David P. Winters

Mr. Winters’ practice focuses on aviation, public procurement, real estate development, construction, litigation, and regulatory matters.

Mr. Winters has held senior legal and executive roles at key agencies in the City of Chicago, including the Department of Aviation and the Department of Procurement Services. Most recently, he served as Managing Deputy Commissioner and Chief Legal and Accountability Officer for the Department of Aviation, where he oversaw all legal affairs and regulatory compliance.  In that capacity, he helped manage legal risk and ensure regulatory alignment on capital projects, including the O’Hare Global Terminal and the capital programs at both O’Hare and Midway Airports.

Previously, Mr. Winters served as Chief Assistant Corporation Counsel for the City of Chicago, where he handled procurement disputes, bid protests, concession agreements, infrastructure contract and complex policy matters. He also served as Senior Counsel and later Managing Director of Construction at the Metropolitan Pier and Exposition Authority (MPEA), leading legal strategy on major capital investments and negotiating financing and design-build agreements for public-private development initiatives.

In addition to his public-sector legal work, Mr. Winters brings significant alternative dispute resolution experience. He serves as a member of the American Arbitration Association’s national commercial and construction panels and draws upon formal training in both mediation and arbitration. His ADR experience complements his legal practice, particularly in resolving multi-party construction disputes, navigating regulatory claims, and fostering collaboration among governmental, corporate, and community stakeholders.

He earned his J.D. from DePaul College of Law, where he also completed a certificate in mediation. He holds an M.A. and A.B. in International Relations, along with doctoral coursework and qualifying exams in sociology. Mr. Winters’ career reflects a sustained commitment to public service, infrastructure development and principled legal stewardship.