Kentucky Derby 2022: The 10 biggest underdogs to win the Run for the Roses by far

Rich Strike caused a huge upset in the 2022 Kentucky Derby by winning at 80-1 odds. The thoroughbred 3-year-old, along with Venezuelan jockey Sonny Leon, became the second-most longshot to win in the event’s 148-year history. There had been no greater upheaval in over 100 years.

Here is a complete list of the 10 Kentucky Derby winners with the longest odds.

1. Donerail (1913), 91-1

Donerail – owned, bred and trained by Thomas P. Hayes – won the 39th race for the Roses by half a length after rallying from fifth at the top of the stretch. This upset paid $184.90 for a $2 bet. Louisville-born jockey Roscoe Goose had a successful career and became one of the first inductees into the Kentucky Athletic Hall of Fame in 1963.

2. Rich Strike (2022), 80-1

Rick Strike won this year’s race by 3/4 length ahead of two favorites, Epicenter and Zandon. Rich Strike wasn’t even supposed to compete, but a spot was open after the Ethereal Road scratch the day before. Here’s CBS Sports’ full story on Rich Strike’s victory.

3. Country House (2019), 65-1

Maximum Security finished the race 1 3/4 lengths ahead but was eventually disqualified after Country House jockey Flavien Prat lodged an objection. He claimed the winning horse ran out of his lane on the final turn and made contact with another horse named War of Will, who then made contact with his horse. It was the first time a horse had been disqualified for a fault during the race.

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

Mine That Bird and jockey Calvin Borel beat Pioneer of the Nile by 6 3/4 lengths after rallying from behind. Although he was a longshot, the horse had victory in his blood as his sire was Birdstone, the winner of Belmont in 2004. The payout was $103.20 for a $2 bet. Mine That Bird was inducted into the Canadian Horse Racing Hall of Fame in 2015.

5. Giacomo (2005), 50-1

If you could use a time machine to bet on any race, this would be it. Closing Argument nearly made that list going 70-1 in 2005, finishing just half a length behind Giacomo and jockey Mike Smith. Betting $2 on Giacomo turned into $102.60. But even more impressive, due to the fact that the top two horses were both by far, a $2 exact bet paid out $9,814.80 and a $1 superfecta brought in $864,253.50.

6. Gallahadion (1940), 35-1

Gallahadion finished 1 1/2 lengths ahead of heavy favorite Bimelech which was quite an achievement as Bimelech won both Preakness and Belmont. Gallahadion and jockey Carroll Bierman moved over the rail and passed the two horses in front after the final turn.

7. Apollo (1882), 32-1

Apollo did not follow the usual path of other Kentucky Derby winners. He did not race as a two-year-old, but still managed in 1882 with a half-victory over Runnymede. He and jockey Babe Hurd were at the back in a field of 14, but then pushed to take sixth place after a mile.

8. Charismatic (1999), 31-1

This race had an exciting end as Charismatic and jockey Chris Antley made a late push down the home straight to take a neck and neck victory over Menifee. Charismatic nearly won the Triple Crown by also winning Preakness. However, he finished third at Belmont and unfortunately suffered a career-ending fracture.

9. Proud Bugler (1967), 30-1

The proud Clarion lost in all three starts in his two-year career, but that was not a good indicator of the kind of career he would have as he got older. He and jockey Bobby Ussery won the 93rd Kentucky Derby by a length, while recording what was the third fastest time at that time at 2:00.60.

10. Exterminator (1918), 29-1

This derby was Exterminator’s first start as a three-year-old and he managed to beat Escoba by a length with jockey William J. Knapp in a muddy track. Ironically, owner Willis Sharpe Kilmer originally bought Exterminator not to race, but to help train Sun Briar, a two-year-old American champion.

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