CHAMPION jockey Raddesh “Sneaky Fox” Roman is on the cusp of breaking Trevor Simpson’s record of 172 wins in a single racing season. Despite a brief setback when he missed the previous race day due to medical clearance issues, Roman bounced back with a vengeance on Saturday, August 16, 2025.

Roman’s determination and skill were on full display as he booted home two winners, Rocket Fire Seb and
Boss Man, in the day’s second and third races, respectively. These wins took Roman’s tally for the season to 83 victories, leaving him just 89 wins shy of equalling Simpson’s record and 90 wins away from breaking it.

With 29 race days remaining in 2025, Roman faces a challenging but achievable target. To break the record he’ll need to average 3.06 wins per day — a feat that will require his signature blend of speed, strategy, and horsemanship.

Rocket Fire Seb easily won the $1.19-million Caymanas 66th Anniversary Trophy, a Restricted Stakes event for three-year-olds and upward over seven furlongs (1,400m). The Spencer Chung trainee won by 11¾ lengths ahead of Fearless Mission and Riches to Rags in a time of 1:25.4.

Boss Man’s victory came in the $1.1-million Caymanas Park 1959 Trophy. Boss Man won the Restricted Allowance II contest for three-year-olds and upward over one mile (1,600m) by a half-length. Perfect Affair finished second and Star Quest came home third as the final time was recorded at 1:43.1.

Roman’s focus remains fixed on defending his title as champion jockey, and he’s confident in his ability to deliver. As he pursues this landmark Roman’s fans and fellow racing enthusiasts will be watching with bated breath, eager to see if he’ll become the new king of Jamaican horse racing.

Will Roman break the record and cement his legacy? Only time will tell.