Barclay Damon
Barclay Damon

Stephen H. Oleskey

Stephen H. Oleskey

Of Counsel

p: 617.274.2909

f: 617.722.6003

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Boston Office

One Financial Center
Suite 1701
Boston, Massachusetts 02111

Stephen 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.  

Representative Experience

  • 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.

Practice Areas


  • New York University School of Law, J.D., Arthur T. Vanderbilt Scholar, 1968
  • Wesleyan University, B.A., magna cum laude, Thesis Honors, Phi Beta Kappa, 1964

Admitted To Practice

  • Massachusetts
  • New Hampshire
  • New York

Memberships & Affiliations

  • American Bar Association
  • American Bar Association Foundation, Fellow
  • Massachusetts Bar Association
  • Boston Bar Association Foundation, Fellow
  • New York Bar Association
  • New Hampshire Bar Association
  • Justice Bridge Advisory Board, Boston MA
  • Board of Directors, Pact, Inc., Immediate Past Chair
  • Greater Boston Legal Services, Past Director and Past President
  • Boston Bar Association's Volunteer Lawyer Project, Past Director and Past Chair
  • Massachusetts Legal Assistance Corporation (Appointed by the Massachusetts Supreme Judicial Court), Past Board Member and Past Chair
  • Massachusetts Equal Justice Coalition, Past Chairman
  • NOW Legal Defense and Education Fund (now Legal Momentum), Past General Counsel and Past National Board Member
  • Trustee, Wesleyan University, 2000-2003

Speaking & Publications

  • Closing Keynote Speaker, ASAE Annual Association Law Symposium, Washington, DC, October, 2015
  • Keynote Speaker, Rhode Island Bar Association Annual Meeting, June 19, 2014
  • New England Journal on Criminal and Civil Confinement, Foreword to Paper Symposium "In Our Name: a Play of the Torture Years," Winter 2013
  • "Reflections on Forty Years of Private Practice and Sustained Pro Bono Advocacy," Maine Law Review Vol. 68.2, 514-530, 2011
  • Speaker, Ancient and Honorable Artillery Company of Boston, JAG Dinner, March 2011
  • Eighteenth Annual Frank M. Coffin Lecturer on Law and Public Service, Portland, Maine, 2010
  • Speaker, Amnesty International USA: 2009 Annual General Meeting, March 2009
  • Community Dispute Settlement Center: Spirit of Mediation Gala, October 2008
  • Presentation, "Indefinitely Imprisoned Without Charge at Guantanamo: A Detainee's Lawyer Describes the Battle for Habeas Corpus After 9/11," Stanford Law School, March 2008
  • Panelist, "Music & Torture: A Discussion on the Use of Popular Music in U.S. Interrogation," Music & Entertainment Industry Student Association, February 2008
  • "Indefinitely Imprisoned Without Charges: Is it Constitutionally Permissible?" Roger Williams University, February 2008


  • Selected to Super Lawyers Massachusetts: Category, 2018
  • Selected by Peer Review for Inclusion in Super Lawyer Directory 2001-2017 for General Litigation
  • The Best Lawyers in America®: Eminent Domain and Condemnation Law, 2015-2019
  • The Best Lawyers in America 2015 Boston Eminent Domain and Condemnation Law "Lawyer of the Year"
  • Recipient of the 2014 Wesleyan University Outstanding Service Award for lifetime service
  • Selected by Peer Review for Inclusion in Super Lawyer Directory 2014 for Civil Litigation: Defense
  • Selected by peers for inclusion in the The Best Lawyers in America, Eminent Domain and Condemnation Law, 2011, 2012, 2013 and 2014
  • Recognized as a Massachusetts leader in the Litigation: General Commercial field in the 2010, 2011, 2012 and 2013 editions of Chambers USA: America's Leading Lawyers in Business 
  • Named a "Lawyer of the Year" by Massachusetts Lawyers Weekly, November 2008 
  • Recipient of the Community Dispute Settlement Center's 2008 Community Peacemaker Award 
  • Recipient of the 2008 Massachusetts Correctional Legal Services' Distinguished Leadership Award for "his remarkable contributions to the legal profession, and most especially for his recent advocacy work on behalf of six clients detained without charges for more than three years at Guantanamo Bay"
  • Recipient of the 2007 Lifetime Achievement Pro Bono Public Award by the American Bar Association 
  • Named "Alumnus of the Month" by New York University School of Law, December 2007
  • Recipient of the Massachusetts Correctional Legal Services' Distinguished Leadership Award for "his remarkable contributions to the legal profession, and most especially for his recent advocacy work on behalf of six clients detained without charges for more than three years at Guantanamo Bay."
  • Named a "New England Super Lawyer" (formerly "Massachusetts Super Lawyer") in civil litigation defense in the 2004-2012 editions of Boston Magazine 
  • Named a "Distinguished Alumnus" for his professional and public service achievements by his alma mater, Wesleyan University, in 1999
  • Awarded Honorary Doctor of Law Degrees by Southern New England School of Law (now University of Massachusetts School of Law) (2009) and Northeastern University School of Law (Commencement Speaker 2009)

Prior Experience

  • Hiscock & Barclay, LLP, Of Counsel
  • WilmerHale, Partner
  • Massachusetts Deputy Attorney General and Chief of the Public Protection Bureau, 1987-1988