John Bailey
John Harry Bailey, beloved husband, father, uncle, and grandfather, passed away on December 5, 2025, at the age of 79, at the home he built, with his loving wife and devoted daughter at his side.
Born in Collingwood, Ontario, and raised in Dundas, John built a respected teaching career in Toronto before retiring to Thornbury—a place he had ties to since the 1960s and where he became a permanent, full-time resident in 2000.
John lived a life defined by service, community, and connection. Beginning as a student executive at McMaster University, he went on to hold executive roles with the Toronto Ski Club, to serve as President of the Thornbury BIA and President of T.C. Rotary, and later became a proud member of Legion 281.
John had two meaningful careers. He was a beloved Math and Geography teacher at York Memorial Collegiate Institute in Toronto, where he found deep fulfillment in teaching and coaching. Through his dedication, encouragement, and steady presence—both in and out of the classroom—he touched the lives of countless students and cared deeply for his colleagues. Later, combining his love of hands-on work with an entrepreneurial spirit, he became the owner-operator of Reliable Handyman and Management Services in Thornbury, working alongside—and mentoring—his stepson, Mark. He took great satisfaction in serving his customers, many of whom became friends.
Through T.C. Rotary, John’s pet project was ShelterBox Canada. With the support of Rotary, he helped raise over $100,000 and was honoured as ShelterBox Ambassador of the Year—an achievement that reflected both his compassion and commitment to helping others.
An enthusiastic athlete, John played and coached many sports, including basketball, skiing, hockey, and baseball, both at school and in the community. He especially cherished the camaraderie and laughter shared with friends in the locker room after hockey at BVCC. A lifelong lover of trains and travel, he held a particular fondness for “riding the rails.”
John loved his family, friends, puppies, and his Christian faith. He was deeply proud of his sobriety of over 31 years and credited Alcoholics Anonymous with providing not only spiritual guidance, but also lifelong friendships and a lasting devotion to helping others.
John lived with resolve and determination despite profound challenges. He thrived for twelve years after being diagnosed with stage four lung cancer and, in his final year, faced a much harder battle with an aggressive form of non-Hodgkin lymphoma, which he could not overcome. Unafraid to the very end, he did not go gently. In the words of Dylan Thomas, he truly did “rage, rage against the dying of the light,” a reflection of his enduring courage, resilience, and spirit.
John is immediately survived by his soulmate and wife of 30 years, Diana; his devoted daughter, Kathryn (John); and his loving stepson, Mark. He is also survived by his son, Kevin (Kerri); and his grandchildren, Alex, Nick, Daniel, Gavin, Myles, Madison, Jack, and Logan. He will be greatly missed by his sister-in-law, Julia (Randy); nieces, Kayla and Liz (Scott); nephews, Christopher (Krystal) and Webster (Jolene); great-nephews, Benson, Bentley, Damon, Owain and Vincent and cousins, Robert MacDairmid (Marie), Tim Dey (Sandra) and Richard Dey (Monika). He is fondly remembered by his honorary children, Kana (Shota) and Caron (Dieter), and by the many good friends who were blessed to know him. He is also remembered by extended family.
John’s family and loved ones wish to thank his oncologists, Dr. Anjum and Dr. Sandhu, and his wonderful nurses, Crystal and Cindy. Please consider a donation to cancer care at Owen Sound Hospital (Brightshores Foundation) or to ShelterBox Canada.
A funeral/celebration of life will be held at St. Paul’s Presbyterian Church, 165 Russell St. E, Thornbury, Ontario N0H 2P0, commencing at noon on Saturday, March 14th, 2026.