Caribbean jockeys racing to the top at Winnipeg's Assiniboia Downs

In recent years, Caribbean riders have become a fixture in Winnipeg's horse-racing community — the result of a strategic effort by Assiniboia Downs to sustain the sport in the city, while also providing the riders who come here an opportunity to grow in their craft.

Assiniboia Downs CEO says he hopes partnership between track and the Caribbean will continue

Antonio Whitehall says he's a 'crowd favorite' at Assiniboia Downs. The Barbadian-born jockey has won the leading rider title at Assiniboia Downs twice, with 41 wins in 2018 and 74 wins in 2020. (Walther Bernal/CBC)

Hearing the jockeys at Winnipeg's Assiniboia Downs racetrack talking to one another in Barbadian, Jamaican and Trinidadian accents while they dress, it may be easy to think you're standing somewhere in the West Indies.

In recent years, Caribbean riders have become a fixture in Winnipeg's horse racing community. 

Thirteen of the 17 jockeys at the racetrack this season are from the Caribbean.  A Caribbean rider has won the leading rider title six of the last seven seasons.

"We get treated fairly here," said Antonio Whitehall, a Barbadian-born jockey who races at Assiniboia Downs. 

"You work hard and you get rewarded. You get good clients here. It is nice and friendly, and they like us," he said.

Whitehall, and two Jamaican riders, Arthur Budhu and Leroy Nelson, prepare their helmets in the jockeys' room at Assiniboia Downs before live racing on Tuesday. (Walther Bernal/CBC)

What may appear at first to be a random connection between two distant places is actually the result of strategic effort by Assiniboia Downs to sustain the sport in Winnipeg, while also providing the riders who choose to come the opportunity to grow in their craft. 

"To be perfectly honest, without the participation from the jockeys in the Caribbean region, we wouldn't be able to race," said Darren Dunn, chief executive officer of Assiniboia Downs.

Since the track opened to the public in 1958, most jockeys have come from Canada and the United States. 

But Dunn says changes in Canadian society have shrunk the pool of homegrown riders.

"The challenge we face in Canada is that with every year that goes by, it's another generation that's separated from the farm," he said.

That means fewer people here with "access to the horses … to the opportunity to train, the exposure to the racetracks and/or the ability to horseback ride," said Dunn, leaving Assiniboia Downs "to go outside of the border to look for talent in the saddle."

Darren Dunn, CEO Assiniboia Downs, says with fewer people in Canada growing up riding horses, the racing industry has to look for talent elsewhere. (Jeff Stapleton/CBC)

Mutual benefits

Riding in Winnipeg has proven to be profitable for Caribbean jockeys. 

Chavion Chow first came to Winnipeg from Jamaica in 2008, when he was in his early 20s. He topped his colleagues in 2015, winning the leading rider title, and is credited with having won 269 races and over $2.4 million in purses. 

Jamaican-born jockey Chavion Chow was the champion jockey at Assiniboia Downs in 2015, with 63 wins. (Walther Bernal/CBC)

Chow says he's glad to ride at Assiniboia Downs, because in Jamaica, there is only one track, but "so many riders."

In Canada, he has more options, he says.

"It's good to get an opportunity like this, and you can spread your wings. It's a life-changing experience," he said. 

Fellow jockey Leroy Nelson said he "felt the riding bug" again after a five-year break from riding, which he mentioned to his cousin, Tyrone Nelson, another Jamaican who used to race at Assiniboia Downs. 

Leroy Nelson is credited with more than 176 wins over his career. The Jamaican-born jockey heard about Assiniboia Downs from his cousin, Tyrone Nelson, who used to race there as well. (Walther Bernal/CBC)

His cousin told him to consider Canada, where riders were needed.

"It is my first time really riding and really enjoying the riding," Nelson said. "Everybody kind of [gives] me a fair chance here."

Finding Caribbean talent

Caribbean riders have done well at other venues across Canada. Patrick Husbands from Barbados, riding at Woodbine Racetrack in Toronto, has earned 3,285 victories and almost $160 million in purses.

Dunn says when Assiniboia Downs went looking for riders in the Caribbean, they were impressed with what they found. 

"The success we've had in the Caribbean — the talent, the skill, year after year that continues to emerge from there — is certainly a testament to the roots of racing in the Caribbean," he said. 

The first Caribbean jockey to come to Winnipeg was Vassell Najair, who came from Jamaica about 20 years ago, according to Dunn. 

Jockey Patrick Husbands, shown in this file photo from his 155th Queen's Plate victory, has earned 3,285 victories and almost $160 million in purses, according to the Woodbine Racetrack in Toronto. (Fred Thornhill/The Canadian Press)

Since that time, the organization has been deliberate about recruiting Caribbean riders. 

"I think we were a little bit more aggressive than most racetracks in reaching out directly, making the local contacts, and then reaching out directly to the talent in the saddle," Dunn said. 

He says his organization was deliberate about things like helping to arrange immigration, flights, and a place to live, and making it "very easy to … get settled and get back in the saddle very quickly."

What the fans want

Fans don't care where riders come from, Dunn says. What they do care about is "if their money is down, or they pick a name, pick a colour, that that horse is being safely cared for and safely rode." 

Whitehall has been crowned the leading rider twice, in 2018 and 2020. He also finished third among all jockeys in Canada in 2020 with 117 victories.

"I'm basically a fan favourite. I have been here for a while," he said. 

Like some of the other jockeys, he used to race in Canada for the season and then return to his home in Barbados in the fall. But facing the possibility of a lockout due to flight restrictions at the start of the pandemic, Whitehall decided to move to Winnipeg for good.

The community and the track "feel like home now," he said.

"I see myself here. I like it here, I fit in here perfectly, like here is home," said Whitehall.

"So I think here is the future."

Caribbean jockeys racing to the top at Winnipeg's Assiniboia Downs

12 months ago
Duration 2:31
Horse racing experts say there have been fewer Canadian jockeys each year. To preserve the sport Manitoba's horse racing industry is looking overseas for help. Caribbean riders are answering the call and making their mark in Winnipeg.

For more stories about the experiences of Black Canadians — from anti-Black racism to success stories within the Black community — check out Being Black in Canada, a CBC project Black Canadians can be proud of. You can read more stories here.

BBIC Banner


Andrew Wildes is a reporter at CBC in Manitoba. You can reach him at