John R. "Jack" Gillespie, Jr., best friend and loving longtime companion of Mary Byrnes, passed away on Wednesday, August 20th, 2025.  Born and raised in Derry, New Hampshire, Jack is the son of the late John R. and Evelyn F. (Forbes) Gillespie.

Jack is a graduate of the University of New Hampshire, earning his degree in electrical engineering.  This brought him a long and rewarding career as an engineer and ultimately an executive at various technology companies.  His expertise brought him to many countries around the world, but he was always grateful to come home and pursue his hobbies and passions.

Jack had a love for horses early in his life and became a pilot, owning small plane.  Eventually, however, he traded in his pilot license for his most rewarding passion of all, the open ocean.  Jack was truly his happiest behind the wheel of "Cordial," his beloved Hinckley Bermuda 40 sailboat.  Jack and his first mate Mary enjoyed countless sails on Cordial along the coast of Massachusetts and Maine, creating memories to last a lifetime.

Jack also enjoyed playing tennis and golf and spending time in Hutchinson Island, Florida, his home away from home.  Jack was known for his bellowing laugh that could and would take over a room.  Forever twenty six at heart, he was a kind, compassionate and loving soul who will be deeply missed.

In addition to being the cherished love of Mary, he held a special relationship with her two children, Michael Byrnes of San Francisco, CA, Matthew Byrnes of Middleton, MA, and Matthew's former wife Sarah of Newbury, MA. He was especially devoted to Matthew and Sarah's children Penelope and McKensie.  They will miss "Grampa Jack," his bellowing laugh and soft heart very dearly.  So will Maggie (Matt's French Bulldog) who would dutifully lick away at Jack's hands for hours.

Jack is also survived by his dear nephews and niece Doug, Terrance, Tim and Amy Culver, children of his late sister Priscilla Culver.

Family and friends are cordially invited to visiting hours at the Cota Funeral Home, 335 Park St., North Reading (Corner of Rt. 28 and Park St. at the Reading Line) on Friday, August 29th, from 12 to 2pm.

Following the visitation, a service to celebrate Jack's life will be held at the funeral home at 2:00pm.

In lieu of flowers, please consider making a donation in Jack's Memory to helping kids enjoy his beloved passion for sailing at Sail Salem.  You may donate online at https:// sailsalem.org/donations / or you may mail in at Sail Salem, 23 Glendale St, Salem, MA 01970.