LOUISVILLE, Ky. — Across its 150-year existence, the Kentucky Derby has produced so many storybook results that people have ascribed near-mythical status to the event. Destiny is frequently invoked when lifelong dreams are achieved on the first Saturday in May. References routinely are made to blessings—or curses—from the “Derby gods.” When logical explanations are lacking, the outcome of a two-minute horse race sometimes seems to be guided by unseen hands.
If you believe that such an aura hovers over this race, maybe an untimely death in 2018 is a plausible explanation for how America’s oldest continuous sporting event has gone from storybook to surreal. Perhaps the passing of John Asher—Churchill Downs’ beloved ambassador of Derby cheer—has thrown the Run for the Roses off its karmic bearings.
In his absence, the Kentucky Derby has gotten downright weird.
Asher, the track’s vice president for racing communications, was part historian, part hype man and a full believer in the event’s indefinable magic. His booming bass voice proselytized on behalf of the Derby at every opportunity. Churchill memorialized Asher with a statue of him sitting on a bench adjacent to Col. Matt Winn, the man most responsible for turning the Derby into a national touchstone in the early 20th century. The two men appear to be in conversation, and boy, have they had a lot to talk about lately.
These are the six results since Asher died of a heart attack at age 62:
• Winner Maximum Security was disqualified for impeding other runners in 2019, the first and only DQ of a winner for interference in Derby history. That elevated the 65–1 long shot Country House to Derby champion. Country House never ran another step after the Derby—not even so much as a workout, much less another race—due to illness and injury.
• The race was contested in September 2020, thanks to the COVID-19 pandemic. It was a jolt to the global sporting system that was by no means limited to the Derby. That was the only time it was run outside of spring, and just the third time it took place outside of May. (The Derby was run on April 29 in 1901, and in June in 1945 when a national ban on horse racing was lifted after the Germans surrendered in World War II.) The race, won by Authentic, played out in front of acres of empty seats instead of the usual throng of 150,000.
• The 2021 winner, Medina Spirit, was DQ’d when a post–race drug test revealed the presence of the steroid betamethasone, a banned race–day medication. That prevented Bob Baffert from winning a record seventh Derby and touched off a bitter battle between the famed trainer and the famed racetrack, resulting in a three-year Churchill ban for Baffert. (Baffert returns this year with two Derby entrants.) The DQ elevated 12–1 shot Mandaloun to first place.
• The 2022 race was taken by Rich Strike, at knee-buckling odds of 80–1. He was the second-longest shot ever to capture the roses and could easily be labeled the biggest fluke winner in race history. Rich Strike had just a single, entry-level victory up to that point in his career, then never won again.
• The 2023 winner, 15–1 shot Mage, also had just one prior victory in his career, and never won again after the Derby.
• Last year’s champion was Mystik Dan at 18–1, winning a three-horse photo finish. Mystik Dan has never won again, either, though he isn’t finished yet. He will be running on Derby Day—in the Lake Ouachita Stakes at Oaklawn Park in Hot Springs, Ark., far from the fanfare and elite competition at Churchill Downs. Trainer Kenny McPeek won’t even be in attendance for Mystik Dan’s race, staying in Louisville to see his champion filly Thorpedo Anna compete at Churchill for five times the purse money.

Add it all up, and that’s two winners who didn’t cross under the wire first, one pandemic Derby, and most recently three straight improbable Derby champions who are a combined 0–13 since. “That is an amazing statistic,” said 89-year-old trainer D. Wayne Lukas, winner of 15 Triple Crown races. “That’s really strange.”
There have been plenty of surprise results over 150 years, and plenty of middling horses who were simply on their game at exactly the right time. But three upsets in a row of this magnitude are unprecedented: Parimutuel wagering was introduced at Churchill in 1908, and this is the first time three consecutive Derbies have been won at odds of 15–1 or greater.
In all three cases, the underdog winners rallied from off the lead in the stretch, suddenly looming in contention as tens of thousands of patrons asked, “Who’s that??”
Rich Strike was the ultimate lightning strike, passing 14 horses in the final quarter mile with a daring ride by obscure jockey Sonny Leon to weave through traffic and find daylight in the final strides. Mage was in 14th place with half a mile remaining in the 1 1/4-mile race, and still was sixth heading into the final quarter mile before charging to the front in mid-track. Mystik Dan had a ground-saving trip along the rail behind the leaders before jockey Brian Hernandez Jr. made an incredibly bold move through a tight spot to take over in the final quarter mile, then held off two charging challengers by mere inches at the wire.
“Ninety percent of the time, it’s not going to work out perfectly,” Hernandez says of his trip on Mystik Dan. “That time, it did. You need racing luck and good decisions. Mostly, you need the right horse on the right day.”
For Rich Strike and Mage, the racing luck came in the form of withering early paces that wore down the leaders in the stretch. The 2022 and ’23 Derby leaders went through the first half mile in less than 46 seconds — when 45 and change flashes up on the scoreboard, the race favors the closers. The ’24 pace was stout but slightly more moderate at 46.63 seconds, allowing Mystik Dan to hold up at the end after staying near the front throughout.

Beyond pace scenarios that can junk up the race, there are a plethora of other factors that could be contributing to the weirdness of recent Derbies. The most obvious is that American thoroughbreds don’t race as often as they used to, which leads to many inexperienced young colts being thrown into a chaotic situation on Saturday.
In this year’s Derby, there is a horse with three career starts (Grande) and two with four (Final Gambit and Chunk of Gold). Another horse with just three starts, Tappan Street, was injured over the weekend and dropped out. The top two choices in the morning line, Journalism and Sovereignty, have made five starts. The average for the 20–horse field is 6.1.
The fewer races they’ve had, the less they’ve experienced in terms of varying track conditions, traffic issues, and pace scenarios. Then the variables are compounded by the unprecedented elements that come with the Derby: the longest race any of them have yet contested; the largest field they will ever be part of; and the largest crowd they will ever see (and hear).
Some horses might be freaked out by the noise that accompanies the walk over, or in the Churchill Downs paddock—now a multi-level semicircle that has almost a Roman Colosseum feel to it. Some might be bothered by the size of the herd, being in tight quarters with that many competitors. And some might simply get slammed by another horse in the anarchy when the starting gate opens, or be shuffled back during the charge into the first turn. Bad racing luck can loom anywhere, as can good luck.
“When you prepare your horse, there’s not a lot of things that are just completely out of your hands,” says trainer Brad Cox, who won the 2021 Derby by DQ with Mandaloun. “And when the gate opens in the Kentucky Derby, it's out of your hands. It's a race like no other. It’s a massive field, and we're asking all of them to do something they've never done by going a mile and a quarter. So it's odd. None of us know what we have until they run the race.”
The unknown is the essential conflict underlying the Derby. It is the biggest prize in North American horse racing, but it is also subject to wildly random results—now seemingly more than ever. So much time and thought and expense go into breeding, purchasing, and training horses of Derby caliber, and then the race itself can become an absolute crapshoot.
No trainer is more painfully familiar with that dynamic than Steve Asmussen. The 59-year-old has the most wins in North American history, but he’s never won the Derby. His 26 starters in the race are the most for a trainer who has never captured the Run for the Roses. That gnaws at him.
“I don't know if it's healthy to want something that bad,” Asmussen says. “And maybe that's why it has eluded me.”
Twice, Asmussen has had the best horse in the world—Curlin in 2007-08 and Gun Runner in 2016-17—yet they both finished third in the Derby. (Both have become acclaimed sires as well.) On three other occasions, an Asumussen trainee has finished second—Nehro in 2011, Lookin At Lee in 2017, and most memorably Epicenter in 2022. Epicenter looked like the winner until being passed in deep stretch by—who’s that?—Rich Strike, a former claiming horse, whose place in the race wasn’t secured until another entry scratched the day before.
“Not only have I had Curlin and Gun Runner beat in it when I didn't think that was possible,” Asmussen says. “When Epicenter gets beat by a horse that scratches in—I mean, man, the circumstances that create a Derby winner. …”
Immediately after the Rich Strike jaw dropper three years ago, Asmussen’s only reaction was a disbelieving laugh.
“It’s as improbable as any scenario any of us ever imagined,” he said that day. “As they were loading into the gates, I was thinking how much goes into this exact moment and all of the buildup. And all the scenarios my rambling can come up with? That wasn’t one of them.
“At the head of the stretch (as Epicenter rolled into the lead), this is what you’re dreaming about. Oh, and by the way, you’re about to be run down by a claimer.”
One trade-off, Asmussen says he's unwilling to make is pushing a talented horse too fast, too soon, in an all-out effort to win the Derby. When told that the last three winners have never won again, he said, "That ain't going to happen to me. Maybe it's keeping too much ahead of us, but how we got where we're at, we believe in what we do. We do it as hard as we can and with the philosophy that everything matters or nothing matters, but as disappointed as we are having not won the Derby, (I am) freakishly proud of what we've gotten done (afterwards) with horses that ran in the Derby."
If this recent run of long-shot Derby winners continues, Asumussen is better positioned this year than he was in years when he entered with a proven contender.
His two entries, Publisher and Tiztastic, both are 20–1 in the morning line odds. Perhaps the Hand of Asher guides him to the winner’s circle when he least expects it.
Upset triumphs by the likes of Mystik Dan, Mage and Rich Strike have only stoked the ardor of owners to nudge their own long shots into the race. Derby Fever is real and rampant in this field, where 14 of the 20 horses are at 20–1 odds. They’re hoping the Kentucky Derby stays weird for at least one more year.
“The second those gates open, anything can happen,” says Whit Beckman, trainer of 20–1 shot Flying Mohawk. “It’s up to the elements of the universe.”
This article was originally published on www.si.com as Why the Kentucky Derby Has Never Felt Weirder.