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Rich Strike and the 5 biggest long-shots ever to win the Kentucky Derby

Everybody likes an underdog. Especially in horse racing, right?

Long-shots have had success at the Kentucky Derby more often in the past two decades. Indeed, Donerail in the 1913 is still the biggest long-shot to win, but the next four have all come in the 21st century. The most recent entry into this group was Rich Strike, who won in a ridiculous upset last year.

This year, a handful of horses have 50-1 odds. Perhaps Raise Cain or Sun Thunder will shock the field and come out on top and join the group of the biggest long-shots to win.

Before this year’s Derby, let’s take a look at the biggest long-shots to win it all.

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Mine That Bird

Like Giacomo, Mine That Bird entered the 2009 race with 50-1 odds. He trailed by more than 20 lengths at one point, then rallied and went on to win by nearly seven lengths. At the time, it was the largest margin of victory since 1946. Unfortunately, the film inspired by the unlikely win has a 29% rating on Rotten Tomatoes.

Giacomo

In 2005, this horse was overlooked by bettors because he had won just one of the seven races he had previously run in. Giacomo entered with 50-1 odds. It was a big win for the horse’s owner, Jerry Moss, who was inducted into the Rock and Roll Hall of Fame in 2006. Moss named the horse after Sting’s son.

Country House

This is kind of a weird one. In 2019, Country House wasn’t the first horse to cross the finish line; Maximum Security was. However, after a 22-minute deliberation, Maximum Security was controversially disqualified for interference because he swerved into the path of fellow horses War of Will and Long Range Toddy. It was the first time in Kentucky Derby history that a winning horse had been disqualified for an on-track infraction. And so, Country House, at 65-1 odds, was crowned the winner. Due to various ailments, Country House never ran another race. What a way to go out.

Rich Strike

Entering the race with 80-1 odds, this horse shocked the world in 2022. Remember, this horse wasn’t even in the Derby field until Ethereal Road scratched the morning of the race.

Donerail

This horse won in 1913 with 91-1 odds. A $2 bet would’ve cashed in at $184.90, which was quite a bit of money in those days. According to media accounts at the time, Donerail and his trainer made a three-mile walk the morning before the race because of a lack of stable space at Churchill Downs. As it turns out, that long walk was just a good warm-up.

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