Remembering Winston George Gregory

Winston George Gregory, affectionately known as George—a gifted Engineer Millwright, entrepreneur, and deeply respected member of the Toronto and Mississauga communities, passed away peacefully on January 22, 2026.

George’s story began in Jamaica, continued through his formative years in England, and ultimately brought him to Canada, where he built a life defined by dedication, and service. He moved through the world with a deep curiosity for how things worked, a trait that shaped both his career and his character.

For decades, George was a cornerstone at Peek Freans (Nabisco/Mondelēz), where his skill, reliability, and professionalism formed the backbone of a long and distinguished career.

Even after a full day at the plant, George’s entrepreneurial heart never rested. In the evenings, he dedicated his time to an investment group, where he worked alongside thirteen others to help create economic growth within the community. A licensed barber, George also worked side by side with his wife, Winniefred, helping to establish one of Toronto’s first Black-owned hair salons. That same spirit of building from the ground up continued when he supported his sister in opening Sharon’s Hair Design in Brampton. He was also a devoted and long-standing supporter of the Miss Black Ontario pageant.

Retirement did not slow George down—it simply shifted his focus. He embraced the joy of travel, especially the adventure of cruising, but his greatest happiness was found closer to home, cheering enthusiastically from the side-lines at his grandchildren’s soccer games. Family was the centre of his world. He took immense pride in being present for every milestone and celebration, always offering a welcoming heart and an open door to all.

Predeceased by his beloved wife, Winniefred and brother Desmond Gregory also known as ‘Fitzy” (Hazel), George leaves behind a large and loving family who will miss him dearly. He is lovingly remembered by his children, Joan Willis (Ron) and Wayne Gregory (Mallory) and his siblings, Marva Forbes, Glen Gregory (Ingrid), Sharon Dedrick (Vernal), and Lolleta Cunningham (Barry).

George was a proud and devoted grandfather to Jameel, Rochelle and Janine. He was also a cherished uncle to David, Christine, Delroy, Mark, Marvin, Nicola, Gareth, Paul, Michael, Andre, and Felecia, and was further blessed as a great-grand-uncle to five and a great-great-grand-uncle to five.

A faithful and trustworthy friend to many, George will be deeply missed by his extended family and friends across the globe. His legacy of hard work, generosity, and community spirit will live on in all who knew and loved him.


Service Details

Please join the family in celebrating a life well lived:

Friday, February 13, 2026
Viewing: 10 a.m.
Funeral Service: 11 a.m.
Burial and Reception to follow onsite

Meadowvale Funeral Centre
7732 Mavis Road, Brampton, ON L6Y 5L5

In Honour of George

In lieu of flowers, the family kindly suggests donations be made to the Alzheimer Society of Peel.

The family would also like to extend their heartfelt gratitude to the personal support workers and healthcare teams who cared for George with such compassion and respect. A special thank you is extended to Barbara and Michael for their exceptional dedication, while sincerely acknowledging all those who supported and assisted George so kindly over the years. Your care, kindness, and commitment did not go unnoticed and will always be remembered.