Most Unforgettable Longshots in the History of Kentucky Derby
Most Unforgettable Longshots in the History of Kentucky Derby
Jun 18, 2024 11:38 AM

The finest thoroughbred horses across the U.S. and abroad compete in the Kentucky Derby to start their bid in the Triple Crown Series. The Triple Crown Series is known to be the most prominent horse racing competition in the whole world.

Like any other sports event, the crowd favorites who eventually win the title get extensive media exposure. That’s expected given that spectators have anticipated the horse to win the race.

Let’s discuss some of the unforgettable longshots in the history of the Kentucky Derby and how they managed to clinch the title even without the initial cheers of fans.


Donerail was a colt owned, trained, and bred by Thomas P. Hayes. He triumphed in the 1913 Kentucky Derby with unbelievable 91-1 odds. No other horse in the history of Derby surpassed and even got close to Donerail’s longshot record.

Roscoe Goose, the jockey who mounted Donerail in the Derby, became one of the most popular riding mentors of other successful jockeys like Eddie Arcaro and Charlie Kurtsinger.

Mine That Bird

With 50-1 odds, Mine That Bird was not expected to win the 2009 Kentucky Derby. However, the colt didn’t just prevail in the race. He won the Kentucky Derby by a shockingly large margin.

His longshot record was only second to Donerail, who won the race in 1913. But Mine That Bird’s record was knocked off by Rich Strike (80-1) in 2022 and Country House (65-1) in 2019, first- and second-highest, respectively.

He finished the Kentucky Derby by 6 3/4 lengths, topping one of the most astonishing come-from-behind victories in the history of Run for the Roses.

Animal Kingdom

Trained by H. Graham Motion, Animal Kingdom won both the 2011 Run for the Roses and the 2013 Dubai Cup. The chestnut stallion was awarded the American Champion Three-Year-Old Male Horse in the same year he won the Kentucky Derby.

Animal Kingdom has a 30–1 morning-line odds in the Derby and was 21–1 by post time. Nonetheless, the long shot managed to guarantee a 2+3⁄4 length victory.

He was mounted by the Puerto Rican jockey John R. Velazquez who was supposed to ride the early favorite Uncle Mo, who had suffered from gastrointestinal illness and failed to compete in the Derby. That time, Uncle Mo has topped FanDuel’s kentucky derby picks, among other betting sites. But, he was stripped of the field because of his health condition, giving way to the long-shot victory of Animal Kingdom.


Giacomo was a 50-1 longshot, tied with Mine That Bird as the second-best longshot record of a Kentucky Derby champion. This colt is owned by Jerome Moss and trained by John Sheriffs. Giacomo holds the second-highest Kentucky Derby payout with $102.60 on a $2 bet.

Donerail’s payout in the 1913 Derby is in the top spot, with $184.90. This colt’s bid for the Triple Crown title was derailed when he placed third in Preakness Stakes and seventh in the Belmont Stakes.


Owned by Ethel V. Mars’ Milky Way Farm Stable, Gallahadion was mounted by jockey Carroll Bierman in his 1940 Kentucky Derby win. This stallion was trained by Roy Waldron and bred by Robert A. Fairbairn. He was a 36:1 long shot in the Kentucky Derby. Nonetheless, he won the Derby against the heavy favorite, Bimelech, a 1939 U.S. 2-Year-Old Champion.

However, the overwhelming favorite has captured both Preakness Stakes and Belmont Stakes, frustrating Gallahadion. The iconic long short in the 1940 Kentucky Derby finished third in the second leg of the Triple Crown and fell short of securing a place in the Belmont Stakes.


Charismatic won both the Kentucky Derby and Preakness Stakes in 1999. He failed to ace in the Belmont Stakes and finished third instead. Bob and Beverly Lewis owned this stallion, and the legendary D. Wayne Lukas trained him. He was a 31-1 longshot in the first leg of the Triple Crown Series as he competed with 18 other horses.

With a 1:55.20 record for the 1+3⁄16-mile distance, Charismatic also triumphed in the Preakness Stakes, hopeful of nailing the Triple Crown title by winning the last leg of the series. There has been a long Triple Crown drought, and if Charismatic can manage to defeat Manifee, a strong contender in the Belmont field, he would be the first horse to claim the title after 21 years. However, he only placed third in the Belmont Stakes after fracturing his foreleg.

Country House

Country Horse was a chestnut colt who won the 2019 Kentucky Derby. He was trained by Bill Mott and bred by Joseph V. Shields. With odds of 65–1, Country Horse went on to win the Kentucky Derby after jockey Flavien Prat’s objection call, claiming Maximum Security, the supposed winner of the race, caused a near-spill. His longshot record was the third-highest, trailing Donerail (1913) and Rich Strike (2022).


Sports events as big as the Kentucky Derby sometime come with big surprises. These could either be awful injuries, unexpected attendance of prominent people, or iconic long shots winning the race. Upsets happen in any sport, but they hit differently in the Most Exciting Two Minutes in Sports.

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