Derrick Smith’s journey in horse racing has been a roller-coaster of emotions, with moments of pure joy and crushing heartbreak. His memories of Seeking My Dream, the talented colt who won the 2015 Jamaica Derby and the first two editions of the Diamond Mile, still bring a smile to his face. However, 2015 also brought a painful reminder of the sport’s unpredictability.

Seeking My Dream’s disqualification from the Jamaica St Leger, despite crossing the finish line first, left a lasting scar. Smith’s appeal against the stewards’ decision was unsuccessful, and the pain of that loss lingered. Yet, Smith’s determination to rewrite the narrative never wavered. He vowed to one day claim the St Leger, a race he still believes was unjustly taken from him.

Years later, Smith’s perseverance paid off. On July 6, 2025, I Dream Again, trained by Jason DaCosta and ridden by Robert Halledeen, surged ahead with a furlong to go and crossed the line as champion of the Jamaica St Leger. Smith’s eyes must have welled up with tears as he watched his dream become a reality. The wait was worth it, and the sweetness of victory was all the more poignant given the painful memories of the past.

As Smith basked in the glory of I Dream Again’s triumph, he must have felt a deep sense of satisfaction and vindication. The St Leger, a race that had once slipped through his fingers, was now firmly in his grasp.

Smith, emotional yet resolute, found partial healing in the win.

“Ten years later I have won the Jamaica St Leger, an honour taken away from me 10 years ago. That is the main reason why I named this horse I Dream Again,” Smith said.

He then recounted the moment the colt first caught his attention.

“On the morning of the 2023 yearling sale, I was going through the catalogue and saw this bay colt by Soul Warrior out of Lady Najariya,” Smith shared.

“Two things struck me at the time; Soul Warrior is a proven Classic producing sire and Lady Najariya is by
Legal Process the sire of Alsafra, who is the dam of Seeking My Dream. I called trainer DaCosta and asked him to take a look at the horse and if satisfactory, then he should purchase not going beyond a certain price,” he said.

The purchase was made. And now, Smith is the proud owner of a Jamaica St Leger winner — a dream revived and realised.

“DaCosta made the purchase and now I have my St Leger winner. Thanks and appreciation go out to the team at the DaCosta stables, and to jockey Halledeen who rode what I consider to be a well-judged and timed race,” Smith said.