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the biggest kentucky derby upsets

The Biggest Kentucky Derby Upsets

The Kentucky Derby, known as the “Run for the Roses,” is a prestigious horse racing event that captures the hearts of enthusiasts worldwide. While favorites often dominate the track, the Derby has seen its fair share of unexpected victories that have left both bettors and spectators stunned. In this article, we’ll delve into some of the most significant Kentucky Derby upsets that have etched their place in the annals of racing history.

fonerail 1913 a shocking triumph

1. Donerail (1913): A Shocking Triumph

The 39th Kentucky Derby witnessed one of the most remarkable upsets in its history when Donerail, a 91-1 underdog, emerged victorious. Against the odds, jockey Roscoe Goose piloted Donerail to a stunning finish, passing his competitors in the final stretch and securing a thrilling victory. Donerail’s triumph remains a testament to the unpredictable nature of horse racing, proving that any contender can seize the glory on Derby day.

2. Mine That Bird (2009): A Cinderella Story

In 2009, the Kentucky Derby witnessed another monumental upset with the victory of Mine That Bird. At 50-1 odds, Mine That Bird’s triumph stands as one of the most improbable in Derby history. Under the skillful guidance of jockey Calvin Borel, Mine That Bird navigated through a crowded field, surging ahead in the final stretch to seize the win. The victory served as a reminder that underdogs can defy expectations and write their triumphant narratives.

3. Giacomo (2005): From Obscurity to Glory

The 2005 Kentucky Derby introduced the world to Giacomo, a longshot contender with odds at 50-1. Despite his underdog status, Giacomo surged ahead in the final moments of the race, overtaking favorites like Bellamy Road and Afleet Alex. Jockey Mike Smith guided Giacomo to an unforgettable victory, showcasing that perseverance and determination can lead to unexpected triumphs even in the most prestigious racing events.

4. Charismatic (1999): Seizing the Spotlight

In 1999, Charismatic delivered a stunning upset by winning the Kentucky Derby at odds of 31-1. Charismatic’s victory marked a story of resilience and determination, as he had previously raced in claiming races before his ascent to the Derby stage. Jockey Chris Antley expertly guided Charismatic to victory, capturing the hearts of racing fans and proving that the Derby is a stage where underdogs can emerge as champions.

5. Orb (2013): A Muddy Miracle

The 2013 Kentucky Derby showcased the unpredictable nature of the sport when Orb, a 5-1 favorite, claimed victory on a wet and muddy track. The challenging conditions didn’t deter Orb, who surged ahead in the final stretch to secure the win. Orb’s triumph highlighted the influence of factors beyond odds and favorites, reminding us that Derby’s outcome can be shaped by the elements and the grit of the contenders.

6. Exterminator (1918): The Iron Horse’s Triumph

Exterminator, affectionately known as the “Iron Horse,” is a legendary figure in horse racing history. In 1918, he defied his 30-1 odds to clinch victory in the Kentucky Derby. Exterminator’s ability to outlast his competitors earned him the nickname, and his unexpected Derby win solidified his place as a true champion. Exterminator’s story resonates as a testament to the tenacity and heart required to achieve the seemingly impossible.

The Kentucky Derby’s history is peppered with unforgettable moments, and some of the most remarkable are the upsets that have left spectators in awe. These victories remind us that the spirit of competition is alive on the racetrack, where underdogs can rise to the occasion and capture the glory against all odds. The stories of Donerail, Mine That Bird, Giacomo, Charismatic, Orb, and Exterminator serve as a testament to the essence of horse racing, where anything can happen and the thrill of victory is often found in the most unexpected places. As racing enthusiasts gather to witness the next Kentucky Derby, they’ll do so with the knowledge that the race’s history is paved with the hoofprints of the greatest upsets that have graced the track.