Stephen Oleskey is Of Counsel in the firm’s Commercial Litigation practice area, and a member of the Real Property Tax & Condemnation practice area. Stephen has represented a wide range of corporations, partnerships, joint ventures, individuals and government entities, in civil jury and jury-waived trials, arbitrations and mediations in Massachusetts state and federal courts and in many other jurisdictions. He has lectured and spoken on these topics. Stephen has argued before the U.S. Supreme Court, as well as before the Massachusetts Supreme Judicial Court, the Massachusetts Appeals Court, the New Hampshire Supreme Court, the Maine Supreme Court, the U.S. Tax Court, the U.S. Court of Claims, and the District of Columbia, First, Third and Ninth Circuit U.S. Courts of Appeals.

Significant litigation representations have included The Gale Companies, Stockbridge Real Estate Fund, Mondev International, Equity Office Properties, New England Life Insurance Company, Gerald D. Hines Interests, Sears Roebuck, Silverleaf Resorts, Inc., and Suez North America.

From 1968 to 1987, and 1988 to 2012, he practiced at WilmerHale (formerly Hale and Dorr).

Stephen served as Massachusetts Deputy Attorney General and Chief of the Public Protection Bureau in 1987 and 1988. He supervised 140 attorneys, investigators, paralegals and support personnel in the Antitrust, Civil Rights, Consumer Protection, Environmental Protection, Insurance, Public Charities, Utilities, Nuclear Safety and Special Litigation Divisions. He was responsible for all civil litigation and enforcement proceedings in the Bureau.

Stephen co-chaired Massachusetts’ Attorney General Maura Healey's election campaign and then chaired her transition team.  

• Successfully defended a joint venture owning a new office tower against a $40M claim by a former partner. 
• Established that a client operating a large building under a long-term lease from a public authority was entitled to the same statutory exemption from real property taxes enjoyed by the authority. 
• Represented the owner of a large parking garage in a lease re-set arbitration over a long-term parking contract and established that the lease value had increased dramatically. 
• Defeated minority partners’ claims for breach of fiduciary duty by general partners and then obtained a judgment for over $2M in legal fees from the plaintiffs for instigating and pursuing a frivolous suit. 
• Enjoined a wind farm developer from completing its project until it established compliance with its development permit.