Obituaries

Robert “Rob” Thomson
April 11, 1961 – November 27, 2025

Rob was born in Winnipeg, Manitoba, to Mary and “Red” Thomson, the second youngest of four children. As a military family, they moved often throughout his early life, including postings in Oromocto, New Brunswick, and time in Germany—where both his oldest and youngest brothers were born—before eventually returning to Winnipeg.

After completing three years of military service, Rob joined Canpar Transport, where he worked for nearly three decades until retirement.

Before marriage and children, Rob built a tight-knit circle of friends and, of course, the Sessionaires—relationships forged through shared experiences. Among those friendships was Cheryl. What began as camaraderie grew slowly, naturally, into love. They married in 1987, and at the heart of their life together remained the simple foundation it had always been: friendship first. Every season of life—work, raising kids, travel, retirement—was approached side by side. Nothing was “his” or “hers.” It was always “theirs.”

He was a hands-on dad, and his dedication to family was unmistakable. He once looked after Laura, Brian, and the children of one of Cheryl’s girlfriends so they could get away on a trip to Mexico. He handled it the way he handled everything: with a shrug, a smirk, and the steady confidence that he’d “figure it out.” And of course, he did.
Rob believed in strong morals, the value of a dollar, and the importance of staying calm. Think it through. Don’t panic. There is always a solution. And if it required duct tape, a screwdriver, and a late-night run to Canadian Tire—so be it.

He was happiest with a game on: the Blue Jays, the Winnipeg Jets, curling, or golf—and even happier when the people he loved were nearby. Throughout the years, Rob was a fierce competitor, and he played to win. He never stuck to a single activity. He played sponge hockey, baseball, curling, and golf; yard games, board games, cards, and puzzles; and he accompanied his mom to bingo on Sundays. He was clever, calm, and always planning one move ahead.

Rob was a tinkerer through and through. He fixed, adjusted, rebuilt, and improved anything he could get his hands on—or anything Cheryl could dream up. He completed countless projects: sunrooms, new kitchens, stairs, decks, and fences for family and friends. He was known for perfectly timing the steak on the BBQ, and everyone close to him knew the unspoken truth: Rob handled the meat, and Cheryl made the meal complete. The sides, the salads, the details—always a partnership. The plate wasn’t “his” or “hers.” It was theirs. And if you knew him, you knew he made a mean deep-fried turkey in the backyard—crisp, golden, carved with quiet confidence. It wasn’t simply food; it was a “Rob moment” that drew people in. If you were lucky enough to be there, you know exactly how it felt.

For nearly a decade, Arizona was one of the most joyful chapters of Rob’s life. He and Cheryl owned a trailer in Mesa and surrounded themselves with friends old and new, activities, and easy laughter. Cards with the guys, live music at the pool, and twenty-five-cent drafts weren’t just ways to pass the time—they were rituals that made community feel simple and real. Mesa wasn’t where their dreams began; it was simply another place where they lived them. They dreamed, planned, and tinkered together no matter where they were— the trailer, the kitchen table, or the backyard.

Rob and Cheryl also took yearly road trips to the East Coast to visit family. They had their familiar stops and favourite restaurants along the way—the places where the meals were good, the beer was cold, and the company felt easy. Rob loved those journeys because they were slow, steady, and filled with the people he cared about. A glass of wine with dinner, a rye when the moment called for it—never loud, never showy—just simple and good.

Family was the heart of Rob’s world.
He leaves behind his loving wife, Cheryl; his children, Brian (with wife Kayla) and Laura (with partner Stephen).
Rob is survived by his siblings: Willy (with Kathy), Darlene (with Gary), and Larry (with Dana).

He also leaves behind Cheryl’s parents, Joann and Jerry Gillis, and his sister-in-law Tricia (with husband Joe), whom he considered as much family as his own.

Rob was an uncle through many chapters of his life— to Bobby and Gary, to Rebecca and Kimberly, to Myleigh and Morgan—and later, a great-uncle as well.

After a courageous battle with cancer, Rob passed away surrounded by love. He tried one more time to play to win.

Those who knew him were lucky to have known him.
He lives on in the people he shaped, the lessons he taught, the memories he created, and the quiet steadiness he brought into every room.

A private ceremony is planned.

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