95 Years of the Winnipeg Futurity – In Pictures

Jun 19, 2025 | ASD History, The Inside Track

Winnipeg Futurity Announcement – Manitoba Free Press, March 19, 1928.

by Track Historian Bob Gates

As the end of June isn’t far off, we can look forward to seeing the “babies” (two-year-olds) make their way to the races. The stakes races for the youngsters include the Debutante, Graduation, Osirus, Buffalo, CTHS Sale Stakes and of course the Winnipeg Futurity.

The Futurity is the oldest continuously run race in western Canada. The race was inaugurated in 1930 by Robert James Speers for two-year-olds bred in western Canada. From 1936 to 1985 the race was opened to two-year-olds foaled in Canada. In 1986 the Canadian breeding restriction was removed, and the race became an open event. Over the years the Futurity has showcased the finest young horses and nine decades later it remains a highlight on the racing calendar.

This week lets take a pictorial trip back in time to review highlights from the 95 years of the race. Trying to select photos to adequately represent the race was a challenge. Here, for your viewing enjoyment is a photographic sampling of the history of the Winnipeg Futurity.

Hot Whittier, September 11, 1930. (Wpg Tribune photo)

Hot Whittier of the Winnipeg Stable owns the bragging rights as the winner of the inaugural running of the Winnipeg Futurity. The bay gelding, bred by Jim Speers’ Whittier Park Stock Farm, was sent postward as the prohibitive favourite. The second and third place finishers also happened to be “Whittier” horses, Lauretta Whittier and Book Whittier with the latter being ridden by one of racings early iconic jockeys, Johnny Longden.

1942 Omar's Gift Winnipeg Futurity. (Kennedy Family photo)

The 13th running of the Futurity proved to be a lucky one for a young A. G. “Scotty” Kennedy. Kennedy had purchased the filly earlier that spring from Jim Speers “for all of the money he had in his pocket”. The story goes that Kennedy had been in an all-night crap game and all he was carrying that morning was 37-cents. Speers knew all too well what he was doing and desperately wanted Scotty in racing and what better way to achieve that goal than to “sell” him a young and talented Omar’s Gift.

New Flag, Winnipeg Futurity, August 14, 1965. (Bob Barnes photo)

In 1965 Max Bell’s Golden West Farms, New Flag won the 36th running of the Winnipeg Futurity.  New Flag was the only filly in the race and was ridden by Dickie Armstrong who would win four Downs’ leading jockey titles (1962, 64, 65 and 67).

Ruling Lark, Winnipeg Futurity, August 17, 1968. (Gerry Hart photo)

Ruling Lark, known as the “Flying Filly” was the fleet-footed darling two-year-old champion of 1968. She was a $3,700 yearling who was purchased by veteran trainer George Howell for the partnership of Morris Kaplan and Parry Orestes. Following the filly’s win in the 39th Futurity an evening of celebration took place at Orestes’ Paddock Restaurant where Ruling Lark and jockey Bobbie Dimma were the stars of the evening.

1974 Winnipeg Futurity winner, L'Enjoleur with Sandy Hawley up. (Gerry Hart photo)

The City of Winnipeg turned 100 years old in 1974, and Assiniboia Downs paid tribute to the city by naming the 45th renewal of the race the Winnipeg Centennial Futurity. The runaway winner of the race, L’Enjoleur was truly one of racing’s royalty. The bay colt was the son of Buckpasser, out of Fanfreluche, who was by Northern Dancer. The overwhelming favourite thrashed his opponents, winning by 12-lengths. Sandy Hawley, who rode the Johnny Starr-trained blue blood, described L’Enjoleur as one of the best two-year-olds he had ever ridden.

King Midas, Winnipeg Futurity, August 22, 1982. (Gerry Hart photo)

King Midas won the 53rd edition of the Futurity and deserved full marks for his performance in the 1982 race. However, the bay colt had to share the limelight with his rider, Flavio Martinez. Martinez lost a stirrup out of the gate and was forced to navigate most of the race with only one stirrup.

In an effort to gain some degree of balance, he kicked his other foot free and rode “sitting loose.” In spite of the highly undesirable riding style King Midas and Martinez bettered race favourite One and Only by 1½ lengths.

Balooga Bull, Winnipeg Futurity, September 10, 2011. (Gerry Hart photo)

Balooga Bull went undefeated in his two-year-old season, but you could tell there was something special about his win in the 82nd running of the Futurity. The $2,000 bargain yearling covered the six panels in a sharp 1:10 3/5. You’d be hard-pressed to find any sub 1:11 six-furlong time during the Bull’s “hay-day,” and he was only a two-year-old!

The Ardell Sayler-trained champion would go on to win the Manitoba Derby and Gold Cup at three. At four and five he repeated as Gold Cup winner, making him the only horse to win the distinguished Cup three times, not to mention that his wins were consecutive!

First Cavalry and Laura with the Winnipeg Futurity trophy.

We will conclude our time travel tour of the Futurity with 2006 winner, First Cavalry. When Cav’s time of the track was done, he found a second career on the racetrack. He became a fine pony horse. Together with Laura McIvor, the pair took the thoroughbreds to the starting gate for many years, and did their best to ensure the safety of all horses and riders. Cav is seen here in 2019 with his old friend, the historic Winnipeg Futurity trophy.

Have we missed a few photos, for sure! If only there was room for all 95 winners!