Document:

Purchase Agreement

 Exhibit 10.2 
 EXECUTION COPY 
 PURCHASE AGREEMENT 
 THIS PURCHASE AGREEMENT (this “Agreement”) is made and entered into as of August 7, 2009 between DUANE READE HOLDINGS, INC., a
corporation organized and existing under the laws of the State of Delaware (the “Company”), and OHCP DR CO-INVESTORS 2009, LLC, a Delaware limited liability company (the “Purchaser”). Capitalized terms used but not
otherwise defined herein shall have the meanings assigned to them in Section 1.1. 
 WHEREAS, the Company desires to finance the
reduction of certain indebtedness of the Company and its subsidiaries (the “Financing”); and 
 WHEREAS, in order to effect
the Financing, subject to the terms and conditions set forth in this Agreement, the Company desires to issue and sell to the Purchaser and the Purchaser desire to acquire from the Company (the “Transaction”): (i) one million
two hundred fifty thousand (1,250,000) shares (the “Shares”) of the Company’s Series B Redeemable Preferred Stock, par value $0.01 per share (the “Preferred Stock”), and (ii) a Warrant to Purchase
Shares of Common Stock of the Company (the “Warrant”), annexed as Exhibit A hereto, exercisable initially to purchase an aggregate of up to one million one hundred ninety six thousand two hundred sixty one
(1,196,261) shares of the Company’s common stock, par value $0.01 per share (the “Common Stock”), representing 25% of the capital stock of the Company on a fully diluted basis (after giving effect to the issuance of the
Warrant but without giving effect to the conversion of the Preferred Stock and the Company’s Series A Redeemable Preferred Stock), to be issued upon the exercise of the Warrant (including any additional shares of Common Stock issuable upon
exercise of the Warrant as a result of adjustments to the number of shares of Common Stock issuable under the Warrant in accordance with the terms thereof, the “Warrant Shares”). 
 IN CONSIDERATION of the mutual covenants contained in this Agreement, the Company and the Purchaser hereby agree as follows: 
 ARTICLE I 
 CERTAIN DEFINITIONS 

 1.1 Certain Definitions. As used in this Agreement, and unless the context requires a different meaning, the following terms
have the meanings indicated: 
 “Affiliate” means, with respect to any Person, any Person that, directly or indirectly,
controls, is controlled by or is under common control with such Person. For the purposes of this definition, “control” (including, with correlative meanings, the terms “controlling”, “controlled by”
and “under common control with”), as used with respect to any Person, shall mean the possession, directly or indirectly, of the power to direct or cause the direction of the management and policies of such Person, whether through
the ownership of voting securities or by contract or otherwise. 

 “Agreement” shall have the meaning set forth in the preamble to this Purchase Agreement.

 “Business Day” means any day other than Saturday, Sunday and any day which is a legal holiday or a day on which banking
institutions in the State of New York are authorized or required by law or other government actions to close. 
 “Certificate of
Designations” means the Certificate of Designations, Powers, Preferences and Rights of Series B Redeemable Preferred Stock of the Company annexed as Exhibit B hereto. 
 “Closing” shall have the meaning set forth in Section 2.2(a). 
 “Common Stock” shall have the meaning set forth in the recitals to this Agreement. 
 “Company” shall have the meaning set forth in the preamble to this Agreement. 
 “Company SEC Reports” means the forms, reports and documents which are required to be filed with the SEC pursuant to the federal
securities laws and the SEC rules and regulations thereunder. 
 “Equity Interests” means shares of capital stock,
partnership interests, membership interests in a limited liability company, beneficial interests in a trust or other equity ownership interests in a Person, and any warrants, options or other rights entitling the holder thereof to purchase or
acquire any such equity interest. 
 “Exchange Act” means the Securities Exchange Act of 1934, as amended, and the rules and
regulations promulgated thereunder. 
 “Execution Date” means the date of this Agreement first written above. 
 “Issuers” means Duane Reade Inc., a Delaware Corporation, and Duane Reade, a New York general partnership. 
 “Material Adverse Effect” means as determined by the Purchaser in its sole discretion, any change, event, circumstance, fact, condition
or development that has had or could reasonably be expected to have an adverse effect that is material on the business, property, financial condition, projections or prospects of the Company and its subsidiaries, in each case, either on a short-,
medium- or long-term basis, which shall include, for the avoidance of doubt and without limitation, (i) any material increase in the liabilities of the Company and its subsidiaries, (ii) changes in laws, regulations or their enforcement,
(iii) changes generally affecting the industry of the Company and its subsidiaries, (iv) changes in general economic, financial and market conditions, (v) the loss of key managers, labor disputes and other labor disruptions,
(vi) increases in the cost of goods and services, (vii) adverse litigation or arbitration proceedings and (viii) natural and man-made disasters, acts of war or terrorist attacks. 
  

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 “New Notes Offering” means the Issuers’ offering of new senior secured notes and
new senior subordinated notes, each as further described in the Issuers’ Offer to Purchase and Solicitation of Consents, dated July 8, 2009. 
 “Notes” means the Issuers’ (i) $210 million outstanding aggregate principal amount of their Senior Secured Floating Rate Notes due 2010 and (ii) $195 million outstanding aggregate
principal amount of 9.75% Senior Subordinated Notes due 2011. 
 “Offers and Consent Solicitations” means the offer to
purchase for cash the Notes and the solicitation of consents for proposed amendments to the related indentures governing the Notes, each as further described in the Issuers’ Offer to Purchase and Solicitation of Consents, dated July 8,
2009. 
 “Person” means an individual, corporation, partnership, limited liability company, joint venture, incorporated or
unincorporated association, joint stock company, trust, unincorporated organization, government (or an agency or political subdivision thereof) or other entity of any kind. 
 “Preemptive Rights Agreement” means the Preemptive Rights Agreement, dated July 30, 2004, by and amount Oak Hill Capital Partners,
L.P., Oak Hill Capital Management Partners, L.P., OHCP DR Co-Investors, LLC, Duane Reade Shareholders, LLC, the Company, Anthony J. Cuti and certain members of the management of Duane Reade, Inc. 
 “Preferred Stock” shall have the meaning set forth in the recitals to this Agreement. 
 “Purchase Price” shall have the meaning set forth in Section 2.1(b). 
 “Purchaser” shall have the meaning set forth in the preamble to this Agreement. 
 “SEC” means the Securities and Exchange Commission. 
 “Securities Act” means the Securities Act of 1933, as amended, and the rules and regulations promulgated thereunder. 
 “Shares” shall have the meaning set forth in the recitals to this Agreement. 
 “Transaction” shall have the meaning set forth in the recitals to this Agreement. 
 “Transaction
Documents” means this Agreement, the Certificate of Designations, the Warrant and all exhibits hereto and all other documents, instruments and writings required pursuant to this Agreement. 
  

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 “Warrant” shall have the meaning set forth in the recitals to this Agreement.

 “Warrant Shares” shall have the meaning set forth in the recitals to this Agreement. 
 “Warrant Strip” means a Warrant initially exercisable to purchase 0.9570088 shares of Common Stock, and corresponding to one share of
Preferred Stock. 
 ARTICLE II 
 PURCHASE AND SALE OF CONVERTIBLE PREFERRED SHARES 
 2.1 Purchase and Sale; Purchase Price. 
 (a) Subject to the terms and conditions set forth herein, the Company shall issue and sell to the Purchaser, and the Purchaser shall
purchase from the Company, (i) one million two hundred fifty thousand (1,250,000) Shares of Preferred Stock and (ii) the Warrant Strips. The Preferred Stock shall have the respective rights, preferences and privileges as set forth in
the Certificate of Designations to be filed by the Company with the Secretary of State of the State of Delaware on or before the Execution Date. The Warrant shall have the respective rights, preferences and privileges as set forth in the Warrant.

 (b) The purchase price shall be seventy-seven United States dollars and sixty cents ($77.60) for each share of Preferred
Stock and twenty-two United States dollars and forty cents ($22.40) for each Warrant Strip (collectively, the “Purchase Price”). 
 2.2 Closing; Delivery. 
 (a) Subject to the terms and conditions set forth in this Agreement being
satisfied, the closing of the Transaction shall take place at the offices of Paul, Weiss, Wharton, Rifkind & Garrison LLP, 1285 Avenue of the Americas, New York, NY, 10019-6064, at 10:00 a.m. local time, and shall take place
simultaneously with the execution and delivery of this Agreement (which time and place are designated as the “Closing”). At the Closing, the Company shall issue and deliver to the Purchaser one million two hundred fifty thousand
(1,250,000) shares of Preferred Stock and the Warrant, and the Purchaser shall deliver to the Company the Purchase Price in an aggregate amount equal to one hundred twenty five million United States dollars ($125,000,000). 
 (b) At the Closing, the Company shall deliver to the Purchaser (i) a certificate representing the Shares and (ii) the Warrant,
in each case, duly executed and in proper form, and the Purchaser shall deliver to the Company the full amount of the Purchase Price by wire transfer of immediately available U.S. funds. 
  

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 ARTICLE III 
 REPRESENTATIONS AND WARRANTIES 
 3.1 Representations, Warranties and Agreements of the
Company. The Company hereby makes the following representations and warranties to the Purchaser, all of which shall survive the Closing: 
 (a) Organization and Qualification. The Company is a corporation, duly incorporated, validly existing and in good standing under the laws of the State of Delaware, with the requisite corporate power and
authority to own and use its properties and assets and to carry on its business as currently conducted. The Company and each of its subsidiaries are duly qualified to do business and are in good standing in each jurisdiction in which the nature of
the business conducted or property owned by the Company or such subsidiary makes such qualification necessary. Except as set forth in the Company SEC Reports, the Company does not own, directly or indirectly, any equity or debt securities of any
corporation, partnership, or other entity. 
 (b) Authorization, Enforcement. The Company has the requisite corporate
power and authority to enter into this Agreement and each other Transaction Document and to consummate the transactions contemplated hereby and thereby and to otherwise carry out its obligations hereunder and thereunder. The execution and delivery
of this Agreement and each of the other Transaction Documents by the Company and the consummation by it of the transactions contemplated hereby and thereby has been duly authorized by all necessary action on the part of the Company. Each of this
Agreement and the other Transaction Documents has been or will be duly executed by the Company and when delivered in accordance with the terms hereof or thereof will constitute the valid and binding obligation of the Company enforceable against the
Company in accordance with its terms, except as such enforceability may be limited by applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or similar laws relating to, or affecting generally the enforcement of, creditors’
rights and remedies or by other equitable principles of general application. 
 (c) Capitalization.
Schedule 3.1(c) sets forth a complete and accurate list of the authorized, issued and outstanding Equity Interests of the Company immediately prior to the Transaction. Except as set forth on Schedule 3.1(c), there are no
shares of capital stock or other Equity Interests of the Company issued, reserved for issuance or outstanding and no outstanding or authorized options, warrants, convertible or exchangeable securities, subscriptions, rights (including any preemptive
rights), stock appreciation rights, calls or commitments of any character whatsoever to which the Company is a party or may be bound requiring the issuance, sale or redemption or purchase of shares of any Equity Interests of the Company. 

(d) Issuance of Securities. The Shares and Warrant have been duly and validly authorized for issuance, offer and sale pursuant
to this Agreement and, when issued and delivered as provided hereunder against payment in accordance with the terms hereof, shall be valid and binding obligations of the Company enforceable in 

  

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accordance with their respective terms. When issued in accordance with the terms hereof, the Shares and Warrant will be duly authorized, validly issued,
fully paid and non-assessable, and, except pursuant to the Preemptive Rights Agreement, not subject to any preemptive rights. At the Closing, the Company will have the requisite number of shares of Common Stock duly authorized and reserved for
issuance to satisfy the Company’s obligations upon the exercise of the Warrant and conversion of the Preferred Stock, and when issued such shares of Common Stock shall be validly issued, fully paid and non-assessable. 
 (e) No Conflicts. The execution, delivery and performance of this Agreement and the other Transaction Documents by the Company and
the consummation by the Company of the transactions contemplated hereby and thereby, do not and will not (i) conflict with or violate any provision of its certificate of incorporation or bylaws (each as amended through the date hereof) or
(ii) be subject to obtaining any consents, conflict with, or constitute a default (or an event which with notice or lapse of time or both would become a default) under, or give to others any rights of termination, amendment, acceleration or
cancellation of, any material agreement, indenture or instrument to which the Company or any of its subsidiaries is a party, or (iii) result in a violation of any material law, rule, regulation, order, judgment, injunction, decree or other
restriction of any court or governmental authority to which the Company is subject, or by which any property or asset of the Company is bound or affected. The business of the Company is not being conducted in violation of any material law, ordinance
or regulation of any governmental authority. 
 (f) Consents and Approvals. The Company is not required to obtain any
material consent, waiver, authorization or order of, or make any filing or registration with, any court or other federal, state, local or other governmental authority or other Person in connection with the execution, delivery and performance by the
Company of this Agreement and each of the other Transaction Documents, except for the filing of the Certificate of Designations with respect to the Preferred Stock with the Secretary of State of the State of Delaware, which filing shall be effected
on or before the Execution Date. 
 3.2 Representations and Warranties of the Purchaser. The Purchaser hereby represents and
warrants to the Company as follows: 
 (a) Authority. The Purchaser has the requisite power and authority to enter into
this Agreement and any Transaction Document to which it is a party and to consummate the transactions contemplated hereby and thereby and otherwise to carry out its obligations hereunder and thereunder. The acquisition of the Shares and Warrant to
be purchased by the Purchaser hereunder has been duly authorized by all necessary action on the part of the Purchaser. This Agreement and any Transaction Document to which the Purchaser is a party has been duly executed and delivered by the
Purchaser and constitutes the valid and legally binding obligation of the Purchaser, enforceable against it in accordance with its terms, except as such enforceability may be limited by applicable bankruptcy, insolvency, reorganization, moratorium
or similar laws relating to, or affecting generally the enforcement of, creditors rights and remedies or by other general principles of equity. 
  

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 (b) Investment Intent. The Purchaser is acquiring the Shares and Warrant to be
purchased by it hereunder for its own account for investment purposes only and not with a view to or for distributing or reselling such Shares or Warrant, or any part thereof or interest therein, without prejudice, however, to the Purchaser’s
right, subject to the provisions of this Agreement, at all times to sell or otherwise dispose of all or any part of such Shares and Warrant in compliance with applicable federal and state securities laws. 
 (c) Experience of Purchaser. The Purchaser, either alone or together with its representatives, has such knowledge, sophistication
and experience in business and financial matters so as to be capable of evaluating the merits and risks of an investment in the Shares and Warrant to be acquired by it hereunder, and has so evaluated the merits and risks of such investment.

 (d) Access to Information. The Purchaser acknowledges that it has been afforded (i) the opportunity to ask such
questions as it has deemed necessary of, and to receive answers from, representatives of the Company concerning the terms and conditions of the Shares and Warrant offered hereunder and the merits and risks of investing in such securities,
(ii) access to information about the Company and the Company’s financial condition, results of operations, business, properties, management and prospects sufficient to enable it to evaluate its investment in the Shares and Warrant and
(iii) the opportunity to obtain such additional information which the Company possesses or can acquire without unreasonable effort or expense that is necessary to make an informed investment decision with respect to the investment and to verify
the accuracy and completeness of the information that it has received about the Company. 
 (e) Reliance. The Purchaser
understands and acknowledges that (i) the Shares and Warrant that are being offered and sold to it hereunder are being offered and sold without registration under the Securities Act in a private placement that is exempt from the registration
provisions of the Securities Act under Section 4(2) of the Securities Act and (ii) the availability of such exemption depends in part on, and that the Company will rely upon the accuracy and truthfulness of, the foregoing
representations and the Purchaser hereby consents to such reliance. 
 ARTICLE IV 
 OTHER AGREEMENTS OF THE PARTIES 
 4.1 Manner of Offering. The Shares and Warrant are being issued pursuant to Section 4(2) of the Securities Act. 
 4.2 Blue Sky Laws. The Company shall cooperate with the Purchaser in connection with the exemption from registration of the Shares and Warrant under the securities or Blue Sky laws of such jurisdictions as the Purchaser may
request; provided, 
  

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however, that the Company and its subsidiaries shall not be required in connection therewith to qualify as a foreign corporation where they are not
now so qualified. The Company agrees that it will execute all necessary documents and pay all necessary state filing or notice fees to enable the Company to sell the Shares and Warrant to the Purchaser. 
 4.3 Integration. The Company shall not, and shall use its best efforts to ensure that no Affiliate shall, sell, offer for sale or solicit
offers to buy or otherwise negotiate in respect of any security (as defined in Section 2 of the Securities Act) that would be integrated with the offer or sale of the Shares and Warrant in a manner that would require the registration
under the Securities Act of the sale of the Shares and Warrant to the Purchaser. 
 ARTICLE V 
 CONDITIONS TO THE PURCHASER’S OBLIGATIONS AT CLOSING 
 The obligations of the Purchaser to purchase the Shares and Warrant from the Company at the Closing are subject to the fulfillment, on or before the Closing, of each of the following conditions, unless otherwise
waived: 
 5.1 Representations and Warranties. The representations and warranties of the Company contained in
Section 3.1 shall be true and correct in all material respects as of the Closing. 
 5.2 Performance. The Company
shall have performed and complied with all covenants, agreements, obligations and conditions contained in this Agreement that are required to be performed or complied with by it on or before the Closing. 
 5.3 Satisfaction of Conditions to Offer and Consent Solicitations and New Notes Offering. All conditions precedent to the Offers and
Consent Solicitations and the New Notes Offerings shall have been fulfilled (other than the funding of the Transaction pursuant to this Agreement). 
 5.4 Compliance Certificate. An officer of the Company shall deliver to the Purchaser at the Closing a certificate certifying that the conditions specified in Sections 5.1, 5.2, and 5.3 have been
fulfilled. 
 5.5 No Material Adverse Change. Since December 31, 2008, there shall not have occurred any change, event,
circumstance, fact, condition or development that has had or could reasonably be expected to have a Material Adverse Effect. 
 5.6
Qualifications. All authorizations, approvals or permits, if any, of any governmental authority or regulatory body of the United States or of any state that are required in connection with the lawful issuance and sale of the Shares and the
Warrant pursuant to this Agreement shall be obtained and effective as of the Closing. 
  

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 ARTICLE VI 
 CONDITIONS OF THE COMPANY’S OBLIGATIONS AT CLOSING 
 The obligations of the Company to sell the
Shares and Warrant to the Purchaser at the Closing are subject to the fulfillment, on or before the Closing, of each of the following conditions, unless otherwise waived: 
 6.1 Representations and Warranties. The representations and warranties of the Purchaser contained in Section 3.2 shall be true and correct in all material respects as of the Closing.

 6.2 Performance. The Purchaser shall have performed and complied with all covenants, agreements, obligations and conditions
contained in this Agreement that are required to be performed or complied with by them on or before the Closing. 
 6.3 Compliance
Certificate. An officer of the Purchaser shall deliver to the Company at the Closing a certificate certifying that the conditions specified in Sections 6.1 and 6.2 have been fulfilled. 
 6.4 Qualifications. All authorizations, approvals or permits, if any, of any governmental authority or regulatory body of the United States
or of any state that are required in connection with the lawful issuance and sale of the Shares and Warrant pursuant to this Agreement shall be obtained and effective as of the Closing. 
 ARTICLE VII 
 COVENANTS 
 7.1 Further Assurances; Cooperation. From and after the Closing, each party will execute and deliver such instruments and take such other
actions as the other party or parties, as the case may be, may reasonably require in order to carry out the intent of this Agreement. Without limiting the generality of the foregoing, at any time after the Closing, at the request of the Company or
the Purchaser, and without further consideration, the Company will execute and deliver such instruments of sale, transfer, conveyance, assignment and confirmation and take such action as the Company or the Purchaser may reasonably deem necessary or
desirable in order to more effectively transfer, convey and assign to the Purchaser, and to confirm the Purchaser’s title to, the Shares and Warrant. 
 7.2 No Reporting of Accrued and Unpaid Dividends. The Company will not treat for United States federal income tax purposes the amount of any accrued and unpaid dividends that are added to the Liquidation
Preference (as such term is defined in the Certificate of Designations) as a distribution under Section 301 or 305 of the Internal Revenue Code of 1986, as amended, and will not take any position for United States federal income tax purposes on
any tax return or tax filing (including, without limitation, Internal Revenue Service Form 1099) that is inconsistent with this Section 7.2. 
  

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 ARTICLE VIII 
 MISCELLANEOUS 
 8.1 Fees and Expenses. Except as set forth in this Agreement, the
Company shall pay the fees and expenses of the advisers, counsel, accountants and other experts for the Purchaser. The Company shall pay all stamp and other taxes and duties levied in connection with the issuance of the Shares and Warrant pursuant
hereto. The Purchaser shall be responsible for any taxes payable by the Purchaser that may arise as a result of the investment hereunder or the transactions contemplated by this Agreement or any other Transaction Document. The Company shall pay all
costs, expenses, fees and all taxes incident to and in connection with: (a) the issuance and delivery of the Shares and Warrant, (b) the exemption from registration of the Shares and Warrant for offer and sale to the Purchaser under the
securities or Blue Sky laws of the applicable jurisdictions, (c) the preparation of certificates for the Shares and Warrant (including, without limitation, printing and engraving thereof), and (d) all fees and expenses of counsel and
accountants of the Company. 
 8.2 Entire Agreement. This Agreement, together with all of the Exhibits annexed hereto, and
any other Transaction Document contain the entire understanding of the parties with respect to the subject matter hereof and supersede all prior agreements and understandings, oral or written, with respect to such matters. This Agreement shall be
deemed to have been drafted and negotiated by both parties hereto and no presumptions as to interpretation, construction or enforceability shall be made by or against either party in such regard. 
 8.3 Notices. Wherever provision is made in this Agreement for the giving of any notice, such notice shall be in writing and shall be
delivered personally to such party, or sent by facsimile transmission or overnight courier, in each case to the addresses or facsimile telephone numbers set forth as follows: 
 If to the Company: 
 Duane Reade Holdings,
Inc. 
 440 Ninth Avenue 
 New York, NY 10001 
 Attn: General Counsel 
 Fax: (212) 594-0832 
 If to the Purchaser: 
 OHCP DR Co-Investors 2009, LLC 
 c/o Oak Hill
Capital Partners, L.P. 
 65 East 55th Street, 32nd Floor 
 New York,
NY 10022 
 Attn: John R. Monsky, Esq. 
 Fax: (212) 527-8454 
  

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 or to such other address, in any such case, as any party hereto shall have last designated by notice to the other party.
Notice shall be deemed to have been given on the day that it is so delivered personally or sent by facsimile transmission and the appropriate confirmation of successful transmission is received. If sent by overnight courier, notice shall be deemed
to have been given the next Business Day after such communication is sent to the specified address. The Purchaser may change their address for notices by giving written notice of such change to the Company. 
 8.4 Amendments; Waivers. No provision of this Agreement may be waived or amended except in a written instrument signed, in the case of an
amendment, by both the Company and the Purchaser, or, in the case of a waiver, by the party against whom enforcement of any such waiver is sought. No waiver of any default with respect to any provision, condition or requirement of this Agreement
shall be deemed to be a continuing waiver in the future or a waiver of any other provision, condition or requirement hereof, nor shall any delay or omission of either party to exercise any right hereunder in any manner impair the exercise of any
such right accruing to it thereafter. 
 8.5 Headings. The headings herein are for convenience only, do not constitute a part
of this Agreement and shall not be deemed to limit or affect any of the provisions hereof. 
 8.6 Successors and Assigns; No Third
Party Beneficiaries. This Agreement may not be assigned by either party, directly or indirectly, without the prior written consent of the other. This Agreement shall be binding upon and inure to the benefit of the parties and their respective
successors and permitted assigns. The assignment by a party of this Agreement or any rights hereunder shall not affect the obligations of such party under this Agreement. This Agreement is intended for the benefit of the parties hereto and their
respective permitted successors and assigns and is not for the benefit of, nor may any provision hereof be enforced by, any other person. 
 8.7 Governing Law; Venue. This Agreement shall be governed by and construed in accordance with, the laws of the State of Delaware without reference to conflict of law principles. Any action to enforce the terms of this
Agreement or any of its exhibits, or any other Transaction Document shall be brought exclusively in the State and/or Federal courts situated in the County and State of New York. 
 8.8 WAIVER OF JURY TRIAL. THE COMPANY AND THE PURCHASER HEREBY WAIVE TRIAL BY JURY IN ANY LITIGATION IN ANY COURT WITH RESPECT
TO, IN CONNECTION WITH, OR ARISING OUT OF THIS AGREEMENT OR ANY INSTRUMENT OR DOCUMENT DELIVERED PURSUANT TO THIS AGREEMENT, OR THE VALIDITY, PROTECTION, INTERPRETATION, COLLECTION OR ENFORCEMENT THEREOF, OR ANY OTHER CLAIM OR DISPUTE HOWSOEVER
ARISING, BETWEEN THE COMPANY AND THE PURCHASER. 
  

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 8.9 Survival. The representations and warranties of the Company and the Purchaser contained
in Article III and the agreements and covenants of the parties contained in Article IV, Article VII and this Article VIII shall survive the Closing. 
 8.10 Counterpart Signatures. This Agreement may be executed in two or more counterparts, all of which when taken together shall be
considered one and the same agreement and shall become effective when counterparts have been signed by each party and delivered to the other party, it being understood that both parties need not sign the same counterpart. In the event that any
signature is delivered by facsimile transmission or by electronic mail (a “pdf file”), such signature shall create a valid and binding obligation of the party executing (or on whose behalf such signature is executed) the same with
the same force and effect as if such facsimile or pdf file signature page were an original thereof. 
 8.11 Severability. In
case any one or more of the provisions of this Agreement shall be invalid or unenforceable in any respect, the validity and enforceability of the remaining terms and provisions of this Agreement shall not in any way be affected or impaired thereby
and the parties will attempt to agree upon a valid and enforceable provision which shall be a reasonable substitute therefore, and upon so agreeing, shall incorporate such substitute provision in this Agreement. 
 [Signature Page Follows] 
  

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

			
	 COMPANY:
  
 DUANE READE HOLDINGS, INC.

		
	By:	 	/s/ John K. Henry
		 	Name: John K. Henry
		 	Title: Senior Vice President and Chief Financial Officer

  

			
	 PURCHASER:
  
 OHCP DR CO-INVESTORS 2009, LLC

	
	 By: OHCP GenPar, L.P., 
         its Managing Member

	
	 By: OHCP MGP, LLC, 
         its General Partner 

		
	By:	 	/s/ Kevin Levy
		 	Name: Kevin Levy
		 	Title: Vice President

  

 [Signature Page to Purchase Agreement] 

 Schedule 3.1(c) 
 Equity Interests of 
 Duane Reade Holdings, Inc.

  

							
	 Equity Interest
	  	Authorized	  	Issued and
Outstanding	  	Reserved
	 Common Stock
	  	4,205,600	  	2,615,077	  	0
	 Series A Redeemable Preferred Stock
	  	600,000	  	525,334	  	0
	 Phantom Stock
	  	—  	  	—  	  	23,738
	 Options
	  	—  	  	—  	  	575,893
	 Warrants
	  		  		  	384,174

 Exhibit A 
 Warrant to Purchase 
 Shares of Common Stock 
 [Attached] 

 Exhibit B 
 Certificate of Designations, Powers, Preferences and Rights of  
 Series B Redeemable Preferred
Stock 
 [Attached]Warrant to Purchase Shares of Common Stock

 Exhibit 10.3 
 EXECUTION COPY 
 THIS WARRANT AND ANY SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE NOT BEEN REGISTERED
UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND HAVE BEEN ACQUIRED FOR INVESTMENT AND NOT WITH A VIEW TO, OR IN CONNECTION WITH, THE SALE OR DISTRIBUTION THEREOF. NO SUCH SALE OR
DISTRIBUTION MAY BE EFFECTED WITHOUT AN EFFECTIVE REGISTRATION STATEMENT RELATED THERETO OR AN APPLICABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT OR SUCH LAWS. 
 THIS WARRANT AND THE SECURITIES UNDERLYING THIS WARRANT ARE SUBJECT TO THE TRANSFER RESTRICTIONS AND CERTAIN OTHER AGREEMENTS SET FORTH IN THE TRANSACTION DOCUMENTS (AS DEFINED IN THE PURCHASE AGREEMENT DATED AS OF
THE DATE HEREOF). A COPY OF SUCH DOCUMENTS MAY BE OBTAINED BY THE HOLDER HEREOF AT THE COMPANY’S PRINCIPAL PLACE OF BUSINESS WITHOUT CHARGE. 
  

			
	Warrant No. B-1	  	 Number of Shares: 1,196,261
 (subject to
adjustment)

	  
 Date of Issuance: August 7, 2009
	  

 DUANE READE HOLDINGS, INC. 
 WARRANT TO PURCHASE SHARES 
 OF COMMON STOCK 
 THIS WARRANT TO PURCHASE SHARES OF COMMON STOCK (this “Warrant”) certifies that, for value received, OHCP DR CO-INVESTORS 2009, LLC, a Delaware limited
liability company, or its permitted assigns (collectively, the “Holder”) is entitled to subscribe for and purchase from DUANE READE HOLDINGS, INC., a Delaware corporation (the “Company”) 1,196,261 shares of validly
issued, fully paid and nonassessable common stock of the Company, par value $0.01 per share (the “Common Stock”), as adjusted from time to time pursuant to the provisions of this Warrant (the “Warrant Shares”), at
the exercise price per share and subject to the terms and conditions set forth below. Capitalized terms used but not defined herein have the meanings ascribed to them in the Purchase Agreement between the Company and the Holder, dated as of
August 7, 2009 (the “Purchase Agreement”). 
 1. Number of Warrant Shares, Exercise Price and Term: 

In relation to the exercise of this Warrant, the number of shares of Common Stock, the Exercise Price and the term are as set forth
below: 
  

						
	 Number of Shares
	  	Exercise Price per Share	  	Last Day to Exercise
with Respect to these Shares
	1,196,261	  	$	0.01	  	August 7, 2019

 2. Exercise Price. The exercise price per share at which this Warrant may be exercised shall be as
set forth in Section 1, provided that if the par value per share of Common Stock on the date on which this Warrant is duly exercised in accordance with its terms is greater than $0.01, then the Exercise Price per share will be
equal to that par value (the “Exercise Price”). 
 3. Method of Exercise; Payment; Issuance of New Warrant. Subject
to the terms and conditions set forth herein, the purchase right represented by this Warrant may be exercised by the Holder, in whole or in part at any time, or from time to time, on or after the date hereof and on or prior to 5:00 p.m.,
New York City local time, on August 7, 2019 (the “Expiration Date”): 
 (a) by the presentation and
surrender of this Warrant (with the notice of exercise substantially in the form attached hereto as Exhibit 1 duly completed and executed) to the principal office of the Company and accompanied by the payment to the Company of an amount
equal to the Exercise Price multiplied by the number of Warrant Shares as to which this Warrant is then being exercised by (i) cash, (ii) certified or bank check or wire transfer to an account designated by the Company (a “Wire
Transfer”), (iii) the cancellation by the Holder hereof of indebtedness or other obligations of the Company to such Holder in an amount equal to the then applicable Exercise Price multiplied by the number of Warrant Shares then being
purchased, or (iv) the surrender (which surrender shall be evidenced by cancellation of the Warrant represented by any Warrant certificate presented in connection with a Cashless Exercise (as defined below)) of this Warrant, and without the
payment of the Exercise Price in cash or certified check in return for the delivery to the surrendering Holder of such number of shares of Common Stock equal to the number of shares of Common Stock for which such Warrant is exercisable as of the
date of exercise (if the Exercise Price were being paid in cash or certified or official bank check) reduced by that number of shares equal to the quotient obtained by dividing (x) the aggregate Exercise Price to be paid by (y) the Market
Price (as defined below) of one (1) share of Common Stock on the Business Day immediately preceding the day of exercise of the Warrant. An exercise of this Warrant in accordance with clause (iii) or (iv) is herein referred to as a
“Cashless Exercise.” “Market Price” shall mean, per share of Common Stock, on any date specified herein: (a) if the Common Stock is listed on a national securities exchange, the closing price per share of
Common Stock on such date published in The Wall Street Journal (National Edition); or (b) if the Common Stock is not then listed or admitted to trading on any national securities exchange but is designated as a national market system
security by the National Association of Securities Dealers, Inc. (the “NASD”), the average of the closing bid and asked prices of the Common Stock on such date, as officially reported on the principal national securities exchange on
which the Common Stock is then listed or admitted to trading; or (c) if there shall have been no trading on such date or if the Common Stock is not designated as a national market system security by the NASD, the average of the reported closing
bid and asked prices of the Common Stock on such date as shown by NASDAQ and reported by any member firm of the NYSE selected by the Company; or (d) if none of (a), (b) or (c) is applicable, the fair market value per share of Common
Stock as determined by the Board of Directors of the Company in good faith. 
  

 2 

 (b) in connection with a registered public offering of the Company’s securities, by
the presentation and the surrender of this Warrant (with the notice of exercise form attached hereto as Exhibit 1 duly completed and executed) to the principal office of the Company together with notice of (i) arrangements
reasonably satisfactory to the Company for payment to the Company either by certified or bank check or Wire Transfer from the proceeds of the sale of securities to be sold by the Holder in such public offering of an amount equal to the then
applicable Exercise Price per share multiplied by the number of shares of Common Stock then being purchased or (ii) the Holder’s intent to effect a Cashless Exercise of this Warrant. 
 The person or persons in whose name(s) any certificate(s) representing shares of Common Stock shall be issuable upon exercise of this
Warrant shall be deemed to have become the holder(s) of record of, and shall be treated for all purposes as the record holder(s) of, the shares represented thereby (and such shares shall be deemed to have been issued) immediately prior to the close
of business on the date or dates upon which this Warrant is exercised. In the event of any exercise of the rights represented by this Warrant, certificates for the shares of Common Stock so purchased shall be delivered to the Holder hereof by the
Company at the Company’s expense as soon as possible and in any event within thirty (30) days after such exercise and, unless this Warrant has been fully exercised or expired, a new Warrant representing the portion of the shares of Common
Stock, if any, with respect to which this Warrant shall not then have been exercised shall also be issued to the Holder hereof as soon as possible and in any event within such thirty (30)-day period. 
 4. Stock Fully Paid; Reservation of Shares. All Warrant Shares that may be issued upon the exercise of the rights represented by this Warrant
will, upon issuance pursuant to the terms and conditions herein, be duly authorized, validly issued, fully paid and nonassessable, and free from all taxes, liens and charges with respect to the issue thereof. During the period within which the
rights represented by this Warrant may be exercised, the Company will at all times have authorized, and reserved for the purpose of the issue upon exercise of the purchase rights evidenced by this Warrant, a sufficient number of shares of Common
Stock to provide for the exercise of the rights represented by this Warrant and from time to time, will take all steps necessary to amend its Certificate of Incorporation to provide sufficient shares of its Common Stock for issuance on exercise of
this Warrant (and reserves of shares of Common Stock issuable upon exercise of the Warrant). 
 5. Anti-dilution Adjustment. The
number of Warrant Shares to be received upon the exercise of this Warrant shall be subject to adjustment from time to time upon the occurrence of certain events, as follows: 
 (a) Dividend, Subdivision, Combination or Reclassification of Common Stock. If the Company shall, at any time or from time to time
after the issuance of this Warrant but prior to the exercise hereof: (i) make a dividend or distribution on the outstanding shares of Common Stock payable in capital stock, (ii) subdivide or reclassify or reorganize its outstanding shares
of Common Stock into a greater number of shares or (iii) combine or reclassify or reorganize its outstanding shares of Common Stock into a 

  

 3 

 
smaller number of shares, then in each such case, the number and kind of Warrant Shares shall be automatically adjusted so that the Holder upon exercise
hereof shall be entitled to receive the kind and the number of Warrant Shares or other securities of the Company that the Holder would have owned or have been entitled to receive after the happening of any of the events described above had this
Warrant been exercised immediately prior to the happening of such event or any record date with respect thereto. Any adjustment made pursuant to this Section 5(a) shall become effective retroactively (A) in the case of any
such dividend or distribution, on the close of business on the record date for the determination of holders of shares of Common Stock entitled to receive such dividend or distribution or (B) in the case of any such subdivision, combination or
reclassification, on the close of business on the day upon which such corporate action becomes effective. 
 (b) Issuance
of Common Stock or Common Stock Equivalents Below Market Price. 
 (i) If the Company shall at any time or from time to
time, after the issuance of this Warrant but prior to the exercise hereof, issue or sell any shares of Common Stock or Common Stock Equivalent (as defined below) (excluding any such issuance or sale for which an adjustment is made under the
foregoing Section 5(a)) (any such issuance, a “New Issuance”), for a price per share of Common Stock (the “New Issue Price”) that is less than the Market Price as of the close of business on the
last Business Day immediately prior to the announcement of such issuance or, if no such announcement is made, the record date for the determination of stockholders entitled to receive such shares of Common Stock or Common Stock Equivalents (the
“Relevant Date”) (treating the price per share of Common Stock, in the case of the issuance of any Common Stock Equivalent, as equal to the sum of the lowest amounts of consideration (if any) received or receivable by the Company
with respect to any one share of Common Stock (1) upon granting or sale of the Common Stock Equivalent, (2) upon exercise of the Common Stock Equivalent and (3) upon conversion or exchange or exercise of any convertible security
issuable upon exercise of such Common Stock Equivalent), other than (x) issuances or sales for which an adjustment is made pursuant to another subsection of this Section 5 and (y) issuances in connection with an Excluded
Transaction (as defined below), then in such event, the number of Warrant Shares shall be increased to a number equal to the product of (A) the number of Warrant Shares immediately prior to the Relevant Date multiplied by (B) the quotient
of: (I) the sum of (x) the number of shares of Common Stock (determined on a fully-diluted basis) outstanding on the Relevant Date, plus (y) the number of additional shares of Common Stock (determined on a fully-diluted basis)
issued or to be issued in such New Issuance (including the maximum number of shares of Common Stock into which the Common Stock Equivalents issued or to be issued in such New Issuance initially are convertible, exchangeable or exercisable);
divided by (II) the sum of (x) the number of shares of Common Stock (determined on a fully-diluted basis) outstanding on the Relevant Date, plus (y) the number of shares of Common Stock which the aggregate consideration
received by the Company for the total number of such additional shares of Common Stock so issued in such New Issuance would purchase at the Market Price on the date of such New Issuance, and/or, in the case of Common Stock Equivalents, the number of
shares of Common Stock which the aggregate consideration received by the Company 

  

 4 

 
upon the issuance of such Common Stock Equivalents and receivable by the Company upon the conversion, exchange or exercise of such Common Stock Equivalents
(as calculated in accordance with this Section 5(b)) issued or to be issued in such New Issuance would purchase at the Market Price on the date of such New Issuance. 
 (ii) Such adjustment shall be made whenever such shares of Common Stock or Common Stock Equivalents are issued, and, in the case of an
issuance to the stockholders of the Company, shall become effective retroactively to the close of business on the record date for the determination of stockholders entitled to receive such shares of Common Stock or Common Stock Equivalents;
provided, however, that the determination as to whether an adjustment is required to be made pursuant to this Section 5(b) shall only be made upon the issuance of such shares of Common Stock or Common Stock Equivalents, and not upon
the issuance of any security into which the Common Stock Equivalents convert, exchange or may be exercised. 
 (iii) In case
at any time any shares of Common Stock or Common Stock Equivalents shall be issued or sold for cash, the consideration received therefor shall be deemed to be the amount received by the Company therefor, without deduction therefrom of any expenses
incurred or any underwriting commissions or concessions or discounts paid or allowed by the Company in connection therewith. In case any shares of Common Stock or Common Stock Equivalents or any rights or options to purchase any Common Stock or
Common Stock Equivalents shall be issued or sold for a consideration other than cash, the amount of the consideration other than cash received by the Company shall be deemed to be the fair market value of such consideration, without deduction
therefrom of any expenses incurred or any underwriting commissions or concessions or discounts paid or allowed by the Company in connection therewith, as determined by the Board of Directors of the Company in good faith. 
 (iv) If from time to time any Common Stock Equivalents (or any portions thereof) which shall have given rise to an adjustment pursuant to
this Section 5(b) shall have expired or terminated without the exercise thereof and/or if by reason of the terms of such Common Stock Equivalents there shall have been an increase or decrease, with the passage of time or otherwise, in
the price payable upon the exercise or conversion thereof, then the number of Warrant Shares shall be readjusted (but to no greater than originally adjusted), in order to (x) eliminate from the computation any additional shares of Common Stock
corresponding to such Common Stock Equivalents as shall have expired or terminated, (y) treat the additional shares of Common Stock, if any, actually issued or issuable pursuant to the previous exercise of such Common Stock Equivalents as
having been issued for the consideration actually received and receivable therefor and (z) treat any of such Common Stock Equivalents which remain outstanding as being subject to exercise or conversion on the basis of such exercise or
conversion price as shall be in effect at the time. 
  

 5 

 “Common Stock Equivalent” means any security or obligation which is by
its terms convertible into or exchangeable or exercisable into shares of Common Stock or another Common Stock equivalent, and any option, warrant or other subscription or purchase right with respect to Common Stock. 
 “Excluded Transactions” mean (i) Common Stock issued upon exercise of Common Stock Equivalents outstanding as of the
date hereof (after giving effect to the issuances contemplated by the Purchase Agreement), (ii) Common Stock and/or Common Stock Equivalents issued or sold in connection with a strategic transaction by the Company or any of its Affiliates, and
(iii) options for Common Stock of the Company issued from time to time to directors, officers, employees or consultants of the Company and any Subsidiary pursuant to any qualified or non-qualified stock option plan, employee stock ownership
plan, employee benefit plan, stock plan, or such other options, arrangements, agreements or plans intended principally as a means of providing compensation or incentive compensation for employment or services approved by the Board of Directors of
the Company. 
 (c) Certain Distributions. If the Company shall at any time or from time to time, after the issuance of
this Warrant but prior to the exercise hereof, distribute to all holders of shares of Common Stock (including any such distribution made in connection with a merger or consolidation in which the Company is the resulting or surviving Person and the
Common Stock is not changed or exchanged) cash, evidences of indebtedness of the Company or another issuer, securities of the Company or another issuer or other assets (excluding dividends payable in shares of Common Stock for which adjustment is
made under another paragraph of this Section 5), rights or warrants to subscribe for or purchase any of the foregoing, then, and in each such case, the number of Warrant Shares shall be increased to a number equal to the product of
(i) the number of Warrant Shares immediately prior to the date of such distribution multiplied by (ii) the quotient of: (I) the Market Price of the Common Stock as of the Business Day immediately prior to the announcement of such
distribution (or, if no such announcement is made, the record date for the determination of the stockholders entitled to receive such distribution); divided by (II) the excess of the amount of (which amount shall be greater than zero)
(x) the Market Price determined pursuant to the clause (I) above over (y) the amount of cash distributed per share of Common Stock and/or, as applicable, the fair market value per share of Common Stock (as determined in good
faith by the Board of Directors) of any cash, evidence of indebtedness of the Company or another issuer, securities of the Company or another issuer, or other assets (excluding dividends payable in shares of Common Stock for which adjustment is made
under another paragraph of this Section 5), rights or warrants to subscribe for or purchase any of the foregoing distributed to the holders of Common Stock; provided, however, that no adjustment shall be made with respect
to any distribution of rights or warrants to subscribe for or purchase securities of the Company if the Holder would otherwise be entitled to receive such rights or warrants upon the exercise of this Warrant. Such adjustment shall be made whenever
any such distribution is made and shall become effective retroactively to the close of business on the record date for the determination of stockholders entitled to receive such distribution). 
 (d) Other Changes. If the Company shall at any time or from time to time, after the issuance of this Warrant but prior to the
exercise hereof, take any action affecting its Common Stock similar to or having an effect similar to any of the actions described in any of Section 5(a) through (c) above (but not including any action described in any such
section) and the Board of Directors in good faith determines that it would be 

  

 6 

 
equitable in the circumstances to adjust the number of Warrant Shares as a result of such action, then, and in each such case, the number of Warrant Shares
shall be adjusted in such manner and at such time as the Board of Directors in good faith determines would be equitable in the circumstances (such determination to be evidenced in a resolution, a certified copy of which shall be mailed to the
Holders). 
 (e) Rights. The rights applicable to the shares of Common Stock issuable hereunder are set forth in the
Company’s Certificate of Incorporation, as amended through the date of issuance of this Warrant, a true and complete copy of which has been supplied to the Holder (the “Charter”). Following the initial public offering of shares
of Common Stock, the Company shall promptly provide the Holder with any restatement, amendment, modification or waiver of the Charter promptly after the same has been made. 
 (f) No Adjustments. Notwithstanding anything herein to the contrary, no adjustment under this Section 5 need be made to
the number of Warrant Shares if the Company receives written notice from all the Holders that no such adjustment is required. 
 6.
Certificate of Adjustments. Whenever the number of Warrant Shares issuable upon exercise of this Warrant is adjusted pursuant to Section 5 hereof, the Company shall deliver a certificate signed by its chief financial officer
setting forth, in reasonable detail, the event requiring the adjustment, the amount of the adjustment, the method by which such adjustment was calculated, and the number of Warrant Shares after giving effect to such adjustment, and shall cause
copies of such certificate to be mailed (without regard to Section 13 hereof, by internationally recognized overnight courier, specifying next day delivery) to the Holder. 
 7. Fractional Shares. No fractional shares of Common Stock will be issued in connection with any exercise hereunder, but in lieu of such
fractional shares the Company shall make a cash payment therefor based on the Market Price on the date of exercise of this Warrant. 
 8.
Notice of Proposed Actions. Following the initial public offering of shares of Common Stock, in the event the Company proposes at any time or from time to time (a) to declare or pay any dividend payable in stock or to make any other
distribution to the holders of the shares of Common Stock (other than a regularly scheduled cash dividend), (b) to offer to the holders of the shares of Common Stock or Common Stock Equivalent, rights or warrants for or to purchase any
additional shares of Common Stock or Common Stock Equivalents or shares of stock of any class or any other securities, rights or options, (c) to effect any combination, reorganization or reclassification of its Common Stock, (d) to effect
any consolidation, merger or sale, transfer or other disposition of all or substantially all of the property, assets or business of the Company, (e) to effect the liquidation, dissolution or winding up of the Company, or (f) to take any
other action that would require a vote of the Company’s stockholders, then, in each such case, the Company shall give to the Holder, in accordance with Section 13, a written notice of such proposed action, which shall specify
(i) the record date for the purposes of such stock dividend, distribution of rights or warrants or vote of the stockholders of the 
  

 7 

 
Company, or if a record is not to be taken, the date as of which the holders of shares of Common Stock of record to be entitled to such dividend,
distribution of rights or warrants, or vote is to be determined, or (ii) the date on which such combination, reorganization, reclassification, consolidation, merger, sale, transfer, disposition, liquidation, dissolution or winding up is
expected to become effective, and such notice shall be so given as promptly as possible but in any event at least twenty (20) Business Days prior to the applicable record, determination or effective date specified in such notice. 
 9. No Impairment. The Company will not, by amendment of its Certificate of Incorporation or through any reorganization, transfer of assets,
consolidation, merger, dissolution, issue or sale of securities or any other action, avoid or seek to avoid the observance or performance of any of the terms of this Warrant, but will at all times in good faith assist in the carrying out of all such
terms and in the taking of all such action as may be necessary or appropriate in order to protect the rights of the Holder of this Warrant against dilution or other impairment. 
 10. Registration Rights. In connection with the exercise of this Warrant pursuant to Section 3, the Company shall provide the
holder(s) of the shares of Common Stock issuable upon exercise of this Warrant with customary registration rights in respect of the shares of Common Stock delivered upon such exercise consisting of (a) one demand registration right in the
aggregate and (b) piggyback registration rights, in each case, subject to blackout, cutback, lock-up and other customary provisions. Such demand registration right shall be exercised only by the holders of at least a majority of the outstanding
shares of Common Stock issued upon exercise of this Warrant pursuant to Section 3. 
 11. Rights as Stockholders;
Information. Holder, as such, shall not be entitled to vote or receive dividends or be deemed the holder of shares of Common Stock or any other securities of the Company which may at any time be issuable on the exercise hereof for any purpose,
nor shall anything contained herein be construed to confer upon the Holder, as such, any of the rights of a stockholder of the Company or any right to vote for the election of directors or upon any matter submitted to stockholders at any meeting
thereof, or to receive notice of meetings, or to receive dividends or subscription rights or otherwise until this Warrant shall have been exercised and the shares of Common Stock issuable upon the exercise hereof shall have become deliverable, as
provided herein. 
 12. Transfer. Subject to any restrictions on transfer contained in the Purchase Agreement and referred to in the
legends endorsed hereon, this Warrant and all rights hereunder are transferable, in whole or in part, without charge to the Holder hereof upon surrender of this Warrant with a properly executed Form of Assignment, attached hereto as
Exhibit 2, at the principal office of the Company. Upon any partial transfer, the Company will at its expense issue and deliver to the Holder a new Warrant of like tenor, in the name of the Holder, which shall be exercisable for such
number of shares of Common Stock with respect to which rights under this Warrant were not so transferred. 
  

 8 

 13. Notices. Except as provided for in Section 6, wherever provision is made in this
Warrant for the giving of any notice, such notice shall be in writing and shall be delivered personally to such party, or sent by facsimile transmission or overnight courier, in each case to the addresses or facsimile telephone numbers set forth as
follows: 
 If to the Company: 
 Duane Reade Holdings, Inc. 
 440 Ninth Avenue 
 New York, NY 10001 
 Attn: General Counsel 
 Fax: (212) 594-0832 
 If to the Holder:

 OHCP DR Co-Investors 2009, LLC 
 c/o Oak Hill Capital Partners, L.P. 
 65 East 55th Street, 32nd Floor 
 New York, NY
10022 
 Attention: John R. Monsky, Esq. 
 Fax: (212) 527-8454 
 or to such other address, in any such case, as any party hereto shall have last designated by notice to the other party.
Notice shall be deemed to have been given on the day that it is so delivered personally or sent by facsimile transmission and the appropriate confirmation of successful transmission is received. If sent by overnight courier, notice shall be deemed
to have been given the next Business Day after such communication is sent to the specified address. The Holder may change their address for notices by giving written notice of such change to the Company. 
 14. Lost Warrants or Stock Certificates. The Company covenants to the Holder hereof that, upon receipt of evidence reasonably satisfactory to the
Company of the loss, theft, destruction or mutilation of this Warrant or any stock certificate and, in the case of any such loss, theft or destruction, upon receipt of an indemnity reasonably satisfactory to the Company, or in the case of any such
mutilation upon surrender and cancellation of such Warrant or stock certificate, the Company will, at its expense, make and deliver a new Warrant or stock certificate, of like tenor, in lieu of the lost, stolen, destroyed or mutilated Warrant or
stock certificate. 
 15. Descriptive Headings. The descriptive headings of the several paragraphs of this Warrant are inserted for
convenience only and do not constitute a part of this Warrant. 
 16. Governing Law. This Warrant shall be governed by and construed
in accordance with, the laws of the State of Delaware without reference to conflict of law principles. 
  

 9 

 17. Amendment. Any provision of this Warrant may be amended and the observance thereof waived only
with the written consent of the Company and the Holder or, if there is more than one Holder, the holders holding a majority of the Warrant Shares. 
 18. Remedies. In case any one or more of the covenants and agreements contained in this Warrant shall have been breached, the Holder hereof (in the case of a breach by the Company), or the Company (in the case of a breach by Holder),
may proceed to protect and enforce their or its rights either by suit in equity and/or by action at law, including, but not limited to, an action for damages as a result of any such breach and/or an action for specific performance of any such
covenant or agreement contained in this Warrant. 
 19. Severability. In case any one or more of the provisions of this Warrant shall
be invalid or unenforceable in any respect, the validity and enforceability of the remaining terms and provisions of this Warrant shall not in any way be affected or impaired thereby and the parties will attempt to agree upon a valid and enforceable
provision which shall be a reasonable substitute therefore, and upon so agreeing, shall incorporate such substitute provision in this Warrant. 
 20. WAIVER OF JURY TRIAL. THE COMPANY AND THE HOLDER HEREBY WAIVE TRIAL BY JURY IN ANY LITIGATION IN ANY COURT WITH RESPECT TO, IN CONNECTION WITH, OR ARISING OUT OF THIS WARRANT OR ANY INSTRUMENT OR DOCUMENT DELIVERED PURSUANT TO
THIS WARRANT, OR THE VALIDITY, PROTECTION, INTERPRETATION, COLLECTION OR ENFORCEMENT THEREOF, OR ANY OTHER CLAIM OR DISPUTE HOWSOEVER ARISING, BETWEEN THE COMPANY AND THE HOLDER. 
 21. Consent to Jurisdiction. The Company hereby irrevocably consents to the exclusive jurisdiction of the courts of the State of New York and
of any Federal court located in such State in connection with any action or proceeding arising out of or relating to this Warrant or any document or instrument delivered pursuant hereto. 
 22. Entire Agreement. This Warrant constitutes the entire agreement between the parties with respect to the subject matter hereof, and supersedes
any prior understanding or agreement (oral or written) concerning such subject matter. This Warrant (together with the Transaction Documents (as defined in the Purchase Agreement)) constitutes the entire agreement among the parties with respect to
the transactions contemplated hereby and by the other Transaction Documents, and supersedes any prior understanding or agreement (oral or written) concerning such transactions. 
 [Signature Page Follows] 
  

 10 

 In witness whereof, the Company has caused this Warrant to be duly executed on this 7
th day of August, 2009. 
  

			
	DUANE READE HOLDINGS, INC.
		
	By:	 	/s/ John K. Henry
		 	Name: John K. Henry
		 	Title: Senior Vice President and Chief Financial Officer

 [Signature Page to Warrant] 

 EXHIBIT 1 
 [FORM OF] 
 ELECTION TO PURCHASE SHARES 
 The undersigned hereby irrevocably elects to exercise the Warrant to purchase
[            ] shares of fully paid and nonassessable common stock (“Common Stock”) of DUANE READE HOLDINGS, INC. (the “Company”) and hereby [makes payment of
$[            ] therefor] [or] [makes payment therefor by the surrender pursuant to Section 3 of a portion of the Warrant with respect to
[            ] shares]. The undersigned hereby requests that certificates for such shares be issued and delivered as follows: 
 ISSUE TO: 
 Name:
                                        

 Address:
                                         
                                         
                                         
                                         
                         
 Social
Security Number (or other Identifying Number):
                                         
                                         
                                 
 DELIVER TO: 
 Name:
                                        

 Address:
                                         
                                         
                                         
                                         
                         
 If the number of shares of Common Stock purchased hereby is less than the number of shares covered by the Warrant, the undersigned requests that a new Warrant representing the number of shares of Common Stock not purchased be issued and
delivered as follows: 
 ISSUE TO: 
 Name:
                                        

 Address:
                                         
                                         
                                         
                                         
                         
 Social
Security Number (or other Identifying Number):
                                         
                                         
                                 
 DELIVER TO: 
 Name:
                                        

 Address:
                                         
                                         
                                         
                                         
                         
 Dated:
                                        

  

			
	[NAME OF HOLDER]
		
	By:	 	 
		 	 Name:
 Title:

 EXHIBIT 2 
 [FORM OF] ASSIGNMENT 
 FOR VALUE RECEIVED, the undersigned hereby sells, assigns, and transfers unto the
Assignee named below all of the rights of the undersigned to purchase shares of fully paid and nonassessable common stock (the “Common Stock”) of DUANE READE HOLDINGS, INC. (the “Company”) represented by Warrant
No. B-1, dated [            ], 2009, with respect to the number of shares set forth below: 
  

					
	 Name of Assignee
	  	 Address
	  	 No. of Shares

 and does hereby irrevocably constitute and appoint any officer of the Company to make such transfer on the books
of the Company maintained for that purpose, with full power of substitution in the premises. 
 Dated:
                             
  

			
	[NAME OF HOLDER]
		
	By:	 	 
		 	 Name:
 Title:

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