Gerard D. DiFiore

Gerard D. DiFiore of Stoneham, formerly of Medford & Malden, passed away with his family by his side on Wednesday, April 13, 2025. He is 85 years of age.

Born on Saturday, January 6, 1940, in Boston, Gerard is the loving son of the late Andrew DiFiore and MaryEllen (Holland) DiFiore. Gerard is a warm, kind, gentle and loyal son, brother, husband, father, grandfather, uncle, and friend who will be deeply missed.

Jerry was an avid sports fan, from golf to football, his knowledge of current sports details was present even in his final weeks. He enjoyed horse racing and had a special talent for picking the losing horse. Golfing on Wednesdays with his friend Dickie was one of his favorite pastimes.

A proud Veteran, Jerry was extremely regimented, likely from years in the military. Time management and organization were important to him. Despite his decline, Jerry never missed reading the Boston Herald every morning, front to back. He typically included his own commentary and colorful remarks of the day’s events that were not always “fit to print.”

Jerry was a resident of Stoneham, frequently visiting Kennedy's for coffee or Felicia's and Gaetano's for dinner on a Friday night. You could often find him at the corner high top, or the bar with his dear friends Andy, Chickie, Pat, Fitzy. His storytelling was endless, and memories were vivid. He spoke fondly of his childhood in South Medford, his time spent in the army, or his many trips to Las Vegas and Saratoga. Jerry worked for many years at UPS and had endless stories of the characters he met along his routes in the North End and Chinatown. He was a proud member of the Teamsters Union Local 25.

Jerry enjoyed dinners with his son-in-law Mark, with whom he shared a special bond. He cherished moments with his beloved daughter-in-law, Allison, who he adored.

Jerry was a great cook and calamari salad was one of his specialties. He enjoyed scotch on the rocks, a boiled (not grilled) hot dog, and he never met a sweet he didn't like.

Jerry's style was unmatched. He was often dressed to the nines, no matter the occasion and he only wore shorts twice in his life. He wasn't afraid of bright colors, and his hand was often adorned with a gold pinky ring.

Despite being in his eighties, he taught himself how to use a laptop and smartphone, though he frequently called for IT assistance from his son-in-laws, Bob and Dave. You could often find him watching some of his favorite Westerns, and “The Duke” was his favorite Cowboy. He also enjoyed watching The Big Bang Theory and Bar Rescue.

Jerry was the truest friend, brother, son, father, and grandfather. A gentleman that will be missed by his friends and family.

Gerard is the beloved father of Maria O’Halloran and her husband Mark, Lisa DiFiore and David Teixeira, Andrea Lewis and her husband Robert and Gerard DiFiore and his wife Allison Huang. He is the cherished grandfather of Jaclyn O’Halloran-Carrillo and her husband Dante, Caitlyn Tripodi and her husband Patrick, Michael DiFiore, and Andrew DiFiore. The dear brother of Elaine Anderson and her late husband Poogie, Debra Smith and the late James DiFiore, Ellen Airhart, Sandra Ward and her husband Billy and Barbara Champion, Gerard is also survived by many loving nieces and nephews and mother of his four children, Joan DiFiore.

Family and friends are cordially invited to gather and share memories with Gerard’s Family on Tuesday, April 22nd from 4-7pm in the Barile Family Funeral Home, 482 Main St. (RT 28) STONEHAM. Parking attendants and elevator are available.

A Funeral Mass Celebrating Gerard’s Eternal Life will be held on Wednesday, April 23rd at 10am in St. Patrick Church, 71 Central St. Stoneham. Interment Lakeside Cemetery, Wakefield.

In lieu of flowers, please consider making donations in Gerard’s memory to Sawtelle Family Hospice House, c/o Office of Philanthropy, Beth Israel Deaconess Medical Center, 330 Brookline Avenue (OV), Boston, MA 02215 or by referring to Beth Israel Lahey Health Philanthropy

For more information, www.facebook.com/BarileFamilyFuneralHome