the completion of a sale of any Capital Stock of the Company pursuant to a registration statement which has become
effective under the Securities Act; or 
 (d) a “change of control” (or any comparable term or provision) (i) as defined in
any Company Senior Debt document, or any term of similar effect under any document executed in connection with any other Company Senior Debt document or (ii) under or with respect to any documents or agreements governing the Capital Stock of
the Company. 
 “Company Senior Debt” means all principal of, premium (if any), interest (including, without limitation,
interest accruing or that would have accrued but for the filing of a bankruptcy, reorganization or other insolvency proceeding whether or not such interest constitutes an allowable claim in such proceeding) on, and any and all other fees, expense
reimbursement obligations, and other amounts due pursuant to the terms of all agreements, documents and instruments providing for, creating, securing or evidencing or otherwise entered into in connection with (i) indebtedness for borrowed money
of the Company (including, without limitation, guarantees and other contingent obligations with respect to indebtedness for borrowed money of its Subsidiaries) of the type typically held by commercial banks, investment banks, insurance companies and
other recognized lending institutions, entities and funds or subsidiaries thereof, whether now outstanding or hereafter created, incurred, assumed or guaranteed which is not by its terms on parity with or subordinated to the Company’s
obligations under this Note, (ii) obligations evidenced by bonds, debentures, notes or similar instruments, or upon which interest payments are customarily made, of the type typically held by commercial banks, investment banks, insurance
companies and other recognized lending institutions, entities and funds or subsidiaries thereof, whether now outstanding or hereafter created, incurred, assumed or guaranteed which is not by its terms on parity with or subordinated to the
Company’s obligations under this Note, or (iii) capital leases and similar types of financing, together with renewals, extensions, refundings, refinancings, deferrals, restructurings, amendments and modifications of the items described in
(i), (ii), or (iii) above; provided that Company Senior Debt shall not include any of the foregoing to the extent owing to an Affiliate of the Company. 

  
 4 

 “Contribution Agreement” means that certain Contribution and Distribution
Agreement, dated as of June 28, 2019, as amended, amended and restated, modified or supplemented, by and among Emmis Communications Corporation, an Indiana corporation, the Holder and the other parties identified therein. 

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

 “Insolvency Event” means the occurrence of any of the following: (i) the Company makes a general assignment for the
benefit of creditors; (ii) an order, judgment or decree is entered adjudicating the Company bankrupt or insolvent; (iii) any order for relief with respect to the Company is entered under any applicable bankruptcy law; (iv) the Company
petitions or applies to any tribunal for the appointment of a custodian, trustee, receiver or liquidator of the Company or of any substantial part of the assets of the Company, or commences any proceeding relating to the Company under any
bankruptcy, reorganization, arrangement, insolvency, readjustment of debt, dissolution or liquidation law of any jurisdiction; or (v) any such petition or application is filed, or any such proceeding is commenced, against the Company and not
dismissed or stayed within 60 days. 
 “Maturity Date” means the date that is six (6) months after the fifth (5th) anniversary of the Original Unsecured Note Issuance Date. 
 “Original Unsecured
Note” means that certain Unsecured Convertible Promissory Note dated as of November 25, 2019, executed by the Company in favor of the Holder, as amended by that certain Amended and Restated Unsecured Convertible Promissory Note, dated
as of February 28, 2020 and that certain Second Amended and Restated Unsecured Convertible Promissory Note dated as of March 27, 2020. 

“Original Unsecured Note Issuance Date” means November 25, 2019. 

“Person” means an individual, a partnership, a corporation, a limited liability company, an association, a joint stock
company, a trust (including any beneficiary thereof), a joint venture, an unincorporated organization or a governmental entity or any department, agency or political subdivision thereof. 

“Sale of the Company” means the sale of the Company to a third party or group of third parties pursuant to which such party
or parties acquire all or substantially all of the assets or business of the Company on a consolidated basis. 
 “Securities
Act” means the Securities Act of 1933, as amended, and the rules and regulations promulgated thereunder. 
 “Senior
Lender” means any holders of Company Senior Debt. 
 “SG Affiliates” means Standard General, L.P. and the funds
for which is serves as an investment advisor and their respective Affiliates. 
 “Subsidiary” means, with respect to any
Person, any corporation, limited liability company, partnership, association or other business entity of which (i) if a corporation, a majority of the total voting power of shares of stock entitled (without regard to the occurrence of any
contingency) to vote in the election of directors, managers or trustees thereof is at the time owned or controlled, directly or indirectly, by that Person or one or more of the other Subsidiaries of that Person or a combination thereof, or
(ii) if a limited liability company, partnership, association or other business entity, a majority of the partnership or other similar ownership interest thereof is at the time owned or controlled, directly or indirectly, by that

  
 5 

 
Person or one or more Subsidiaries of that Person or a combination thereof. For purposes hereof, a Person or Persons shall be deemed to have a majority ownership interest in a limited liability
company, partnership, association or other business entity if such Person or Persons shall be allocated a majority of limited liability company, partnership, association or other business entity gains or losses or shall be or control any managing
director or general partner of such limited liability company, partnership, association or other business entity. 
 “Trading
Day” means (a) any day on which the Class A Stock is listed or quoted and traded on its Trading Market or (b) if the Class A Stock is not then listed or quoted and traded on any Trading Market, then a day on which
trading occurs on the Nasdaq Global Select Market (or any successor thereto). 
 “Trading Market” means the following
market(s) or exchange(s) on which the 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). 
 “Voting Stock” means, with respect to any
Person, shares of such Person’s Capital Stock having the right to vote for the election of directors (or Persons acting in a comparable capacity) of such Person under ordinary circumstances. 

7. Amendment and Waiver. Subject to any applicable subordination agreement, this Note may be amended only with the written consent of the
Company and the Holder. 
 8. Assignment and Transfer. Except as set forth below, the Holder shall not sell, assign, transfer, pledge,
hypothecate, mortgage, or otherwise encumber this Note; provided, however, that the Holder may assign or transfer all or any portion of this Note with the prior written consent of the Company, in its sole discretion (provided that any
such assignee agrees to be bound by and subject to the terms and conditions of this Note and any applicable subordination agreement executed by the Holder). The Company shall not assign its interest in this Note, either voluntarily or by operation
of law, without the prior written consent of the Holder; provided, that the Company shall be permitted to assign this Note to any Affiliate of equivalent or greater net worth as the Company at the time of such assignment. 

9. Cancellation. After all principal and then accrued interest at any time owed on this Note has been paid in full, this Note shall be
surrendered to the Company for cancellation and shall not be reissued. 
 10. Payments. All payments to be made to the Holder shall be
made in U.S. Dollars by check or wire transfer of immediately available funds. 
 11. Place of Payment. Payments of principal and
interest shall be delivered to the Holder at such address as is specified by timely prior written notice by the Holder. 
 12. Governing
Law. All questions concerning the construction, validity, and interpretation of this Note will be governed by and construed in accordance with the domestic laws of the State of New York, without giving effect to any choice of law or
conflicts of laws provision or rule (whether of the State of New York or any other jurisdiction) that would compel the application of the substantive laws of any jurisdiction other than the State of New York. 

13. Business Days. If any payment is due, or any time period for giving notice or taking action expires, on a day which is not a Business
Day, the payment shall be due and payable on, and the time period shall automatically be extended to, the next day Business Day, and interest shall continue to accrue at the required rate hereunder until any such payment is made. 

  
 6 

 14. Notice. The notice provisions set forth in Section 13.2 of the Contribution
Agreement are incorporated by reference in this Note and made a part hereof as if they were set forth herein. 
 15. Acknowledgement.
The Holder (a) is, by reason of its and its advisors’ business and financial experience, capable of evaluating the merits and risks of this Note and making an informed investment decision with respect hereto and with respect to the
Company’s ability to repay the Note, in each case without reliance upon any Affiliate of the Company, (b) has had full access to such other information (including the opportunity to ask questions and receive answers) concerning the Company
as the Holder has deemed appropriate, and has made its own investigation, without reliance upon the Company (other than as set forth in the Contribution Agreement and the documents referred to therein) or any of its Affiliates, into the business,
prospects, operations, property, financial, and other condition and creditworthiness of the Company, and (c) is able to bear the economic and financial risk of the Note. 

16. Usury Laws. It is the intention of the Company and the Holder to conform strictly to all applicable usury laws now or hereafter in
force, and any interest payable under this Note shall be subject to reduction to the amount not in excess of the maximum legal amount allowed under the applicable usury laws as now or hereafter construed by the courts having jurisdiction over such
matters. The aggregate of all interest (whether designated as interest, service charges, points, or otherwise) contracted for, chargeable, or receivable under this Note shall under no circumstances exceed the maximum legal rate upon the unpaid
principal balance of this Note remaining unpaid from time to time. If such interest does exceed the maximum legal rate, it shall be deemed a mistake and such excess shall be canceled automatically and, if theretofore paid, rebated to the Company or
credited on the principal amount of this Note, or if this Note has been repaid, then such excess shall be rebated to the Company. 
 17. Waiver
of Jury Trial. TO THE EXTENT PERMITTED BY APPLICABLE LAW, EACH OF THE PARTIES TO THIS NOTE HEREBY IRREVOCABLY WAIVES ALL RIGHT TO TRIAL BY JURY IN ANY ACTION, PROCEEDING OR COUNTERCLAIM ARISING OUT OF OR RELATING TO THIS NOTE OR THE
TRANSACTIONS CONTEMPLATED HEREBY. 
 18. Funding Commitments. The Holder hereby agrees to contribute to the Company $3,000,000 as of the
date hereof and $1,000,000 on or before June 1, 2021 (such $1,000,000 contribution, the “Second Contribution”). For the avoidance of doubt, the Second Contribution shall not be considered part of the Outstanding Principal Amount under
this Note until it is disbursed to the Company by the Holder pursuant to the terms of this Note. The additional $3,000,000 evidenced by this Note shall be committed through June 30, 2022, but shall be funded only if all or a portion of such
amount is disbursed by the Holder to the Company prior to such date (any such additional amount, a “Subsequent Contribution”). For the avoidance of doubt, no Subsequent Contribution shall be considered part of the Outstanding Principal
Amount under this Note until it is disbursed to the Company by the Holder pursuant to the terms of this Note. 
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INTENTIONALLY LEFT BLANK] 

  
 7 

 IN WITNESS WHEREOF, each of the Company and the Holder has executed and delivered
this Amended and Restated Unsecured Convertible Promissory Note on the date first above written. 
  

			
	MEDIACO HOLDING INC.
		
	By:	 	 /s/ J. Scott Enright

	Name: J. Scott Enright
	Title: Executive Vice President, General Counsel and Secretary

  

			
	ACCEPTED AND AGREED:
	
	SG BROADCASTING LLC
		
	By:	 	 /s/ Soohyung Kim

	Name: Soohyung Kim
	Title: Managing Member

 [Signature Page to Unsecured Convertible Promissory Note]

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