Hobbies Card Games & Gambling 10 Biggest Kentucky Derby Long Shots Unlikeliest Kentucky Derby Winners That Beats the Odds Share PINTEREST Email Print A rider attempts a win at the Kentucky Derby. Tobias Titz / Getty Images Card Games & Gambling Sports Gambling Gambling Strategies & Tips Casinos Poker Blackjack By Cindy Pierson Dulay Cindy Pierson Dulay is a horse-racing expert, journalist and award-winning photographer. She is the owner and editor of Horse-Races.Net. our editorial process Cindy Pierson Dulay Updated January 13, 2019 The Kentucky Derby is undeniably the most important race in North America for 3-year-old thoroughbreds. There have been some real upsets over the years, with unsung heroes rushing from the back of the pack to overtake favorites. Here's a list of the 10 long shots that paid the most money when they won the "Run for the Roses" seemingly against all odds. 01 of 10 Donerail Donerail's sign on the grandstand at Churchill Downs. Cindy Pierson Dulay Donerail paid $184.90 on a $2 bet to win the Derby in 1913. He's still the highest paying winner ever. He was sent off at odds of 91-1. Each Kentucky Derby winner has its name on a sign at the back of the grandstand at Churchill Downs. Donerail's sign is to the left. 02 of 10 Mine That Bird Al Bello/Staff/Getty Images Mine That Bird trailed most of the race before rallying down the inside in the stretch to win by 6 3/4 lengths. He did it at odds of 50-1, paying $103.20 to win the 2009 Kentucky Derby. He went on to finish second to Rachel Alexandra in the Preakness, and third behind Summer Bird and Dunkirk in the Belmont. Mine That Bird was a gelding who continued to race until November 2010, but he never recaptured his Kentucky Derby glory. He raced nine more times but never won again, then he retired. He has made several appearances as the resident horse at the Kentucky Derby Museum and his story was immortalized in the movie "50 to 1." 03 of 10 Giacomo Giacomo wins the 2005 Kentucky Derby. Cindy Pierson Dulay Giacomo seemed to come out of nowhere when he closed late on the far outside to win the 2005 Kentucky Derby at odds of 50-1. He paid $102.60 to win, the second highest payout on a $2 bet in Kentucky Derby history. 04 of 10 Gallahadion Postcard of Gallahadion after winning the 1940 Kentucky Derby. Cindy Pierson Dulay Gallahadion won the Derby at odds of 36-1 in 1940. His lack of popularity among Kentucky racegoers might have had something to do with him being a California horse, or it might have been the fact that he ran horrifically in his first two races. But he excelled in the Kentucky Derby, paying $72.40 to win, the third highest winning payout in Kentucky Derby history. 05 of 10 Charismatic Matthew Stockman/Staff/Getty Images Charismatic is something of a Cinderella story. He was a "claimer" not long before the Derby, running in some of the weakest races against the poorest competition in the country. No wonder he went off at odds of 31-1. He just got up by a neck to win, paying $64.60 in the 1999 Kentucky Derby. He went on to win the Preakness and was third in the Belmont, where he broke his leg just after the finish. Jockey Chris Antley pulled him up and kept his leg off the ground until the vet arrived. He had surgery the next day and is currently standing at stud in Japan at Iburi Stallion Station. 06 of 10 Proud Clarion Patrick Smith/Staff/Getty Images Proud Clarion won the Derby in 1967 at odds of 30-1. He paid $62.20 to win. It was the fifth highest winning-ticket payout in Kentucky Derby history. He also had the sixth fastest time for a Derby win with a final time of 2:00.60 for the mile and a quarter. 07 of 10 Exterminator Rob Carr/Staff/Getty Images Exterminator might have surprised the world when he won the Kentucky Derby at odds of 29-1 in 1918, paying $61.20 to win, but he went on to have a stellar career. Racing until age 9, the gelding won 50 of his 100-lifetime starts, including many stakes races. He was a fan favorite. 08 of 10 Dark Star Dark Star's sign on the grandstand at Churchill Downs. Cindy Pierson Dulay Dark Star won at odds of 25-1 in 1953, paying $51.80 on a $2 bet to win. This was the seventh highest winning payout ever in the Kentucky Derby. He ran in the Preakness but he didn't make it into the money and was retired after that race. 09 of 10 Thunder Gulch Thunder Gulch at Ashford Stud in 2007. Terence Dulay Sent off at odds of 25-1, Thunder Gulch had the longest odds of the three horses that trainer D. Wayne Lukas entered in the 1995 Kentucky Derby. He drew off to win by 2 1/4 lengths and paid $51. He was third in the Preakness before he went on to win the Travers Stakes and the Kentucky Cup. He retired to stud at the end of his 3-year-old season. 10 of 10 Stone Street Harry How/Staff/Getty Images Stone Street went off at odds of 24-1 in the 1908 Kentucky Derby and paid $123.60 on a minimum bet, which was $5 at that time. That would be $49.40 for the modern-day $2 bet. The Derby was the only stakes win of his career. Is There a Long Shot in Your Betting Future? Long shots are out there and they can win the "Run for the Roses" at any time, in any year. Watch this year's entries closely for the horse who might surprise everyone.