Skip to content Stephen J. Orlando


28 State Street
Suite 1050
Boston, MA 02109


J.D., summa cum laude, Suffolk University Law School, 2013

  • Suffolk University Law Review, Note Editor (2011 - 2013)
  • National Trial Team (2011 - 2013)
  • National Constitutional Law Appellate Team (2011 - 2013)
  • National Health Law Appellate Team (2011)
  • Prosecutor’s Clinic (2012 - 2013)

B.S., Health Policy and Management, Providence College, 2010

B.A., Philosophy, Providence College, 2010


Best Lawyers in America® Ones to Watch distinction in Commercial Litigation (2021-2024)

Super Lawyers Rising Star (2018-2023)


Stephen J. Orlando is a Partner in GRSM’s Boston office.  His practice areas include construction litigation, employment litigation, tenancy disputes, and professional malpractice defense.  Stephen also advises clients as to the negotiation of employment agreements, construction agreements, and lease agreements.  

Stephen has conducted trials in Massachusetts Superior Courts, the United States District Court – District of Massachusetts, and the United States District Court – District of New Hampshire.  Along with his trial experience, Stephen has litigated appeals in the Massachusetts Appeals Court, Supreme Judicial Court, and Court of Appeals for the First Circuit.  

Stephen’s trial advocacy has resulted in significant verdicts for his clients.  Following a two-week trial involving a complex construction dispute, he obtained a $10.6 million judgment for his client.  Following a four-day trial arising out of a lease dispute, Stephen obtained a $1.4 million judgment for his client.  In both cases, Stephen recovered an award for his client’s legal fees and costs.  Stephen has also represented defendants facing multi-million dollar claims, and has successfully defeated those claims through dispositive motions prior to trial or defense verdicts following trial.  

Stephen also represents clients in matters involving the Massachusetts Commission Against Discrimination (MCAD), the State Ethics Commission, and the Division of Occupational Licensure.  

Stephen graduated summa cum laude from Suffolk University Law School, ranking seventh out of 350 students. 


  • Massachusetts
  • U.S. District Court, District of Massachusetts
  • U.S. Court of Appeals, First Circuit 


  • Massachusetts Defense Lawyers Association
  • Massachusetts Bar Association – Business Law Section Council (2019-2020)
Publications & Presentations