Kentucky Derby: The $10 million gamble on a 1000-1 longshot

Amr Zedan, right, paid a hefty price of $10.5 million for a 2027 Kentucky Derby hopeful that the odds say will not be at Churchill Downs next May. (Photo by Andy Lyons/Getty Images)

(Andy Lyons via Getty Images)

Finding a needle in a haystack

When the process for the 2026 Kentucky Derby began roughly a year ago with the arrival of a new 2-year-old crop, Yahoo Sports identified 34 colts bought at auctions in 2024 and 2025 intended for Baffert’s renowned Triple Crown program that cost a total of $26.7 million.

The most expensive of that group, a horse named Faran — purchased by Zedan for $3.4 million — still hasn’t raced and hasn’t recorded a public workout since last November. Another $3 million Zedan purchase named Brant started with promise, winning the Grade 1 Del Mar Futurity last fall at seven furlongs, but was knocked off the Kentucky Derby trail in March after a fifth-place finish in a prep race for the Santa Anita Derby.

And while Litmus Test — an $875,000 purchase — emerged from the mega-partnership between SF Racing, Starlight Racing, Madaket Stables and others as a Derby horse, some of their more expensive purchases like Kelce ($850k) and Stellenbosch ($1.05 million) have yet to race. Others like Falcon Jet ($750,000) proved to not be capable of running at that level and were transferred to other trainers.

“We probably buy 20 to 22 yearlings every year,” Ryan said. “And we probably end up with four or five horses that we would think have the ability to run around in [Derby] preps.”

That doesn’t mean the strategy is a waste of money. Some of those horses could develop later and become a factor in the fall or as 4-year-olds. Some that failed on the Derby trail will find more success as sprinters or milers, divisions that have plenty of lucrative races. If even one is good enough to become a stallion prospect, the partnership will recoup millions and make up for some of the horses that don’t live up to their purchase price.

“You’re thinking Derby, but you’re buying 20 horses so you need 19 other options,” Ryan said. “It doesn’t make them any less valuable, but they can’t win the Triple Crown. We try our best. It’s a game where you’re wrong a lot more than you’re right. You have to be right enough times to stay in business.”

And despite the millions spent in pursuit of one horse race, the paradox of the Derby is that there’s often very little relationship between purchasing power and being right.

Instead of looking for Derrick Henry at running back, I’m looking for 5-foot-10 LeSean McCoy and hope I’m seeing things in terms of athleticism or something not so obvious in the pedigree.

Ramiro Restrepo

Just ask Ramiro Restrepo. His job as a bloodstock agent is to identify and purchase horses for his clients. Restrepo does not have the bankroll of a Zedan or Ryan to go buy 20 expensive colts at auction, but many of his clients are just as enchanted with the idea of winning a Kentucky Derby as someone who can spend $10.5 million on one horse without batting an eye.

“It’s the straw that stirs the drink,” Restrepo said. “So when you have either existing people in the game who are chasing the Holy Grail or a new person who wants to get in the game, the high, high majority of times they’re saying, ‘That’s the race I want to win.’ “

Restrepo, a University of Miami alum and massive college football fan, compares it to the dynamic in recruiting. Baffert and a small group of other trainers like Todd Pletcher, Brad Cox and Chad Brown are like Nick Saban, Kirby Smart and Urban Meyer in their heyday: Whether they won because they got the most five-star prospects or they got the most five-star prospects because they won, it’s a self-perpetuating cycle. The vast majority of the top high school recruits — or, in this case, the most physically impressive horses with the best breeding — are going to end up in a handful of top programs.

Their sheer numbers give them an advantage and margin for error that someone like Restrepo and his clients do not have if the end goal is trying to win a Derby. .

“There are certain sales where I don’t even try to participate in their division,” Restrepo said. “I can’t afford these, I can’t battle them, so I’m not even going to shop there. Instead of finding the 6-foot-4 quarterback, I look for the 6-foot-1 or 6-foot quarterback. Instead of looking for Derrick Henry at running back, I’m looking for 5-foot-10 LeSean McCoy and hope I’m seeing things in terms of athleticism or something not so obvious in the pedigree. You’re looking for those angle plays. You have to get a little more creative in your thought process.”

At a 2-year old sale four years ago, Restrepo made one of those angle plays on a smallish horse by Good Magic, who finished second in the 2018 Kentucky Derby but at that point was an unproven sire. The purchase price ended up being $290,000 — well over his intended budget. While Restrepo and business partner Gustavo Delgado, Jr., were able to recruit some co-owners to defray the cost, Restrepo ended up keeping a piece of the horse for himself.

That colt, eventually named Mage, ended up winning the 2023 Kentucky Derby.

Though the ownership is structured differently this time, there’s a decent chance by Saturday night that Ramiro will have identified his second Derby winner in The Puma, an homage to the nickname of trainer Gustavo Delgado, Sr. Merely having a second chance at it, this time with a horse he bought for $150,000, is such a longshot it’s almost hard to comprehend.

“The window is just so tiny and there is so much capital out there chasing those dreams,” Restrepo said. “It’s like you’re in the movie Cannonball Run and there’s a race to get the treasure. And then about 1 percent of the foal crop of 18,000 is going to end up being a (stakes) winner. So just do the math on that.”

Trainer Chad Brown thought Paladin would be his Kentucky Derby favorite, but an injury felled his run for the roses. So instead he's at Churchill Downs with Emerging Market. (AP Photo/Charlie Riedel)

(ASSOCIATED PRESS)

High hopes don’t always pan out

Though still just 47 years old, Chad Brown is already among the three or four most successful trainers in history yet to win a Kentucky Derby.

Like Baffert, every year brings a new crop of high-priced prospects to Brown’s barn. But even out of 120 total 2-year olds that came under his care last summer, he only made it into the race this year with Emerging Market by the skin of his teeth.

“Half of them are female, then half the males are turf horses, then half the dirt horses are sprinters and when you start to tear it down, you don’t have that many chances,” he said. “Even for someone like me that has a lot of 2-year olds to work with, you probably end up with eight-to-10 candidates and you just have to hope you’ve got the right eight-to-10.”

Before Emerging Market even made his first start in February, Brown had high hopes for Paladin, a $1.9 million yearling who was 4-for-4 until suffering an injury in March. Canaletto, a $1 million horse, finished third in the Tampa Bay Derby before being knocked out by an injury. Iron Honor, who was purchased for $475,000, looked like a Derby horse in late February but just didn’t perform like expected in his key prep race at the Wood Memorial.

Brown’s program is a bit different because he’s mostly known for being the best grass trainer in America. He’s also won the Preakness twice with Cloud Computing and Early Voting, horses owned by billionaire hedge fund manager Seth Klarman.

Despite having the means to go head-to-head with the heaviest hitters, Klarman is a value investor in both the stock market and the horse market. The philosophy, in general, is to take more shots with horses priced under $500,000 than to aim for the top end of the sales. That includes Emerging Market, whom he purchased for just $185,000.

So while Brown’s clients are not necessarily as focused on the Derby as someone like Baffert, he’ll probably have enough at-bats to break through at some point. Maybe even this weekend.

“All my accounts that I have now, they appreciate an honest, objective, patient approach both to try to get there but not to hurt the overall career of the horse,” Brown said. “I have a lot of horses in my care, and annually we’re participating in a lot of the top races even after the Triple Crown so I’m fortunate to have some chances to get to the Derby. This year I had a particularly good group, but I have a very diverse stable. Other trainers might be more focused on just dirt racing or just Derby colts.”

It puts into perspective how insanely against the odds it is that Baffert has won the race six times with his would-be seventh victory in 2021 taken away as a result of Medina Spirit testing positive for betamethasone in his post-race sample.

That incident led to Baffert being banned from Churchill for two years, which extended into a third due to ongoing litigation and his refusal to admit fault. Baffert maintained the ointment that caused the positive test was being used to treat a skin condition, but the two sides made up last year.

Now, with California racing on the decline due to low purses and small fields, Baffert plans to buy a house in Louisville and have a string of horses permanently based at Churchill Downs.

There’s a good chance Zedan, the $10.5 million horse, might be one of them. After all, the 2027 Derby picture will start to take shape pretty soon and Baffert is going to have a loaded barn as always.

But when the goal is to win a race that happens once a year, there is no amount of money that guarantees success.

“We’re all lined up in the same barn and it’ll be interesting to see where the cards fall,” Ryan said. “The good thing about the system is there’s enough to go around for everyone. If he turns out to be a superstar, he can only win one race at a time. We’ll pick up the crumbs if we have to.”