Thomas F. O’Reilly, Esq., of South Boston, left this world a far less witty place on October 9, 2025. He is survived by his siblings: Dr. Joseph G. O'Reilly and his wife Carolyn, Robert E. O'Reilly and his former wife Francine Dwyer, Diane M. McManama and her husband Robert, Donna M. Matteodo and her husband David, William J. O'Reilly and his wife Elizabeth, and an eldest brother lost in infancy; in addition, he is remembered with love by 15 nieces and nephews and 10 great-nieces and great-nephews. Tom was known for his sharp humor, unwavering integrity, and brilliant mind — qualities that defined both his career and his life.
Son of the late Brookline Fire Department Captain Thomas F. O’Reilly and Anne M. (Donoghue) O’Reilly, Tom studied at Boston College before serving as a Captain in the United States Marine Corps, including a tour in Vietnam. He later served at the U.S. Naval Activity Command in London, England, as a Guard Officer for the Naval Nuclear Training Facility, and stateside as Infantry Company Commander at Camp Lejeune. He concluded his military service with a Navy Commendation Medal for composure under enemy fire, a Vietnamese Service Medal, and a Presidential Unit Citation.
Back in Massachusetts, Tom joined the State Department Security Division, guarding heads of state around the world while pursuing his law degree at Suffolk University. Over decades of legal service, Tom built a career defined by skill, integrity, and dedication, culminating in his role as Assistant District Attorney in Middlesex County, where he handled numerous high-profile cases and commanded respect as a formidable yet fair prosecutor.
Beyond his professional accomplishments, Tom was deeply devoted to his family. He was the go-to 2 a.m. call for his nieces and nephews, a fiercely loyal brother, and a steadfast uncle - always ready to offer honest guidance, debate any topic, or find the perfect gift. A South Boston resident for decades, Tom could often be found on his front balcony, taking in his slice of the Boston Harbor view with his police scanner on full volume.
Tom’s legacy is one of service, grit, and love - a brilliant man who lived life guided by a strong moral compass and left a lasting mark on all who knew him.
Funeral Services private.