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Top Upsets at the Kentucky Derby

Anything can happen on the first Saturday in May, and each edition of the Kentucky Derby provides the opportunity for the underdogs to shine. We’ve revisited some of the more recent upsets at Churchill Downs, and look forward to many more in the future.


#5 – Animal Kingdom, 2011

Odds – 21-1

This one went from normal to chaotic overnight as the overwhelming favorite Uncle Mo bowed out of the day before, opening up all kinds of possibilities for the race odds. At the time of posting, Dailed In was the favorite at 5-1 odds.

Animal Kingdom was an unexperienced entry who took advantage of the opportunity, stormed to the lead with 200m left and left Louisville a champion.


#4 – Charismatic, 1999

Odds – 31-1

Man, this was a fun race. Charismatic was lucky to be in the field, earning a place in the race at the Lexington Stakes just two weeks before. The late jockey Chris Antley patiently waited for the opportunity and Charismatic  went eye-to-eye with Cat Thief down the straightaway. However, if the race were 20 meters longer, a late charging Menifee might have walked away with the title. The last 200m of this race are great to rewatch. After Antley’s death, ESPN made a 30 for 30 about Charismatic, which can be seen HERE.


#3 – Giacomo, 2005

Odds – 50-1

2005 was the year of the underdog, as Giacomo made a late charge and held off fellow long shot Closing Argument to win by half a length. The finish was fabulous, as three horses took the lead as the finish line approached. What will get lost in history is the horse that was in the lead with 50 yards to go, Afleet Alex, would go on to win the Preakness and Belmont Stakes.


#2 – Mine That Bird, 2009

Odds: 50-1

Admittedly, a lot of these races tend to blend together, but the 2009 edition will never escape memory. Yes, the upset was monumental, but the move against the rail that jockey Calvin Borel executed to perfection on the final straightaway is still remarkable to watch.  As the finish line neared, Mine That Bird proceeded to pull away the field to a 6 ½ length victory. Rewatching the broadcast, it’s comical to hear how long it took announcer Tom Durkin to not only recognize the charge, but identify the horse. You can tell he absolutely didn’t see Mine That Bird coming.


#1 – Country Home, 2019*

Odds: 64-1

Although we were 10 months away from a global pandemic, the 2019 Kentucky Derby feels like it should have taken place in 2020. For the first time in the history of the Kentucky Derby, the horse that crossed the finish line first was not declared the winner. It was strange to follow and comprehend watching on TV, and had to be even more confusing to those in the stands.

Maximum Security, a horse who entered the race already under suspicion for how much he improved race to race, defeated the muddy and rainy elements to cross the finish line first. As seen in the video we shared above, it looks like the winning jockey is the one who accidentally triggered a probe with a candid post race comment turned confession. However, a protest would have been launched anyway as the jockey of Country Home received encouragement from another jockey to launch a protest. Winning bet tickets were temporarily frozen, and the race results remained “unofficial.”

The next half hour was tense and confusing as several judges broke down the race like the Zabruder film from five difference angles.  In the end, it was deemed that the “box out” move executed by Maximum Security, whether intentional or not, was against the rules and resulted in a disqualification. By being the next horse to cross the line, Country Horse, who was not impacted by Maximum Security’s impediment, was crowned champion.

The controversy didn’t end on the first Saturday in May, either. Maximum Security and his trainers have had quite a go at it since, including positive doping tests, further disqualifications, and lawsuits.


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Top 5 Upsets at the Kentucky Derby

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