The Biggest Kentucky Derby Upsets

No horse racing event in the United States is more attention-grabbing than the Kentucky Derby, a contest that is now a hallmark of American sporting tradition. It draws millions of eyeballs to screens, and it has been the stage for multiple adrenaline-inducing shock wins. Below, we detail the ten ones that got racing fans’ jaws to drop to the floor, making some bookies very angry in the process.

1. Donerail

According to many experts, the most stunning Kentucky Derby win happened over a hundred and ten years ago, in 1913, when Donerail became the upset winner of the 1913 Kentucky Derby. Regarding the odds in play, this stallion was the biggest longshot winner in the race’s history, at 91:1. Donerail did not find much success elsewhere after his massive underdog win three years after his birth, retiring in 1917 with a record of ten wins in sixty-two races. He died in 1918 as a cavalry horse.

2. Rich Strike

In 2022, the second-biggest Kentucky Derby upset occurred when Rich Strike, owned by the Calumet Farm, took first place in the Derby as an 80:1 longshot. Called Richie by his close circle, Rich Strike is a chestnut colt that did not take first place in other major contests he ran after the miraculous feat he pulled off in 2022. But he did take second place at the Lukas Classic Stakes held at Churchill Downs the same year he won the iconic twenty-two-inches-tall KD trophy.

3. Country House

Here is a win that stemmed from a disqualification. In 2019, this Kentucky chestnut colt bred by Joseph V. Shields Jr. got awarded first place in the Derby following a controversial event – the disqualification of Maximum Security, ridden by Luis Saez, which crossed the finish line first. Yet, after the race had concluded, other participating jockeys complained that Maximum Security impeded their horses. Most notably, the later proven claim that he caused interference with three horses by veering out of his land in the final turn. The affected competitors were War of Will, Long Range Toddy, and Bodexpress. Flavien Prat, Country House jockey, filed an official objection, and it got Maximum Security disqualified, making Country House the winner as it crossed the line second, becoming the winner at pre-race odds of 65:1.

4. Giacomo

Jerry Moss is best recognized as the co-founder of A&M Records and for his career as a recording executive. But something that few fans of this New Yorker who passed away in 2023 know is that he owned racehorses. One of these was Giacomo, a grey stallion that won the 2005 Kentucky Derby ridden by Mike E. Smith at 50:1 odds. For those not into horse racing, Smith is one of the best US jockeys ever, winning more most Breeders’ Cup competitions than any other person, and two years before winning the Derby with Giacomo, he got inducted into the National Museum of Racing and Hall of Fame.

5. Mine That Bird

Four years following Giacomo’s unanticipated victory, Kentucky’s Mine That Bird triumphed in the Kentucky Derby, with bookmakers giving him the same winning odds as Giacomo, 50:1. However, many have tried to downplay this horse’s success by stating that the overnight rain had made the track sloppy, giving the favorites trouble coming out the gate and racing on the wet natural dirt field. Still, its jockey, Calvin Borel, credited his ground-saving/rail-skimming riding technique for the win.

6. Charismatic

Without question, one of the saddest racing stories in history is the one of Charismatic, a four-white-leg stocking horse that created a shocker in the 1999 Derby by beating 31:1 odds. Unfortunately, this thoroughbred failed to complete that year’s Triple Crown after he suffered an injury at the Belmont Stakes (he was a 2-1 favorite). X-rays revealed that he had cracked his sesamoid bone in the ankle of the same leg where he fractured his cannon one. He had successful surgery that repaired his leg, but his racing days were over after this unfortunate event, causing a stop to what could have been a stunning career.

7. Thunder Gulch

Thunder Gulch captured the 1995 Derby while coming into it as a 24:1 underdog. He was conditioned by D. Wayne Lukas, a Hall of Fame trainer, and ridden by Gary Stevens, considered one of his generation’s best tactical riders. Thunder Gulch’s lifetime race earnings hovered close to $3 million, and his most notable offspring was Point Given, a Hall of Famer that went down in history as the first to win four $1 million races in a row.

8. War Emblem

Bred in Kentucky by Charles Nuckols, Jr. & Sons., War Emblem was a magnificent black colt that won the Preakness Stakes and Kentucky Derby in 2002. He pulled off the latter by posting a time of 2:01.13 in a race where he took an early lead. The odds for him triumphing stood at 21:1.

9. Animal Kingdom

Before a then-record crowd of 164,858 (surpassed in 2015 – 170,513), Animal Kingdom overcame bookmakers not believing in him by giving him 21:1 odds to win by crossing the finish line first in his debuting dirt race at the 2011 Derby. Ridden by John R. Velasquez., Animal Kingdom got a stroke of luck in that year’s race, as Uncle Mo, one of the competition’s main contenders, got ruled out from competing due to a stomach infection.

10. Lil E. Tee

In 1992, the half-brother of Great Impulse and My Big Sis, Lil E. Tee, bred in Pennsylvania, led the field in Churchill Downs, upsetting the much-vaunted Arazi. Lil E. Tee is an uplifting tale of a prize-winning horse that had to survive immune deficiency and stomach problems en route to becoming a consistent runner. On top of his Derby win, he snagged two Grade 2 ones. He had issues with ankle chips and a lung infection as a four-year-old, which ended his racing days, leaving him with an earning tally of $1.4 million and a lifetime record of 7-4-1 from thirteen starts.

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