Biggest Longshots to Win the Kentucky Derby

50-1 odds: One of the wildest Kentucky Derby runs in modern history, Giacomo, ridden by hockey Mike E. Smith, entered with 15th best odds among the 20 horses entered. He won by 1/2 length over second-place Closing Argument, who carried the worst odds of any horse in the field. Favorite Bellamy Road finished in seventh. Had you placed a $2 exacta bet, you’d have won $9,814.80.

4. Mine That Bird - 2009

50-1 odds: Mine That Bird’s odds to win the Kentucky Derby in 2009 were even lower than Giacomo’s considering only two horses had a lower chance, by the betting numbers. But Calvin Borel, who had won the Derby in 2007 and would win it again in 2010, jockeyed the horse to a first-place finish.

3. Country House - 2019

65-1 odds: Country House did not cross the finish line first in 2019 as Maximum Security, the horse with the second-best odds entering the race, managed to do it. But the horse was disqualified because judges determined it shifted its position in a manner that impeded another horse. The controversy marked the first time an otherwise winning horse was disqualified from the Derby because of an on-track infraction.

MORE: What Is the Payout for the Kentucky Derby Winner?

2. Rich Strike - 2022

80-1 odds: No horse in the gates had worse odds to win the 2022 Kentucky Derby than Rich Strike. The horse had not even been in the field until the day before the race, taking the place of Ethereal Road, who was scratched. Rich Strike became just the second horse to ever win the Derby from the 20th post, while jockey Sonny Leon won his first graded stakes race of any kind.

1. Donerail - 1913 

91-1 odds: Donerail’s odds to win the Kentucky Derby were well longer than any other winner’s. So high, in fact, it’s hard to imagine another horse ever registering such a small betting chance. As such, the horse remains a legend, a testament to the craziness that can happen in the sport when taking part in “the most exciting two minutes in sports.”