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                                                                    EXHIBIT 10.4

                                    GUARANTY

         THIS GUARANTY (as may be amended, supplemented or otherwise modified
from time to time, the "GUARANTY") is made as of this 13th day of June, 2005 in
favor of the Covered Persons (as defined herein) by Gray Television, Inc., a
Georgia corporation ("GRAY").

                                    RECITALS

         A. Triple Crown Media, Inc., a Delaware corporation ("TCM") is a newly
formed, wholly-owned subsidiary of Gray.

         B. TCM was capitalized with $.10, and has no other assets.

         C. Gray is considering spinning off all of the shares of capital stock
of TCM to its shareholders (the "SPIN-OFF").

         D. Immediately prior to the Spin-Off, Gray would contribute
substantially all of the assets of its newspaper publishing business and
Graylink Wireless business to TCM, and TCM would assume certain liabilities.

         E. TCM and Gray, as the sole shareholder of TCM, are considering the
merger of Bull Run Corporation, a Georgia corporation ("BULL RUN"), with and
into a wholly-owned subsidiary of TCM immediately following the Spin-Off (the
"MERGER").

         F. TCM is considering refinancing all of its and Bull Run's
indebtedness immediately following the Merger (the "REFINANCING", and with the
Spin-Off and the Merger, the "PROPOSED TRANSACTIONS").

         NOW, THEREFORE, to induce the Covered Persons to serve and act for TCM,
and in consideration of the substantial benefit Gray will derive from the acts
and service of such Covered Persons, and other good and valuable consideration,
the receipt and sufficiency of which is hereby acknowledged, and intending to be
legally bound hereby, Gray hereby agrees as follows:

         1.01 "COVERED PERSON" means any person who was or is made or is
threatened to be made a party or is otherwise involved in any action, suit or
proceeding, whether civil, criminal, administrative or investigative (a
"PROCEEDING"), by reason of the fact that he or she, or a person for whom he or
she is the legal representative, is or was a director or officer of TCM at
anytime from the date of this Guaranty through date of the consummation of the
Proposed Transactions or, while a director or officer of TCM during such period,
is or was serving at the request of TCM as a director, officer, employee or
agent of another corporation or of a partnership, joint venture, trust,
enterprise or nonprofit entity, including service with respect to employee
benefit plans.

         1.02 Gray irrevocably and unconditionally guarantees to the Covered
Persons the prompt, punctual and full performance of all of TCM's
indemnification and contribution obligations (including the advancement of
expenses) arising under, in accordance with and

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subject to, the Delaware General Corporation Law, TCM's certificate of
incorporation, TCM's bylaws, any resolutions of TCM's board of directors or any
committee thereof, or otherwise, as they may exist from time to time, in respect
of actions or omissions by the Covered Persons occurring at or prior to the
consummation of the Proposed Transactions ("GUARANTEED OBLIGATIONS").

         1.03 At or prior to the consummation of the Proposed Transactions, it
shall not be necessary or required that any Covered Person exercise any right,
assert any claim or demand or enforce any remedy whatsoever against TCM before
or as a condition to the obligations of the Gray under this Guaranty.

         1.04 After the consummation of the Proposed Transactions, a Covered
Person may not assert any claim or demand or enforce any right or remedy against
Gray in respect of the Guaranteed Obligations, unless and until such Covered
Person has exhausted all rights and remedies against TCM in respect of the
Guaranteed Obligations.

         1.05 After the consummation of the Proposed Transactions, sole recourse
and exclusive remedy that the Covered Person shall have to satisfy any claims
for the Guaranteed Obligations, shall be against TCM; provided however, if TCM
is unable to perform the Guaranteed Obligations, then the Covered Persons may
satisfy any such claims against Gray.

         1.06 Notwithstanding paragraphs 1.03, 1.04 and 1.05 hereto, Gray shall
have the right to recover from TCM for any payments made by Gray to the Covered
Persons in satisfaction of any claims against TCM or Gray under this Guaranty.

         1.07 Gray hereby acknowledges and agrees that the terms, covenants and
provisions contained in TCM's certificate of incorporation and bylaws may be
altered, modified and amended without any agreement or consent of Gray, and Gray
agrees that this Guaranty and its liabilities hereunder shall be in no way
affected, diminished or released by any such alteration, modification or
amendment.

         1.08 This Guaranty is a continuing guaranty and will remain in full
force and effect.

         1.09 Gray represents and warrants to the Covered Persons that (i) it is
a corporation duly organized, validly existing and in good standing under the
laws of the State of Georgia, (ii) it has all requisite corporate power and
authority to enter into this Guaranty, (iii) the execution and delivery of this
Guaranty and the performance by Gray of its obligations hereunder have been duly
authorized by all necessary corporate action on the part of Gray, (iv) this
Guaranty has been duly executed and delivered by Gray and (v) this Guaranty
constitutes a valid and binding obligation of Gray, in accordance with its
terms.

         1.10 No invalidity, irregularity or unenforceability of this Guaranty
shall affect, impair or be a defense to this Guaranty.

         1.11 The obligations of Gray are subject to any defenses available to
TCM (other than defenses of bankruptcy, reorganization, insolvency, moratorium
or other laws affecting the enforcement of creditors' rights generally) and Gray
is entitled to all rights of set off, counterclaims, claims for indemnity or any
other rights that may be exercised by TCM.

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         1.12 No delay or failure on the part of a Covered Person to exercise
any power or right given under TCM's certificate of incorporation or bylaws or
under this Guaranty shall be a waiver and no right or remedy of a Covered Person
shall be considered abridged or modified by any course of conduct.

         1.13 This Guaranty and all claims arising hereunder shall be governed
by and construed and enforced in accordance with the laws of the State of
Delaware, without giving effect to the principals of conflicts of laws thereof.

         1.14 This Guaranty is binding upon Gray and its successors or assigns.

                            [SIGNATURE PAGE FOLLOWS.]

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         IN WITNESS WHEREOF, the undersigned hereby sign, seal and deliver this
Guaranty.

                                               GRAY TELEVISION, INC.

                                               By:  /s/ Robert S. Prather
                                                   ----------------------------
                                                   Name: Robert S. Prather
                                                   Title: President

                                               Address for Notice:
                                               Gray Television, Inc.
                                               4370 Peachtree Road, NE
                                               Atlanta, GA 30319
                                               Attn: James C. Ryan
                                               Fax: (404) 261-9607<PAGE>
                                                                    EXHIBIT 10.5

                           AMENDMENT NO. 1 TO GUARANTY
                             AS OF OCTOBER 18, 2005

         The GUARANTY (the "GUARANTY") made as of the 13th day of June, 2005 in
favor of the Covered Persons (as defined in the Guaranty) by Gray Television,
Inc., a Georgia corporation ("GRAY"), is amended as follows:

         1.       Section 1.03 is hereby amended in its entirety to read as
                  follows:

                  "It shall not be necessary or required that any Covered Person
                  exercise any right, assert any claim or demand or enforce any
                  remedy whatsoever against TCM before or as a condition to the
                  obligations of the Gray under this Guaranty."

         2.       Section 1.04 is hereby deleted.

         3.       Section 1.05 is hereby deleted.

         4.       Section 1.06 is hereby amended in its entirety to read as
                  follows:

                  "Notwithstanding paragraph 1.03, Gray shall have the right to
                  recover from TCM for any payments made by Gray to the Covered
                  Persons in satisfaction of any claims against Gray under this
                  Guaranty."

                            [Signature page follows.]

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         IN WITNESS WHEREOF, the undersigned hereby sign, seal and deliver this
Amendment No. 1 to the Guaranty.

                                               GRAY TELEVISION, INC.

                                               By: /s/ Robert S. Prather, Jr.
                                                   ----------------------------
                                                   Name: Robert S. Prather, Jr.
                                                   Title: President and Chief
                                                   Operating Officer

                                               Address for Notice:
                                               Gray Television, Inc.
                                               4370 Peachtree Road, NE
                                               Atlanta, GA 30319
                                               Attn: James C. Ryan
                                               Fax: (404) 261-9607

FOR PURPOSES OF SECTION 1.06 ONLY:

TRIPLE CROWN MEDIA, INC.

By: /s/ James C. Ryan
    ----------------------------
    Name: James C. Ryan
    Title: Chief Financial Officer and Secretary

Address for Notice:
Triple Crown Media, Inc.
546 East Main Street
Lexington, KY 40508
Attn: James C. Ryan
Fax: (859) 226-4356

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