For those in the game, horse racing is an accrual of scar tissue. It’s a steady layering of disappointments that is blessedly alleviated by the soothing balm of occasional victory. If hitters in baseball are celebrated for being successful 30% of the time at the plate, that’s still better than horsemen—none of the top 25 North American trainers for 2024 has a win percentage higher than 29.

And no race is harder to capture than the biggest of them all, the Kentucky Derby. Chad Brown is one of the most successful trainers in the sport and Mike Repole is one of the most successful owners, yet the Derby has kicked them around plenty. They’re a combined 0-for-14 in the Run for the Roses—but that stat only scratches the surface of their scars.

This year, maybe, one of them will break through. The irrepressible Repole owns the Derby favorite, Fierceness. The pensive Brown trains the Derby second choice, Sierra Leone. On paper, they appear to loom over their 18 rivals. But paper can be shredded quickly when the starting gate springs open Saturday evening at Churchill Downs.

They know better than to get overly optimistic. It’s all too fragile.

Repole has seen his blue-and-orange racing silks—the colors of his beloved New York Mets and Knicks—go to post seven times in the Derby. His best finish is fifth. But the real heartache came in 2011 and again last year, when his best colts were scratched late in the lead-up to the race. 

Thirteen years ago, 2-year-old champion Uncle Mo was the second choice in the morning-line odds, having won four out of five career races. But the day before the Derby, Repole and trainer Todd Pletcher pulled Uncle Mo out of the race after he developed an illness that caused him to lose weight.

“I don’t think I’ve ever had a horse as good as Uncle Mo,” Pletcher said at the time, one year after winning his first Derby with Super Saver.

“Uncle Mo, in my opinion, he’s five to seven lengths better than any horse in this race,” Repole said. “As bad as I want [to] win this race, [Pletcher] is 43 and I’m 42. He looks a lot older than I do, but the bottom line is that we’re going to be around a while.”

Pletcher and Repole hung around long enough to see gut-punch history repeat in 2023, when favored 2-year-old champion Forte was stunningly scratched by Churchill veterinarians the morning of the Derby. Forte had stumbled slightly during a Thursday breeze on the track and was diagnosed with a foot bruise. In a week rife with racing tragedy, with a dozen horses dying due to a variety of issues, caution prevailed and the colt was sidelined.

“I’m devastated,” Repole said last year. “I’m shocked. I think they were overly cautious, but I have to respect the fact that they’re overly cautious.”

Last year’s devastation has been rinsed away. An entrepreneur who has made a lot of money in a variety of ways, Repole is a font of optimism. He’s fourth among North American thoroughbred owners in earnings for 2024 and is always looking for his next score. He is not easily discouraged.

“A year after Forte, and I got Fierceness?” Repole said last week. “What great luck. Like, what the f—? There’s 20,000 foals born every year, and the Derby favorite was one out of 20,000 and now you come back a f—ing year later and you have one out of 20,000 again? What great luck. I’m humbled by this. This is not normal. Three 2-year-old champions.

“No one should feel bad for Mike Repole. I’ve got a pretty awesome life. I’ve got an awesome family—my parents, my daughter, my wife, my friends from childhood. I’m 0-for-7 with [Derby] starters, 0-for-2 with [scratched] favorites, 0-for-9. This will be No. 10. Who would have thought that growing up in Queens and going to Aqueduct, I’d be on my 10th Derby entry? It’s all great.”

Brown has been teased by the Derby gods even more than Repole. On three separate occasions, he’s felt the massive adrenaline rush of seeing his horse enter the home stretch with a chance to win—Normandy Invasion was on the lead in 2013, while Good Magic and Zandon were giving chase in second place in ’18 and ’22. None hit the wire first.

Normandy Invasion faded to fourth after chasing a hot early pace. Good Magic couldn’t catch Justify, a monster on his way to winning the Triple Crown. Zandon dueled with Epicenter before both were passed in deep stretch by a certifiable fluke, 80–1 long shot Rich Strike.

“What a feeling both ways,” Brown says. “I’ve had the fortune of having the feeling that most trainers will never get—when you turn for home in the Derby, three times I thought I was going to win. 

“That long walk [to the barn] afterwards, each time I walked back on the track thinking, ‘I’m not positive I’ll be back with a horse quite as good.’ It’s one thing to get a horse to the Derby, but can you get to the quarter pole in the Derby? By the quarter pole, most of them can’t win. That’s a hard spot to get to.”

The only spot harder to reach is the Derby winner’s circle. If either Repole or Brown is going to get there this year, it will be via distinctly different race scenarios.

The 5–2 morning-line favorite, Fierceness’s weapon is sheer speed. A slight, wiry colt, the Repole homebred doesn’t look like much until he’s in full flight. Fierceness has lost two of five lifetime races after poor starts, breaking poorly in the Champagne Stakes as a 2-year-old and being pinballed by other horses after the break in the Holy Bull Stakes. But when he breaks cleanly and avoids trouble, it’s over.

The most recent evidence of that was a 13½-length blowout in the Florida Derby. Fierceness got to the front, dictated terms and then drew off in a jaw-dropping performance.

“When he runs his race, he’s just faster than these horses,” Brown says of his top competition. “If he gets the position early in the race he likes, and he gets away from there cleanly and he takes to the Churchill track, he’s going to be tough to run down. He’s just running a bit faster than these horses. So I respect the horse a lot, and we’ll just see how it plays out into that first turn. I’d say that he’s a deserving favorite for sure.”

Sierra Leone, 3–1 in the morning line, is a closer who will come from off the pace. The regally bred son of 2017 Horse of the Year Gun Runner looks the part of a champion—he’s a physical specimen. His pedigree and conformation led a deep-pocketed ownership group to spend a whopping $2.3 million on him as a yearling in ’22.

“You could breed literally many thousands of horses and not get one to come out that perfect, in every regard,” Brown says.

From there, it was up to Brown not to blow it—something that happens more often than you might think with pricey horses. (The most expensive yearling of all time, The Green Monkey, fetched a preposterous $16 million at auction in 2006 and never won a race.) Brown earned the opportunity with a résumé that includes 18 Breeders’ Cup victories, two Preakness triumphs and leading North America in earnings five different years.

“There’s a lot of pressure associated when the ownership group chooses you to train a sale-topping yearling like this,” Brown says. “They have a lot of choices. When they pick you as a trainer, you take a lot of responsibility with that. They don’t apply pressure; you apply pressure yourself. It’s a wonderful group to train for, very experienced ownership. But yes, the expectations are high, so it’s extra rewarding to get to at least this moment, to confirm that they made a good decision.”

Sierra Leone has lost only once, by just a nose, last December. His two 3-year-old races have been stirring stretch wins in the Risen Star and Blue Grass Stakes, displaying the requisite stamina to handle the Derby’s 1¼-mile distance. 

The question for Sierra Leone will be traffic, since he will be starting from the problematic No. 2 post and coming from well back in a 20-horse field. There figures to be a lot in the way for jockey Tyler Gaffalione to weave through.

“A big horse with his running style, it does make the trip more challenging,” Brown says. “Ironically in this race, you’d probably prefer a handier horse that maybe has a little more speed and is not quite as big, because of the 20-horse field and tight turns at Churchill. But he does have other attributes that you like.”

Sierra Leone has many attributes. So does Fierceness. Their accomplishments to date have moved them to the forefront of the 150th Kentucky Derby—so close they can almost touch it. Mike Repole and Chad Brown are just two minutes and change away from a breakthrough victory in a race that has haunted them. But only one can get there, and maybe neither will.

This is the game. Even the most successful horsemen lose far more often than they win, and no race is harder to win than this one.