Most Surprising Kentucky Derby Betting Winners

The 141st Kentucky Derby is less than two weeks away, and horse racing fans all over the world will be flocking to Louisville, Kentucky, to witness the most popular horse racing event of the year. In honor of this year’s Kentucky Derby betting, lets take a quick look at some of the most surprising winners of the “fastest two minutes in sports.”

Closer Look at the Most Surprising Kentucky Derby Betting Winners

#5. Charismatic and the Horse Racing Betting Odds (1999)

Charismatic was one of the biggest underdogs to ever win the Kentucky Derby with one of the best horse racing stories ever. In a sport where yearlings sell for millions of dollars, Charismatic was available for $62,500 the year he won the Derby. Going into the race, the odds of him winning were 31-1, but the horse lived up to his name and shocked the world by winning. He followed it up with a win at the Preakness and came close to winning the Triple Crown, taking the lead in the final furlong. Unfortunately, he ended up breaking a bone in his leg in two places, failing to win the race. Charismatic ended up paying out $64.60 to win.

#4. Gallahadion (1940)

The son of Reigh Count, the winner of the 1928 Kentucky Derby, pulled off one of the biggest upsets in the history of the race by winning the Derby despite the 36-1 odds he faced. At the time, Gallahadion was considered the second biggest upset in Derby history. He paid out $72.40 to win.

#3. Giacomo (2005)

The 2005 Kentucky Derby has one of the strangest finishes ever. Giacomo had the second longest odds of winning the race at 50-1, and ended up pulling off the second biggest upset in Kentucky Derby history. What makes it even crazier was that Closing Argument, the horse with the longest shot of winning, came in second. Whoever was lucky enough to place bets on those two horses coming in first and second, is probably still laughing all the way to the bank right now, with Giacomo paying out $102.60 to win, and Closing Argument paying out $70 to place.

#2. Mine That Bird (2009)

Mine That Bird tied Giacomo’s four year old record in spectacular fashion. The horse started out at 50-1 and trailed the leaders for most of the race. He eventually rallied back to the front and ended up winning the race by 6 3/4 lengths, capping a very wild event. Like Giacomo, he failed to win the Preakness, but his Derby win is still the second highest longshot win at the Kentucky Derby. Mine The Bird paid out $103.21 to win.

#1. Donerail (1913)

Since this race happened a long time ago, there isn’t too much information on the horse’s racing career, but from the information available, Donerail started the Kentucky Derby as a 91-1 longshot to win the race, which was higher than the 6-5 odds the leading contender –Ten Point– was given. Apparently, he was ridden by a jockey named Roscoe Goose, who liked riding longshots and was very familiar with the track at Churchill Downs. They were able to win the race, which ended up paying out $184.90 to win. These upsets are just a small reminder of why you shouldn’t put all your money on favorites, especially at the Kentucky Derby. At the upcoming race, make sure to put something on one or two longshots to win… you never know when the next big upset might happen.