One of the biggest upsets in horse racing history took place in 2009 when Mine That Bird (50-1) won the Kentucky Derby. That thoroughbred’s career began at Woodbine Racetrack in Toronto.

Twelve years later, a Canadian-born trainer and owner hope to pull off another massive upset in the annual Run for the Roses.

Robertino Diodoro, originally from Calgary, is one of North America’s leading trainers. His first-ever appearance in the opening leg of the Triple Crown this Saturday at Churchill Downs is with Keepmeinmind. The three-year-old colt is co-owned by Whiterock, B.C. native Arnold Bennewith.

“It’s every trainer’s dream to have a horse running in the Kentucky Derby,” Diodoro said from Louisville, K.Y., earlier this week. “I don’t even know how to put it in words to be honest. And to be here with Arnie… whose son Lance coached me in hockey when I was 12 years old… it’s pretty special.”

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