Stephen J. Orlando


  • Office Contact Info
  • Biography

    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)
  • Practice Areas
  • Representative Experience

    Stephen's trial experience includes the following:

    • Successfully defended client against multi-million dollar claim for breach of employment contract and violation of ERISA, 2023.
    • Obtained directed verdict for client in lawsuit alleging violations of M.G.L. c. 93A and Attorney General Regulations, 2023.
    • Won $1.4 million verdict, including an award for client’s legal fees, in a commercial eviction dispute, 2022.
    • Defended client against $150,000 claim for breach of contract, 2021.
    • Represented homeowners in multi-million dollar lawsuit against an international corporation, 2020.
    • Won $10.6 million verdict following a two-week jury trial, including an award for punitive damages and attorney’s fees, 2019.
    • Obtained defense verdict in multi-million dollar wrongful death lawsuit following three-week jury trial, 2017.
    • Obtained defense verdict in medical malpractice / wrongful death lawsuit, 2017.

    In addition to his trial experience, Stephen has repeatedly defeated lawsuits against his clients through successful dispositive motions.  His experience includes:

    • Obtained summary judgment in favor of client defending against $1.7 million defamation claim.
    • Defeated claim of discriminatory termination through motion for summary judgment, 2024.
    • Prevailed in motion to dismiss claim for employment discrimination, 2023.
    • Obtained summary judgment for client in $550,000 claim for profession malpractice, breach of contract, and violation of M.G.L. c. 93A, 2022.
    • Obtained dismissal of Complaint, filed in United States District Court, alleging violations of the Fair Debt Collection Practices Act, 2022.
    • Prevailed on motion to dismiss Complaint alleging civil rights violation, 2021.
    • Defeated $700,000 claim for professional malpractice through successful motion for summary judgment, 2020.

    Finally, Stephen has litigated appeals in the Massachusetts Appeals Court, Massachusetts Supreme Judicial Court, and Court of Appeals for the First Circuit.  In 2023, Mr. Orlando obtained a First Circuit decision affirming dismissal of a Complaint filed against his client in the United States District Court.

  • Publications & Presentations


    Avoid Delay or Get Ready to Pay: The Risks of “Time-is-of-the-Essence” Clauses, GRSM Construction Blog (August 10, 2018)

    The Doctor Will See You For the Last Time Now: Physician-Assisted Suicide in Massachusetts, 46 Suffolk U. L. Rev. 243, Suffolk University Law Review (February 2013)

  • Education


    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)