March 17, 2026
Alright, horse racing might not be the first thing that comes to mind when you think of the Caribbean, but here we are. To the surprise of most people, many countries in the Caribbean actually have a healthy horse racing scene.
And we’re not talking about “healthy” in a way that there are some decent local races. We’re talking about a way where many Caribbean jockeys travel the world, and they are winning big international multi-million-dollar races.
Horse racing in the Caribbean doesn’t sound natural, and it is a weird combo. But if you look more closely, you can see a thriving horse-racing scene, and the people have a strong passion for the sport. Maybe that’s why there are so many Caribbean jockeys showing up on the global scene.
We’ve seen them win titles, enter big races, and travel far with their riding talent.
So, who are these jockeys, and does the Caribbean really produce many racing legends?
Small Islands, Big Ambition
So, what’s so special about Caribbean racing? Well, these islands are known for producing riders who learn fast, and they are incredibly tough. The racing culture in places like Jamaica, Barbados, Trinidad and Tobago, and especially Puerto Rico, is a serious business.
And remember, these aren’t just casual little hobby tracks where everyone shows up for some fun riding times. The competition here may not be at the same level as the Kentucky Derby, but it doesn’t mean it is easy. The best thing about horse racing in the Caribbean is that the crowds support the sport, and they love it. That’s exactly what pushes young talent towards becoming a jockey.
And the pressure that jockeys feel here is quite different from other places. They risk a lot chasing a jockey career, and it is literally a ride-or-die scenario. That’s why when you see Caribbean jockeys on the international scene doing well, it makes sense. They are already used to that pressure.
That’s exactly the case with Shaun Bridgmohan, who, to the surprise of most people, became the second Jamaican to enter the Kentucky Derby back in 2006, and he has won the Kentucky Cup Classic Stakes.
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Yes, there aren’t many jockeys from the Caribbean entering the Kentucky Derby, but there are enough of them to prove that the Caribbean Islands are no joke when it comes to racing.
That’s why you should always research the jockey’s history when you’re looking for ways to bet on the 2026 Kentucky Derby. This can give you a lot of helpful information and lead you to a more accurate bet.
The People Who Opened Doors
We are here for the professionals that managed to reach the highest level of international racing. Yes, compared to other places like the UK or the United States, there aren’t as many high-level jockeys as possible from the Caribbean, but some managed to reach international waters and even win big multi-million-dollar international racing events.
These people represent Caribbean racing culture and history, and they show how passionate they are for the sport.
Now, we cannot talk about Caribbean jockeys without mentioning riders like Patrick Husbands or Emile Ramsammy. These are easily one of the most recognizable names that have Caribbean roots.
Husbands is a Barbadian legend who managed to build an elite career in Canada after already making a name for himself back home. He has won multiple Sovereign Awards as Canada’s outstanding jockey and was even inducted into the Canadian Horse Racing Hall of Fame in 2024. So, he is the real Caribbean horse racing ambassador.
Then we have Ramsammy, one of the toughest champion jockeys that reached the highest level of Canadian racing. But his professional career started early, and before moving to Canada, he already had more than 500 wins. Then he went to dominate the Canadian scene and managed to win the Queen’s Plate twice, and if that’s not enough, he got his hands on two Sovereign Awards.
And when riders like these manage to succeed abroad, in a much bigger horse racing market, younger jockeys from the region notice and get inspired. Wouldn’t you do the same?
Puerto Rico: The Biggest Jockey-Producing Machine
We can all agree that Puerto Rico deserves its own little section here. After all, the island has long been one of the strongest talent-production areas in the wider Caribbean. Puerto Rico has produced the most high-level jockeys who managed to enter the U.S. and Canadian racing scene.
Here are a few examples. The first name that pops up is Jevian Toledo, and if you follow the U.S. horse racing scene closely, you’ve definitely heard of him. He is a Puerto Rico native and began his professional racing career in 2013. After a few short years, he already built quite a reputation in Maryland.
Toledo managed to compete in the most popular horse racing events in the world, like the Preakness Stakes, and won a lot of races in his first years. Then the injuries came, which were a major setback in his career. But being a Puerto Rican, he showed that people from the Caribbean don’t wave the white flag easily, as he got back to professional racing in 2024.
Next, we have Rafael Hernandez, who is another Puerto Rican rider, but instead of the U.S., he managed to build a strong career in Canada. He is the leading jockey with 148 wins in the 2025 Woodbine season, and this is his second time topping the standings after a successful 2020 season.
He has won many major Canadian races, including multiple editions of the King’s Plate.
So, next time when you see a Caribbean jockey entering a big race, do some more research. He might be a good bet for winning the race considering their hard-core dedication to the sport.