A Day to Remember: Halledeen’s Historic Wins at Caymanas Park

On a sun-drenched Wednesday, August 6, 2025, the atmosphere at Caymanas Park was electric. Trainer Jason DaCosta and jockey Robert “Hard Ball” Halledeen took a moment to soak in the glory of their recent triumphs in the winners’ enclosure. The duo had just teamed up with the impressive I Dream Again to clinch victory in the 105th Jamaica Derby Classic, a race that would be etched in the annals of Jamaican horse racing history.

A Milestone Moment

Earlier that day, Halledeen made headlines by riding his 500th career winner aboard H Two O in the Independence Day Stakes Trophy. The three-year-old American-bred chestnut colt dominated the Restricted Allowance II contest, winning by an astonishing 8 ½ lengths in a swift time of 1:26.3. The excitement had already begun when Halledeen secured a win on Girvano in the $1.25-million Emelio “Bimbo” Rodriquez Trophy, setting the stage for a day filled with celebration.

Standing in the winner’s circle, Halledeen reflected on his journey. “Honestly, 500 is a good number, but I wasn’t paying it any mind. I wasn’t even thinking about it,” he shared with a humble smile. “My family is important to my success. They depend on me, and that motivates me to be the best I can be.”

The Thrill of the Derby

But the day didn’t end there. In the very next race, Halledeen and DaCosta joined forces once more, this time with I Dream Again. The stakes were high, and the crowd was on its feet as the horses thundered down the stretch. I Dream Again, owned by Derrick Smith, found itself neck and neck with Burning Hedge, ridden by Dick Cardenas. With the finish line in sight, Halledeen urged I Dream Again forward, and the horse responded, crossing the wire a length ahead of its competitor.

“The feeling hasn’t soaked in as yet,” Halledeen admitted, his joy palpable. “I am happy for my family, for Jason’s family, for Mr. Smith and his family, all I Dream Again’s supporters, and fans. I am really grateful.”

Praise for the Team

DaCosta, who had initially been surprised by I Dream Again’s early lead, quickly regained confidence thanks to Halledeen’s expert handling. “I was kind of surprised I Dream Again went to the lead, but I know ‘Hard Ball’ always makes the right decisions in the big races,” he praised.

As the race unfolded, DaCosta’s nerves kicked in when Burning Hedge began to challenge I Dream Again. However, he remained hopeful, recognizing Halledeen’s skill. “From she couldn’t go away from him, I know Burning Hedge was never going to outfinish him,” DaCosta noted, emphasizing Halledeen’s tactical prowess.

A Community Celebration

The day was not just about individual achievements; it was a celebration of community and support. Halledeen took a moment to express gratitude to his sponsors, particularly Thurston Elite Services, a luxury concierge company that has been instrumental in his career. “I have to big up my sponsor,” he said, acknowledging the vital role they play in his success.

Elizabeth DaCosta, the matriarch of the DaCosta family, beamed with pride for Halledeen. “I am really happy for Robert Halledeen. He is a very good jockey and he deserves a lot more,” she said, her admiration evident.

As the sun set on a historic day at Caymanas Park, the excitement lingered in the air. With Halledeen’s remarkable achievements and the support of his team, the future looks bright for this talented jockey. What other milestones await him on the track? Only time will tell.