The Top 5 biggest Upsets in Kentucky Derby History

The Top 5 biggest Upsets in Kentucky Derby History

The Top 5 biggest Upsets in Kentucky Derby History

By Fan Arch March 12, 2024 22:30

The Kentucky Derby is an iconic event in American sports culture, known for producing unforgettable moments and showcasing the incredible athleticism of Thoroughbred racehorses. While most memorable Kentucky Derby moments involve heavily favored horses securing victory, the race has also seen its fair share of stunning upsets. Let's delve into the top 5 biggest upsets in the history of the Kentucky Derby, each of which left a lasting mark on the sport.

1) Donerail, 1913

How It Happened:

In 1913, Donerail shocked the nation with a stunning upset at odds of 91-1, rallying from off the pace to win by half a length.

Why It Was Shocking:

Donerail's upset victory returned $184.90 on a $2 win wager, which remains the biggest $2 win payout in Kentucky Derby history to date.

Why It's Here:

At astronomical odds, Donerail holds the title as the longest shot to ever win the Kentucky Derby, cementing his permanent place in the history books.

2) Gallahadion, 1940

How It Happened:

In 1940, Gallahadion, a 35.20-1 longshot, rushed up along the rail to overtake the heavy favorite, Bimelech, and won going away by 1 ½ lengths.

Why It Was Shocking:

Gallahadion's unexpected victory over the champion 2-year-old, Bimelech, in the Kentucky Derby stands as one of the most shocking results in the race's history.

Why It's Here:

Despite finishing third and fifth in the subsequent Preakness Stakes and Belmont Stakes, Gallahadion's Kentucky Derby win remains a remarkable upset in the annals of horse racing.

3) Dark Star, 1953

How It Happened:

In 1953, Dark Star, a 25.20-1 longshot, won the Kentucky Derby after Native Dancer, the overwhelming favorite, faced a nightmarish trip, settling farther back than expected.

Why It Was Shocking:

Dark Star's victory over the highly regarded Native Dancer, who entered the race with 11 consecutive wins, stands as one of the biggest upsets in Kentucky Derby history.

Why It's Here:

Dark Star's triumph over the heavily favored Native Dancer is widely regarded as one of the most significant upsets in the history of the Kentucky Derby, showcasing the unpredictable nature of the sport.

4) Giacomo, 2005

How It Happened:

In 2005, Giacomo rallied desperately at odds of 50-1 to hold off fellow long shot Closing Argument and etch his spot in the history books, prevailing by half a length.

Why It Was Shocking:

Giacomo's victory over the much-hyped Bellamy Road, sent off as the favorite and finishing a non-threatening seventh, marked one of the most thrilling finishes in Kentucky Derby history.

Why It's Here:

With only a maiden win to his credit prior to the Derby and a fourth-place finish in his most recent prep race, Giacomo's stunning form reversal was a true shock to bettors and racing fans alike.

5) Rich Strike, 2022

How It Happened:

In 2022, Rich Strike, an 80-1 longshot, shocked the field with a dramatic win, jolting ahead out of nowhere to claim an unlikely victory.

Why It Was Shocking:

Rich Strike's win was the most unlikely result in nearly 150 years of the Kentucky Derby, with his entry into the race requiring a fortunate turn of events.

Why It's Here:

Rich Strike's victory in the Kentucky Derby in 2022 stands as the most shocking upset in 109 years, solidifying its place among the most remarkable moments in the history of the race.

These monumental upsets in the Kentucky Derby have demonstrated the unpredictable and thrilling nature of horse racing. From Donerail's historic win in 1913 to Rich Strike's astonishing upset in 2022, these races have left an indelible mark on the sport and continue to captivate racing enthusiasts around the world.

As the Kentucky Derby remains an essential part of American sports culture, these upsets serve as a testament to the enduring allure and excitement of Thoroughbred racing, where anything can happen, and underdogs can defy the odds to etch their names in the annals of racing history.

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