Robert J. O'Regan



Bob O'Regan has successfully represented clients involving commercial and employment matters, fiduciary duties of corporate officers and directors, trustees, and guardians. He also represents clients in complex divorce cases in which the valuation and division of business or trust assets are a primary issue.

Bob's expertise in civil and commercial litigation includes directors' and officers' liability, fidelity bond claims, real estate title issues, and discharges from employment. He has successfully represented businesses and individuals before the Massachusetts Commission Against Discrimination. His practice also includes representing professionals before licensing and disciplinary authorities.


J.D., Georgetown University Law Center

M.A., Economics, Tufts University

B.A., magna cum laude, Tufts University



U.S. Supreme Court

U.S. Court of Appeals for the First Circuit

U.S. Court of Appeals for the Ninth Circuit

U.S. District Court for the District of Massachusetts

honors & awards

Named a 2019 “Family Law Trailblazer” by The National Law Journal

Named a 2016 “Lawyer of the Year” by Massachusetts Lawyers Weekly

Massachusetts Super Lawyers (2004, 2010, 2014-2021)


Boston Bar Association

  • Fiduciary Litigation Committee, Co-Chairman

Massachusetts Council for Public Justice

Massachusetts Probate and Family Inn of Court

  • Treasurer



“The Fiduciary Litigation Session,” Boston Bar Journal, March 2019


“Widow Gets Appreciation on Her Share of Estate,” Massachusetts Lawyers Weekly, July 2021

speaking engagements

“Trustee Removal No Fault and For Cause,” Panelist, MBA 6th Annual Probate Law Conference, November 2018