Remembering Jack Robertson
December 7, 1938 – February 4, 2026
A Horseman’s Horseman
By G.S. Thompson
Highly respected Assiniboia Downs trainer Jack Robertson passed away on Wednesday, February 4, at the age of 87. The multiple stakes-winning trainer was well known as one of the best caretakers of horses in the history of Assiniboia Downs, and his horses always gave their best.
Jack’s reputation, as a man who could take a horse that others had given up on and bring out the very best in it, was the hallmark of a 43-year career at the Downs that produced more than 600 victories, nearly $4 million in purse earnings, and a legacy that will endure for generations among Manitoba horsemen.
Born on December 7, 1938, in Winnipeg, Jack spent his early years on the family farm at Lynch’s Point before moving to Harcus in 1953. Horses were always a part of Jack’s life, both for farm work and for pleasure. He was one of the first breeders of Paint horses in the 1950s and showed them successfully in both Canada and the United States, winning more than 100 trophies in the show ring before he ever saddled a thoroughbred.
Jack trained and competed with western pleasure horses before transitioning to thoroughbreds in the early 1970s, first racing horses at local “Sports Days” before taking out his trainer’s licence in 1976. He saddled his first starter at Assiniboia Downs on May 28, 1976, and recorded his first win as a trainer with From the Heart on August 24, 1976, at Regina Exhibition Race Track.
A student of pedigree who gained an edge understanding thoroughbred bloodlines through studying the more complicated pedigrees of purebred cattle, Jack was almost always among the leading percentage trainers at Assiniboia Downs. But it was his extraordinary ability to recondition horses, purchasing cast-offs and horses that couldn’t compete at major American tracks and rejuvenating them mentally and physically, that set him apart from his peers.
The most notable among his reconditioning successes was local Champion and Horse of the Year Uene, a former claimer who won the 1988 Gold Cup Handicap, along with the Inaugural Handicap and the Manitoba Crocus Stakes that same season.
Jack’s all-time leading money-earner at the Downs was Manitoba-bred Pete’s Surprise, who won the R.C. Anderson Stakes, the Distaff Stakes, and the Canada Day Stakes in 2003–2004 and earned US$132,468.
One of the major indicators of a top horseman is the ability to guide horses through long, consistent careers at the track. Jack showcased his skills in that area with the game campaigner Bobby Q, who won seven stakes over the course of an eight-year career at the Downs and compiled a record of 20-12-8 from 80 starts for earnings of US$131,784.
Bobby Q counted the Free Press Handicap, the Wheat City Handicap, the Harry Jeffrey Handicap, and the R.J. Speers Handicap among his stakes triumphs, a testament to the kind of patient, meticulous horsemanship that was Jack’s trademark.
Jack won the R.J. Speers an amazing five times—with Kapalua (1989), Portage (1990), Feudal (1991), Bobby Q (1984), and Copa De Ore (1997)—a record that speaks to his consistency at the highest level of racing at the Downs. His other major stakes victories included the Assiniboia Oaks with Imarunaway (1993), the Derby Trial Stakes with Dazzling Beau (1995), the Winnipeg Sun Stakes with Vox Neneme (1996), the Buttons and Bows Handicap with Villa Girl (1993), and multiple editions of the Hugh Jackson Memorial, Harry Jeffrey, and Duchess Stakes.
Jack retired from training horses in 2018 after compiling a career record of 684-658-674 from 4,727 starts for purse earnings of US$3,964,105. Those numbers tell one story. The respect he earned from his fellow horsemen tells another.
In a game where horses can’t speak for themselves, the highest praise one horseman can bestow upon another is that he took care of his animals first and foremost. Jack Robertson earned that praise every single day.
Rest easy, horseman.
A Celebration of Life will be held for Jack at 3 p.m. on Wednesday, May 27, 2026, at Assiniboia Downs. Read Jack’s Full Obituary here.