On Saturday, September 27, 2025, the winners’ enclosure at Caymanas Park erupted in jubilation as Dick Cardenas — the whip-smart jockey with a story etched in triumph – rode Midnight Flight to victory, clinching his 800th career win in Jamaica.

This landmark was achieved in the ninth race, a three-year-old and upward Claiming ($1.5m-$1.2) over 5 furlongs straight. Trained by Byron Davis, Midnight Flight won the race by 1½ lengths in 59.3 seconds.

Cardenas’s path since debuting in 2008 had been paved with grit, passion, and an unwavering gaze toward greatness. He won his first race aboard St Bess, trained by Percival Hussey, at odds of 19-1.

Cardenas spoke with heartfelt conviction after Midnight Flight propelled him to his 800th career win. His words reflected the dedication behind this milestone.

“It wasn’t easy to win 800 races. I worked very hard for this and so I am very happy that I could win my 800th here at Caymanas Park”, he shared with the Jamaica Observer’s The Supreme Racing Guide.

“To be honest, I never really thought that I would have won so many races here. And so I must thank the owners, trainer, grooms, everybody that supported me during my career. This [Jamaica] is my second home. I met my wife here and I really like Jamaica,” Cardenas said.

Cardenas didn’t stop there. He went on to win three races on Sunday, September 28. Cardenas won aboard
Brompton Boy for trainer Anthony Nunes, Hickory Slim for trainer Donovan Phillipps, and SmartAsset for trainer Oral Hayden to bring his tally to 803 winners.

Cardenas currently sits in 10th place on Caymanas Park’s all-time jockey winners’ list, an impressive feat considering his achievements. Only Winston “Fanna” Griffiths (1,663 winners), Trevor “Slicer” Simpson (1,509 winners), Shane “Canter Man” Ellis (1,369 winners), Omar “Hot” Walker, Charles “Boggle Man” Hussey (1,239 winners), Dane “Warrior Chief” Nelson (1,219 winners), Andrew “Nanny Cartoon” Ramgeet (1,149 winners), Emilio “Binbo” Roderquez (1,084 winners), and Paul “Country” Francis (825 winners) have won more races than Cardenas.

Cardenas said that he is absolutely driven to hit that 1,000-win milestone in Jamaica. He’s got his eyes firmly fixed on the horizon, and you can sense the determination in his words.

“I want to win 1,000 races here in Jamaica. That’s my milestone target. I passed 1,000 races overall because I have won many races in America and Panama but I want to win 1,000 races here in Jamaica. That’s my goal,” said Cardenas, who has over 300 winners in his homeland.

Among his many winners in Jamaica, Cardenas said that Mark My Word stood out for him.

“My Triple Crown winner, Mark My Word in 2010, really stands out for me. I mean, I have ridden Classic winners, ridden talented racehorses but Mark My Word stood out for me,” Cardenas said.

Cardenas’s American racing career took off in 2014, and he’s racked up over 100 wins in the US. His first winner was aboard Red Rond, trained by Norman Pointer, on January 28, 2015, at Gulfstream Park — a great start to his Stateside journey.

In addition to Gulfstream Park, Cardenas rode at top race tracks including Hawthorne, Turfway Park, Horseshoe at Indianapolis, Churchill Downs, Mahoning Valley Race Course, and Keeneland, among others. He has ridden top horses in the US such as Tornado, Expect Indy, Sweet N Wicked, and Capture the Glory, among others.

Jockey Dick Cardenas celebrates his 500th career winner in Jamaica on Saturday, September 27, 2025.Garfield Robinson

Dick Cardenas wins aboard Midnight Flight, his 800th career winner in Jamaica on Saturday, September 27, 2025. (Photo: Garfield Robinson)