Each of the 20 horses set to start Saturday’s Grade 1, $5 million Kentucky Derby at Churchill Downs in Louisville will bring plenty of notable storylines to the table for horse racing’s biggest event.

But none will offer as many as Final Gambit, a 30-1 long shot on the morning line who is set to leave the same starting gate — post position No. 3 — as last year’s Derby winner, Mystik Dan.

Final Gambit, a Kentucky bred, brings together the kind of Derby narrative that holds intrigue for racing fans of all interest levels.

He’s one of three gray horses in the field. He will be ridden by a first-time Kentucky Derby jockey. All four of his previous races have come inside the commonwealth. His biggest win to date — the Grade 3 Jeff Ruby Steaks over a synthetic surface on March 22 at Turfway Park in Florence — came in a contest that has produced several recent Derby contenders.

And let’s not forget about the connections. Final Gambit is a Juddmonte Farms homebred who is conditioned by Brad Cox, a Louisville native. Cox and Juddmonte teamed up to win the Kentucky Derby in 2021 with Mandaloun, but that victory only came after the horse that finished first — Bob Baffert’s Medina Spirit — was disqualified for failing a postrace drug test.

Final Gambit is far from the experts’ top choice to win this year’s Run for the Roses. But he’s the horse with the most interesting context ahead of Saturday’s showcase.

“There’s a question mark with the dirt, but he’s moving great and he seems to be getting over it well. … He’s in a good spot,” Cox said about Final Gambit over the weekend. “He’s moving fantastic. His energy is through the roof, in a positive way. Not in a cheap way. He’s shown a lot of class and we’ve loved what we’ve seen from him since we moved him to Churchill.”

Kentucky Derby hopeful Final Gambit has two wins from four career starts, including in the Grade 3 Jeff Ruby Steaks in March at Turfway Park. Coady Media

Final Gambit enters Kentucky Derby after winning Jeff Ruby Steaks

Final Gambit’s close ties to the commonwealth are a good place to start when it comes to his fascinating Derby backstory.

A son of Not This Time and Pachinko (a Tapit mare), Final Gambit was foaled in February 2022 at Juddmonte in Lexington. Final Gambit’s Kentucky connections only grow stronger when you study his racing career.

Cox, the trainer, grew up near Churchill Downs and attended both Fairdale High School and Iroquois High School in the Derby City.

Another distinct Kentucky quirk on Final Gambit’s résumé?

He’s the only runner in this year’s Kentucky Derby to have never left the commonwealth for a race. Final Gambit’s racing debut came with a third-place effort in a maiden special weight race on the turf course at Churchill Downs last November.

Final Gambit’s other three starts have all been at Turfway Park in Northern Kentucky. He was second in a maiden special weight race there in January and won a maiden special weight at Turfway in February. Then came his big break, prevailing in the Jeff Ruby Steaks by more than 3 lengths in March over a field of 12 runners.

“Honestly, we were not thinking Derby before (the Jeff Ruby win). That’s being perfectly honest,” said Garrett O’Rourke, the general manager of Juddmonte’s American operation. “But again, you’re learning about these horses and horses change so much at that point and time. (We) always knew he had some talent, but didn’t know what level of talent. … But the Derby is the Derby. We want to win it. Brad wants to win it. We’ve got to give (Final Gambit) his shot.”

Final Gambit will be Juddmonte’s first Derby runner since Mandaloun, the eventual 2021 winner.

The Jeff Ruby Steaks — which is run on Turfway Park’s synthetic Tapeta track — has been on a hot streak of late when it come to producing Derby horses.

In 2022, long-shot Kentucky Derby champion Rich Strike ran third in that year’s Jeff Ruby. In 2023, Kentucky Derby runner-up Two Phil’s won that year’s Jeff Ruby.

Last year’s Jeff Ruby Steaks featured two horses — Endlessly (ninth) and West Saratoga (12th) — who went on to compete in the Kentucky Derby. This year, the Jeff Ruby will also send two runners to the Derby in winner Final Gambit (post position No. 3) and runner-up Flying Mohawk (post position No. 11).

To this point, Cox cited the example of Idiomatic — another Juddmonte homebred who was trained by Cox — who won four of five career starts at Turfway Park before then winning two graded stakes at Churchill Downs.

“Horses can definitely come off the Turfway surface and perform well here at Churchill,” said Cox, who added that stamina and the Kentucky Derby distance of 1 1/4 miles isn’t a concern for Final Gambit, who will be making his dirt debut on Saturday.

“People are saying that, ‘Well, he never ran on dirt. That should be a problem,’” added Machado, Final Gambit’s jockey. “The way I think, it’s, ‘What if he likes (dirt) better?’ I’m being positive, and it can happen because he’s showing it. He’s showing that he’s comfortable.”

Final Gambit is bathed after morning workouts out at Churchill Downs on Tuesday. The winner of Turfway Park’s Jeff Ruby Steaks is a 30-1 shot on the morning line for Saturday’s 151st Kentucky Derby. Ryan C. Hermens [email protected]

While it can be difficult to determine the correlation between prep races and success, or lack thereof, in the Kentucky Derby, it’s clear that the Jeff Ruby Steaks now commands more respect as a Derby prep race than it previously did.

“That day, we had a lot of speed going on that helped us a lot. We kind of knew the way (the race) was going to set up for us. It actually set up a little better than I thought,” said Machado, who guided Final Gambit to the far outside to win the Jeff Ruby Steaks after being shuffled to the back of the field at the start.

“Because he was just following the pace very easily. I thought I was going to have to ask a lot of him to go on or not to be too far back. And actually, he proved to me he was better than I even thought.”

“He made it easier (winning the Jeff Ruby) than when he broke his maiden,” Machado added. “So I was impressed.”

Jockey Luan Machado, shown at right, will make his Kentucky Derby debut this year aboard Final Gambit. Tasha Poullard [email protected]

Luan Machado to make Kentucky Derby debut with Final Gambit

Machado himself is very much part of Final Gambit’s story as the 2025 Kentucky Derby nears.

A native of Brazil, Machado — who was aboard Final Gambit for all three of his starts at Turfway Park — will be making his Kentucky Derby debut Saturday.

“In this business we just try to live day after day. It’s just about the momentum and making sure everything’s going to be good for the next day,” Machado said of managing his emotions ahead of his first Derby start. “… We’re just waiting to try our best every day to get ready for the moment. That’s all. No big secrets. Keep it simple and helpful for the horse, too.”

Machado — whose father was a jockey in Brazil — is a fixture on the Kentucky racing circuit. This includes riding five winners during the recently completed Keeneland Spring Meet. Last year, Machado led all jockeys with 142 wins in Kentucky.

“It’s very tough to be competing with this colony of great jockeys (in Kentucky),” said Machado, who rode another Derby horse, East Avenue, to a second-place finish in last month’s Blue Grass Stakes at Keeneland. “I’m very blessed to be part of this colony and to be able to show my work and what I live for every day.”

Another reason for public sentiment to potentially be behind Final Gambit come Saturday evening?

He’s one of three gray horses in the Derby field, along with Sandman (post position No. 17) and Chunk of Gold (post position No. 19). A gray horse hasn’t won the Kentucky Derby since 50-1 long shot Giacomo in 2005, and only eight gray horses have won the Run for the Roses all time.

Final Gambit will start this year’s Kentucky Derby at Churchill Downs from post position No. 3. That’s the same starting gate that housed last year’s Derby champion, Mystik Dan. Coady Media

This story was originally published April 29, 2025 at 6:00 AM.