Donald Alexander Gregory

Donald Alexander Gregory, Age 74 of Medford, MA, passed away on March 4, 2026 with his family around him. Born on September 27, 1951, in Dorchester, he was son of John Vincent Gregory II of Boston and Mary Catherine (Beaton) Gregory of Cape Breton, Nova Scotia.

Don was raised in Allston, MA, and graduated from Boston University in 1983. He built a meaningful career in health care administration and human resources, primarily in long-term care, where he was especially gifted at working with the elderly. Throughout his life, Don found deep purpose in helping others, drawing inspiration from listening to their stories, challenges, and triumphs. He fought passionately to support those seeking to improve their circumstances.

Don spent many happy years in Sutton, MA with his first wife, Susan, and their daughter, Becky, surrounded by a household full of beloved dogs and cats. He had a lifelong passion for all things related to Scotland, Nova Scotia, and Cape Breton—especially their rich musical traditions. A dedicated and longtime member of the New Hampshire Highland Games, Don cherished attending annually with his wife Theresa.

In addition to his parents, Don was predeceased by his first wife, Susan Louise (Forget) Gregory (2005), and his older brother, John Vincent Gregory III (2022). He is survived by his wife, Theresa Stapleton of Medford; his daughter, Rebecca Gregory (Joel Van Gorder) and his grandchildren, Graham and Isla of Milwaukee, WI. He also leaves behind his stepdaughters, Heather Cabral (Dren Ibrani) and grand-dog, Penny, of Wakefield, and Jillian (Andrew) Fleming and grandchildren Cody, Micayla, Wesley, and Natalie of Medford. Don is further survived by his loving sister, Anne Isberner of Milwaukee, WI, along with numerous nieces, nephews, extended family members, and dear friends.

In lieu of flowers, memorial contributions may be made to Father Bill's & Mainspring, 430 Belmont Street, Brockton, MA 02301. Services will be private.