A billionaire businessman from New York City’s Queens borough, Mike Repole, is back at Churchill Downs with another horse favored to win the Kentucky Derby and finally conquer the “Run for the Roses” after repeated disappointments and setbacks.

Mr. Repole owns Fierceness, the betting favorite to win the 150th running of the Kentucky Derby on Saturday afternoon at historic Churchill Downs at Louisville. Trained by a two-time Derby winner, Todd Pletcher, Fierceness was listed at 5-2 after drawing the no. 17 post in an expected field of 20 for the $5 million race set to start at 6:57 p.m. EST.

Owning the front-runner is familiar territory for Mr. Repole, who had two favorites scratched only hours before the start of the 2023 Kentucky Derby. Uncle Mo, the second choice in the race, scratched the day before due to illness, and the 3-1 favorite, Forte, was scratched by the Kentucky Horse Racing Commission over concerns about a bruised right foot. The safety of horses was highly scrutinized last year after seven horses died the week of the race.

It was a heartbreaking series of events for Mr. Repole, who grew up wanting to be the head basketball coach at St. John’s, then yearned to own the New York Mets. He also had a passion for horse racing, spending frequent afternoons at Aqueduct Racetrack at Jamaica, New York. He admits what happened last year “made me feel bad,” but the ultra-successful entrepreneur believes in embracing adversity and considers himself fortunate to be back for a 10th chance to win America’s ultimate horse race.

“I’m zero for seven with starters and zero for two with favorites and this will be no. 10,” Mr. Repole told reporters at Churchill Downs. “Who would have thought that growing up in Queens going to Aqueduct, I would be in my 10th Derby entry? It’s all great.”

Sired by City of Light, Fierceness looked invincible in dominating the Grade 1 Florida Derby at Gulfstream Park, leading from start to finish and winning by 13 and a half lengths. A winner in three of five starts, Fierceness is saving his best for the biggest races with a three-time Derby winner, John Velazquez, aboard.

“This horse is just different,” Mr. Repole said. “He does everything so easy, so calm, so collected. I’ve been through this a lot and a horse like this calms you down. He calms me down. He just gets it.”

Fierceness, who can start fast and finish fast, must fend off a group of worthy challengers. An impressive Blue Grass Stakes winner, Sierra Leone, is listed at 6-1 and a Japanese entry, Forever Young, is 7-1. Dornoch, 50-1, is capable of a strong run, while Catching Freedom, who went to first from last at the Louisiana Derby, is 12-1. Honor Marie, 14-1, and Just a Touch also could be in the mix. Just Steel, trained by D. Wayne Lukas, is also a threat at 25-1.

Ron Flatter of Horse Racing Nation is picking Fierceness, telling the Sun he is “the best horse in the field and the most likely winner as long as he gets out of the gate. Whether keying him or using him defensively, he must be included. Just a Touch, an impressive second in the Blue Grass and Domestic Product, who has been under the radar since finishing first in the Tampa Bay Derby are the price plays.”

Sierra Leone is trainer Chad Brown’s best chance to win his first Kentucky Derby. He went for $2.3 million as a yearling and has not disappointed as a 3-year-old. He had trouble getting into the gate for the start of the Blue Grass but had plenty left after running down four horses, including Just a Touch in the stretch to win by a length and a half.

“He’s a naturally rare borne talent. He’s been that way his entire life,” Mr. Brown said of Sierra Leone, adding, “He’s got a tremendous amount of power and endurance. He might not be the fastest horse early, but once he gets moving it seems like his stride is two compared to the horses next to him.”

Sierra Leone isn’t helped by drawing the no. 2 post after Mr. Brown had said, “I don’t know that anyone wants to be buried down in the first couple of posts.” Yet, if his horse can get a decent start out of that gate, “he’s going to be tough to beat,” Mr. Brown said.

Forever Young, unbeaten in five starts, is considered by many the best Japanese horse to enter a Derby. A cousin of Sierra Leone — their mothers are half-sisters — Forever Young won the UAE Derby and Saudi Derby to earn a chance to become the first Japanese horse to win the roses. Trained by the fashionable Yoshito Yahagi, Forever Young drew a favorable no. 11 post in a race that often defies predictability.

Mage, who didn’t win a race as a 2-year-old and had just one win in three starts, won the 2023 Kentucky Derby at 15-one. Rich Strike, who is an 80-1 long shot, won in 2022. “You can visualize it until you’re blue in the face,” the trainer of Catching Freedom and Just a Touch, Brad Cox, said. “When the gates come open it normally unfolds a different way.”

The Sun’s Picks:
1. Sierra Leone
2. Fierceness
3. Catching Freedom
4. Just Steel