Meet the 15 Biggest Long Shot Horses to Ever Win the Kentucky Derby

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Written by Justin Zipprich

Updated: May 4, 2023

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There are many reasons why people attend the Kentucky Derby. Some just want to see the gorgeous horses in their full glory, and some like the idea of wearing the festive outfits and hats. Then there are those who like to place a friendly wager on the race and try to win some money. If you’re in that final category, and you ever bet on the underdog for the races below, then you won a pretty penny. Let’s look at some of the biggest long shot horses to ever win the Kentucky Derby.

Horse Racing and Odds Explained

In order to understand when we tell you about the biggest long shot horses to ever win the Kentucky Derby, you must know a bit about gambling and how the odds work

If you just make a regular bet and you see that the odds are something like 5-1, that means that for every dollar you bet, you will make five dollars. So, $1 will win you $5. If you bet $100, then you’ll win $500. You would also get the initial money that you bet in the first place back as well. In the case of the horses on this list, they had much larger odds. In the case of the horses that had odds of 50-1, where $1 gets you $50, you can see how profitable that would be. Just imagine if you bet $100 instead of $1.

Of course, the chances of a horse with such long shot odds actually winning is incredibly rare, and winning money in these instances requires luck that most people typically don’t have. So, don’t go to the track expecting to get rich on one visit. Of course, you should also always gamble responsibly.

Without further ado, here are some of the most famous long shot horses to ever win the Kentucky Derby.

Donerail (1913). Odds: 91-1

Our first of the biggest long shot horses to ever win the Kentucky Derby is the famous Donerail, who raced all the way back in 1913. This is the biggest long shot to ever win the Derby, and we may not see something like this again. Bred and trained by Thomas P. Hayes, Donerail won the race by an incredible half-length. The incredible odds of 91-1 mean that for every dollar bet, the gambler got $91 in return. 

Rich Strike (2022). Odds: 80-1

It took over 100 years to get odds almost as unbelievable as the record set by Donerail, but Rich Strike was close by winning the Kentucky Derby with odds of 80-1. Part of the reason for the big odds is that Rich Strike wasn’t even supposed to race, but another horse, Ethereal Road, had to drop out. Betters probably thought that Rich Strike wouldn’t have a chance since the horse was added so abruptly.

Country House (2019). Odds: 65-1

Our next of the wildest long shot horses to ever win the Kentucky Derby is the amazing Country Horse, with crazy odds of 65-1. There’s a crazy story that goes along with this one. 

When the race originally came to an end in 2019, it appeared that the horse named Maximum Security had won. However, the jockey for Country Horse, Flavien Prat, filed an objection. He said that Maximum Security left his lane and hit another horse during the final turn, which is a foul in this sport. Because of that foul, Maximum Security was disqualified and the long shot Country Horse won the race with wild 65-1 odds.

Mine That Bird (2009). Odds: 50-1

There are two athletes on this list of the biggest long shot horses to ever win the Kentucky Derby who won with 50-1 odds, and the first is Mine That Bird. Although the horse had these crazy odds, betters should have known better, especially since his father, Birdstone, was the 2004 Belmont winner. Part of the reason may have been that his trainer was a complete unknown and didn’t have a track record of success. 

Still, the odds were in place, and Mine That Bird ended up winning the Kentucky Derby by 3/4 lengths after a hard-fought race, mostly because jockey Calvin Borel was able to sneak between two other horses to eke out the win. Later on, Mine That Bird found his way into the Canadian Horse Racing Hall of Fame in 2015.

Jockeys storm down the homestretch in a claiming race.

Many amazing underdogs have won the Kentucky Derby, including the awesome Giacomo at 50-1 odds.

Giacomo (2005). Odds: 50-1 

The other horse to win the Kentucky Derby at 50-1 odds was Giacomo. During the race of 2005, all of the underdogs were having great success. On top of the fact that Giacomo won the race with such crazy odds, another horse, Closing Argument, came in second, and he had 70-1 odds. If someone was at that race and chose both of those horses to come in first and second place, they would have won thousands of dollars. 

Gallahadion (1940). Odds: 35-1

As we hit this point in the list, we will see that the odds start to go down quite a bit. Still, if you happened to have bet on a horse like Gallahadion in 1940, $1 would have still made you $35, and that was a ton of money back in the 40s. Gallahadion really set the world on fire during that year’s derby, winning by 1 1/2 lengths ahead of Bimelech, which was the heavy favorite that year. Gallahadion kept pace the entire time, until the final turn, when he and his jockey raced past two horses to get the win.

Apollo (1882). Odds: 32-1

Next on our list of the craziest long-shot horses to ever win the Kentucky Derby is Apollo who beat the odds way back in 1882. Apollo was a long shot because unlike the other competitors, he had not professionally raced until he was three years old. Apollo took the win by a half-length at odds of 32-1. 

Charismatic (1999). Odds: 31-1

Spectators at the 1999 Kentucky Derby didn’t know that long shot Charismatic would pull off a victory until the very end. Towards the conclusion of the race, jockey Chris Antley put his golden horse into full gear to pull off a tight victory against frontrunner Menifee. What else should we have expected from famous trainer D. Wayne Lukas? Betters were probably put off because Charismatic barely qualified for the Derby in the first place, but nonetheless, he pulled it off. Although that was a happy moment, unfortunately Charismatic suffered from a career-ending fracture later on at the Belmont Stakes. 

Proud Clarion (1967). Odds: 30-1

If you were around in 1967, then no one would hold it against you if you bet against Proud Clarion. A horse’s prime comes during the first two years of its life, and during Proud Clarion’s first two years, the horse lost all three starts, so it wasn’t looking good. However, like a fine wine, Proud Clarion got better with age and was able to get a win during the 1967 Kentucky Derby by a length. 

As an added piece of trivia, Proud Clarion also won in the third fastest time in Derby history at just over two minutes.

Exterminator (1918). Odds: 29-1

Another of the most insane long-shot horses to ever win the Kentucky Derby was the boldly named Exterminator, who was yet another older horse entering the race at three years old. Once again, age meant nothing in this case because Exterminator was able to beat Escoba, who was the favorite, and went on to win by a full length and on a muddy track to boot! What makes the win more interesting is that Exterminator wasn’t raised to race at all, but owner Willis Sharpe Kilmer saw something in the horse, and the rest is history. 

Thunder Gulch (1995). Odds: 25-1

The spectators had no faith that Thunder Gulch would become one of the many long shot horses to ever win the Kentucky Derby, and they considered him to be a generally untalented horse. However, you should never underestimate a good horse or the unpredictability of the Kentucky Derby. In the end, Thunder Gulch was able to cross the finish line first at a record pace of 2:01.2

Gato Del Sol (1982). Odds: 21-1

Though he wasn’t the longest-shot on the card during the 1982 Kentucky Derby, Gato Del Sol wasn’t exactly setting the world on fire during his three year career. The horse had some small victories, but no one expected him to win the big Derby. However, he pulled off the victory while winning by a whopping 2 ½ lengths. Some experts say that the lineup of horses was especially weak that year and that any horse had a chance to win. Still, you can’t take anything away from Gato Del Sol because the horse put on an amazing performance.

Animal Kingdom (2011). Odds: 21-1

This was yet another example of how gamblers at the Kentucky Derby likely could not have known that the winning horse was a contender. At 21-1 odds, most betters passed by Animal Kingdom. Part of the reason was that they were in a panic when former favorite, Uncle Mo, suddenly had to exit out of the race. Once that happened, another horse, Dialed In, became the favorite. 

On top of the craziness of the day, Animal Kingdom was also unproven up until this point since he had only run on turf and synthetics and had not yet run on conventional dirt. After this amazing win, Animal Kingdom went on to win the Dubai World Cup when he was 4-years-old.

Lil E Tee (1992). Odds: 17-1

Gamblers at the 1992 Kentucky Derby didn’t think much about Lil E Tee. Instead, all eyes were on the hot horse Arazi, who spectators thought was the newest star on the block that was close to unbeatable. Money spent on Arazi was wasted as the horse ended up placing in eighth. On top of that, potential second favorite, A.P. Indy, had to be removed from the race. 

What they forgot to remember is that Lil E Tee had jockey Pat Day riding up top, who was known for his patience and prowess on the track. Because of his strengths, Lil E Tee was able to win by a length and wow the crowd.

Go for Gin (1994). Odds: 9-1

Seeing Go for Gin become the winner during the 1994 Kentucky Derby was shocking, to say the least. Among other horses, Go for Gin was going against Holy Bull, who had won eight of his last nine starts and was on a hot streak. Well, every steak has to come to an end. It didn’t help that a massive rain storm had just come through the area and left the track a slippery and muddy mess. Needless to say, Holy Bull put on a poor performance, which led the way for Go for Gin to win by two lengths at 9-1 odds. 

Conclusion

There’s your list of some of the most amazing long shot horses to ever win the Kentucky Derby. These are horses that beat the odds and proved that even animals can make an awesome claim to victory when they want to succeed. Of course, the jockeys were pretty helpful as well. The next time you attend the Kentucky Derby, consider betting on a long shot!


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About the Author

Justin Zipprich is a writer at A-Z Animals, where his primary focus is travel, state facts, pets, and mammals. Justin has been writing and editing animal content for over 7 years, though he holds a Bachelor’s Degree in Instructional Technology from Western Illinois University, which he earned in 2005. As a resident of Texas, he loves discovering local animals and spending time with his wife and two kids.

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