Jockey Robert “Hard Ball” Halledeen etched his name in the record books on a memorable day at the track on Wednesday, August 6, 2025.

Halledeen’s remarkable achievement began with a milestone moment: riding his 500th career winner aboard H Two O, trained by Jason DaCosta, in the Independence Day Stakes Trophy.

H Two O, a three-year-old American-bred chestnut colt, won the Restricted Allowance II contest over 7 furlongs by 8 ½ lengths in a smooth 1:26.3. The stage was earlier set for Halledeen’s day with a win on Girvano in the $1.25-million Emelio “Bimbo” Rodriquez Trophy earlier.

As Halledeen stood in the winner’s circle, basking in the glory of his 500th career win, he couldn’t help but feel a sense of gratitude and humility.

“Honestly, 500 is a good number, but I wasn’t paying it any mind. I wasn’t even thinking about it but it’s a good number to reach as a jockey in Jamaica where we have few race days,” Halledeen told the Jamaica Observer.

For Halledeen, the milestone was more than just a number – it was a testament to the countless hours he’d spent honing his craft, the sweat and tears shed, and the unwavering support of his loved ones.

“My family is important to my success. They depend on me, and that motivates me to be the best I can be. My career has been blessed and so I can’t complain about anything,” he said, his words infused with gratitude. “I can do way more but I’m at peace with where I am, and I’m thankful for every moment I’ve had on the track,” Halledeen noted.

One moment that stood out in his mind was his thrilling win of the 2024 Mouttet Mile with Funcaadun for Jason DaCosta and Carlton Watson.

“That was legendary,” he recalled, his eyes lighting up with excitement. “It’s moments like those that make all the hard work worth it.”

Halledeen didn’t forget to express his heartfelt gratitude to his sponsors, acknowledging the crucial support they’ve shown him.

“I have to big up my sponsor Thurston Elite Services. Thurston Elite Services is a luxury concierge company that provides lifestyle management services,” Halledeen ended.

Elizabeth DaCosta, the matriarch of DaCosta, couldn’t be prouder of Halledeen.

“I am really happy for Robert Halledeen,” she said, beaming with admiration. “He is a very good jockey and he deserves a lot more.”

But Halledeen wasn’t done yet. The very next race, he teamed up again with DaCosta and I Dream Again to win the Jamaica Derby.

Owned by Derrick Smith, I Dream Again, under strong urgings, rallied in deep stretch to beat Burning Hedge (Dick Cardenas) by a length in the 105th running of the $7.5-million blue riband event over 12 furlongs (2,400m).

The crowd was on its feet, cheering on the horses as they thundered down the stretch. I Dream Again and Burning Hedge were nose to nose, with the outcome hanging precariously in the balance. Burning Hedge pointed on I Dream Again but Halledeen wasn’t done yet. He urged I Dream Again forward, and the horse found an extra burst of speed, rallying to cross the wire a length ahead of Burning Hedge. Pretty Perfect (Oneil Mullings) finished third.

The feeling of triumph still hadn’t fully sunk in for Halledeen, but one thing was certain – he was overjoyed for everyone involved with I Dream Again. His happiness extended far beyond his own family to Jason DaCosta’s family, Mr Smith and his family, and the entire team of supporters and fans who had backed the talented colt.

“The feeling hasn’t soaked in as yet. 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 and thanks everyone for their input,” Halladeen said.

DaCosta’s initial surprise at I Dream Again taking the lead quickly turned to 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,” DaCosta said, praising Halledeen’s tactical skills.

As Burning Hedge challenged I Dream Again at the top of the lane, DaCosta’s nerves kicked in. However, seeing I Dream Again’s determination and Halledeen’s masterful ride, he remained hopeful.

“From she couldn’t go away from him, I know Burning Hedge was never going to out finish him, and they weren’t going to outride ‘Hard Ball’,” DaCosta said, acknowledging Halledeen’s superior skill in securing the win.

Jockey Robert “Hard Ball” Halledeen celebrates after riding his 500th career winner aboard H Two O on Wednesday, August 6, 2025. (Photo: Naphtali Junior)

H Two O easily wins the Independence day Stakes Trophy on Wednesday, August 6, 2025, giving jockey Robert Halledeen his 500th career winner. (Photo: Naphtali Junior)