Document:

Limited Guarantee

 Exhibit 10.1 
 Execution Version 
 LIMITED GUARANTEE 

This LIMITED GUARANTEE (this “Limited Guarantee”), dated as of January 9, 2011, is made by Rizvi Opportunistic
Equity Fund, L.P. (“ROEF”), Rizvi Opportunistic Equity Fund I-B, L.P. (“ROEF I-B”), Rizvi Opportunistic Equity Fund (TI), L.P. (“ROEF TI”), Rizvi Opportunistic Equity Fund I-B (TI), L.P.
(“ROEF I-B TI”), Rizvi Traverse Partners LLC (“RTP”), and Rizvi Opportunistic Equity Fund II, L.P. (“ROEF II”, together with ROEF, ROEF I-B, ROEF TI, ROEF I-B TI, and RTP, the
“Guarantors”) in favor of Playboy Enterprises, Inc., a Delaware corporation (the “Guaranteed Party”). 
 1. Limited Guarantee. To induce the Guaranteed Party to enter into that certain Agreement and Plan of Merger, dated as of January 9, 2011, by and among ICON Acquisition Holdings, L.P.,
a Delaware limited partnership (the “Purchaser”), Icon Merger Sub, Inc., a Delaware corporation (“Sub”), and the Guaranteed Party (as may be amended, the “Merger Agreement”) pursuant to which and
subject to the terms and conditions of which the Guaranteed Party will become a wholly owned subsidiary of Purchaser (the “Merger”), the Guarantors, intending to be legally bound, hereby jointly and severally, absolutely,
irrevocably and unconditionally guarantee to the Guaranteed Party, on the terms and conditions set forth herein the due and punctual payment as and when due of the payment obligations of Purchaser as set forth in Section 8.2(c),
Section 8.2(f) and 9.12(c) of the Merger Agreement (the “Obligations”), provided that notwithstanding anything to the contrary contained in this Limited Guarantee (except as provided in the third paragraph of this
Section 1), in no event shall the Guarantors’ aggregate liability under this Limited Guarantee exceed $20 million plus the amount, if any, due to the Guaranteed Party under Section 8.2(f) of the Merger Agreement (which
amount may not exceed $1 million), less the portion of the foregoing amounts, if any, indefeasibly paid to the Guaranteed Party by Purchaser, Sub or any other Person that is not rescinded or otherwise returned or repaid (the “Cap”),
it being understood that this Limited Guarantee may not be enforced without giving effect to the Cap. The Guaranteed Party hereby agrees that in no event shall the Guarantors be required to pay any amount to the Guaranteed Party under, in respect
of, or in connection with this Limited Guarantee, the Equity Commitment Letter, the Merger Agreement or the transactions contemplated hereby and thereby other than as expressly set forth herein or therein. All payments hereunder shall be made in
lawful money of the United States, in immediately available funds. Each capitalized term used but not defined herein shall have the meaning ascribed to it in the Merger Agreement, except as otherwise provided. 

If Purchaser fails to pay the Obligations when due, then all of the Guarantors’ liabilities to the Guaranteed Party hereunder in
respect of such Obligations shall, at the Guaranteed Party’s option, become immediately due and payable and the Guaranteed Party may at any time and from time to time, at the Guaranteed Party’s option, take any and all actions available
hereunder or under applicable Law to collect the Obligations from the Guarantors. 
 The Guarantors agree to pay on demand all
reasonable and documented out-of-pocket expenses (including reasonable fees and expenses of counsel) incurred by the Guaranteed Party in connection with the enforcement of its rights hereunder if the Guarantors fail or refuse to make any payment to
the Guaranteed Party hereunder when due and payable following the earlier of (a) Purchaser’s written acknowledgment that it has become obligated to make any 

 
payment hereunder, including to pay the Purchaser Termination Fee or (b) the time that it is judicially determined by a court of competent jurisdiction in a final, non-appealable order that
Purchaser is obligated to make any payment hereunder, including to pay the Purchaser Termination Fee; provided, that the amounts payable by the Guarantors pursuant to this paragraph shall not be considered in determining the Guarantors
aggregate liability under this Limited Guarantee for purposes of the Cap. 
 2. Nature of Guarantee. In the event
that any payment to the Guaranteed Party in respect of the Obligations or under the last paragraph of Section 1 is rescinded or must otherwise be returned for any reason whatsoever, the Guarantors shall remain liable hereunder with
respect to the Obligations (subject to the Cap) as if such payment had not been made. This Limited Guarantee is an absolute, irrevocable, unconditional and continuing guarantee of payment and not of collection and shall be absolute, unconditional,
irrevocable and continuing irrespective of any modification, amendment, waiver or consent to departure from the Merger Agreement that may be agreed to (subject to the Cap), and the Guaranteed Party shall not be required to proceed against Purchaser
or Sub before proceeding against any of the Guarantors hereunder nor shall the Guaranteed Party be required to proceed against all of the Guarantors. 
 3. Changes in Obligation. The Guarantors agree that the Guaranteed Party may, in its sole discretion, at any time and from time to time, without notice to or further consent of the
Guarantor, extend the time of payment of the Obligations, and may also make any agreement with Purchaser or Sub for the change in manner, place or terms of payment or performance, or the extension or renewal thereof, or otherwise, in whole or in
part, without in any way impairing or affecting the Guarantors’ obligations under this Limited Guarantee or affecting the validity or enforceability of this Limited Guarantee. The Guarantors agree that the obligations of the Guarantors
hereunder shall not be released or discharged, in whole or in part, or otherwise affected by (a) the failure or delay on the part of the Guaranteed Party to assert any claim or demand or to enforce any right or remedy against Purchaser or Sub;
(b) the addition or substitution of any entity or other Person now or hereafter liable with respect to the Obligations or otherwise interested in the transactions contemplated by the Merger Agreement; (c) any change in the corporate
existence, structure or ownership of Purchaser, Sub or any Person now or hereafter liable with respect to the Obligations or otherwise interested in the transactions contemplated by the Merger Agreement; (d) the existence of any claim, set-off
or other right which the Guarantors may have at any time against Purchaser, Sub or the Guaranteed Party or any of their respective Affiliates, whether in connection with the Obligations or otherwise except as provided herein; (e) the adequacy
of any other means the Guaranteed Party may have of obtaining payment related to the Obligations; (f) any insolvency, bankruptcy, reorganization or other similar proceeding affecting Purchaser, Sub or any other Person now or hereafter liable
with respect to the Obligations or otherwise interested in the transactions contemplated by the Merger Agreement; and (g) any discharge of the Guarantors as a matter of applicable Law (other than as a result of, and to the extent of, payment of
the Obligations in accordance with the terms of the Merger Agreement). The Guarantors acknowledge that they will receive substantial direct and indirect benefits from the transactions contemplated by the Merger Agreement and that the agreements,
covenants, obligations and other terms in this Limited Guarantee are knowingly made and agreed to in contemplation of such benefits. The Guaranteed Party hereby covenants and agrees that it shall not institute, directly or indirectly, and shall
cause its Affiliates not to institute, directly or indirectly, any proceeding or bring any other claim arising under, in respect 

  
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of or in connection with the Merger Agreement or the transactions contemplated thereby, against the Guarantors or any Non-Recourse Party (as defined in Section 10 herein), except for
claims against the Guarantors under this Limited Guarantee (subject to the limitations described herein); provided, that notwithstanding anything to the contrary contained in this Limited Guarantee, the Guarantors acknowledge, and nothing
herein shall restrict, the Guaranteed Party’s rights against Purchaser and Sub to specific performance to which it is entitled under the Merger Agreement to require Purchaser to enforce certain equity commitments that the Guarantors may owe to
RT-ICON Holdings, LLC, a Delaware limited liability company (“RT-ICON”), in connection with the Contemplated Transactions in accordance with the terms thereof. RT-ICON is entering into a certain equity commitment to the Purchaser in
connection with the Contemplated Transaction. Each of the Guarantors hereby covenants and agrees that it shall not assert, directly or indirectly, in any proceeding that this Limited Guarantee is illegal, invalid or unenforceable in accordance with
its terms. To the fullest extent permitted by applicable Law, each Guarantor hereby expressly waives any and all rights or defenses arising by reason of any applicable Law which would otherwise require any election of remedies by the Guaranteed
Party. Each Guarantor waives promptness, diligence, notice of the acceptance of this Limited Guarantee and of the Obligations, notice of or proof of reliance by the Guaranteed Party upon this Limited Guarantee, acceptance of this Limited Guarantee,
presentment, demand for payment, notice of non-performance, default, dishonor and protest, notice of the Obligations incurred and all other notices of any kind (except for notices to be provided in accordance with the Merger Agreement), all defenses
which may be available by virtue of any valuation, stay, moratorium or other similar applicable Law now or hereafter in effect, and all suretyship defenses generally (other than defenses to the payment of the Obligations that are available to
Purchaser or Sub under the Merger Agreement). 
 4. No Waiver; Cumulative Remedies. For so long as this Limited
Guarantee shall remain in effect in accordance with Section 9 hereof, no failure to exercise, and no delay in exercising, any right, remedy or power hereunder shall operate as a waiver thereof; nor shall any single or partial exercise of
any right, remedy or power hereunder preclude any other or future exercise of any right, remedy or power hereunder. Each and every right, remedy and power hereby granted to the Guaranteed Party shall be cumulative and not exclusive of any other, and
may be exercised by the Guaranteed Party at any time or from time to time. The Guaranteed Party shall not have any obligation to proceed at any time or in any manner against, or exhaust any or all of the Guaranteed Party’s rights against,
Purchaser, Sub or any other Person now or hereafter liable for any Obligation or interested in the transactions contemplated by the Merger Agreement prior to proceeding against one or more of the Guarantors. 

5. Right of Contribution. Each of the Guarantors agrees that to the extent that a Guarantor shall have paid more than its
proportionate share (based on the percentages such Guarantor’s equity commitment to RT-ICON bears to the total equity commitments to RT-ICON made by the other Guarantors) of any payment made hereunder, such Guarantor shall be entitled to seek
and receive contribution from and against any other Guarantor hereunder which has not paid its proportionate share of such payment. The provisions of this Section 5 shall in no respect limit the obligations and liabilities of any
Guarantor to be jointly and severally liable to the Guaranteed Party for the Obligations. 

  
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 6. Representations and Warranties. Each of the Guarantors hereby represents
and warrants that: 
 (a) it has all requisite power and authority to execute, deliver and perform this Limited
Guarantee; the execution, delivery and performance of this Limited Guarantee have been duly and validly authorized by all necessary action, and do not contravene any provision of the Guarantor’s charter, partnership agreement, operating
agreement or similar organizational documents, or any applicable Law or resulting in any violation of, or default (with or without notice, lapse of time or both) under, or give rise to a right of termination, cancellation or acceleration of any
material obligation or to the loss of any material benefit under any material contract to which such Guarantor is a party or to which its assets are bound; and the Person executing and delivering this Limited Guarantee on behalf of such Guarantor is
duly authorized to do so; 
 (b) all consents, approvals, authorizations, permits of, filings with and
notifications to, any Governmental Entity necessary for the due execution, delivery and performance of this Limited Guarantee by such Guarantor have been obtained or made and all conditions thereof have been duly complied with, and no other action
by, and no notice to or filing with, any Governmental Entity is required in connection with the execution, delivery or performance of this Limited Guarantee; 
 (c) this Limited Guarantee constitutes a legal, valid and binding obligation of such Guarantor enforceable against such Guarantor in accordance with its terms, subject to (i) the effects of
bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium or other similar applicable Laws affecting creditors’ rights generally, and (ii) general equitable principles (whether considered in a proceeding in equity or at
law); and 
 (d) such Guarantor has the financial capacity to pay and perform its obligations under this Limited
Guarantee, and all funds necessary for such Guarantor to fulfill its obligations under this Limited Guarantee shall be available to such Guarantor (or its permitted assignee pursuant to Section 7 hereof) for so long as this Limited
Guarantee shall remain in effect in accordance with Section 9 hereof. 
 7. No Assignment. Neither
this Limited Guarantee nor any right or obligation hereunder may be assigned by any party (by operation of law or otherwise) without the prior written consent of the other parties hereto, except that, without the prior written consent of the
Guaranteed Party, this Limited Guarantee may be assigned, in whole or in part, by a Guarantor to one or more of its Affiliates or to one or more investment funds sponsored or managed by such Guarantor or one or more of its Affiliates;
provided, that any such assignment will not release the such Guarantor from its obligations hereunder. Any attempted assignment in violation of this section shall be null and void. 

  
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 8. Notices. All notices, requests, claims, demands and other communications
hereunder shall be given by the means specified in the Merger Agreement (and shall be deemed given as specified therein), as follows: 
 if to the Guarantors: 
 c/o Rizvi Traverse Management, LLC

 260 East Brown Street, Suite 380 

Birmingham, MI 48009 
 Attention: John A. Giampetroni and Suhail Rizvi 
 Telecopy:
(248) 594-4751 
 with a copy to (which alone shall not constitute notice): 

Honigman Miller Schwartz and Cohn LLP 

2290 First National Building 
 660 Woodward Avenue 
 Detroit, MI 48226 

Attention: Michael D. DuBay 
 Telecopy: (313) 465-7393 
 If to the Guaranteed Party, as provided in the
Merger Agreement. 
 9. Continuing Guarantee. This Limited Guarantee may not be revoked or terminated and shall
remain in full force and effect and shall be binding on the Guarantors, and each of their respective successors and permitted assigns until the Obligations have been paid in full. Notwithstanding the foregoing, this Limited Guarantee shall terminate
and the Guarantors shall have no further obligations under this Limited Guarantee as of the earliest of (i) the Closing in accordance with the terms of the Merger Agreement, including payment of the Merger Consideration and Option
Consideration, (ii) the valid termination of the Merger Agreement in accordance with its terms under circumstances set forth in the Merger Agreement in which Purchaser would not be obligated to pay the Purchaser Termination Fee, (iii) the
twelve (12) month anniversary of any other termination of the Merger Agreement in accordance with its terms, except as to a claim for payment of any Obligation or expenses due under the third paragraph of Section 1 presented by the
Company to Purchaser, Sub or the Guarantors on or prior to such twelve (12) month anniversary; provided, that such claim shall set forth in reasonable detail the basis for such claim and the Guarantors shall not be required to pay any claim not
submitted on or before the twelve (12) month anniversary of such termination of the Merger Agreement, in which case such claim shall survive until the earlier of (A) the indefeasible payment or satisfaction in full of the full amount of
the Obligations and expenses due under the third paragraph of Section 1 (as the same may be finally determined by a court of competent jurisdiction or mutually agreed by the parties) and (B) the final determination by a court of
competent jurisdiction that no amounts are payable hereunder, and (iv) the payment to the Guaranteed Party by any combination of Purchaser and/or the Guarantors of the full amount of the Obligations and expenses due under the third paragraph of
Section 1. If any payment or payments made by Purchaser or Sub or any part thereof, are subsequently invalidated, declared to be fraudulent or preferential, set aside or are required to be repaid to a trustee, receiver, or any other
person under any bankruptcy act, state or federal law, common law or equitable cause rescinded or otherwise returned or repaid, then to the extent of such payment or payments, the Obligations and expenses due under the third paragraph of
Section 1, or part thereof, hereunder intended to be satisfied shall be revived and continued in full force and effect as if said payment 

  
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or payments had not been made. Notwithstanding any other term or provision of this Limited Guarantee, in the event that the Guaranteed Party or any of its Affiliates asserts in any litigation or
other proceeding that the provisions of Section 1 hereof limiting the Guarantors’ liability to the Cap or any other provisions of this Limited Guarantee are illegal, invalid or unenforceable in whole or in part, or asserting any
theory of liability against the Guarantors or any Non-Recourse Party with respect to the transactions contemplated by the Merger Agreement other than liability of the Guarantors under this Limited Guarantee (as limited by the provisions of
Section 1), then (x) the obligations of the Guarantors under this Limited Guarantee shall terminate ab initio and shall thereupon be null and void, (y) if the Guarantors have previously made any payments under this
Limited Guarantee, they shall be entitled to recover such payments from the Guaranteed Party, and (z) neither the Guarantors, nor any Non-Recourse Parties shall have any further liability to the Guaranteed Party or any of its Affiliates with
respect to the Merger Agreement or the transactions contemplated by the Merger Agreement or under this Limited Guarantee. The Guarantors agree not to assert in any litigation or other proceeding that this Limited Guarantee is illegal, invalid or
unenforceable in whole or in part. 
 10. No Recourse. Notwithstanding anything that may be expressed or implied
in this Limited Guarantee or any document or instrument delivered in connection herewith, by its acceptance of the benefits of this Limited Guarantee, the Guaranteed Party covenants, agrees and acknowledges that no Person other than the Guarantors
have any obligation hereunder and that, notwithstanding that the Guarantors and/or certain investment managers, managers or general partners of it or its Affiliates may be partnerships or limited liability companies, the Guaranteed Party has no
right of recovery under this Limited Guarantee, or any claim based on such obligations against, and no personal liability shall attach to, the former, current or future equity holders, controlling persons, directors, officers, employees, agents,
Affiliates (other than the Guarantors or any assignees under Section 7), members, managers or general or limited partners of the Guarantors or Purchaser, or any former, current or future equity holder, controlling person, director,
officer, employee, general or limited partner, member, manager, Affiliate (other than the Guarantors or any assignees under Section 7) or agent of any of the foregoing (collectively, each of the foregoing but not including Purchaser, the
Sub or their respective assignees themselves, a “Non-Recourse Party”), through Purchaser or otherwise, whether by or through attempted piercing of the corporate veil, by or through a claim by or on behalf of Purchaser against any
Non-Recourse Party, by the enforcement of any assessment or by any legal or equitable proceeding, by virtue of any statute, regulation or applicable Law, or otherwise, and the Guaranteed Party further covenants, agrees and acknowledges that the only
rights of recovery that the Guaranteed Party has in respect of the Merger Agreement or the transactions contemplated thereby against any Non-Recourse Party are its rights to recover from the Guarantors (but not any Non-Recourse Party) under and to
the extent expressly provided in this Limited Guarantee and subject to the Cap and the other limitations described herein. The Guaranteed Party acknowledges and agrees that Purchaser has no assets other than certain contract rights and cash in a
de minimis amount and that no additional funds are expected to be contributed to Purchaser unless the Acceptance Time or, if the Merger is to occur pursuant to Section 6.7 of the Merger Agreement, the Closing occurs, and in each
case the funding will occur prior to such occurrence. Recourse against the Guarantors under and pursuant to the terms of this Limited Guarantee shall be the sole and exclusive remedy of the Guaranteed Party and all of its Affiliates against the
Guarantors and the Non-Recourse Parties in respect of any liabilities or obligations arising under, or in connection with, the Merger Agreement or the transactions 

  
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contemplated thereby, including by piercing of the corporate veil or a claim by or on behalf of Purchaser; provided, that nothing in this Limited Guarantee shall restrict the Guaranteed
Party’s rights against Purchaser and Sub to specific performance to which it is entitled under the Merger Agreement. The Guaranteed Party hereby covenants and agrees that it shall not institute, and it shall cause its Affiliates not to
institute, any proceeding or bring any other claim arising under, or in connection with, the Merger Agreement or the transactions contemplated thereby against the Guarantors or any Non-Recourse Party except for (i) claims against the Guarantors
under this Limited Guarantee, (ii) claims against Purchaser or Sub under and in accordance with the Merger Agreement, (iii) claims against RT-ICON and Purchaser under the Equity Commitment Letter, including specific enforcement if
applicable thereunder, and (iv) claims against Purchaser under and in accordance with the Confidentiality Agreement. Nothing set forth in this Limited Guarantee shall confer or give or shall be construed to confer or give to any Person other
than the Guaranteed Party (including any Person acting in a representative capacity) any rights or remedies against any Person including the Guarantors, except as expressly set forth herein. 

11. Governing Law; Jurisdiction. This Limited Guarantee shall be governed by and construed in accordance with the internal
laws of the State of Delaware without giving effect to any conflict of law provision or rule (whether of the State of Delaware or any other jurisdiction) that would cause the application of laws of any jurisdictions other than those of the State of
Delaware. Each of the parties to this Limited Guarantee (a) consents to submit itself to the personal jurisdiction of the Court of Chancery of the State of Delaware in any action or proceeding arising out of or relating to this Limited
Guarantee, (b) agrees that all claims in respect of such action or proceeding may be heard and determined only in such court, (c) agrees that it shall not attempt to deny or defeat such personal jurisdiction by motion or other request for
leave from such court, (d) agrees not to bring any action or proceeding arising out of or relating to this Limited Guarantee in any other court, and (e) agrees that service of process upon such party in any action or proceeding shall be
effective under any manner permitted under the laws of the State of Delaware. Each of the parties hereto waives any defense of inconvenient forum to the maintenance of any such action or proceeding so brought and waives any bond, surety or other
security that might be required of any other party with respect thereto. 
 12. Waiver of Jury Trial. EACH PARTY
ACKNOWLEDGES AND AGREES THAT ANY CONTROVERSY WHICH MAY ARISE UNDER THIS LIMITED GUARANTEE IS LIKELY TO INVOLVE COMPLICATED AND DIFFICULT ISSUES, AND THEREFORE EACH SUCH PARTY HEREBY IRREVOCABLY AND UNCONDITIONALLY WAIVES ANY RIGHT SUCH PARTY MAY
HAVE TO A TRIAL BY JURY IN RESPECT OF ANY LITIGATION DIRECTLY OR INDIRECTLY ARISING OUT OF OR RELATING TO THIS LIMITED GUARANTEE. EACH PARTY CERTIFIES AND ACKNOWLEDGES THAT (I) NO REPRESENTATIVE, AGENT OR ATTORNEY OF ANY OTHER PARTY HAS
REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF LITIGATION, SEEK TO ENFORCE THE FOREGOING WAIVER, (II) EACH PARTY UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (III) EACH PARTY MAKES THIS
WAIVER VOLUNTARILY, AND (IV) EACH PARTY HAS BEEN INDUCED TO ENTER INTO THIS LIMITED GUARANTEE BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS EXPRESSED ABOVE. 

  
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 13. Counterparts. This Limited Guarantee may be executed in any number of
counterparts (including by facsimile and via email by .pdf delivery), each such counterpart when executed being deemed to be an original instrument, and all such counterparts shall together constitute one and the same agreement. 

14. No Third Party Beneficiaries. Except as provided in Section 10, the parties hereby agree that their
respective representations, warranties and covenants set forth herein are solely for the benefit of the other party hereto and its successors and permitted assigns, in accordance with and subject to the terms of this Limited Guarantee, and this
Limited Guarantee is not intended to, and does not, confer upon any Person other than the parties hereto and their respective successors and permitted assigns any rights or remedies hereunder, including the right to rely upon the representations and
warranties set forth herein. 
 15. Confidentiality. This Limited Guarantee shall be treated as confidential and
is being provided to the Guaranteed Party solely in connection with the Contemplated Transactions. This Limited Guarantee may not be used, circulated, quoted or otherwise referred to in any document by the Guaranteed Party or its Affiliates except
with the prior written consent of the Guarantors in each instance; provided that no such written consent is required for any disclosure of the existence of this Limited Guarantee to the legal, financial and accounting advisors to the
Guaranteed Party, or to the extent required by applicable Law, by the applicable rules of any national securities exchange, in connection with any SEC filing relating to the Contemplated Transactions or in connection with any litigation relating to
the Merger, the Merger Agreement or the transactions contemplated thereby and hereby. 
 16. Miscellaneous.

 (a) This Limited Guarantee, together with the Merger Agreement contains the entire agreement between the
parties relative to the subject matter hereof and supersedes all prior agreements and undertakings between the parties with respect to the subject matter hereof. No amendment, modification or waiver of any provision hereof shall be enforceable
unless approved by the Guaranteed Party and the Guarantor in writing. 
 (b) Any term or provision hereof that
is prohibited or unenforceable in any situation in the agreed-upon jurisdiction shall be ineffective solely to the extent of such prohibition or unenforceability without invalidating the remaining provisions hereof; provided, however,
that this Limited Guarantee may not be enforced without giving effect to the limitation of the amount payable hereunder to the Cap provided in Section 1 hereof and the provisions of Sections 9 and 10 and this
Section 16(b). 
 (c) When a reference is made in this Limited Guarantee to a Section, such
reference shall be to a Section of this Limited Guarantee unless otherwise indicated. The headings contained in this Limited Guarantee are for reference purposes only and shall not affect in any way the meaning or interpretation of this Limited
Guarantee. Whenever the words “include,” “includes” or “including” are used in this Limited Guarantee, they shall be deemed to be followed by the words “without limitation”. The words “hereof,”
“herein” and “hereunder” and words of similar import when used in this Limited Guarantee shall refer to this Limited Guarantee as a whole and not to any particular 

  
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provision of this Limited Guarantee. The definitions contained in this Limited Guarantee are applicable to the singular as well as the plural forms of such terms and to the masculine as well as
to the feminine and neuter genders of such term. References to a “person” will be interpreted broadly to include, without limitation, any individual, corporation, company, group, partnership, limited liability company, other entity or any
governmental representative or authority, as well as such person’s permitted successors and assigns. 
 (d)
All parties acknowledge that each party and its counsel have reviewed this Limited Guarantee and that any rule of construction to the effect that any ambiguities are to be resolved against the drafting party shall not be employed in the
interpretation of this Limited Guarantee. 
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 IN WITNESS WHEREOF, the Guarantors and the Guaranteed Party have caused this Limited
Guarantee to be duly executed and delivered as of the date first written above. 
  

			
	GUARANTORS:
	
	RIZVI OPPORTUNISTIC EQUITY FUND, L.P.,
	RIZVI OPPORTUNISTIC EQUITY FUND I-B, L.P.,
	RIZVI OPPORTUNISTIC EQUITY FUND (TI), L.P.,
	RIZVI OPPORTUNISTIC EQUITY FUND I-B (TI), L.P., and
	RIZVI TRAVERSE PARTNERS LLC
		
	By:	 	Rizvi Traverse Management, LLC
	Its:	 	General Partner or Manager
		
	By	 	 /s/ Bernhard L. Kohn III

	Name:	 	 Bernhard L. Kohn III

	Title:	 	Managing Director and Partner

  

			
	RIZVI OPPORTUNISTIC EQUITY FUND II, L.P.
		
	By:	 	Rizvi Traverse GP II, LLC
	Its:	 	General Partner
		
	By	 	 /s/ Bernhard L. Kohn III

	Name:	 	Bernhard L. Kohn III
	Title:	 	Managing Director and Partner

  

			
	GUARANTEED PARTY:
	
	 PLAYBOY ENTERPRISES, INC.

		
	By:	 	 /s/ Sol Rosenthal

	Name:	 	Sol Rosenthal
	Title:	 	Chairman of the Special CommitteeTender and Support Agreement

 Exhibit 10.2 
 TENDER AND SUPPORT AGREEMENT 
 THIS TENDER AND SUPPORT AGREEMENT dated as
of January 9, 2011 (this “Agreement”), by and among (i) Playboy Enterprises, Inc., a Delaware corporation (the “Company”) and (ii) the stockholders of the Company and their affiliates signatory hereto
(each a “Stockholder” and collectively the “Stockholders”). 
 WHEREAS, each Stockholder is
the beneficial and record owner of the number of shares of Class A common stock of the Company (“Class A Common Stock”), par value one cent ($.01), set forth opposite the name of such Stockholder on Schedule 1 hereto (together
with any shares of Class A Common Stock acquired or purchased by such Stockholder after the date of this Agreement and any other New Shares (as defined below), the “Owned Shares”); 

WHEREAS, the Board of Directors of the Company (the “Board”) has established a special committee (the
“Committee”) to evaluate, consider, review and respond to any proposal that has been or may be received by the Company, the Board or the Committee (an “Offer” or the “Offers”) for an acquisition of,
or other business combination with, the Company (any such transaction, a “Transaction”); and 
 WHEREAS, to
support and facilitate the Company entering into the Merger Agreement related to the Transaction identified on Exhibit A hereto (the “Subject Offer”), constituting a Recommended Third Party Offer (as defined below), each Stockholder
has agreed to take the actions and refrain from other actions each as described in this Agreement. 
 NOW THEREFORE, in
consideration of the premises and for other good and valuable consideration given to each party, the receipt of which is hereby acknowledged, and intending to be legally bound, the parties agree as follows. Certain capitalized terms used herein are
defined in ARTICLE V below. 
 ARTICLE I. 
 Restrictions on Transfer 
 Section 1.01 Restriction on Transfer. During the Term (as
defined below), except for any action required or permitted pursuant to this Agreement, each Stockholder shall not, directly or indirectly, (i) offer, sell, transfer, tender, pledge, encumber, create a Lien, assign, hypothecate or otherwise
dispose of, or enter into any contract, option, Constructive Sale (as defined below) or other agreement, arrangement or understanding with respect to the offer, sale, transfer, tender, pledge, encumbrance, assignment, hypothecation or other
disposition of, any or all of the Owned Shares held beneficially or of record by such Stockholder, or grant any proxy, power of attorney or other authorization or consent in or with respect to any of its Owned Shares that would be inconsistent with
such Stockholder’s obligations under this Agreement (any such action, a “Transfer”); or (ii) enter into any swap, hedge or other agreement, arrangement or understanding that transfers, in whole or in part, any of the
economic consequences of voting rights or ownership of the Owned Shares, or (iii) commit or agree to take or publicly announce an intention to commit or agree to take any of the foregoing actions. Any purported Transfer not permitted under this
Section 1.01 shall be null and void. 

 Section 1.02 Additional Shares. Each Stockholder agrees that, in the event
(i) of any stock dividend, stock split, recapitalization, reclassification, combination or exchange of the Common Stock affecting the Owned Shares held beneficially or of record by such Stockholder, or (ii) that after the date of this
Agreement such Stockholder purchases or otherwise acquires or obtains beneficial or record ownership of or an interest in any Common Stock (any such shares referred to in the foregoing clauses “(i)” or “(ii),” collectively,
“New Shares”), that such Stockholder shall deliver promptly (but no later than the second
(2nd) Business Day following such acquisition) to the
Company written notice of its purchase, acquisition or ownership of New Shares which notice shall state the number of New Shares so purchased, acquired or owned. Each Stockholder agrees that any New Shares purchased, acquired or owned during the
Term by such Stockholder shall be subject to the terms of this Agreement and shall constitute Owned Shares of such Stockholder to the same extent as if those New Shares were owned by such Stockholder on the date of this Agreement. 

Section 1.03 Further Assurances. In furtherance of the foregoing, (i) each Stockholder also agrees and consents to the entry of stop transfer
instructions with the Company, any record holder of any Owned Shares beneficially held by such Stockholder (or DTC participant holding Owned Shares in “street name” (a “Broker”)) and any duly appointed transfer agent for
the registration or transfer of such Stockholder’s Owned Shares against the transfer thereof except in compliance with the restrictions in ARTICLE I and in accordance with the obligations set forth in Section 2.01 and in compliance
with the other terms of this Agreement, and (ii) the Company, any such record holder or Broker and any duly appointed transfer agent for the registration or transfer of Owned Shares are hereby authorized to decline to make any transfer thereof
if such transfer may constitute a violation or breach of this Agreement. From time to time, at the request of the Company and without further consideration, each Stockholder shall execute and deliver such additional documents and take all such
further action as may be necessary or desirable to consummate and make effective the restrictions, provisions and transactions contemplated by this Agreement. 
 ARTICLE II. 
 Agreement to Tender 

Section 2.01 Obligation to Tender. Each Stockholder shall duly tender, or cause to be tendered, in the Subject Offer, all of the Owned Shares
pursuant to and in accordance with the terms of the Subject Offer. Promptly, but in any event no later than five (5) Business Days after the commencement of the Subject Offer, each Stockholder shall (i) deliver or cause to be delivered to
the depositary designated in the Subject Offer (the “Depositary”) (A) a letter of transmittal with respect to such Owned Shares complying with the terms of the Subject Offer, (B) a certificate or certificates representing
such Owned Shares or an “agent’s message” (or such other evidence, if any, of transfer as the Depositary may reasonably request) in the case of a book-entry transfer of any Owned Shares and (C) all other documents or instruments
required to be delivered pursuant to the terms of the Subject Offer, and/or (ii) instruct its Broker to tender such Owned Shares on a timely basis and in accordance herewith pursuant to and in accordance with the terms of the Subject Offer.
Each Stockholder agrees that once its Owned Shares are so tendered, such Stockholder will not withdraw, nor permit the withdrawal of, any tender of such Owned Shares, unless and until (i) the Subject Offer shall have been terminated in
accordance with the terms of the Merger Agreement, or (ii) this Agreement shall have been terminated in 

 
accordance with Section 4.01. In the event that the Merger Agreement entered into in connection with the Subject Offer is terminated in accordance with its terms and another Third
Party Agreement is entered into with respect to another Recommended Third Party Offer during the Term, the provisions of this Section 2.01 shall apply to such other Recommended Third Party Offer in the same fashion as they apply to the
Subject Offer, unless the Company (acting through the Committee, if applicable) shall have advised the Stockholders in writing that this Section 2.01 shall not apply to such other Recommended Third Party Offer. For the avoidance of
doubt, Stockholders are not required to tender into any Recommended Third Party Offer which does not have an offer price of at least $6.15 in cash for each Owned Share, subject to equitable adjustment as a result of any stock split (including a
reverse stock split) or combination, exchange or readjustment of shares, or any stock dividend or stock distribution, in each case after the date hereof and prior to consummation of the Subject Offer or, if applicable, any other relevant Recommended
Third Party Offer to which the Owned Shares are otherwise required to be tendered pursuant hereto. 
 Section 2.02
Obligation to Enter Into Other Tender Support Agreements. In the event that the Merger Agreement entered into in connection with the Subject Offer is terminated in accordance with its terms, subject to the terms of this Agreement, and during
the Term, each Stockholder agrees that if the Company (acting through the Committee, if applicable) advises such Stockholder that it has received an Offer which it determines is a Recommended Third Party Offer and requests that each Stockholder, in
lieu of such Stockholder’s obligations to the Company under Section 2.01, enter into a tender support agreement in customary form with the Third Party under such Recommended Third Party Offer pursuant to which each Stockholder will
agree with the applicable Third Party that it irrevocably tender (subject to the provisions of Section 2.03 below) into such Recommended Third Party Offer, all of the Owned Shares held beneficially or of record by such Stockholder in
accordance with the terms of the Recommended Third Party Offer, then each Stockholder shall enter into such support agreement as promptly as practicable and in no event later than the second
(2nd) Business Day following such notice and request.

 Section 2.03 Termination of Third Party Agreement or Change in Company Recommendation. Notwithstanding anything to the contrary in
Section 2.01, Section 2.02 or any other provision of this Agreement, no Stockholder shall be required to (and any other tender support agreement shall not require such Stockholder to) Transfer any Owned Shares held
beneficially or of record by such Stockholder pursuant to a Recommended Third Party Offer (including the Subject Offer) if the Merger Agreement (in the case of the Subject Offer) or the related Third Party Agreement for such other Recommended Third
Party Offer, as the case may be, has been terminated in accordance with its terms. 
 Section 2.04 Voting, Written Consents. Nothing
herein shall restrict the right, if any, of each Stockholder to vote the Owned Shares held beneficially or of record by it in favor or against any matter submitted by the Board for a vote by the Company’s stockholders. 

Section 2.05 Waiver of Appraisal and Dissenters’ Rights and Actions. Each Stockholder hereby (i) waives and agrees not to exercise any
rights of appraisal or rights to dissent from the merger contemplated by a Recommended Third Party Offer (including the Subject Offer) that Stockholder may have and (ii) agrees not to commence or join in, and agrees to take all actions

 
necessary to opt out of any class in any class action with respect to, any claim, derivative or otherwise, against the Company, any Third Party or any of their respective officers, directors,
general partners, managers, affiliates or successors (x) challenging the validity of, or seeking to enjoin the operation of, any provision of this Agreement or (y) alleging a breach of any fiduciary duty of any person with respect to any
Recommended Third Party Offer, including in connection with the negotiation and entry into the Merger Agreement or any other applicable Third Party Agreement. 
 ARTICLE III. 
 Representations and Warranties 

Section 3.01 Representations and Warranties of the Stockholders. Each Stockholder hereby represents and warrants to the Company as follows as to
itself, as of the date of this Agreement and during the Term: 
 (a) Power; Due Authorization; Binding Agreement. Such
Stockholder is a corporation, limited partnership or limited liability company, as applicable, duly formed under the laws of its jurisdiction of incorporation, formation or organization and has full entity power and authority to execute and deliver
this Agreement and to perform its obligations hereunder and consummate the transactions contemplated hereby. The execution and delivery of this Agreement by such Stockholder and the performance of its obligations hereunder and the consummation of
the transactions contemplated hereby have been, if necessary, duly and validly authorized by the appropriate governing body of such Stockholder, and, no other entity proceedings on the part of such Stockholder are necessary to authorize the
execution, delivery and performance of this Agreement by such Stockholder and the consummation of the transaction contemplated hereby. Such Stockholder has duly and validly executed this Agreement and this Agreement constitutes a legal, valid and
binding obligation of such Stockholder enforceable against such Stockholder in accordance with its terms. 
 (b) Ownership of
Shares. The Owned Shares listed on Schedule 1 opposite such Stockholder’s name are owned beneficially and of record by such Stockholder and constitute all of the Owned Shares and any other securities of the Company owned beneficially
or of record by such Stockholder. All of the Owned Shares are free and clear of any Liens except as provided hereunder or pursuant to restrictions on transfer under applicable securities laws. Except as set forth in the Stockholder SEC Filing, such
Stockholder has sole voting power, sole power of disposition and sole power to issue instructions with respect to the matters set forth in this Agreement, in each case with respect to all of the Owned Shares set forth opposite Stockholder’s
name on Schedule 1 with no limitations, qualifications or restrictions on such rights, subject to applicable securities laws and the terms of this Agreement (and except that no representation or warranty is made as to any restrictions arising under
the Company’s certificate of incorporation or by-laws). No Stockholder is a party to any swap, hedge or other agreement, arrangement or understanding that transfers, in whole or in part, any of the economic consequences or voting rights of
ownership of the Owned Shares. 
 (c) No Conflicts. The execution and delivery of this Agreement by such Stockholder does
not, and the performance of the terms of this Agreement by such Stockholder will not, (i) require such Stockholder to obtain the authorization, consent or approval of, or make any 

 
filing with or notification to, any Governmental Authority (other than any required filing under the U.S. federal securities laws) that has not already been obtained or made, (ii) require
the authorization, consent or approval of, or make any filing with or notification to, any other Person that has not already been obtained or made, (iii) violate any agreement, arrangement or understanding to which such Stockholder is a party,
including any voting agreement, stockholders agreement, irrevocable proxy or voting trust, (iv) violate any order, writ, injunction or decree of any Governmental Authority that is applicable to such Stockholder or any of such Stockholder’s
properties or assets, in each case, except for any violation, default or conflict which would not adversely effect in any material respect the ability of such Stockholder to perform its obligations hereunder or consummate the transactions
contemplated hereby. The Owned Shares held beneficially or of record by such Stockholder are not, with respect to the voting or Transfer of such Owned Shares, subject to any other agreement, arrangement or understanding including any voting
agreement, stockholders agreement, irrevocable proxy or voting trust. 
 (d) No Litigation. There is no suit, claim,
action, investigation or proceeding pending or, to the knowledge of such Stockholder, threatened against such Stockholder at law or in equity before or by any Governmental Authority that could reasonably be expected to impair the ability of such
Stockholder to perform its obligations hereunder or consummate the transactions contemplated hereby. 
 (e) No Material
Non-Public Information. Each Stockholder acknowledges that the Company has not provided any material non-public information regarding the Company that has not been previously disclosed other than, based upon Stockholder’s entering into a
confidentiality agreement and agreement not to trade, the terms of the Merger Agreement. 
 ARTICLE IV. 

Term 
 Section 4.01
Term. The term of this Agreement (the “Term”) shall commence on the date hereof and expire on March 31, 2011. However, if the Subject Offer has commenced by such date, then until such time (but in no event later than
June 3, 2011) as the Subject Offer (or any other Recommended Third Party Offer commenced during the Term) remains open and has not been consummated or terminated in accordance with the Merger Agreement or other Third Party Agreement, as the
case may be, the provisions of Section 2.01, Section 2.05 and ARTICLE VI, including Section 6.12, shall continue to apply. Notwithstanding anything to the contrary in Section 6.07, any Transfer by any
Stockholder after March 31, 2011 shall be subject to the agreement by the transferee to the foregoing continuing obligations in form reasonably satisfactory to the Company. No termination of the Term shall relieve any party from any liability
for any breach of this Agreement. 
 ARTICLE V. 
 Definitions 
 Section 5.01 Definitions. As used in this Agreement, the
following terms shall have the meanings set forth below: 
 “Business Day” shall mean a day, other than a
Saturday, Sunday or another day on which commercial banking institutions in New York are authorized or required by Law to be closed. 

 “Common Stock” shall mean, collectively, the shares of Class A Common
Stock and the shares of the Company’s Class B common stock, par value one cent ($.01) per share. 
 “Constructive
Sale” shall mean a short sale with respect to such security, entering into or acquiring a derivative contract with respect to such security, entering into or acquiring a futures or forward contract to deliver such security or entering into
any transaction that has substantially the same effect as any of the foregoing. 
 “Governmental Authority”
shall mean any national government or the government of any state or other political subdivision, and departments, courts, commissions, board, bureaus, ministries, agencies or other instrumentalities of any of them. 

“Law” means any federal, state, provincial, local or foreign law, statute, ordinance, regulation, judgment, order,
decree, injunction, arbitration award, franchise, license, agency requirement or permit of any Governmental Authority. 

“Lien” shall mean any lien, mortgage, charge, pledge, security interest, encumbrance, any conditional sale or other
title retention agreement or the filing of or any agreement, arrangement or understanding to give any financing statement under the Laws of any jurisdiction including with respect to any account with the Broker containing any Owned Shares.

 “Merger Agreement” means the Third Party Agreement related to the Subject Offer. 

“Person” shall mean any individual, corporation, limited liability company, partnership, association, trust,
unincorporated organization, other entity or group (as defined in the Securities Exchange Act of 1934, as amended). 

“Recommended Third Party Offer” shall mean the receipt of an Offer from a Third Party to be made as a tender offer that
(i) the Board (acting through the Committee, if applicable) determines is in the best interests of the Company’s stockholders, (ii) which the Board (acting through the Committee, if applicable) intends to recommend to the
Company’s stockholders, subject to the application of Section 2.03, and (iii) provides that each outstanding share of Common Stock (other than shares of Common Stock held directly or indirectly by such Third Party or its
affiliates, members, owners or other related parties and dissenting shares) will be entitled upon consummation of such Recommended Third Party Offer to receive at least $6.15 per share in cash, free and clear of all Liens created by the Company or
such applicable Third Party. 
 “Subsidiary” means any Person (i) of which the Company directly or
indirectly owns securities or other equity interests representing more than fifty percent (50%) of the aggregate voting power or (ii) of which the Company possesses directly or indirectly more than fifty percent (50%) of the right to
elect directors or Persons holding similar positions. 

 “Third Party” shall mean the offeror under a Recommended Third Party Offer
including the Subject Offer (other than the Company). 
 “Third Party Agreement” shall mean an agreement
(including the Merger Agreement) entered into with the Company providing for a Recommended Third Party Offer, as the same may be amended from time to time in accordance with its terms. 

ARTICLE VI. 

Miscellaneous 
 Section
6.01 Entire Agreement; Amendments. This Agreement constitutes the entire agreement among the parties with respect to the subject matter of this Agreement and supersedes all other prior agreements and understandings, both written and oral,
among the parties with respect to the subject matter of this Agreement. Nothing in this Agreement, express or implied, is intended to or shall confer upon any other person any right, benefit or remedy of any nature whatsoever under or by reason of
this Agreement. This Agreement may not be modified, amended, altered or supplemented, except upon the execution and delivery of a written agreement executed by each of the parties to this Agreement. 

Section 6.02 Notices. All notices, requests and other communications to any party shall be in writing and shall be deemed given if delivered
personally, facsimiled (which is confirmed) or sent by recognized overnight courier (providing proof of delivery) to the parties at the following addresses: 
 If to the Company, to: 
 Playboy Enterprises, Inc. 

680 North Lake Shore Drive 
 Chicago, IL 60611 
 with a copy (which shall not constitute notice) to:

 Kaye Scholer LLP 
 1999 Avenue of the Stars 
 Suite 1600 

Los Angeles, CA 90067 
 If to any Stockholder, to the address of such Stockholder on the Company’s books and records: 

or such other address or facsimile number as such party may hereafter specify by like notice to the other parties. All such notices, requests and other
communications shall be deemed received on the date of receipt by the recipient if received prior to 5:00 p.m., New York city time, and such day is a Business Day in the place of receipt. Otherwise, any such notice, request or communication
shall be deemed not to have been received until the next succeeding Business Day in the place of receipt. 

 Section 6.03 Governing Law. This agreement shall be governed by, and construed in accordance with,
the Laws of the State of Delaware, applicable to contracts executed in and to be performed entirely within that state, regardless of the Law that might otherwise govern under applicable principles of conflicts of laws. 

Section 6.04 Expenses. All expenses incurred by the Company in connection with or related to the authorization, preparation or execution of this
Agreement and the consummation of the transactions contemplated hereby, shall be borne solely and entirely by the Company, and all such expenses incurred by any Stockholder shall be borne solely and entirely by such Stockholder. 

Section 6.05 Jurisdiction. All actions and proceedings arising out of or relating to this Agreement shall be heard and determined in the Chancery
Court of the State of Delaware or, in the event that such court does not have subject matter jurisdiction over such action or proceeding, any federal or state court sitting in the State of Delaware, and the parties to this Agreement irrevocably
submit to the exclusive jurisdiction of such courts (and, in the case of appeals, appropriate appellate courts therefrom) in any such action or proceeding and irrevocably waive the defense of an inconvenient forum to the maintenance of any such
action or proceeding. The consents to jurisdiction set forth in this paragraph shall not constitute general consents to service of process in the State of Delaware and shall have no effect for any purpose except as provided in this paragraph and
shall not be deemed to confer rights on any Person other than the parties. Each of the parties to this Agreement consents to service being made through the notice procedures set forth in Section 6.02 and agrees that service of any
process, summons, notice or document by registered mail (return receipt requested and first-class postage prepaid) to the respective addresses set forth in Section 6.02 shall be effective service of process for any suit or proceeding in
connection with this Agreement or the transactions contemplated by this Agreement. 
 Section 6.06 WAIVER OF JURY TRIAL. EACH OF THE
PARTIES TO THIS AGREEMENT HEREBY IRREVOCABLY WAIVES ANY AND ALL RIGHTS TO TRIAL BY JURY IN ANY ACTION, PROCEEDING OR COUNTERCLAIM (WHETHER BASED IN CONTRACT, TORT OR OTHERWISE) ARISING OUT OF OR RELATING TO THIS AGREEMENT OR THE TRANSACTIONS
CONTEMPLATED HEREBY OR THE ACTIONS OF COMPANY OR SHAREHOLDER IN THE NEGOTIATION, ADMINISTRATION, PERFORMANCE AND ENFORCEMENT OF THIS AGREEMENT. 

Section 6.07 No Assignment. Neither this Agreement nor any of the rights, interests or obligations under this Agreement shall be assigned, in
whole or in part, by any of the parties without the prior written consent of the other parties; provided that the Company may assign any or all of its rights, interests and obligations under this Agreement to a Third Party in connection with a
Recommended Third Party Offer. Subject to the preceding sentence, this Agreement shall be binding upon, inure to the benefit of, and be enforceable by, the parties and their respective successors and permitted assigns. Any purported assignment not
permitted under this Section 6.07 shall be null and void. 
 Section 6.08 Counterparts. This Agreement may be executed in
counterparts (including by facsimile) (each of which shall be deemed to be an original but all of which taken together shall 

 
constitute one and the same agreement) and shall become effective when one or more counterparts have been signed by each of the parties and delivered to the other parties. Copies of executed
counterparts transmitted by telecopy, telefax or electronic transmission shall be considered original executed counterparts for purposes of this Section 6.08 provided that receipt of copies of such counterparts is confirmed. 

Section 6.09 Severability. If any term or other provision of this Agreement is determined by a court of competent jurisdiction to be invalid,
illegal or incapable of being enforced by any Law or public policy, all other terms, provisions and conditions of this Agreement shall nevertheless remain in full force and effect. Upon such determination that any term or other provision is invalid,
illegal or incapable of being enforced, the parties shall negotiate in good faith to modify this Agreement so as to effect the original intent of the parties as closely as possible to the fullest extent permitted by Law in an acceptable manner to
the end that the transactions contemplated by this Agreement are fulfilled to the extent possible. 
 Section 6.10 No Ownership Interest.
Nothing contained in this Agreement shall be deemed to vest in the Company or any other Person any direct or indirect ownership or beneficial ownership or incidence of ownership or beneficial ownership of or with respect to any Owned Shares until
the Owned Shares are accepted by a Third Party in a Recommended Third Party Offer. Until such time, all rights, ownership and economic benefits of and relating to the Owned Shares shall remain vested in and belong to the Stockholders, subject to the
Stockholders’ obligations under this Agreement. 
 Section 6.11 Time of the Essence; Publicity. Time is of the essence in the
performance of the obligations under this Agreement. The Company and/or any relevant Third Party may issue a press release announcing the execution of this Agreement, in a form reasonably satisfactory to the Stockholders. Nothing herein shall limit
any party from complying with its disclosure obligations under applicable securities laws or stock exchange rules. 
 Section 6.12 Liquidated
Damages. The Stockholders acknowledge that in the event of a material breach of this Agreement by any Stockholder the Company will suffer significant damages. The Stockholders further acknowledge and agree that the amount of such damages is
uncertain and incapable of estimation at this time and that any attempt to estimate such damages would be extremely difficult, time-consuming and impracticable. Therefore, the parties agree that, in the event that any Stockholder materially breaches
its obligations under this Agreement (other than as a result of the Company’s failure to take actions required by Section 1.03) and as a direct result the transactions contemplated by the Subject Offer) cannot be consummated in
accordance with the terms of the Merger Agreement or the consummation of such contemplated transactions is delayed in any material respect, the Stockholders shall be joint and severally obligated to pay the Company as liquidated damages an aggregate
of $2.5 million, it being agreed and acknowledged that such amount represents a reasonable estimate of the damages the Company will sustain and does not constitute a forfeiture or penalty. Such liquidated damages shall be payable regardless of
whether (a) the Subject Offer is ultimately consummated, (b) another Recommended Third Party Offer occurs or (c) the Company enters into Third Party Agreement in connection with any another Recommended Third Party Offer. 

 The parties have caused this Agreement to be duly executed as of the day and year first
above written. 
  

					
	 PLAYBOY ENTERPRISES, INC.

		
	By:	 	 /s/ Sol Rosenthal

	 Name:
	 	Sol Rosenthal
	 Title:
	 	Chairman of the Special Committee
	
	 PLAINFIELD CAPITAL LIMITED

		
	By:	 	 /s/ Thomas X. Fritsch

		 		 	Thomas X. Fritsch
	
	 PLAINFIELD SPECIAL SITUATIONS MASTER FUND II LIMITED

		
	By:	 	 /s/ Thomas X. Fritsch

		 		 	Thomas X. Fritsch
	
	 PLAINFIELD OC MASTER FUND LIMITED

		
	By:	 	 /s/ Thomas X. Fritsch

		 		 	Thomas X. Fritsch

 SCHEDULE 1 
 Details of Ownership 
  

							
	 	 	              Stockholder	  	Owned Shares	 
			
	 1.
	 	 Plainfield Capital Limited
	  	 	757,595	  
			
	 2.
	 	 Plainfield Special Situations Master Fund II Limited
	  	 	104,298	  
			
	 3.
	 	 Plainfield OC Master Fund Limited
	  	 	64,807	  

 EXHIBIT A 
 Agreement and Plan of Merger by and among Icon Acquisition Holdings, L.P., Icon Merger Sub, Inc. and the Company dated as of January 9, 2011

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