Born in Lynn, MA on Sept. 4, 1960, he is the son of Janice E. (Furey) and the late Timothy J. O'Leary. He grew up in Lynn and Saugus, MA and settled down in North Billerica with his wife and children. He graduated from Saugus High School in 1978, then went on to UMass Amherst earning his Bachelor’s Degree in Communications. Craig moved to Chicago and worked for a video production company where he met many celebrities and musicians, some of whom he formed friendships and kept in touch with over the years. After five years in Chicago, he moved back to Massachusetts where he had a long career with the Social Security Administration. He also was a Blood Driver Transport for a Medical Courier Company.
Craig was a loving, kind, thoughtful, gentle soul who truly was one of a kind. Making new friends came easily for Craig with his many interests throughout his lifetime. Craig was a music enthusiast, and a die-hard fan of the Grateful Dead would be an understatement. As a "Dead Head" he would travel in his younger years, catching every show in every city. He also saw his lifelong idol Bob Dylan perform on the last show of David Letterman in NY with his sister Karen. He was a huge Stephen King fan and was lucky enough and very proud to have met him.
Craig also enjoyed photography and videography and developed his own film in his dark room as a teenager. He was a big fan of Star Trek and known to have a few tribbles. He was an avid collector of unusual and rare items. Craig enjoyed watching the Patriots, Red Sox, and especially the Lowell Spinners, loved Dunkin Donuts, Lobster Rolls and Indian Cuisine. He enjoyed traveling and taking trips to Disney World with his family, but what Craig cherished the most was spending time with his family and his beloved K9 friends, Mieko and Walter.
In addition to his mother, he leaves behind his daughter Amoreena O’Leary of Beverly, MA and his son Sean O’Leary of North Billerica, both who he adored and loved very much. He also leaves his sister Mary-Ellen Chaves of Kingston, MA, his sister Karen O'Leary of Danvers, MA, his brother Christopher O'Leary of Saugus, MA; and a special Uncle, Robert Furey of Saugus. He also leaves the mother of his two children, Tara Vaccarello, his niece Caitlin Silvia of Plymouth, his nephew Brian Chaves of Kingston, his aunt Ann Furey of S. Hamilton, and many cousins...
The family will receive visitors in the Cuffe McGinn Funeral Home, 157 Maple St., Lynn on Sunday, April 13, 2025 from 2-5pm with a service to follow at 5pm.
Craig fought a long and courageous battle with Parkinson's Disease. His bright joyful light will be missed and may the memory of his laughter and smile bring comfort to those who mourn his passing.
In lieu of flowers, and in honor of Craig and others please donate to the Michael J. Fox Foundation for Parkinson's Research.
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