17 Kentucky Derby Upsets That Shocked Bettors
Few sporting events match the excitement and pageantry of the Kentucky Derby. The thundering hooves, colorful silks, and mint juleps create an atmosphere unlike any other in American sports. But what truly makes the Derby magical are those unexpected moments when long shots cross the finish line first, leaving bettors stunned and bookmakers thrilled.
Here is a list of 17 remarkable Kentucky Derby upsets that left the betting world reeling and proved that in the ‘Run for the Roses,’ anything can happen.
Mine That Bird
Nobody saw this one coming. At odds of 50-1, Mine That Bird stunned the racing world with a phenomenal stretch run through the mud at Churchill Downs.
Jockey Calvin Borel guided his mount along the rail, bursting through to win by nearly seven lengths. The gelding had been purchased for just $9,500 and ended up paying out more than $100 for every $2 bet.
Rich Strike
Talk about last-minute drama! Rich Strike wasn’t even supposed to be in the race, entering only after another horse scratched the day before.
At 80-1 odds, this colt pulled off the second-biggest upset in Derby history, weaving through traffic in the final stretch. Trainer Eric Reed and jockey Sonny Leon celebrated their first Derby victory while bewildered bettors tore up their tickets.
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Donerail
The ultimate long shot in Derby history, Donerail shocked America with odds of 91-1. Jockey Roscoe Goose piloted the colt to victory in a time that was actually quite fast for the era.
The payout was astronomical for 1913 standards—$184.90 on a $2 bet, equivalent to over $5,000 in today’s money.
Giacomo
The betting public dismissed Giacomo at 50-1 odds, but the gray colt had other plans. He charged from 18th place to win in a heart-pounding photo finish over a strong field.
Jockey Mike Smith earned his first Derby win while bettors who believed in the underdog collected $102.60 for a $2 bet.
Gallahadion
The racing world was firmly behind Bimelech, the overwhelming favorite with a perfect record. Gallahadion, at 35-1 odds, wasn’t given much attention until he powered past the favorite in the stretch.
Owner Ethel V. Mars (of the candy company fame) enjoyed a sweet victory that paid $72.40 on a $2 wager.
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Charismatic
Just three months before the Derby, Charismatic was running in claiming races where any owner could have purchased him. At 31-1 odds, this former claimer surged to victory under jockey Chris Antley.
Trainer D. Wayne Lukas looked like a genius while stunned racing experts scrambled to explain how they’d overlooked this copper-colored champion.
Thunder Gulch
Despite being trained by the legendary D. Wayne Lukas, Thunder Gulch was largely ignored at 24-1 odds. The chestnut colt responded with a powerful performance, demonstrating why odds aren’t always the best predictor of ability.
Many fans who bet on his more heralded stablemate Timber Country were left wondering how they missed the signals.
Dust Commander
At 15-1 odds, Dust Commander wasn’t the longest shot on the board, but few gave him serious consideration. Jockey Mike Manganello guided him to a decisive five-length victory on a track that had been drying out from earlier rain.
His owners, the Lehmann family, had purchased him for just $6,500 as a yearling—a true bargain for a Derby winner.
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I’ll Have Another
Despite winning the Santa Anita Derby, I’ll Have Another was sent off at 15-1 odds, overshadowed by favorites Bodemeister and Union Rags. Jockey Mario Gutierrez, riding in his first Kentucky Derby, timed his move perfectly to run down Bodemeister in the stretch.
The victory signaled the start of a Triple Crown bid that would end with a scratch before the Belmont Stakes.
Iron Liege
This race is remembered not only for Iron Liege’s 8-1 upset but for what happened to Bill Shoemaker aboard the favorite, Gallant Man. Shoemaker misjudged the finish line and stood up too early, allowing Iron Liege to triumph by a nose.
The greatest jockey error in Derby history resulted in one of its most unexpected outcomes.
Country House
Though Country House crossed the wire second at 65-1 odds, he was declared the winner after Maximum Security was disqualified for interference—the first such disqualification in Derby history. The controversial outcome left bettors either ecstatic or furious, depending on their tickets.
Trainer Bill Mott earned his first Derby win under circumstances no one could have predicted.
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Animal Kingdom
With no previous experience on dirt tracks, Animal Kingdom seemed an unlikely Derby contender at 20-1 odds. The versatile colt silenced doubters with a brilliant stretch run that left handicappers questioning their assumptions.
First-time Derby jockey John Velazquez found himself in the winner’s circle after a remarkably clean trip.
Exterminator
Nicknamed ‘Old Bones’ for his gangly appearance, Exterminator was a last-minute substitute for his injured stablemate. At 30-1 odds, this overlooked gelding splashed through a muddy track to victory.
He went on to become one of the most beloved horses in American racing history, winning 50 races during his remarkable career.
Gato Del Sol
Coming from dead last in the field, the gray Gato Del Sol stunned the crowd at 21-1 odds. Jockey Eddie Delahoussaye navigated through traffic with remarkable patience, saving ground along the rail before swinging wide for the win.
The victory was especially sweet for 80-year-old trainer Eddie Gregson, who had waited decades for Derby success.
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Canonero II
The ultimate outsider, Canonero II, came from Venezuela with little fanfare and was dismissed at 39-1 odds. His unorthodox training included gallops along the beaches of Venezuela, far from traditional Derby preparation.
The South American mystery horse became an overnight sensation, paying $19.40 to win and creating one of racing’s most unlikely success stories.
Funny Cide
As a New York-bred gelding owned by a group of high school buddies who traveled to the race in a school bus, Funny Cide embodied the underdog spirit. At 12-1 odds, he wasn’t the longest shot, but his victory over the highly regarded Empire Maker resonated with everyday racing fans.
His ownership group, Sackatoga Stable, became instant celebrities for their humble approach to the sport of kings.
Dark Star
Native Dancer entered the 1953 Derby with an unblemished record and overwhelming favoritism. Dark Star, at 25-1 odds, shocked the racing world by defeating the ‘Gray Ghost’ in what would be Native Dancer’s only career loss.
Jockey Hank Moreno executed a perfect front-running strategy that caught the favorite and his jockey off guard.
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Racing’s Unpredictable Magic
The Kentucky Derby continues to captivate us precisely because of these incredible moments when conventional wisdom falls short. These 17 remarkable upsets remind us that racing formulas and statistics can never fully account for the heart of a thoroughbred or the chemistry between horse and jockey on the first Saturday in May.
Whether you’re a serious handicapper or casual fan, the Derby’s long history of surprising results offers hope that sometimes, just sometimes, the impossible becomes gloriously real beneath the twin spires of Churchill Downs.
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