The 5 Most Dramatic Finishes in Preakness Stakes History

The Preakness Stakes is a crucial leg in the race for the Triple Crown, captivating fans each year with thrilling moments. It’s where the best horses compete, creating unforgettable memories.

Dramatic finishes at the Preakness have become legendary tales, showcasing the power and beauty of horse racing. These heart-pounding moments define careers and engrave stories into the sport’s history, making every race a potential page-turner.

Cloud Computing’s Upset Victory, 2017

In 2017, Cloud Computing entered the Preakness Stakes with the odds stacked against him. Having not competed in the Kentucky Derby, many critics doubted his potential for success in such a competitive field. But anyone watching the race closely, just like people looking at the Preakness 2024 live odds now, knows that horse racing is always full of surprises and thrills.

On the race day, his team had a plan. They paced him perfectly, keeping him close but not in the lead too early. In a thrilling final stretch, Cloud Computing surged ahead, beating the favorites to the finish line.

This unexpected win shocked many and proved that underdogs could triumph. The victory boosted Cloud Computing’s reputation and reminded everyone in horse racing that surprises could come from anywhere. It showed the importance of strategy and heart. Cloud Computing’s win is now a favorite story for fans, adding depth to his legacy and the rich history of the Preakness Stakes.

War of Will’s Redemption, 2019

War of Will faced a tough time at the Kentucky Derby in 2019, where a controversial moment left him without the win many thought he deserved. Despite this setback, he and his team didn’t lose heart. Arriving at the Preakness Stakes, they were determined to prove their mettle.

With skilled navigation through a crowded field, War of Will showcased his speed and agility, overcoming obstacles to claim victory. This win was more than just a race result. It was a powerful statement about resilience and the spirit of redemption in sports.

It also highlighted how setbacks can set the stage for comebacks, turning disappointment into a driving force for success. War of Will’s triumphant moment at the Preakness is an inspiring lesson that, with determination and perseverance, anyone can overcome challenges and achieve greatness.

Exaggerator’s Rainy Comeback, 2016

The 2016 Preakness Stakes was marked by relentless rain, turning the race into a test of adaptability and endurance. The soggy track conditions were challenging, yet they set the stage for Exaggerator’s unforgettable performance. Starting from the middle of the pack, he didn’t seem like the favorite at first.


However, as the race progressed, Exaggerator’s strength in muddy conditions became evident. His jockey skillfully navigated through the slippery track, using Exaggerator’s proven ability to handle wet surfaces. With a stunning burst of speed in the final stretch, he dramatically moved past his competitors, clinching victory.

This race was a masterclass in strategic racing, showing how critical it is to adapt strategies based on conditions. Exaggerator’s win underscored the importance of preparation, resilience, and seizing opportunities, proving that no obstacle is too great when skill and strategy align perfectly.

Swiss Skydiver vs. Authentic, 2020

The 2020 Preakness Stakes was notable for the thrilling showdown between Swiss Skydiver, a formidable female contender, and Authentic, a top male competitor. This rare male vs. female matchup captured the imagination of racing fans worldwide.

Swiss Skydiver competed and excelled against the odds, demonstrating incredible speed and tenacity. In the final stretch, she took on Authentic head-to-head, demonstrating unmatched speed and an indomitable will to win. In those final moments, with the audience holding its breath, Swiss Skydiver pushed forward, outpacing Authentic by a slim margin and crossing the finish line in a victory that would be talked about for years.


This win wasn’t just a personal triumph for Swiss Skydiver. It was a landmark achievement for female horses in major races, challenging traditional perceptions and showcasing the competitive spirit regardless of gender.

Rombauer’s Surprising Surge, 2021

Rombauer, entering the 2021 Preakness Stakes, was not the name on every racing enthusiast’s lips. With odds stacked against him and predictions favoring other contenders, his underdog status was clear. However, as the race unfolded, Rombauer defied the odds.

In an astonishing move during the final turn, Rombauer displayed an explosive burst of speed, surging past the leaders in a dazzling display of power and strategy. This incredible maneuver clinched the win and left spectators and commentators in awe.

Rombauer’s win did more than secure a trophy. It served as a powerful narrative about the unpredictability and beauty of horse racing. It demonstrated that races aren’t just won on paper but on the racetrack, where conditions, determination, and sometimes the heart of the underdog can lead to unforeseen victories.

Final Thoughts

Recent years have provided some of the most dramatic finishes in the Preakness Stakes, each adding to the legacy of this prestigious race. These finishes remind us why we watch and love horse racing – for the unpredictability, the competition, and the stories of triumph that emerge.