Kentucky Derby Long Shots: 5 Biggest Winners in History

Mike Schultz | Fri. May 06 2016, 03:05 pm

charismatic kentucky derby long shot winner

Some of the greatest stories throughout sports history are the inspiring tales of the long shots. The unknown underdogs that were never expected to win, let alone become household names and legends in their respective sports. Horse racing has it’s share of long shots who defied the odds to win, and the Kentucky Derby has provided some of the most astounding and inspiring examples of this phenomenon.

As the 142nd Kentucky Derby approaches, we wanted to take a look at history’s five biggest underdogs at this legendary race at Churchill Downs in Louisville, Kentucky. This year, the odds have two horses as the longest shots to win, Trojan Nation and Oscar Nominated. Will one of them astound horse racing fans around the world and shatter expectations when they enter the winner’s circle?

Top 5 Kentucky Derby Longshot Winners

donerail long shot kentucky derby winner

1. Donerail

In 1913, Donerail set a record that has yet to be beaten. With odds set at 91-1, a $2 bet on Donerail provided a $184.90 payoff for the lucky few who took a chance on him. In 62 races, Donerail only won 10 times. When he retired in 1917, his stud services cost breeders $50. Eventually he was used to sire cavalry horses for the Remount Service, a general horse-breeding program started by the the US Department of Agriculture.

mine that bird long shot kentucky derby

2. Mine That Bird

In 2006, Mine That Bird was more than just a long shot winner at 50-1, with a 2$ wager paying out $103.20. He was also only the second gelding since 1929 to win the Kentucky Derby, and one of only nine geldings to win in the entire history of the race. Racehorses are not usually gelded, but if the horse displays erratic behavior, gelding can often help calm them. Mine That Bird, whose sire Birdstone won the 2004 Belmont Stakes, went on to place second in the Preakness Stakes and third in the Belmont Stakes.

giacomo kentucky derby long shots

3. Giacomo

Giacomo and Mine That Bird tie each other for being the second biggest long shots in Derby history, with 50-1 odds. Giacomo accomplished this feat in 2005, and what was just as remarkable that year was that the second place finisher behind Giacomo was another 50-1 long shot named Closing Argument. He went on to place third in the Preakness Stakes, but had a disappointing seventh place finish in the Belmont Stakes. Giacomo is owned by Jerry Moss, founder of A&M Records, who named his odds-defying horse after the son of rock legend Sting.

Gallahadion kentucky derby upset long shot

4. Gallahadion

Even though Gallahadion came from an impressive legacy of winners – his sire was Sir Gallahad III, and his damsire was the winner of the 1928 Kentucky Derby, Reigh Count – he was not considered a real contender at the 1940 Kentucky Derby, where he was given 36-1 odds after not placing in two prep races. Owned by Ethel Mars, a founder of the famous Mars’ candy company, Gallahadion got his name from one of the chocolate bars they produced.

charismatic kentucky derby long shot winner

5. Charismatic

Charismatic was another horse with an impressive bloodline who entered the Kentucky Derby as a long shot. Charismatic’s was a third generation descendant of both Secretariat and Northern Dancer, and his sire, Summer Squall, was the winner of the 1990 Preakness Stakes. Charismatic’s odds at the Derby were 31-1, and he went on to win the Preakness Stakes as well. By the time he entered the Belmont Stakes that year, Charismatic was a 2-1 favorite. Charismatic broke his leg in the final furlong of that race, but still managed to place third.

Kentucky Derby Betting

To bet on the long shots in this year’s Race to the Roses, visit our betting page on the 2016 Kentucky Derby race.