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On May 17, 1875, 15 horses and their riders assembled at the Louisville Jockey Club to compete in the first iteration of the race known as the Kentucky Derby.
That venue was eventually rechristened as “Churchill Downs,” and the hallowed racetrack that’s home to the one-mile dirt oval where the equally legendary event is held in May each year has hosted it (and the 170,000 fans who gather for the spectacle) close to 150 times.
The Kentucky Derby is widely referred to as “The Most Exciting Two Minutes in Sports” (a nickname that stems from the amount of time it takes the competitors to complete the circuit), and the first leg of the Triple Crown has spawned some truly incredible moments and sagas over the years.
That includes the more than a dozen horses that have eventually gone on a claim the Triple Crown after winning The Run for the Roses—a list that’s home to some legendary names like War Admiral, Secretariat, and Seattle Slew.
There are also plenty of others that have defied some pretty astronomical odds (and made anyone who decided to place a bet on them very happy) by crossing the finish line before the rest of the field—although one horse stands out from the pack when it comes to the biggest upset to ever unfold.
What’s the biggest longshot to ever win the Kentucky Derby?
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That particular question certainly sprung to the mind of countless people who witnessed what unfolded when the 148th running of the Kentucky Derby took place in 2022.
Taiba and Epicenter headed into the race as odds-on favorites at 5-1, which put them all the way on the other end of the spectrum where Rich Strike (which had opened at 99-1) ended up after officially closing at 80-1.
However, the dark horse stunned the world by surging down the final stretch to take the lead before walking away with the win by around a length.
It was an underdog story for the ages—although it was actually the second-most impressive upset at the Kentucky Derby thanks to what had transpired more than a century before.
Ten Points was the favorite to win the Kentucky Derby in 1913 after closing at 11/5. The relatively small field of eight horses meant the race was a fairly wide-open one, although there was one entrant who seemed to be out of the running before it even started: Donerail, who headed to the post as a 91-1 longshot.
Donerail almost didn’t compete in the race in the first place, as owner, trainer, and breeder Thomas P. Hayes unsuccessfully lobbied jockey Roscoe Goose to find another mount before agreeing to let the colt run after a friend of his offered to pay the entry fee.
That turned out to be a very good call, as Donerail was ultimately able to outdo Ten Points by half a length in a race where the winner ran what was then the fastest time ever recorded at the Kentucky Derby en route to securing the $5,475 purse reserved for the first place finisher.
As Rich Strike proved, it’s foolish to ever count out the darkest of the dark horses, but other thoroughbreds have their work cut out for them if they want to unseat Donerail.