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GEOFF MCCULLOUGH
Born: Aug 31, 1947
Date of Passing: Nov 23, 2023
Send Flowers to the Family Offer Condolences or MemoryGEOFF MCCULLOUGH
The youngest of three boys, Geoff was born and raised in a post war veterans survey in the heart of Spring Valley, in Ancaster, Ontario by Howard and Grace McCullough. He grew up wreaking havoc and having fun in the valley with his big brothers, Howie, and Wes, and their many friends, including his third “brother”, Jim Flood. From a young age, Geoff was an accomplished athlete and scholar (he was so smart he even skipped kindergarten!).
Though a skilled multi-sport athlete, his true love was hockey. As Ancaster was too small for its own league, he played in Dundas – and though his hockey career started as a goalie (remember, he was the youngest of three, they needed someone in net!), he spent his formative years as a defenseman, culminating as left winger for the Dundas Blues – being on the highest scoring line in the division his last two years as the Blues won two straight league titles. The winning didn’t stop there though, as, after he married the love of his life, Sandra Anne McCullough (Sam) and they had bought their first house, he joined the Aurora Old Timers. Along with many friendships, he brought home the league championship seven times over the course of his nine year run with the team – and he’s got all the jackets to prove it, much to Sam’s chagrin! Let’s just say they weren’t always on the same page when it came to his fashion choices, especially in his retirement years – Bomber’s jersey, shorts (even in -50˚ Winterpeg weather) and crocs – no socks, so as not to be mistaken for his stylish teenage grandson!
Geoff started university at McMaster but left before earning a degree and followed his brother Wes to Hamilton Teachers College where he graduated in 1969. He taught for three years at Dundana Elementary School, in Dundas, Ontario. He was acknowledged as a great teacher, but when his outside of the box thinking and avant-garde teaching ways didn’t fit the federation’s mold, he quit - and thus, the impetus into his illustrious 45-year career in Real Estate Administration.
Geoff was hired by the Ontario Real Estate Association in 1972 to teach the real estate course, having never even owned a house. He knew that if they taught him real estate, that he could teach anyone how to sell a house or broker a deal – and he was right! He was promoted to Director of Education of OREA in 1975 and the rest, as they say, is history. Throughout his career, he had the privilege of not only working for OREA, but also for the Canadian Real Estate Association, the Toronto Regional Real Estate Board, and the Winnipeg Real Estate Board, where he spent the final 19 years of his career as CEO.
He was a positive and gentle role model. He was cool and conscientious. He was logical, practical, and dependable. He was a calm, reliable, loving force. He wasn't chatty, but he was quietly charming. He was a confident leader, a true gentleman – just ask any woman who ever extended a hand in greeting (having it met with a kiss followed by a suave enchanté), and a devoted and generous family man. He lived to work, but no one knew how to have more fun than Geoff (or how to get his kids into more trouble) – and there were never any problems, only opportunities: no toboggan?, use your body and have everyone pile on top; no curling rock?, find the smallest child (just watch out for the thin ice); bored listening to speeches at a convention or a wedding?, try hanging a spoon from your nose; long wait at a restaurant?, play a game of coin and sugar packet football; want to achieve master bubble blower status?, leave your chewed bubble gum on the counter to “rest” awhile before popping it back in your mouth.
Known in the real estate world as the education, constitution, by-law, and strategic planning king, at home, he was known for supporting Sam’s many hairstyles; for teaching his 2 daughters how to use a kybo, the difference between “can I” and “may I”, and the importance of a strong work ethic; and for imparting to his grandchildren that an assist is often greater than a goal, where to find Waldo, and the fine art of crokinole (a skill he inherited from his grandmother Nina). He was a master poet, and his friend the EB will miss his expert prose at Easter! There wasn’t an art show or hockey game Papa would miss (unless of course, he couldn’t find the arena), and there was nothing he loved more than spending time with his grandkids watching them live their best lives. He was a provider - of love, of time, of experiences, of fun, of cherished memories.
Left to mourn his quick wit, his dry sense of humour, his legendary grasp of the English language and associated grammar rules (once an English teacher, always an English teacher), and his dedication are his vibrant wife of 50 years, Sandy (Sam); their two daughters, Kyla and Paige, and two sons-in-law, Rob Stewart and Dave McWilliams; their four cherished grandchildren, McKenna and Braeden, and Spencer and Bodie; along with their extended family in the Ancaster area and the many friends and colleagues whose lives he touched over the course of his life.
As per Geoff’s wishes, cremation has taken place and the family will be holding a private service. Not one for fuss, you can honor Geoff’s life in many ways, most conveniently by lighting up a moderately priced cigar or by challenging yourself to a sudoku, most impactfully by enjoying a meal with the ones you love, and most importantly, by not giving up hopes that the Montreal Canadiens will bring home a Stanley Cup.
Geoff, Dad, Papa: Thank you for ensuring we were all “Set for Life”, even if none of us ever scratched the big one; we most certainly won the lottery having you in our lives - now Hit the Road, Jack.

As published in Winnipeg Free Press on Nov 30, 2023, Nov 30, 2023
Condolences & Memories (9 entries)
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It is with great sadness to learn of the passing of Geoff. We remember him as a great teammate and person. You will be missed Geoff. Rest in peace. Your former teammates from the Aurora Old Chiefs - Posted by: Aurora Old Chiefs (hockey team) on: Feb 16, 2024
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Geoff, his brothers and his Mum and Dad were the heart and soul of the Spring Valley Community in Ancaster. While I was younger than the three boys it didn't prevent Geoff's Dad from inviting me in and whipping my butt at chess. All the while being fed endless cups of tea by Mrs. Mccullough. My fondest memories are of Sunday morning Touch Football with Geoff, his brothers, my brother Jim and Geoff's cousins. That's 50 or 60 years ago now but I will always remember Geoff's outstretched hand to lift me out of the dirt after being "touched". God bless him and my sincere condolences to his family. - Posted by: Kevan Flood (neighbour) on: Dec 14, 2023
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Geoff--You were an awesome role model at the Wpg Real Estate Board and a true friend. You helped me so much when I was the EO at Brandon Board. The greeting was as was said reach out your hand and he would kiss my hand. (true gentleman). You will be missed! Susan Enns - Posted by: Susan Enns (Real estate and Board mtgs) on: Dec 04, 2023
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Condolences to Geoff’s family and friends. A terrific man, true friend and great colleague. He will be missed by many. 🙏🙏🙏 - Posted by: Bill Benoit (Friend, mentee, colleague, etc.) on: Dec 03, 2023
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So saddened to hear that such a wonderful and talented man has left us. Having had the pleasure of working with Geoff on so many meetings at the Winnipeg Board and knowing that I could always call on him for a ruling ..my thoughts sincerely go out to Geoff's family on the loss of such respected husband and father . - Posted by: Mel Boisvert (Friend and colleague ) on: Dec 01, 2023
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Geoff was a one of a kind! As already stated he was a true gentleman and knew when to give advice which many of us in the real estate association longed for. As a past president of the Board I appreciated his wisdom. We ushered this man too soon and will miss him. Go Habs Go!! - Posted by: Ron Derksen (Friend in Real Estate ) on: Nov 30, 2023
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Geoff was one of a kind! Consummate gentleman, and master of many talents. Geoff, was an active board member of the Children's Rehabilitation Foundation during my tenure as the Executive Director. He assisted in rewriting all the by-laws of the foundation. He always kept our meetings on task and in order with Roberts Rules. Thank you Geoff for your wisdom, guidance and friendship over the years. My deepest sympathy to Sam, Kyla, Paige and families. - Posted by: Christine Schollenberg (Friend ) on: Nov 30, 2023
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Every so often, a person comes into ones life that sees something that we don't see, Geoff was that person who mentored me and so many others with career advice and pushed one to follow their dreams they may not even realized they had. Geoff was a gifted speech writer during my presidency with the real estate board as well as the calming voice during board meetings. In real estate your acquaintances become a friend, And Geoff was that friend that opened his home and was a great guy to travel with. Always professional and contributed so much to organized real estate to the benefit of all. - Posted by: wes schollenberg (friend) on: Nov 30, 2023
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I am Geoff’s youngest girl cousin on his Mother’s side. What a beautiful tribute written about him. I will always remember his smile and his soft demeanour. Love to all of you 😞💚 - Posted by: Roberta Hunt (Cousin) on: Nov 30, 2023