Form of Executive Option Agreement



 Exhibit 10.42 
 EXECUTIVE OPTION AGREEMENT 
 Optionee: Tom Casey

 This Option and any securities issued upon exercise of this Option are subject to restrictions on transfer and
requirements of sale and other provisions as set forth below. 
 CC MEDIA HOLDINGS, INC.  

NON-QUALIFIED STOCK OPTION AGREEMENT 
 This stock option (the “Option”) is granted by CC Media Holdings, Inc., a Delaware corporation (the “Company”), to the Optionee, pursuant to the Company’s 2008
Executive Incentive Plan (as amended from time to time, the “Plan”). For the purpose of this Executive Option Agreement (the “Agreement”), the “Grant Date” shall mean December 31, 2010.

 1. Grant of Option. The Agreement evidences the grant by the Company on the Grant Date to the Optionee of an option to
purchase, in whole or in part, on the terms provided herein and in the Plan, 250,000 shares of Class A Common Stock, par value $.001 per share (the “Shares”) from the Company at the price per share of $10. 

The Option evidenced by this Agreement is not intended to qualify as an incentive stock option under Section 422 of the Code.

 2. Vesting. 
 (a) During Employment. During the Optionee’s Employment, this Option shall vest and become exercisable with respect to 25% of the Option on the Grant Date and each of the first, second and
third anniversaries of the Grant Date. 
 (b) Termination of Employment. 

(i) Notwithstanding any other provision of this Section 2 and subject to Section 2(c)(ii) below, automatically
and immediately upon the cessation of Employment, the then outstanding and unvested portion of the Option shall terminate. 
 (ii) Notwithstanding Section 2(c)(i), in the event the Optionee’s Employment is terminated by the Company without Cause during the twelve (12) months following a Change of Control, 100% of
the then outstanding and unvested portion of the Option will vest and become exercisable in accordance with Section 3(a) below. 

  
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 Notwithstanding the foregoing (but subject to any contrary provision of this Agreement or any other written
agreement between the Company and the Optionee with respect to vesting and termination of Awards granted under the Plan), no Options shall vest or shall become eligible to vest on any date specified above unless the Optionee is then, and since the
Grant Date has continuously been, an Employee. 
 3. Exercise of Option. Each election to exercise this Option shall be
subject to the terms and conditions of the Plan and shall be in writing, signed by the Optionee or by his or her executor or administrator or by the person or persons to whom this Option is transferred by will or the applicable laws of descent and
distribution (the “Legal Representative”), and made pursuant to and in accordance with the terms and conditions set forth in the Plan. In addition to the methods of payment otherwise permitted by the Plan, the Administrator shall,
at the election of the Optionee, hold back Shares from an Option having a Fair Market Value equal to the exercise price in payment of the Option exercise price. The latest date on which this Option may be exercised (the “Final Exercise
Date”) is the date which is the tenth anniversary of the Grant Date, subject to earlier termination in accordance with the terms and provisions of the Plan and this Agreement. Notwithstanding the foregoing, and subject to the provisions of
Section 2(b) above, the following rules will apply if Optionee’s Employment ceases in all circumstances: automatically and immediately upon the cessation of Employment, this Option will cease to be exercisable and will terminate, except
that: 
 (a) any portion of this Option held by the Optionee or the Optionee’s Permitted Transferees, if
any, immediately prior to the termination of the Optionee’s Employment by reason of a termination by the Company without Cause, to the extent then vested and exercisable, will remain exercisable for the shorter of (i) a period of 90 days
or (ii) the period ending on the Final Exercise Date, and will thereupon terminate; and 
 (b) any portion
of this Option held by the Optionee or the Optionee’s Permitted Transferees, if any, immediately prior to the termination of the Optionee’s Employment by reason of death or Disability, to the extent then vested and exercisable, will remain
exercisable for the shorter of (i) the one year period ending with the first anniversary of the Optionee’s death or Disability, as the case may be, or (ii) the period ending on the Final Exercise Date, and will thereupon terminate.

 4. Withholding. No Shares will be transferred pursuant to the exercise of this Option unless and until the person
exercising this Option shall have remitted to the Company an amount sufficient to satisfy any federal, state, or local withholding tax requirements, or shall have made other arrangements satisfactory to the Company with respect to such taxes. The
Administrator may, in its sole discretion, hold back Shares otherwise receivable upon exercise of the Option or permit an Optionee to tender previously owned shares of Stock in satisfaction of tax withholding requirements (but not in excess of the
applicable minimum statutory withholding rate). 

  
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 5. Nontransferability of Option. This Option is not transferable by the Optionee
other than by will or the applicable laws of descent and distribution, and is exercisable during the Optionee’s lifetime only by the Optionee. 
 6. Restrictions on Shares. 
 (a) Transferability of
Shares. Except as provided in this Section 6, no Transfer of Shares received upon exercise of the Option (“Received Shares”) by the Optionee is permitted: 

(i) Permitted Transferees. The Optionee may Transfer any and all Received Shares to a Permitted Transferee,
provided that such Permitted Transferee shall become a party to and subject to the terms and conditions of this Agreement. Prior to the initial Transfer of any Received Shares to a given Permitted Transferee pursuant to this Section 6(a) and as
a condition thereto, the Permitted Transferee shall execute a written agreement in a form provided by the Company under which such Permitted Transferee shall become subject to all provisions of this Agreement to the extent applicable to the Received
Shares, including without limitation Sections 6, 7, and 10. 
 (ii) Public Transfers. After the third
anniversary of the closing of a Qualified Public Offering, the Optionee may Transfer any or all Received Shares to the public pursuant to Rule 144 under the Securities Act of 1933, as amended (“Rule 144”). 

(iii) Sale Rights on Termination Due to Death or Disability. Upon the Optionee’s termination of Employment due
to death or Disability, the Optionee and his or her Permitted Transferees will have the right, subject to Sections 6(a)(v) and 6(a)(vi), to sell to the public pursuant to Rule 144 at any time during the one-year period following the effective date
of such termination all or any portion of the Received Shares, notwithstanding that such a Transfer might not otherwise then be permitted by Section 6(a)(ii). 

(iv) Release of Received Shares. If prior to the third anniversary of the closing of a Qualified Public Offering,
any Investor makes a Transfer of its Equity Shares to any Person (other than a Transfer to any other Investor or Sponsor or to any of the respective Affiliates or Affiliated Funds of any such Investor or Sponsor), then the Optionee will be permitted
to Transfer, pursuant to Rule 144, that portion of the Optionee’s Received Shares that bears the same proportion to the total number of Shares with respect to which this Option is then vested and exercisable and Received Shares then owned by
the Optionee as the number of Equity Shares that were Transferred by such Investor bears to the total number of Equity Shares that were owned by all Investors immediately prior to such Transfer. 

  
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 (v) Legal Restrictions; Other Restrictions. The restrictions on
Transfer contained in this Agreement, including those specified in this Section 6, are in addition to any prohibitions and other restrictions on transfer arising under any applicable laws, rules or regulations, and the Optionee may not Transfer
Received Shares to any other Person unless the Optionee first takes all reasonable and customary steps, to the reasonable satisfaction of the Company, to ensure that such Transfer would not violate, or be reasonably expected to restrict or impair
the respective business activities of the Company or any of its subsidiaries under, any applicable laws, rules or regulations, including applicable securities, antitrust or U.S. federal communications laws, rules and regulations. The restrictions on
Transfer contained in this Agreement are in addition to any other restrictions on Transfer to which the Optionee may be subject, including any restrictions on Transfer contained in the Company’s certificate of incorporation (including
restrictions therein relating to federal communications laws), or any other agreement to which the Optionee is a party or is bound or any applicable lock-up rules and regulations of any national securities exchange or national securities
association. 
 (vi) Impermissible Transfers. Any Transfer of Received Shares not made in compliance with
the terms of this Section 6 shall be null and void ab initio, and the Company shall not in any way give effect to any such Transfer. 
 (vii) Period. Upon the occurrence of a Change of Control, all the Transfer restrictions of this Section 6 shall terminate. 

(b) Drag Rights. 
 (i) Sale Event Drag Along. If the Company notifies the Optionee in writing that it has received a valid Drag Along Sale Notice (as defined in the Stockholders Agreement) pursuant to the
Stockholders Agreement and that Capital IV has informed the Company that it desires to have the Optionee participate in the transaction that is the subject of the Drag Along Sale Notice, then the Optionee shall be bound and obligated to Transfer in
such transaction the percentage of the aggregate number of Shares with respect to which this Option is then vested and exercisable and Received Shares then held by the Optionee that the Company notifies the Optionee is equal to the percentage of
Equity Shares held by the Sponsors and their Affiliates that the Sponsors and Affiliates are transferring in such transaction, on the same terms and conditions as the Sponsors and their Affiliates with respect to each Equity Share Transferred. With
respect to a given transaction that is the subject of a Drag Along Notice, the Optionee’s obligations under this Section 6(b) shall remain in effect until the earlier of (1) the consummation of such transaction and
(2) notification by the Company that such Drag Along Sale Notice has been withdrawn. 
 (ii) Waiver of
Appraisal Rights. The Optionee agrees not to demand or exercise appraisal rights under Section 262 of the Delaware General Corporate Law, as amended, or otherwise with respect to any transaction subject to this Section 6(b), whether or
not such appraisal rights are otherwise available. 

  
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 (iii) Further Assurances. The Optionee shall take or cause to be
taken all such actions as requested by the Company or Capital IV in order to consummate any transaction subject to this Section 6(b) and any related transactions, including but not limited to the exercise of vested Options and the execution of
agreements and other documents requested by the Company. 
 (iv) Period. The foregoing provisions of this
Section 6(b) shall terminate upon the occurrence of a Change of Control. 
 (c) Lock-Up. The Optionee
agrees that in connection with a Public Offering, upon the request of the Company or the managing underwriters(s) of such Public Offering, the Optionee will not Transfer, make any short sale of, loan, grant any option for the purchase of, pledge,
enter into any swap or other arrangement that transfers any of the economic ownership, or otherwise encumber or dispose of the Option or any portion thereof or any of the Received Shares for such period as the Company or such managing
underwriter(s), as the case may be, may request, commencing on the effective date of the registration statement relating to such Public Offering and continuing for not more than 90 days (or 180 days in the case of any Public Offering up to and
including the Qualified Public Offering), except with the prior written consent of the Company or such managing underwriter(s), as the case may be. The Optionee also agrees that he or she will sign a “lock up” or similar arrangement in
connection with a Public Offering on terms and conditions that the Company or the managing underwriter(s) thereof deems necessary or desirable. 
 7. Grant of Proxy. To the extent permitted by law, the Optionee hereby grants to Capital IV an irrevocable proxy coupled with an interest, with full power of substitution, to vote such
Optionee’s Received Shares as Capital IV sees fit on all matters related to (i) the election of members of the Board, (ii) any transaction subject to Section 6(b) herein or (iii) any amendment to the Company’s
certificate of incorporation to increase the number of shares of common stock authorized thereunder. Such proxy shall be valid and remain in effect until the earlier of (1) the occurrence of a Change of Control and (2) with respect to any
particular matter, the latest date permitted by applicable law. 
 8. Status Change. Upon the termination of the
Optionee’s Employment, this Option shall continue or terminate, as and to the extent provided in the Plan and this Agreement. 
 9. Effect on Employment. Neither the grant of this Option, nor the issuance of Shares upon exercise of this Option, shall give the Optionee any right to be retained in the employ of the Company or
its Affiliates, affect the right of the Company or its Affiliates to discharge or discipline such Optionee at any time, or affect any right of such Optionee to terminate his or her Employment at any time. 

  
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 10. Non-Competition, Non-Solicitation, Non-Disclosure. The Board shall have the right
to cancel, modify, rescind, suspend, withhold or otherwise limit or restrict this Option, including, without limitation, canceling or rescinding this Option if the Board determines that the Optionee is not in compliance with any non-competition or
non-solicitation or non-disclosure agreement with the Company and such non-compliance has not been authorized in advance in a specific written waiver from the Company. In addition, in the event of any such violation of such agreement (without the
advance written consent of the Company) that occurs during the period following termination of employment covered by any such agreement, the Company may require that (i) the Optionee sell to the Company Received Shares then held by the Optionee
for a purchase price equal to the aggregate exercise price of the Options and (ii) the Optionee remit or deliver to the Company (1) the amount of any gain realized upon the sale of any Received Shares, and (2) any consideration
received upon the exchange of any Received Shares (or the extent that such consideration was not received in the form of cash, the cash equivalent thereof valued at the time of the exchange). The Company shall have the right to offset, against any
Shares and any cash amounts due to the Optionee under or by reason of Optionee’s holding this Option, any amounts to which the Company is entitled as a result of Optionee’s violation of the terms of any non-competition, non-solicitation or
non-disclosure agreement with the Company or Optionee’s breach of any duty to the Company. Accordingly, Optionee acknowledges that (i) the Company may withhold delivery of Shares, (ii) the Company may place the proceeds of any sale or
other disposition of Shares in an escrow account of the Company’s choosing pending resolution of any dispute with the Company, and (iii) the Company has no liability for any attendant market risk caused by any such delay, withholding, or
escrow. The Optionee acknowledges and agrees that the calculation of damages from a breach of an agreement with the Company or of any duty to the Company would be difficult to calculate accurately and that the right to offset or other remedy
provided for herein is reasonable and not a penalty. The Optionee further agrees not to challenge the reasonableness of such provisions even where the Company rescinds, delays, withholds or escrows Shares or proceeds or uses those Shares or proceeds
as a setoff. 
 11. Provisions of the Plan. This Option is subject in its entirety to the provisions of the Plan, which
are incorporated herein by reference. A copy of the Plan as in effect on the date of the grant of this Option has been furnished to the Optionee. By exercising all or any part of this Option, the Optionee agrees to be bound by the terms of the Plan
and this Agreement. In the event of any conflict between the terms of the Plan and this Agreement, the terms of this Agreement shall control. 
 12. Definitions. The initially capitalized terms Optionee and Grant Date shall have the meanings set forth on the first page of this Agreement; initially capitalized terms not otherwise defined
herein shall have the meaning provided in the Plan, and, as used herein, the following terms shall have the meanings set forth below: 
 “Affiliate” means, with respect to any specified Person, any other Person that directly or indirectly through one or more intermediaries controls, or is controlled by, or is under
common control with, such specified Person. For the purposes of this Agreement, “control” (including, with correlative meanings, the terms “controlling,” “controlled by” and “under common control with”), as
used with respect to any Person, means the possession, directly or indirectly, of the power to direct or cause the direction of the management or policies of such Person, whether through the ownership of voting securities, by agreement or otherwise.
For purposes of this Agreement, none of the Company or any of its subsidiaries will be considered an Affiliate of any Sponsor or any of their respective Affiliates or Affiliated Funds. 

  
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 “Affiliated Fund” means, with respect to any specified Person,
(a) an investment fund that is an Affiliate of such Person or that is advised by the same investment adviser as such Person or by an Affiliate of such investment adviser or such Person or, with respect to a Person that is a Sponsor or an
Affiliate of a Sponsor, (b) any partnership, limited liability company or other legal entity controlled (i) jointly by the Sponsors and/or their respective Affiliates or (ii) individually by a single Sponsor and/or its Affiliates, in
each case (i) and (ii) that is formed to invest directly or indirectly in the Company. 
 “Capital
IV” means Clear Channel Capital IV, LLC, a Delaware limited liability company formed and jointly controlled by the Sponsors, and its successors and/or assigns. 
 “Capital V” means Clear Channel Capital V, L.P., a Delaware limited partnership formed and jointly controlled by the Sponsors, and its successors and/or assigns. 

“Change of Control” means (a) any consolidation or merger of the Company with or into any other corporation or
other Person, or any other corporate reorganization or transaction (including the acquisition of capital stock of the Company), whether or not the Company is a party thereto, after which the Sponsors and their respective Affiliated Funds and
Affiliates do not directly or indirectly control capital stock representing more than 25% of the economic interests in and 25% of the voting power of the Company or other surviving entity immediately after such consolidation, merger, reorganization
or transaction; (b) any stock sale or other transaction or series of related transactions, whether or not the Company is a party thereto, after which in excess of 50% of the Company’s voting power is owned directly or indirectly by any
Person and its “affiliates” or “associates” (as such terms are defined the Securities Exchange Act of 1934, as amended and the rules thereunder), other than the Sponsors and their respective Affiliated Funds and Affiliates (or a
group of Persons that includes such Persons); or (c) a sale of all or substantially all of the assets of the Company to any Person and the “affiliates” or “associates” of such Person (or a group of Persons acting in
concert), other than the Sponsors and their respective Affiliated Funds and Affiliates (or a group of Persons that includes such Persons). 
 “Disability” (a) has the meaning given to such term in the Optionee’s employment agreement then in effect, if any, between the Optionee and the Company or any of its
subsidiaries, or (b) if there is no such term in such employment agreement or there is no such employment agreement then in effect, means the disability of an Optionee during his or her Employment through any illness, injury, accident or
condition of either a physical or psychological nature as a result of which, in the judgment of the Board, he or she is unable to perform substantially all of his or her duties and responsibilities, notwithstanding the provision of any reasonable
accommodation, for 6 consecutive months during any period of 12 consecutive months. 
 “Equity Shares” means
Shares as such term is used in the Stockholders Agreement. 
 “Investors” means Capital IV and Capital V and
their “Permitted Transferees,” as defined in the Stockholders Agreement. 
 “Members of the Immediate
Family” means, with respect to an individual, each spouse or child or other descendant of such individual, each trust created solely for the benefit of one or more of the aforementioned persons and their spouses and each custodian or
guardian of any property of one or more of the aforementioned persons in his or her capacity as such custodian or guardian. 

  
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 “Permitted Transferee” means (a) the Optionee’s estate,
executors, administrators, personal representatives, heirs, legatees or distributees, in each case acquiring the Received Shares in question pursuant to the will or other instrument taking effect at death of such Optionee or by applicable laws of
descent and distribution, or (b) a trust, private foundation or entity formed for estate planning purposes for the benefit of the Optionee and/or any of the Members of the Immediate Family of such Optionee. In addition, the Optionee shall be a
Permitted Transferee of the Optionee’s Permitted Transferees. 
 “Public Offering” means a public offering
and sale of shares of common stock of the Company, for cash pursuant to an effective registration statement under the Securities Act of 1933, as amended. 
 “Qualified Public Offering” means the first underwritten Public Offering after July 30, 2008 pursuant to an effective registration statement (other than on Form S-4, S-8 or a
comparable form) in connection with which the Company or any of the Sponsors or their respective Affiliates or Affiliated Funds receives sale proceeds therefrom. 
 “Sponsors” shall mean Bain Capital (CC) IX L.P. and Thomas H. Lee Equity Fund VI, L.P. 
 “Stockholders Agreement” means the Stockholders Agreement, dated as of July 29, 2008, as amended from time to time, by and among the Company, BT Triple Crown Merger Co., Inc. and
other stockholders of the Company who from time to time may become parties thereto. 
 “Transfer” means any
sale, pledge, assignment, encumbrance, distribution or other transfer or disposition of shares or other property to any other Person, whether directly, indirectly, voluntarily, involuntarily, by operation of law, pursuant to judicial process or
otherwise. 
 13. General. For purposes of this Option and any determinations to be made by the Administrator or
Committee, as the case may be, hereunder, the determinations by the Administrator or Committee, as the case may be, shall be binding upon the Optionee and any transferee. 

  
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 IN WITNESS WHEREOF, the Company has caused this Option to be executed under its corporate
seal by its duly authorized officer. This Option shall take effect as a sealed instrument. 
  

					
	CC MEDIA HOLDINGS, INC.
		
	By:	 	  

		 	Name:	 	Mark P. Mays
		 	Title:	 	CEO


 Dated: 

 

	
	Acknowledged and Agreed
	
	  
	 Name:
  
 Address of Principal Residence:

	
	  

	  

	  



  
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