ShiftPixy (PIXY) S-1/AIPO registration (amended)

EXHIBIT 5.2

July 29, 2024

ShiftPixy, Inc.

4101 NW 25th Street

Miami, FL 33142

Ladies and Gentlemen:

We have acted as counsel to ShiftPixy, Inc., a Wyoming corporation (the “Company”) in connection with the proposed sale and issuance (the “Offering”) of up to $5,000,000 of shares of the Company’s common stock, par value $0.0001 per share (the “Common Stock” and such shares, the “Shares”), Warrants (the “Common Warrants”) to purchase up to $5,000,000 of shares of Common Stock (the “Common Warrant Shares”), and Pre-Funded Warrants (the “Pre-Funded Warrants” and, together with the Common Warrants, the “Warrants”) to purchase up to $5,000,000 of shares of Common Stock (the “Pre-Funded Warrant Shares” and, collectively with the Common Warrant Shares and Pre-Funded Warrant Shares, the “Warrant Shares” and, collectively with the Shares, Common Warrants and Prefunded Warrants, the “Securities”) being issued to the Purchasers (as defined below), pursuant to the Registration Statement on Form S-1 (Registration No. 333-280566) filed by the Company with the Securities and Exchange Commission (the “Commission”) under the Securities Act of 1933, as amended (the “Securities Act”) (as amended, the “Registration Statement”), and the related prospectus contained therein (the “Prospectus”). The Securities are to be sold pursuant to a Securities Purchase Agreement (the “Purchase Agreement”) between the Company and each purchaser signatory thereto (each, a “Purchaser” and collectively, the “Purchasers”).

As counsel to the Company in connection with the proposed potential issuance and sale of the above-referenced Securities, we have reviewed the Registration Statement, Prospectus and the respective exhibits thereto. We have also reviewed such corporate documents and records of the Company, such certificates of public officials and officers of the Company and such other matters as we have deemed necessary or appropriate for purposes of this opinion. In our examination, we have assumed: (i) the authenticity of original documents and the genuineness of all signatures; (ii) the conformity to the originals of all documents submitted to us as copies; (iii) the truth, accuracy and completeness of the information, representations and warranties contained in the instruments, documents, certificates and records we have reviewed; (iv) that, as set forth in a separate opinion delivered to the Company on the date hereof by Bailey | Stock | Harmon | Cottam | Lopez LLP, special Wyoming counsel to the Company, the Warrants have been duly authorized; and (v) the legal capacity for all purposes relevant hereto of all natural persons and, with respect to all parties to agreements or instruments relevant hereto other than the Company, that such parties had the requisite power and authority (corporate or otherwise) to execute, deliver and perform such agreements or instruments, that such agreements or instruments have been duly authorized by all requisite action (corporate or otherwise), executed and delivered by such parties and that such agreements or instruments are the valid, binding and enforceable obligations of such parties. As to any facts material to the opinions expressed herein that were not independently established or verified, we have relied upon oral or written statements and representations of officers and other representatives of the Company.

Based on the foregoing, and subject to the assumptions, limitations and qualifications set forth herein, we are of the opinion that (i) when the Common Warrants are duly executed and delivered by the Company and paid for by the Purchasers pursuant to the Purchase Agreement and in accordance with the terms of the Prospectus, such Common Warrants will constitute the legal, valid and binding obligation of the Company, enforceable against the Company in accordance with their terms, subject to bankruptcy, insolvency or other similar laws affecting creditors’ rights and to general equitable principles and (ii) when the Pre-Funded Warrants are duly executed and delivered by the Company and paid for by the Purchasers pursuant to the Purchase Agreement and in accordance with the terms of the Prospectus, such Pre-Funded Warrants will constitute the legal, valid and binding obligation of the Company, enforceable against the Company in accordance with their terms, subject to bankruptcy, insolvency or other similar laws affecting creditors’ rights and to general equitable principles.

The opinions set forth above are subject to the following exceptions, limitations and qualifications: (i) the effect of bankruptcy, insolvency, reorganization, fraudulent conveyance, moratorium or other similar laws now or hereafter in effect relating to or affecting the rights and remedies of creditors; (ii) the effect of general principles of equity, including without limitation, concepts of materiality, reasonableness, good faith and fair dealing and the possible unavailability of specific performance or injunctive relief, regardless of whether enforcement is considered in a proceeding in equity or at law, and the discretion of the court before which any proceeding therefor may be brought; and (iii) the unenforceability under certain circumstances under law or court decisions of provisions providing for the indemnification of, or contribution to, a party with respect to liability where such indemnification or contribution is contrary to public policy. We express no opinion concerning the enforceability of any waiver of rights or defenses with respect to stay, extension or usury laws.

Any additional Securities registered in reliance on Rule 462(b) under the Securities Act in connection with the Offering are hereby expressly covered by this opinion. As used in this opinion, the term “Registration Statement” shall include any additional registration statement filed pursuant to Rule 462(b) under the Securities Act in connection with the Offering and the term “Prospectus” shall include any prospectus deemed to be included in any such additional registration statement.

Our opinion is limited to the laws of New York. We express no opinion as to the effect of the law of any other jurisdiction. Our opinion is rendered as of the date hereof, and we assume no obligation to advise you of changes in law or fact (or the effect thereof on the opinions expressed herein) that hereafter may come to our attention. We advise you that matters of Wyoming law are covered in the opinion of Bailey | Stock | Harmon | Cottam | Lopez LLP, special Wyoming counsel for the Company, in Exhibit 5.1 to the Registration Statement.

We hereby consent to the filing of this opinion as Exhibit 5.2 to the Registration Statement and to the references to our firm under the caption “Legal Matters” in the Prospectus which is a part of the Registration Statement. In giving such consent, we do not thereby admit that we are in the category of persons whose consent is required under Section 7 of the Securities Act or the rules and regulations promulgated thereunder.