Raymond Stewart, The Pride of Gladstone — Reflections on a Life Well-Lived!

Ray Stewart in Calgary. 1950.

Ray Stewart in Calgary. 1950.

by Bob

It's been more than 75 years since Ray Stewart scored his first win as a jockey on the old western prairie circuit.

I recently had an opportunity to sit down with the 93-year-old Stewart and reminisce about his horse racing past at his home in Brandon where he lives with his son Melvin. What a treat it was!

History buffs are always on the lookout for that special find. There is nothing more gratifying than unearthing a piece of the past and shining a light on it so that all might enjoy. With the assistance of Gladstone horseman Doug Mustard, we present a unique story from the past in this week's trip down memory lane.

The 2015 edition of the Gold Cup, its 58th running, is still three months away, but some stories can't wait that long to be told. The record books reflect that the winner of the Inaugural Gold Cup was Dr. Pat who was owned and trained by I. H. Halverson and ridden by R. Stewart.

It is totally understandable if you believe that Bobby Stewart was the winning jockey. Bobby was a great rider who won consecutive Gold Cups in 1967 and 1968 on Pool To Market and Clique, but Bob didn't get his first win at the Downs until June 1960.

No sir! This R. Stewart isn't Bobby, it is none other than Raymond Stewart the Manitoba-born jockey who came to be known as the Pride of Gladstone.

Young Raymond got his start back on the old western prairie circuit in 1939 that featured train stops at Winnipeg's Whittier and Polo Park, as well as Calgary, Edmonton, Regina and Saskatoon. Stewart signed a three-year contract that ran from 1939 to 1941 with St. Boniface horseman Walter Jarvis, who also hailed from Gladstone. Those Gladstone boys like to stick together!

Stewart rode for seven short years in a career that spanned from 1939 to 1959. In addition to the western circuit he also rode at tracks in B.C. and south of the border.

Ray's Stewart's first. Beauty Warm. June 6, 1940. Whittier Park.

Ray's Stewart's first win at Whittier Park. Beauty Warm. June 6, 1940.

The first win of Stewart's career came on a horse named Jungle Shawl on July 25, 1939 in Saskatoon. Jungle Shawl would become Stewart's all-time favourite horse.

He took a break from racing after the 1941 season, got married on May 19, 1943 and started his stint in Canada's army the following day. He also tried his hand at farming prior to his return to racing in 1950. In the twilight of his career he rode at the "new" Assiniboia Downs in 1958 and 59, but like many before him lost his battle with weight and decided to call it quits in 1959.

Through the years he rode for:

  • Female trainer Peggy Swallow in 1941. (If Miss Swallow wasn't the first female trainer she had to be mighty close to it.)
  • Actress Barbara Stanwyck.
  • Popular Calgary horseman Harold "Spud" Murphy.
  • The Carey Brothers with trainer M. R. "Dick" Carey. (Is there anyone out there who remembers "Carey's Tavern?" I'm told that it was a popular hangout in the old days of the Downs' backstretch.)
  • Canadian Horse Racing Hall of Famer and Fort Qu'Appelle, Saskatchewan's favourite son Captain Stanley "Cap" Harrison.
  • Canadian horseman and trainer extraordinaire Lorne Dupont, who spent some 70 years in the horse racing business.

And those are just a few that Stewart rode for! He wasn't sure if he rode for Downs' Patriarch, Bert Blake, but knew him and said that Blake was "100%" and that "they didn't get any better."

Stewart had many tales from the past, but none more interesting than those relating to the connections of a horse he rode on a regular basis named Misme in 1940.

Misme was owned by George Lamb, who, according to Ray, was a secretary for Al Capone. And the horse's trainer was Vic Vesley, who was reportedly a driver for Capone. Apparently, Vesley didn't like having his picture taken and never posed for any of the traditional winner's circle photographs.

The best horse he ever rode? That was an easy one for Stewart. It was Dr. Pat.

Stewart said that Dr. Pat was a tough horse to gallop, and had a tendency to lug in, but reckoned that for him there were none better, even though he only rode him four times. Dr. Pat, aka the "Montana Killer", was owned by Irwin H. Halverson from Scobey Montana.

Dr. Pat. Sept. 13, 1958. Assiniboia Invitational Handicap.

Dr. Pat. Sept. 13, 1958. Assiniboia Invitational Handicap.

In 1958 Dr. Pat won the Assiniboia Downs Invitational Handicap on September 13, ran third on September 19 and won the 1st running of the Assiniboia Downs Gold Cup on September 24. Stewart scored one final win on Dr. Pat in October 1958 in Spokane before Dr. Pat was retired.

Stewart had kind words and a great deal of respect for fellow jockey "Scotty" Craigmyle. No one has won more Canadian Derbys than Craigmyle, who holds the record with four wins in the big race. Ray spoke of the time he ran second to Scotty - lost by a "whisker" on August 18, 1939, not long after his first win, and offered that "when you get beat that close by Scotty you feel like you won. In my mind he was one of the top riders in Canada."

Stewart took great pride in the work he did in the community. From 1960 to 1977 he held several positions for the Town of Gladstone, including town constable and foreman. He also worked for the Town of Carman before retiring for good in the 1980s.

His wife, Ruth passed in 2009 and tragically he buried a son, Gerald and daughter, Sandra Ann. But he soldiers on!

I'm not sure who enjoyed our afternoon of memories more, him or me? All things considered, his photos were in good shape, but he admits he doesn't have as many as he used to. He explained that his father had a habit of "gifting" his early racing win pictures to friends and relatives when they would visit.

He took pride in saying that he "never pulled a horse." It is important to remember that racing in the 1930s and '40s was a different time, rules were few and enforced even less. Thoroughbred horse racing was, at times, like a battle, where hand-to-hand combat wasn't that unusual.

Stewart had an impeccable memory and our conversation about old Whittier Park centered on the tight turns the track was famous for. I asked him if they were as bad as described. His answer was, "Absolutely! Especially the top turns by the barns." What struck me was that he spoke of Whittier Park's notorious track like he rode there last week, not 75 years ago!

Ray Stewart was a rider from a by-gone era, but being a jockey never defined who he was as a man. Stewart says he never missed racing once he hung up his tack and that he never followed the sport all that much in the years that followed, except for the odd televised events like the Triple Crown races.

Ray with son Mel. May 19, 2015.

Ray with son Mel. May 19, 2015.

Raising a family and contributing to his community was where he devoted his time and efforts.

Ray presented me with his old saddle, which he bought in 1939 from jockey Freddie Soloman for $25. The saddle will go great with his skull cap, which was donated by Doug Mustard. Both are on display in one of the history cases in the "Racing Through Time" display on the main floor at the Downs.

A skull cap and saddle from 75 years ago and a first-hand glimpse of what it was like on the old western prairie circuit, from our very own tour guide in time.

Mr. Ray Stewart. The Pride of Gladstone!

Thank you Sir!

6 Responses

  1. Pat Duncan

    As always, very much enjoyed this story.

  2. Marilyn Stewart

    Sitting talking to my father in law about his brother Raymond Stewart. Very interesting story.

    • helen fostey

      Very interesting Uncle Ray. So amazing that all Uncle Ray’s siblings (7) have been blessed with such sharp minds as if it was a gift. Thank you Doug for doing this fabulous article. We as a family will treasure this for a lifetime.

  3. Bob Gates

    I am so pleased you all enjoyed reading about Ray’s career. He was an interesting man to sit down with and talk about the old days! You don’t often get these kind of opportunities.

  4. Please correct the spelling of my father’s name. It is NOT Solomon. It is SOLOMAN.

    Yes I have memorabilia as well.

    THANKS Beverly Soloman

    • TheBigHorse

      Corrected Beverly. Our apologies. Thanks for letting us know!

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