Matthew S. Olesh

Commercial Litigation Attorney

Matt Olesh is a partner in Obermayer’s Litigation Department with offices in Philadelphia, West Conshohocken, and New York. While Matt’s litigation experience spans the gamut of clients, subjects, and size, he focuses on high-stakes, complex commercial disputes – “bet the company” litigation.  In addition to private clients, his work includes the representation of public entities, including municipal authorities, in litigation of significant consequence.  Matt’s experience has ranged from representing companies and their directors/officers in contractual disputes to defeating injunctions of multi-million dollar transactions and projects to defending against consumer class-action lawsuits.

Matt’s approach to litigation is a holistic one – the legal issues with which he works are always part of a larger picture. He strives to thoroughly understand his clients’ business and strategic situation, and serves as both an advocate and a trusted advisor. His goal is to simultaneously resolve the immediate dispute and anticipate and avoid future issues. He excels at assembling the varying pieces of a strategic puzzle and arriving at a workable, cost-effective solution.

An essential element of Matt’s practice is service. Whether a client is a large corporate entity, small business or an individual, Matt emphasizes accessibility, responsiveness and careful listening as essential tools for a good attorney. While results are critical, they’re not alone sufficient – ongoing, attentive and professional service is also necessary.

Matt strongly believes in the importance and value of pro bono work.  He routinely volunteers his time with a number of legal service organizations in Philadelphia to help those in need of assistance.  Beyond pro bono, Matt also works in his spare time to give back to his neighborhood, the legal community, and the City of Philadelphia.  He can often be found volunteering at his son’s neighborhood public school and has served as part of the Philadelphia Bar Association’s leadership since 2016.

To unwind, Matt can be found having a catch with his son or relaxing with his wife on the stoop of his Philadelphia rowhouse with a drink and good music.  He enjoys all types of craft beer and whiskey, and has curated whiskey and beer tastings.  He also loves exploring the City’s ever-changing food scene with his family.

Commercial litigation is a complex, often ongoing, and varied legal specialty. As a result, Matt has played a variety of roles as a litigator. He has acted as both an aggressive advocate for his clients’ interests and a sophisticated, astute negotiator, often in the course of the same matter. He is a skilled project manager, resulting in exceptional efficiency and cost-effectiveness. He’s also a gifted writer, both of formal legal material and persuasive business and non-legal content.

Matt’s specific accomplishments include:

• Successfully defending the City of Philadelphia’s Beverage Tax against legal challenges in the Philadelphia Court of Common Pleas, Pennsylvania Commonwealth Court and Pennsylvania Supreme Court.
• Representing both employers and employees in disputes pertaining to non-compete agreements and other employment issues, including Fair Labor Standards Act claims.
• Litigating claims pertaining to alleged construction defects and unsafe housing conditions.
• Defending architects and other design professionals in claims alleging negligent or otherwise defective design.
• Representing municipalities and municipal authorities in litigation and administrative proceedings pertaining to the sale of water and wastewater systems.
• Obtaining the dismissal of claims brought under the federal RICO Act and 42 U.S.C. § 1983 in a complex, multi-party case alleging a conspiracy between local government officials and the operators of a professional soccer team.
• Defending a large property management company against claims alleging substandard management as well as handling code violations.
• Representing both landlords and tenants in lease disputes and confession of judgment proceedings.
• Defeating an effort to enjoin a $150 million construction project at the Curtis Center in Philadelphia.
• Defending prominent recording artists against copyright infringement claims.
• Defeating a request for an injunction of the Harleysville/Nationwide insurance company merger.
• Advising a senior corporate executive regarding alleged misappropriation of trade secrets.
• Successfully defending against an attempt to gain ownership of land via adverse possession.
• Recovering a stolen pet via emergency relief and replevin claims.
• Resolving title and other property ownership disputes through civil litigation and negotiation.
• Serving as arbitrator for claims involving personal injury, including premises liability.

Matt’s pro bono work defines who he is as both an attorney and a person.  He volunteers with Philadelphia VIP, the Pennsylvania Innocence Project, the Prisoner Civil Rights Panel of the U.S. District Court for the Eastern District of Pennsylvania, Philadelphia Lawyers for Social Equity, and other legal service organizations.  Matt also strongly believes in second chances and helping those who may have made mistakes but have paid their debt to society.  In addition to personally helping clients who seek expungements and pardons, Matt helped organize a citywide expungement clinic that enabled hundreds of individuals to obtain expunged records.

Matt is extensively involved in a wide range of professional organizations.  He is currently Treasurer of the Philadelphia Bar Association, where he previously served as Assistant Treasurer as well as Chair of its Young Lawyers Division. He also served as Co-Chair of Philadelphia VIP’s Recruitment and Retention Committee. He was in the inaugural class and now helps administer the Philadelphia Bar Foundation’s Board Observer Program. He has been active with several nonprofits, previously serving as a Director of the Lawyer’s Club of Philadelphia and co-founding and serving as a Director of the Friends of Chester A. Arthur School Education Foundation.  Matt has also served as a Committeeperson in the 30th Ward Democratic Executive Committee in Philadelphia since 2014.

In addition, Matt serves as the chair of the Campaign for Qualified Judges.  In that capacity, he helps promote the ratings assigned to candidates for local judicial office by the Philadelphia Bar Association’s Commission on Judicial Selection and Retention. Matt organizes citywide voter outreach initiatives both in advance of and on Election Day, supervising nearly one hundred volunteers at polling places in all parts of Philadelphia.

In 2019, Matt received the Philadelphia Bar Association Chancellor’s Service Award in recognition of his efforts and impact in his role on the Campaign for Qualified Judges. Matt was also named one of Billy Penn’s Who’s Next: Law honorees and a Fellow of the American Bar Foundation in 2017. Matt was also selected for inclusion in Pennsylvania’s Super Lawyers Rising Stars® every year between 2013 and 2022 and was included in The Best Lawyers in America© from 2022 to 2025.

Awards Won*

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