Five of the biggest shocks in Kentucky Derby history

Unlike games of chance that you might encounter in a casino, the result of a Thoroughbred horse race is far from a random outcome event. That’s not to say that there aren’t inexplicable surprises from time to time. In its century and a half of longevity, the Kentucky Derby has seen its share.

Donerail’s Victory in 1913

The most objective criteria at determining what constitutes a “shocking” result is the pari-mutuel payoff. By that standard, Donerail’s victory in the 1913 Derby remains the most surprising of all. For every $2 wagered on Donerail, winning bettors received $184.90, the equivalent of more than $5,700 in purchasing power today.

Even at a time when the Derby was still largely a provincial affair, little chance was afforded Donerail and several others by the 30,000 or so on track at Churchill Downs, where the only legal wagering occurred. In a field of eight, three horses started at odds of 87-1 or higher, with Donerail the second longest shot at 91-1. Proving the old saw that horses don’t know how to read the tote board, Donerail caught longtime leader and 6-5 favorite Ten Point inside the final furlong to post the upset.

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Dark Star’s Upset Over Native Dancer in 1953

There have been longer-priced winners than Dark Star ($51.80) and shorter-priced losers than Native Dancer (7-10 odds), but the result in 1953 still resonates as one of the more unfathomable in Derby history. At a time when the wider public were getting some of their first live glimpses of the Derby via national television, Native Dancer was racing’s first star on the relatively new medium.

Not only was Native Dancer’s gray coat easy to pick out on black and white screens, but he was also easy to spot at the finish as he entered the Derby unbeaten from 11 starts. In contrast, Dark Star barely managed to justify an entry into the Derby itself by winning the Derby Trial just four days beforehand.

Although knocked about entering the first turn, Native Dancer was well within striking range – 2 1/2 lengths – of the front-running Dark Star with a quarter mile to go. Perhaps Native Dancer’s superior class should have willed him to even a narrow victory, but Dark Star managed to cling to a head advantage crossing the finish line.

Native Dancer went on to capture the Preakness and Belmont Stakes and thus was denied a Triple Crown sweep by Dark Star, the only horse that ever finished ahead of him in 22 starts.

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The expansion this century of the Derby win pool to 20 interests, and the worldwide ability to bet on the race, has coincided with several of the more shocking upsets in the race’s history. 

Giacomo’s Surprise Win in 2005

Giacomo’s come-from-behind victory in 2005 was not only surprising, but the longshot-dominated race produced record exotics payoffs, too. Win bettors received $102.60 for every $2 bet on Giacomo, while the $2 exacta with 70-1 outsider Closing Argument returned $9,814.80. The $2 trifecta with 9-2 second choice Afleet Alex returned more than $133,000, and the $1 superfecta with 29-1 Don’t Get Mad was worth more than $864,000.

Like Native Dancer a half century before, Afleet Alex rebounded from this head-scratching loss to win the Preakness and Belmont, in his case by authoritative margins that left no doubt as to who the best three-year-old really was. The connections of Giacomo would go on to enjoy further success in the racing limelight when campaigning the superstar mare Zenyatta later that decade.

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Mine That Bird’s Shocking Win in 2009

Four years after Giacomo, Mine That Bird produced the largest margin of victory in the Derby by a horse who started at 50-1 or higher. Trailing the field of 19 after six furlongs, Mine That Bird skimmed the rail over a sloppy track under jockey Calvin Borel and exploded to win by 6 3/4 lengths over Pioneerof the Nile, who later sired Triple Crown winner American Pharoah.

Although the champion juvenile in Canada, Mine That Bird had lost his two previous attempts on dirt, including a fourth-place finish in the Sunland Derby in New Mexico. Only when his connections were advised by Churchill’s racing secretary that they could still make the field due to defections and attrition did they decide to roll the dice.

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Rich Strike’s Victory in 2022

The biggest shocker in modern times was the $163.60 payoff on Rich Strike in 2022. Stuck on the also-eligible list when entries were drawn, Rich Strike officially made the field of 20 only the day before the race after another horse was scratched.

For a colt whose only previous win had occurred in a $30,000 maiden claimer, and whose three prep races had been moderate efforts over a synthetic track, Rich Strike picked the perfect day to strike it rich with a ground-saving rally at odds of 80-1. As was the case in 1953 and 2005, the eventual champion of the division, Epicenter, settled for a minor share.