Bobby Stewart aboard Ocean Roar in the 1969 Kentucky Derby.
Bobby Stewart and Dick Armstrong had different styles, but got similar results. They won.
by Bob
From 1962 to 1972, two jockeys dominated the leading rider standings at Assiniboia Downs.
In that 11-year period George Richard “Dickie” Armstrong and Robert Roy “Bobby” Stewart won leading rider honours 10 times! Dick won four riding titles (1962, 64, 65 and 67) and Bobby won a record-setting six titles (1966, 68, 69, 70, 71). In 1972 Bobby also tied for the title with Bob Dimma.
The only year the title eluded these two elite jockeys was 1963, when a young upstart named Frank Barroby won the title. Needless to say, back then, if you were looking to cash a win ticket your chances were greatly improved if you bet on a horse that was ridden by Armstrong or Stewart.
It goes without saying that both were accomplished riders and while each had a gift in the saddle they were as different as night and day. Bobby knew he was good and walked with a certain swagger. Dick, on the other hand, was much more reserved and let his riding do the talking. Bob’s riding style was aggressive and he received his fair share of “days” (suspensions), whereas Dick was very seldom penalized.
Stewart’s good friend, Murray Duncan of Carberry, said that Bobby wasn’t afraid of anything – he was absolutely fearless, but not reckless. Downs’ patriarch, the late Bert Blake, said he never met a man who had anything bad to say about Dick Armstrong.
Oddly, both men won the prestigious Manitoba Derby but once. Bob won it on Nice Dancer in 1972 when he had a terrible virus and a temperature of 102. Dick won his Derby in 1969 on Fire N Desire when he outdueled and outwitted Avelino Gomez on Icy Song to the wire. The track was “off” that day and Dick successfully “pinned” Gomez on the rail, while he found better footing for his mount further off the fence.
Armstrong/Stewart Fast Facts:
- On July 2, 1965, Dick became the Downs’ all-time leading jockey when he rode his 247th winner, bettering the record previously held by Winnipeg boy Tommy Stadnyk. Dick would go on to win 478 races at the Downs from 1958 to 1969.
- In late 1970 the all-time leading jockey honours were taken over by Bobby, who closed out his 1970 campaign with 486 career wins at the west end oval. Bobby set a record by winning 724 races at the Downs from 1960 to 1976, a record that would stand until June 15, 1981 when Jimmy Anderson won his 725th race at the Downs.
- On July 18, 1964, Dick established a new record when he rode five winners on an 8-race card. His record stood until June 15, 1971, when Bobby rode six winners on an 8-race card. The latter record wouldn’t be bettered until June 23, 1976, when Jim Sorenson rode seven winners on a 9-race card, a record that still stands.
There just isn’t enough room on this blog to fully describe the talent of these two men. Of all the things written and said about these two brilliant saddlesmiths, the line (attributable to Elman Guttormson I believe) I like best is about Bobby, who “gave the appearance of going nowhere and having all day to get there!”
We have had many great riders at the Downs over the years, and while it can be difficult and possibly unfair to compare riders from different eras (and not that anybody asked); Bobby Stewart would be my pick for the best jockey to ever ride at Assiniboia Downs.
Dick Armstrong wins 1969 Manitoba Derby aboard Fire N Desire.
His record speaks for itself, and the fact remains that he could have ridden anywhere in Canada or the U.S. Possibly the biggest highlight of Bobby’s career was riding in the 1969 Kentucky Derby. His mount, Ocean Roar, was a speedball with little chance of winning the “Run for the Roses” but Bobby had the lead for most of the race before fading to finish sixth.
Bob did many things very well, but above all he knew how to sit still on a horse, and according to Bert Blake “no one could switch sticks like Bobby.”
Bobby was taken from us much too soon, on May 3, 1985, and after helping the Downs celebrate its 50th anniversary in 2008, Dick passed away on November 16, 2009.
For more than a decade this dynamic duo — two icons if you will — dominated their rivals at Assiniboia Downs.
They “owned” the Winner’s Circle.