The Long Shots
Everyone loves an underdog story, and a century and a half of Kentucky Derbies have delivered no shortage of surprise winners. These are three of the Rocky Balboas of the racetrack, horses that went unheralded until they ran for the roses.
Rich Strike 80-1
The horse in the outermost gate in the 2022 Kentucky Derby had the unusual number of 21. It was Rich Strike, and he wasn’t supposed to be there, but got a shot when the No. 20 horse was scratched. “We found out about 30 seconds before the deadline,” owner Rick Dawson told ESPN. The pace was fast, with a track record set by Summer is Tomorrow for the first quarter mile, with Rich Strike stuck in 15th place. He stayed there for the first mile before making his move at the last turn. In the final seconds, Rich Strike—who went off at 80-1—snuck up on the rail, thundering to a slim lead. “Oh my goodness!” shouted announcer Larry Collmus. “The longest shot has won the Kentucky Derby!” He’s had six races since (his last was May 23, 2023) but at press time had not won since his day of glory.
Mine That Bird 50-1
No horse had longer odds in the 2009 Derby than Mine That Bird, a 50-1 long shot with a crooked leg and a taste for peppermint candies. The racetrack was wet that day, and Mine That Bird ran dead last for nearly all of it. “Well behind the rest of them is Mine That Bird,” said announcer Tom Durkin. But suddenly in the final turn, Mine That Bird hit a gear no one thought it owned, ing one horse after another and making a move for the rail that caught Durkin by surprise. “An impossible result here!” he yelled. “A monumental upset.” The horse won by nearly seven lengths, the widest winning margin in more than six decades. He placed in the Preakness and Belmont Stakes, but never won again.
Donerail 91-1
Donerail’s owner, Thomas P. Hayes, had to be convinced by his jockey to enter the horse in the 1913 Kentucky Derby. He thought the feisty but unremarkable racehorse was outclassed. The oddsmakers agreed, putting him at 91-1. With not enough stables at Churchill Downs, Donerail slept some three miles away and had to walk to the track on May 10, 1913. The warmup seemed to do him good. The bay horse came from behind to overtake the favorite Ten Point by half a length in the biggest upset in Derby history. A $2 bet paid $184.90, a record that has endured for more than a century.
