2025 Jockey Inductee
Growing up in Granum, Alberta, horse racing was never on Perry Winters’ radar – until a friend who performed trick riding pointed out that he had the ideal build to be a jockey. A natural athlete who excelled in basketball and baseball, Perry was fearless by nature and decided to give race riding a shot. Not only did he fall in love with the sport, but he also carved out a remarkable career that earned him a place in Canadian horse racing history and a well-deserved spot in the Canadian Horse Racing Hall of Fame.
Perry was just 18 when he received early race-riding lessons from top Alberta Quarter Horse trainer, William Leech. His first competitive races came at the bush tracks of Alberta, Grande Prairie, Medicine Hat and Cochrane.
Perry credits fellow bush track jockeys Elige Bourne and Jim Roebuck for helping him master the tricks of the riding trade. By 1980, he had transitioned to riding Thoroughbreds at Lethbridge, Turf Paradise in Arizona and Marquis Downs in Saskatchewan. He graduated to the Alberta ‘A’ circuit – Stampede Park and Northlands – in the mid 1980s and quickly dominated the jock’s room.
For 11 consecutive seasons, Perry won over 100 races and in 1991 he rode a staggering 1,185 races winning 241 of them, second most in Canada that year and an impressive 20 percent rate.
Perry eventually captured seven riding titles and rode in almost 20,000 races 2,985 winners, putting him 195th on the list of all-time leading jockeys by wins and in the top 10 all-time in Canada. For many of those years, Perry rode against champion riders such as Don Seymour, Rick Hedge and Ron Carrasco.
The accomplished rider is proud of the horses he rode to stakes wins in his home province and says he won virtually every added-money race including the prestigious Canadian Derby in 1993 aboard Cozzy Grey. Perry talks fondly about Chilcoton Blaze, trained by Don Gilkyson. Notoriously tough to train in the morning, Perry got along with the talented gelding in the afternoons, winning more than a dozen stakes races together including 10 in 1987. Gilkyson’s son Kenny, Perry’s long-time agent, praised the rider saying his timing in races was second to none.
Perry retired from riding in 2012, and although years of racing left him with multiple injuries—including a hip replacement—the newly inducted Hall of Fame jockey now enjoys spending his time golfing with his son, Trey.
In a 2021 interview with ShawTV, Perry shared that his favorite parts of racing were the thrill of victory and the beauty of the horses. Given his remarkable career, he experienced plenty of both.