Robert A. Dempsey, Jr.

Robert A. “Bobby” Dempsey, Jr., a resident of the Allston section of Boston passed away unexpectedly at Brigham and Women’s Hospital on August 10, 2026, with his loving family by his side. He was 57 years old.

Born in Lowell, Massachusetts on July 21, 1969, Bobby was the only son of the late Robert A. “Tony” and Mary Ann (White) Dempsey, of Lowell, who survives him.

Bobby grew up in Dracut and graduated from Dracut High School. He was known for his quick wit, sharp intellect, and love of all New England sports teams. He was a skilled prep cook working in restaurants throughout Boston and the North Shore. During family gatherings, he could always be found in the kitchen or at the grill, cooking for everyone.

Though Bobby struggled with substance abuse disorder for many years, he also had extended periods of sobriety, during which his true inner goodness and love of family were impossible to miss. He was a devoted son who remained closely connected to his mother and provided unwavering care for his father during his battle with cancer. He was much more than the challenges he endured and will be remembered by his family as a funny, smart and loving son, brother, and uncle. Bobby recently celebrated a significant recovery milestone with the Devine Recovery Center and took great pride in supporting others in recovery. His family is deeply proud of him and incredibly grateful for the love and support the recovery community extended to Bobby.

Bobby is survived by his mother and by his three sisters, Kathleen A. Ross and her husband, Thomas of Somerville; Mary Ann Dempsey of Merrimack, New Hampshire; and Susan M. de Mari and her husband, Giampaolo of Tyngsboro. He also leaves behind his beloved nieces Sophia and Caroline de Mari of Tyngsboro; his nephew Graham Ross of Somerville; his uncle, Thomas N. White, and his wife, Patricia of Dracut; as well as many cousins and extended family members who held him close.

He was predeceased by his father and by his sister, Elizabeth C. Dempsey; uncle, Richard J. Dempsey; maternal grandparents, Thomas N. and Agnes White; and paternal grandparents, Robert B. and Winifred Dempsey.

The family held a private burial for Bobby, who is now at rest with his father and sister at St. Mary’s Cemetery in Tewksbury. In lieu of flowers, the family requests that donations be made to support the ongoing work of the Devine Recovery Center through the Gavin Foundation Development Department, 675 East 4th Street, PO Box E-15, South Boston, MA 02127. https://gavinfoundation.org