The 8 Biggest Longshots That Managed To Win The Kentucky Derby

There isn’t a single horse race in the United States that attracts more interest than the Kentucky Derby, and the event has spawned plenty of impressive underdog stories over the decades. However, none of them stand out more than the literal dark horses that managed to defy the odds more than any other.

The horse listed as the favorite when the betting closes at the Kentucky Derby has won around 35% of the time since 1908, which means the winner of the first leg of the Triple Crown has defied the odds more often than not.

With that said, most of those victors didn’t have the kind of odds that made a bet on them seem absolutely foolish, but there are more than a few that really managed to stun everyone paying attention to the results at Churchill Downs.

Donerail: 91/1

There were only eight horses in the running at the Kentucky Derby in 1913, and Ten Points entered the race as the favorite at 11/5.

Donerail, on the other hand, was expected to be the ultimate also-ran at 91/1, and owner and breeder Thomas P. Hayes tried to convince jockey Roscoe Goose to go with another mount before he accepted his fate after a friend offered the foot the entry fee.

That turned out to be a pretty good decision, as Donerail was able to edge out Ten Point by half a length as Hayes walked away with the $5,475 purse handed to the winner.

Rich Strike: 80/1

Rich Strike didn’t seem like the horse to bet on if you wanted to strike it rich at the Kentucky Derby in 2022, but anyone who took a gamble on him had to be very pleased with the return on that investment.

Ethereal Road was slated to race from the 20th post but was scratched the day before the race to give Rich Strike and jockey Sonny Leon the opportunity they seized upon after the gates opened.

The duo stayed back of the pack before making a move on the rail in the final quarter mile and edged out Epicenter by 3/4 of a length to win the $1.86 million prize despite having the worst odds of the 20 entrants.

Country House: 65/1

This one is a bit unusual thanks to the circumstances surrounding the outcome of the race, as it appeared Maximum Security had won The Run For The Roses when he crossed the finish line ahead of the rest of the pack in 2019.

However, things took an unexpected and unprecedented turn after two jockeys (including Country House’s Flavien Prat) filed an objection that asserted Maximum Security had illegally interfered with the race by swerving during a turn while knocking other competitors out of position.

The stewards came to the same conclusion after a 22-minute review that led to the initial winner being disqualified, which meant Country House got the win in spite of the 60/1 odds that were the worst on the board that day.

Mine That Bird: 50/1

It didn’t seem like Mine That Bird had a shot to win the Kentucky Derby before it commenced in 2009, and that was still the case more than halfway through the race when you consider he and jockey Calvin Borel were dead last among the 20 horses in contention ahead of the final turn.

However, we were treated to some incredible dramatics in the home stretch as Mine That Bird surged toward the front of the pack that the horse ended up at the front en route to beating Pioneerof the Nile by 6 3/4 lengths as owner Bennie L. “Chip” Woolley Jr. took home over $1.4 million.

Giacomo: 50/1

Mine That Bird technically had slightly worse odds than Giacomo if you dive deeper into the numbers (specifically 50.8 compared to 50.3), but the latter was still a longshot in the 2005 Kentucky Derby where Bellamy Road was the 5/2 favorite.

Giacomo and jockey Mike Smith stayed near the back for the first half of the race before they made their move toward the front and ultimately prevented an even bigger underdog—the 71/1 Closing Argument—from getting the win by edging him out by half a length to get the $1.64 million grand prize.

Gallahadion: 36/1

If you squint hard and look all the way to the right of that picture, you can spot Gallahadion, who was one of the eight horses who lined up in the electronic gate that was deployed in the Kentucky Derby for the first time in 1940.

The odds may not have been in his favor, but jockey Carroll Bierman helped defy them while helming Gallahadion to the finish line during a race he won by one-and-a-half lengths.

Charismatic: 31/1

The legendary (and ultimately disgraced) Bob Baffert headed into the Kentucky Derby in 1999 hoping to become the first trainer to win the race three years in a row, and he was in charge of three different horses who had the chance to help him make history.

However, that trio—and the other 18 horses in the race that year—were ultimately outfoxed by Charismatic and jockey Chris Antley, who pulled off the stunning upset that was the third-largest in Kentucky Derby history at the time.

Proud Clarion: 30/1

Damascus (who would go on to win the Preakness and the Belmont Stakes) was the overwhelming favorite heading into the Kentucky Derby in 1967, and the odds tell you all you need to know about how Proud Clarion was perceived.

However, jockey Bobby Ussery was able to pilot him to victory by a length ahead of Barbs Delight, who took place while Damascus settled for show.