Trainer Ryan Darby achieved a monumental milestone on Saturday, August 2, 2025, when his charge All Together crossed the finish line first, marking Darby’s 500th career winner at Caymanas Park.

Ridden by apprentice jockey Demar Williams, All Together’s victory came in the $1.05-million Beverly Rhoden Memorial Cup, a maiden condition race for native-bred three-year-olds fillies over 5 ½ furlongs. All Together won by half-length ahead of Miss Braeton (Oneil Mullings) and Dreamer’s Corner (Omar Walker) in 1:10.1

Following the win, the excitement was palpable as Darby celebrated this remarkable achievement, a testimony to his unwavering dedication and unrelenting passion for the sport.

As Darby reflected on this incredible feat, his enthusiasm was evident.

“I’m happy and looking forward to another 500,” he exclaimed, his eyes gleaming with anticipation.

Darby’s calm and collected demeanour belies the intense focus and hard work that have been the hallmarks of his career.

“I’ve been telling people that after I reached 499 and my father reached 800, I’ve won a lot of races, so there weren’t any nerves,” he told the Jamaica Observer’s The Supreme Racing Guide.

However, Darby’s humility and gratitude shone through as he acknowledged the journey that has brought him to this point.

“I didn’t have the material like one time and so it [getting to 500 winners] took a little longer than expected. But I’m rebuilding and rebranding, and I’ll pick up the pace for sure. I have done it before and so I will pick up pace and momentum very soon,” Darby said.

As Darby looked back on his remarkable journey, he reminisced about his first winner, a moment that still holds a special place in his heart.

“I would imagine that my first winner was probably a little bit more emotional but I’m appreciative of this 500 winners. Both my first winner and my 500th winner are great accomplishments, and hopefully, when I reach the 1000, I’ll celebrate more,” Darby said.

The significance of Darby’s achievement cannot be overstated. As he continues to strive for greatness, his legacy in the racing world is already cemented. With his sights set firmly on the future, Darby is poised to make an indelible mark on the sport he loves

All Together (#10-Demar Williams) beats Miss Braeton (Oneil Mullings) on Saturday, August 2, 2025 to give trainer Ryan Darby his 500th career winner. (Photo: Naphatli Junior)