John F. "Skip" O'Brien III
September 12, 1949 - September 5, 2025
John F. O’Brien III, lovingly known as “Skip,” passed away peacefully on September 5, 2025, at the age of 75, after a courageous battle with Stage 4 cancer. Born in Dorchester, MA, on September 12, 1949, he was the son of the late Evelyn Griffin O’Brien and John F. O’Brien II “Buddy.” He grew up in Milton, MA, and graduated from Milton High School.
Skip enjoyed a long and successful career in the jewelry business, working for many years in Boston’s Jewelers Building with DePrisco Jewelers and Robinson Jewelers & Co. He later continued his career in New York, Chicago, and Short Hills, NJ, before retiring and briefly driving for Uber and Lyft.
Above all, his greatest joy was spending time with his cherished granddaughter, Alexa Rose, who brought endless light to his life.
He is survived by his sister Jeanne Thomas and his brother Gregory O’Brien, and was predeceased by his siblings Marjorie Calabraro, David O’Brien, and Lynne Mara. He leaves behind his son, John A. Smith, devoted daughter, Courtney Elizabeth O’Brien, her long-term partner, Eric M. Daly, his cherished granddaughter Alexa Rose Daly, and many nieces, nephews, and cousins and their families.
Please join us for a Memorial Mass at St. Mary’s in Hanover, MA, on Sunday, September 28, 2025, at 11:30 a.m. A Celebration of Life will immediately follow.
Skip’s legacy of humor, resilience, and love for family will live on in the hearts of all who knew him.
In honor of his memory, donations may be made to Alcoholics Anonymous (aa.org).