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Of Counsel

"At 13, I decided that trial lawyers did exciting, impactful work in helping resolve disputes, and I've found this to be true in my practice."



A former Massachusetts Deputy Attorney General and Public Protection Bureau chief, Stephen primarily concentrates his practice on representing 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, including the US Supreme Court, the Massachusetts Supreme Judicial Court, the Massachusetts Appeals Court, the New Hampshire Supreme Court, the Maine Supreme Court, the US Tax Court, the US Court of Claims, and US Courts of Appeals for the District of Columbia First, Third, and Ninth Circuits.

Some of Stephen’s representative clients have included Gale Companies, Stockbridge Real Estate Fund, Equity Office Properties, New England Life Insurance Company, Gerald D. Hines Interests, Sears Roebuck, Silverleaf Resorts, Inc, and Trinity Financial.

Bar Associations

  • American Bar Association Foundation, Fellow
  • Boston Bar Association
  • Boston Bar Association Foundation, Fellow
  • New Hampshire Bar Association

Selected Memberships & Affiliations

  • Pact, Inc., Former Director and Chair
  • Massachusetts Legal Assistance Corporation, Former Director and Chair
  • Massachusetts Equal Justice Coalition, Former Director and Chair
  • NOW Legal Defense and Education Fund (now Legal Momentum), Former General Counsel and National Board Member
  • Phi Beta Kappa

Representative Experience

  • Successfully defended a joint venture owning a new office tower against a $40 million 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-reset arbitration over a long-term parking contract and established that the lease value had increased dramatically.
  • Defeated minority partners’ claims for breach of fiduciary duties by general partners and obtained a judgment for over $2 million in legal fees from the plaintiffs for instigating and pursuing their frivolous suit.
  • Enjoined a wind-farm developer from completing its project until it established compliance with its development permit.
  • Secured a $17 million jury verdict against a municipality in favor of the developer of a mixed-use project where the municipality had unlawfully refused to convey the project land.
  • Represented an office-tower developer in the successful defense of all project permits and approvals.
  • Co-led a team for eight years in representing six men detained in Guantanamo Bay Prison without charge or trial, culminating in the first federal district court habeas corpus trial for any such detainees and a ruling that five of the men were being held without legal authority and should be immediately released.

Prior Experience

  • Hiscock & Barclay, LLP, Of Counsel
  • WilmerHale, Partner
  • Massachusetts Deputy Attorney General and Chief of the Public Protection Bureau

Selected Community Activities

  • Justice Bridge Boston Legal Incubator, Advisory Board Member
  • Beacon Hill Civic Association, Former Director and Chair
  • Boston Bar Association Volunteer Lawyers’ Project, Former Director and Chair
  • Community Dispute Settlement Center, Community Peacemaker Award, 2008

Selected Honors

  • The Best Lawyers in America®: Eminent Domain and Condemnation Law, 2009–2023; Commercial Litigation, 2022–2023; and Boston Lawyer of the Year: Eminent Domain and Condemnation Law, 2022
  • Selected to Super Lawyers Massachusetts: General Lit, 2001–2020
  • Inaugural recipient of the Stephen H. Oleskey Award for Excellence in Public Service, 2019
  • Massachusetts Lawyers Weekly, Lawyer of the Year, 2008
  • American Bar Association, Pro Bono Publico Award, 2007


Selected Speaking Engagements

  • ASAE Annual Law Symposium “ Litigation as a Vehicle to Influence and Effect Public Policy” Closing Keynote Speaker
  • Rhode Island Bar Association Annual Meeting, Keynote Speaker, “Habeas Corpus After Boumediene
  • Eighteenth Annual Honorable Frank M. Coffin Lecturer on Law and Public Service, “Reflections on 40 Years of Private Practice and Sustained Pro Bono Advocacy”
  • Connecticut Judges’ Institute, “Boumediene v. Bush
  • American Corporate Counsel Association Chapter, “Arbitration, Mediation, and ADR in Real Estate Disputes”

Selected Media

  • New England Journal on Criminal and Civil Confinement, “In Our Name: A Play of the Torture Years”
  • Maine Law Review, “Reflections on 40 Years of Private Practice and Sustained Pro Bono Advocacy”

Featured Media


US Supreme Court Shrinks Federal Authority Under the Clean Water Act


Supreme Court Strikes Down Taxing Authorities' Right to Retain Surplus Monies in "Strict Foreclosures"


Appellate Division, Third Department, Denies Appeal and Upholds Office of Renewable Energy Siting Regulations


NYS Public Service Commission Formally Initiates Proceeding to Establish What Constitutes "Zero Emission" Under the CLCPA


NYS Appellate Court Dismisses Common Law Claims Against Contractor for Injuries Sustained by "Special Employee"


Child Victim Act Complaint Dismissed for Failure to Sufficiently Allege Special Duty

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