Kentucky Derby: All-Time Biggest Longshots
May 03, 2016 10:18am

Although everyone wants to make some money in the Kentucky Derby, betting the favorite will not provide much of a return. The high payoffs come with the longshots. Since 1911, it’s been tradition to place a $2 bet, and betting $2 on a longshot is a minimum loss compared to what you could win. Below are the 10 horses with the highest payoffs since the $2 bet came into play.


1.) Donerail (1913): No other horse has come close to the longshot win that Donerail had in the Kentucky Derby. He was sent off at odds of 91-1 and paid $184.90. Donerail had a short career at stud in Lexington before being donated to the Remount Service to produce horses for the cavalry.


2.) Mine That Bird (2009): Mine That Bird had four wins as a two-year-old in Canada and finished second and fourth in New Mexico at age three. His trainer loaded the gelding in a trailer attached to his pick-up truck and drove to Churchill Downs with a broken foot. Mine That Bird was given 50-1 odds and paid $103.20 after his shocking win up the rail. He may not have won another race after the Kentucky Derby, but his victory that day is not forgotten.


3.) Giacomo (2005): Giacomo ties with Mine That Bird for having the second highest Kentucky Derby odds at 50-1. He looked promising after breaking his maiden by 10 lengths as a two-year-old, but that was his only win going into the Kentucky Derby. His surprising win paid $102.60. Giacomo only won once more in his racing career when he crossed the wire first by a head in the 2006 San Diego Handicap.


4.) Gallahadion (1940): Gallahadion was owned by Ethel V. Mars’ Milky Way Farm. The farm’s name came from the chocolate bar that Mars’ company produced. Gallahadion was another horse that did not see as much success outside the Kentucky Derby. He was unplaced in two California Derby preps, but the decision was made to enter him for the first Saturday in May after he won the San Vicente and finished second in the Derby Trial. Off at odds of 36-1, his win paid $72.40.


5.) Charismatic (1999): Before winning the Kentucky Derby, Charismatic’s record held 3 wins out of 14 races. Those victories came from a maiden claiming race, another claiming race, and the Lexington Stakes. His 31-1 odds in the Kentucky Derby paid $64.60 to win.


6.) Proud Clarion (1967): Coming from a top pedigree, Proud Clarion was given high expectations that he did not quite live up to. He had no wins from three starts as a two-year-old, and only won a few sprint races before the Kentucky Derby. His best prep for the race was the Blue Grass where he finished second. He went off just over 30-1 in the Kentucky Derby and paid $62.20. He had no wins outside his three-year-old year.


7.) Exterminator (1918): When his owner’s U.S. Champion Two-Year-Old Colt Sun Briar scratched from the Kentucky Derby, Exterminator was grudgingly entered instead. Having been bought merely as a work mate for Sun Briar, no one expected much and Exterminator stunned the field at odds of 30-1 to pay $61.20. The gelding became known as “Old Bones” by his fans and raced 99 times. He retired at age nine with a record of 50-17-17.


8.) Dark Star (1953): Even with odds at 25-1, Dark Star won the Kentucky Derby and handed Native Dancer his only defeat. The upset paid $51.80. Dark Star won 6 of 13 races during his career.


9.) Thunder Gulch (1995): Though he had won both the Fountain of Youth and the Florida Derby, Thunder Gulch was given odds of 25-1 in the Kentucky Derby, where his win paid $51.00. He went on that year to win the Belmont, the Swap Stakes, the Travers, and the Kentucky Cup Classic Handicap, earning Eclipse Champion Three-Year-Old Colt.


10.) Gato Del Sol (1982): With his only two wins before the Kentucky Derby being at two-years-old, Gato Del Sol went off at Churchill Downs with odds of 21-1. His Kentucky Derby victory paid $44.40. He ran 39 times in his racing career, but only won four other races after the Kentucky Derby.

By Christine Oser


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