Document:

Exhibit 4.1

 Exhibit 4.1 

Execution Version 
 FIRST
SUPPLEMENTAL INDENTURE 
 First Supplemental Indenture (this “Supplemental Indenture”), dated as of January 2, 2019,
among Gray Television, Inc., a Georgia corporation (the “Company”), the parties that are signatories hereto as guarantors (each, a “Guaranteeing Subsidiary”) and U.S. Bank National Association, as trustee (in such
capacity, the “Trustee”) to the Indenture (as defined below). 
 W I T N E S S E T H 

WHEREAS, Gray Escrow, Inc. (the “Escrow Issuer”) has heretofore executed and delivered to the Trustee an indenture (the
“Indenture”), dated as of November 16, 2018, pursuant to which the Escrow Issuer has issued an aggregate principal amount of $750,000,000 of 7.000% Senior Notes due 2027 (the “Notes”); 

WHEREAS, the Indenture permits the Acquisition Transactions (including, without limitation, the merger of Escrow Issuer with and into the
Company on the Escrow Release Date upon the condition, among other things, that the Company and each Guaranteeing Subsidiary party hereto shall execute and deliver to the Trustee this Supplemental Indenture (i) which shall evidence the
assumption by the Company of all of the Escrow Issuer’s obligations under the Notes and the Indenture, in each case, on the terms and conditions set forth herein and under the Indenture and (ii) pursuant to which the Guaranteeing
Subsidiaries shall unconditionally guarantee all of the Company’s obligations under the Notes and the Indenture on the terms and conditions set forth herein and under the Indenture; and 

WHEREAS, pursuant to Section 9.01 of the Indenture, the Company, each Guaranteeing Subsidiary and the Trustee are authorized to execute
and deliver this Supplemental Indenture. 
 NOW THEREFORE, in consideration of the foregoing and for other good and valuable consideration,
the receipt of which is hereby acknowledged, the parties mutually covenant and agree for the equal and ratable benefit of the Holders of the Notes as follows: 

(1) Defined Terms. As used in this Supplemental Indenture, terms defined in the Indenture or in the preamble or recital
hereto are used herein as therein defined. The words “herein,” “hereof” and “hereby” and other words of similar import used in this Supplemental Indenture refer to this Supplemental Indenture as a whole and not to any
particular section hereof. 
 (2) Assumption of the Escrow Issuer’s Obligations. The Company hereby confirms
that, pursuant to the merger of the Escrow Issuer with and into the Company, occurring contemporaneous with the execution and delivery of this Supplemental Indenture, it has fully and unconditionally assumed the Escrow Issuer’s obligations
under the Indenture and the Notes on the terms and subject to the conditions set forth therein and to be bound by all other applicable provisions of the Indenture and to perform all of the obligations and agreements of the Escrow Issuer under the
Indenture. 
 (2) Agreement to be Bound. Each Guaranteeing Subsidiary hereby becomes a party to the Indenture as a
Subsidiary Guarantor and as such will have all of the rights and be subject to all of the obligations and agreements of a Subsidiary Guarantor under the Indenture. 

 (3) Guarantee. Each Guaranteeing Subsidiary agrees, on a joint and
several basis with all the other Subsidiary Guarantors, to provide an unconditional Subsidiary Guarantee on the terms and subject to the conditions set forth in Article XI of the Indenture. 

(4) Ratification of Indenture; Supplemental Indentures Part of Indenture. Except as expressly amended hereby, the
Indenture is in all respects ratified and confirmed and all the terms, conditions and provisions thereof shall remain in full force and effect. This Supplemental Indenture shall form a part of the Indenture for all purposes and every Holder of Notes
heretofore or hereafter authenticated and delivered shall be bound hereby. 
 (5) Governing Law. THIS SUPPLEMENTAL
INDENTURE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK, WITHOUT REGARD TO PRINCIPLES OF CONFLICTS OF LAW THAT WOULD INDICATE THE APPLICABILITY OF THE LAWS OF ANY OTHER JURISDICTION. 

(6) Counterparts. The parties may sign any number of copies of this Supplemental Indenture. Each signed copy shall be an
original, but all of them together represent the same agreement. 
 (7) Effect of Headings. The Section headings
herein are for convenience only and shall not affect the construction hereof. 
 (8) The Trustee. The Trustee shall
not be responsible in any manner whatsoever for or in respect of the validity or sufficiency of this Supplemental Indenture or for or in respect of the recitals contained herein, all of which recitals are made solely by the Guaranteeing Subsidiary.

 (9) Benefits Acknowledged. Each Guaranteeing Subsidiary’s Subsidiary Guarantee is subject to the terms and
conditions set forth in the Indenture. Each Guaranteeing Subsidiary acknowledges that it will receive direct and indirect benefits from the financing arrangements contemplated by the Indenture and this Supplemental Indenture and that the guarantee
and waivers made by it pursuant to this Subsidiary Guarantee are knowingly made in contemplation of such benefits. 
 (10)
Successors. All agreements of each Guaranteeing Subsidiary in this Supplemental Indenture shall bind its successors, except as otherwise provided in the Indenture. All agreements of the Trustee in this Supplemental Indenture shall bind its
successors. 
 (11) Execution and Delivery. Each Guaranteeing Subsidiary agrees that its Subsidiary Guarantee set
forth in Article XI of the Indenture shall remain in full force and effect notwithstanding any failure to endorse on each Note a notation of any such Subsidiary Guarantee. 

 IN WITNESS WHEREOF, the parties hereto have caused this Supplemental Indenture to be duly
executed, all as of the date first above written. 
  

			
	GRAY TELEVISION, INC.
		
	By:	 	 /s/ James C. Ryan

		 	Name: James C. Ryan
		 	 Title: Executive Vice President and Chief Financial

          Officer

  

			
	WVLT-TV, INC.
		
	By:	 	 /s/ James C. Ryan

		 	Name: James C. Ryan
		 	Title: Vice President and Chief Financial Officer

  

			
	GRAY TELEVISION GROUP, INC.
		
	By:	 	 /s/ James C. Ryan

		 	Name: James C. Ryan
		 	 Title: Executive Vice President and Chief Financial

          Officer

  

			
	GRAY TELEVISION LICENSEE, LLC
		
	By:	 	 /s/ James C. Ryan

		 	Name: James C. Ryan
		 	Title: Treasurer

 [Signature Page to First Supplemental Indenture to November 2018 Indenture] 

 
			
	RAYCOM MEDIA, INC.
	
	RAYCOM SPORTS NETWORK, INC.
	
	RAYCOM MEDIA LICENSEE, LLC
	
	KNIN LICENSE SUBSIDIARY, LLC 
	
	WBRC LICENSE SUBSIDIARY, LLC
	
	WFLX LICENSE SUBSIDIARY, LLC
	
	WVUE LICENSE SUBSIDIARY, LLC 
	
	WXIX LICENSE SUBSIDIARY, LLC
	
	KYOU RAYCOM LICENSE SUBSIDIARY, LLC
	
	TUPELO HONEY RAYCOM, LLC
		
	By:	 	 /s/ James C. Ryan

		 	Name: James C. Ryan
		 	Title: Treasurer

 [Signature Page to First Supplemental Indenture to November 2018 Indenture] 

 
			
	U.S. BANK NATIONAL ASSOCIATION, as Trustee
		
	By:	 	 /s/ Felicia H. Powell

		 	Name: Felicia H. Powell
		 	Title: Assistant Vice President

 [Signature Page to First Supplemental Indenture to November 2018 Indenture]Exhibit 4.2

 Exhibit 4.2 

FIRST SUPPLEMENTAL INDENTURE 

FIRST SUPPLEMENTAL INDENTURE (this “Supplemental Indenture”) dated as of January 2, 2019, among the parties that are
signatories hereto as guarantors (collectively, the “New Guarantors”), each a subsidiary of Gray Television, Inc. (or its successor), a Georgia corporation (the “Company”) and U.S. Bank National Association, a
national association under the laws of the United States, as trustee under the Indenture referred to below (the “Trustee”). 

W I T N E S S E T H 
 WHEREAS,
the Company and the subsidiaries of the Company existing as such on September 14, 2016 have heretofore executed and delivered to the Trustee an Indenture (the “Indenture”), dated as of September 14, 2016, providing for the
issuance of an aggregate principal amount of $525,000,000 of 5.125% Senior Notes due 2024 (the “Notes”); 
 WHEREAS,
Section 4.17 of the Indenture provides that under certain circumstances the Company is required to cause the New Guarantors to execute and deliver to the Trustee a supplemental indenture pursuant to which the New Guarantors shall
unconditionally guarantee all of the Company’s obligations under the Notes pursuant to a Guarantee on the terms and conditions set forth herein; 

WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee, the Company and the New Guarantors are authorized to execute and deliver
this Supplemental Indenture; and 
 WHEREAS, the Company and the New Guarantors have duly authorized the execution and delivery of this
Supplemental Indenture and all things necessary to make this Supplemental Indenture when executed by each of them a valid and binding agreement of the Company, the Subsidiary Guarantors and the New Guarantors have been done and performed. 

NOW THEREFORE, in consideration of the foregoing and for other good and valuable consideration, the receipt of which is hereby acknowledged,
the New Guarantors, the Company, the Subsidiary Guarantors and the Trustee mutually covenant and agree for the equal and ratable benefit of the holders of the Notes as follows: 

1. Agreement to Guarantee. The New Guarantors hereby agree, jointly and severally with the Subsidiary Guarantors, to unconditionally
guarantee the Company’s obligations under the Notes on the terms and subject to the conditions set forth in Article XI of the Indenture and to be bound by all other applicable provisions of the Indenture and the Notes. 

2. Ratification of Indenture; Supplemental Indentures Part of Indenture. Except as expressly amended hereby, the Indenture is in all
respects ratified and confirmed and all the terms, conditions and provisions thereof shall remain in full force and effect. This Supplemental Indenture shall form a part of the Indenture for all purposes, and every Holder heretofore or hereafter
authenticated and delivered shall be bound hereby. 
 3. GOVERNING LAW. THIS SUPPLEMENTAL INDENTURE SHALL BE GOVERNED BY, AND
CONSTRUED IN ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK BUT WITHOUT GIVING EFFECT TO APPLICABLE PRINCIPLES OF CONFLICTS OF LAW TO THE EXTENT THAT THE APPLICATION OF THE LAWS OF ANOTHER JURISDICTION WOULD BE REQUIRED THEREBY. 

4. Trustee’s Assumption; Trustee Makes No Representation. The Trustee assumes no duties, responsibilities or liabilities under
this Supplemental Indenture other than as set forth in the Indenture. The Trustee makes no representation as to the validity or sufficiency of this Supplemental Indenture. 

5. Counterparts. The parties may sign any number of copies of this Supplemental Indenture. Each signed copy shall be an original, but
all of them together represent the same agreement. 
 6. Effect of Headings. The Section headings herein are for convenience only and
shall not affect the construction thereof. 

 IN WITNESS WHEREOF, the parties hereto have caused this Supplemental Indenture to be duly
executed as of the date first above written. 
  

			
	RAYCOM MEDIA, INC.
	
	RAYCOM SPORTS NETWORK, INC.
	
	RAYCOM MEDIA LICENSEE, LLC
	
	KNIN LICENSE SUBSIDIARY, LLC
	
	WBRC LICENSE SUBSIDIARY, LLC
	
	WFLX LICENSE SUBSIDIARY, LLC
	
	WVUE LICENSE SUBSIDIARY, LLC
	
	WXIX LICENSE SUBSIDIARY, LLC
	
	KYOU RAYCOM LICENSE SUBSIDIARY, LLC
	
	TUPELO HONEY RAYCOM, LLC
		
	By:	 	     /s/ James C. Ryan

	Name: James C. Ryan
	Title: Treasurer
	
	GRAY TELEVISION, INC.
		
	By:	 	     /s/ James C. Ryan

	Name: James C. Ryan
	Title: Executive Vice President and Chief
		 	Financial Officer

 [Signature Page to First Supplemental Indenture to September 2016 Indenture] 

 
			
	 U.S. BANK NATIONAL ASSOCIATION,
 as
Trustee

		
	By:	 	     /s/ Felicia H. Powell

	Name: Felicia H. Powell
	Title: Assistant Vice President

 [Signature Page to First Supplemental Indenture to September 2016 Indenture]

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00290-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00290-of-00352.parquet"}]]