Kentucky Derby 2022: The 10 biggest underdogs to win the Run for the Roses as a long shot

Rich Strike pulled a huge upset during the 2022 Kentucky Derby by winning against 80-1 odds. The 3-year-old thoroughbred, along with Venezuelan jockey Sonny Leon, became the second biggest longshot to win in the 148-year history of the event. There had not been a bigger upset in over 100 years. 

Here is a full 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 Run for the Roses by a half-length after rallying from the fifth spot at the top of the stretch. That upset paid $184.90 for a $2 wager. Jockey Roscoe Goose, a Louisville native, had a successful career and went on to become one of the inaugural class of inductees in the Kentucky Athletic Hall of Fame in 1963.

2. Rich Strike (2022), 80-1

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

3. Country House (2019), 65-1

Maximum Security finished the race ahead by 1 3/4 lengths, but was eventually disqualified after Country House jockey Flavien Prat filed an objection. He claimed that the winning horse had come out of his lane in the final turn and made contact with another horse named War of Will, who then made contact his horse. That was the first time ever that a horse got disqualified for a foul during the race.

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

Mine That Bird and jockey Calvin Borel beat Pioneerof the Nile by 6 3/4 lengths after rallying from behind. Although he was a longshot, the horse did have winning in its blood as his father was Birdstone, the 2004 Kentucky Derby winner. 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 make a bet on any race, this would be the one. Closing Argument almost made this list as a 70-1 shot in 2005, finishing just a half-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 long shots, a $2 exacta bet paid $9,814.80, and a $1 superfecta had a $864,253.50 payout.

6. Gallahadion (1940), 35-1

Gallahadion finished 1 1/2 lengths ahead of heavy favorite Bimelech, which was quite the accomplishment as Bimelech went on to win both Preakness and Belmont. Gallahadion and jockey Carroll Bierman moved up on the rail and shot past the two horses ahead after the final turn.

7. Apollo (1882), 32-1

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

8. Charismatic (1999), 31-1

This race had an exciting finish as Charismatic and jockey Chris Antley made a late push in the homestretch to pull off a neck victory over Menifee. Charismatic almost earned Triple Crown by also winning Preakness. However, he finished third in Belmont and unfortunately suffered a career ending fracture.

9. Proud Clarion (1967), 30-1

Proud Clarion lost in all three starts of his two year-old career, but that was not a good indicator of what type of career he would have when he got older. He and jockey Bobby Ussery won the 93rd Kentucky Derby by a length, while also registering what was the third-fastest time at that point 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 had initially bought Exterminator not to race, but to help train two year old Sun Briar, a U.S. Champion.