4 Biggest Upsets In Kentucky Derby History

Biggest Upsets In Kentucky Derby History

Favorites have a good record in the Kentucky Derby. In fact, if you are used to understanding odds in horse racing, you know they were victorious in every Kentucky Derby from Orb’s 2013 win until Justify in 2018.

They have a good record in most races, all factors considered. Sometimes a horse receives a lot of hype that turns out not to be true, but for the most part, talent and class in a racehorse becomes fairly evident fairly quickly.

However, anything can happen in a horse race, especially when said horse race has as many X factors as the Kentucky Derby.

According to TwinSpires.com, in the Kentucky Derby, horses are asked to run longer than they’ve ever run before, in what is by far the biggest field they will ever face in their careers. They are asked to do this in front of thousands upon thousands of rowdy, screaming, ultimately unpredictable fans.

Sometimes, this leads to a shocking upset, one in which a horse whom nobody expects takes home all of the glory.

Here are the 4 longest shots to ever win the Kentucky Derby. Check out these names and then compare with the current list of contenders in the 2024 event. Do you think any of the current contenders will match these horses’ underdog stories?

1. Mine That Bird (2009, 50-1)

Mine That Bird wasn’t always a long shot. In fact, he was Canada’s 2008 Sovereign Award Champion Two-Year-Old Male, having won Woodbine’s Grade III Grey Stakes in addition to two ungraded stakes races.

However, following a poor effort in the Breeders’ Cup Juvenile, Mine That Bird’s connections moved him to Sunland Park, where minor placings in two more listed stakes granted him enough earnings to qualify for the Kentucky Derby (the points system now in use was not introduced until 2013), albeit without much confidence from the public.

The gelding did, however, have two advantages: he was a deep closer in a field with a ton of early speed, and he had the services of jockey Calvin Borel, a master of navigating rail trips at Churchill Downs. As the frontrunners fell apart, Borel and Mine That Bird scooted through to pick up the pieces- and the roses.

2. Country House (2019, 65-1)

Country House’s Kentucky Derby story is unique not for his long odds, but for the fact that he didn’t actually finish first. In fact, in all seven starts, he only ever finished first once: in a maiden race as a two-year-old. He qualified for the Kentucky Derby by placing third in the Grade I Arkansas Derby, but few saw him as a viable candidate for the nation’s most prestigious horse race.

Instead, it was Grade I Florida Derby winner and second-favorite Maximum Security who appeared to have a lock on the race, leading from gate to wire. However, he failed to keep his path on the far turn and interfered with War of Will and Long Range Toddy. Country House, who was to the outside, appeared unaffected and went on to chase Maximum Security home.

Long Range Toddy’s jockey, Jon Court, lodged a claim of foul against Luis Saez and Maximum Security. After twenty minutes of deliberation, the judges placed Maximum Security behind Long Range Toddy, who had placed seventeenth, thus elevating Country House to the winners’ circle.

3. Rich Strike (2022, 80-1)

Rich Strike’s story is the stuff of legend.

The former claimer fell into the hands of a hard luck trainer who had been all but erased from the business after a barn fire killed most of his charges. He happened to place third in the Grade III Jeff Ruby Steaks, a race on a synthetic surface that had only thst year been named as a 100-point race on the Road To The Kentucky Derby. That left Rich Strike sitting at number 21 on the leaderboard, on the outside looking in as entries were being drawn.

However, the connections didn’t give up hope. Five minutes before the entries were finalized, trainer D. Wayne Lukas elected to withdraw Ethereal Road from the competition. Rich Strike was in, less than 48 hours before post time.

Most of the pre-race attention was focused on Epicenter, the favorite who had easily and professionally won the Grade II Louisiana Derby. The Japanese entry, which consisted of Crown Pride and Summer Is Tomorrow, the top two finishers in the Grade II UAE Derby, also drew considerable notice.

Indeed, these three horses had a major impact on the race. Crown Pride pressed Summer Is Tomorrow to set one of the hottest paces in Kentucky Derby history, with Epicenter stalking. Epicenter held on and took over on the turn, but in a move eerily reminiscent of Borel and Mine That Bird, Rich Strike and jockey Sonny Leon shot through on the rail and stunned everyone, including the track announcer, who barely had time to call the colt’s name before he won.

4. Donerail (1913, 91-1)

Source: courier-journal.com

With all of the above-mentioned Derbies having been run in the last fifteen years, it is curious that the longest shot of all happened nearly a century before any of them.

With much of the records of lower-level racing having been lost to time, there is a lot modern racing fans do not know about Donerail prior to his Derby win. We do know that he was winless to that point as a three-year-old, although like Mine That Bird, he had shown some promise at age two. We also know that although he had placed in the Blue Grass Stakes, his owner/trainer/breeder, Thomas P. Hayes, had considered not running Donerail in the Derby, and that his instructions to jockey Roscoe Goose were to “try to grab a piece of the purse.”

Favored Ten Point was fighting off Yankee Notions, and it seemed as though one of them would prevail. However, Goose and Donerail, like others on this list, popped up at the last second and left their competition astounded- in stakes-record time, at that!

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