The Kentucky Derby is America’s longest-running continuous sporting event, bringing together elite horses and passionate bettors year after year. While the favorites often dominate the headlines, it’s the underdogs that often capture the curiosity of racing fans and bettors alike.
These long shots bring unpredictability to the race, creating some of the most memorable moments in Derby history. The thrill of betting on an underdog comes with its risks, but the potential rewards are significant, with huge payouts for those who correctly spot a dark horse before the odds shift.
Why Underdogs Matter in the Kentucky Derby
In horse racing, an underdog refers to a horse with higher odds, meaning oddsmakers and the public give it a lower probability of winning. Although the chances of winning are low, bettors are in for a jackpot should their chosen underdog win.
These horses often come from smaller stables, have less prestigious pedigrees, or lack high-profile race wins, leading to their underdog status. However, history has shown that Kentucky Derby upsets are not uncommon, and longshots have delivered some of the most unforgettable victories in the sport.
Here are some of the famous underdog wins in Kentucky Derby history:
- Mine That Bird (2009) – Entered at 50-1 odds, this longshot delivered one of the most stunning victories in Derby history, surging from last place to first with an explosive finish, overtaking Pioneerof the Nile, the race favorite, who finished second, and Musket Man, who came in third
- Country House (2019) – At 65-1, this underdog became the second-highest-priced winner in Derby history, thanks to a controversial disqualification of Maximum Security, the original first-place finisher. The ruling reshaped the betting landscape and handed Country House an unexpected but historic victory.
These moments prove that while underdogs are often overlooked, they bring an element of surprise that makes the Kentucky Derby one of the most exciting betting events in sports. For bettors, understanding why certain underdogs have succeeded in the past can provide insights into how to identify future dark horses.
Finding This Year’s Top Underdog Contenders
Identifying underdogs for the 2025 Kentucky Derby requires evaluating past performances, prep races, and trainer-jockey combinations. On the Road to the Kentucky Derby, horses that finish strong in key races like the Arkansas or Florida Derby, even without winning, often signal upset potential. Moreover, a skilled jockey and a smart race strategy can make a crucial difference. As a result, a well-timed late surge can turn an overlooked contender into a serious threat.
Considering these factors, Horse Racing Nation highlights the following as the top two underdog contenders for the 2025 Kentucky Derby.
- Flying Mohawk. Trained by Whit Beckman, this colt has accumulated 50 points on the Road to the Kentucky Derby leaderboard, with earnings of $156,800. Flying Mohawk has shown promise in recent prep races, indicating potential for an upset. Just recently, Flying Mohawk finished second at the Jeff Ruby Steaks just this March 22. Although he didn’t win, a hard-earned 2nd place win was more than enough for him to secure a spot in this year’s Kentucky Derby.
- Journalism. With 47.5 points and $300,000 in earnings, Journalism is trained by Michael W. McCarthy and owned by a partnership including Bridlewood Farm and Eclipse Thoroughbred Partners. His consistent performances position him as a noteworthy underdog. Regardless of how he’ll place in the upcoming Santa Anita Derby this April, Journalism has his spot secured in the upcoming Kentucky Derby.
These horses have demonstrated potential through their performances in prep races, and their connections, specifically, their trainers and owners with histories of success, add to their credibility as underdog contenders. Analyzing their running styles, adaptability to different track conditions, and responses to competition will be crucial in assessing their chances for an upset victory in the 2025 Kentucky Derby.
Strategies for Betting on Underdogs
Placing a bet on an underdog carries both high risks and high rewards, making strategy crucial. Instead of focusing on hype, bettors should analyze value and probability. One key approach is to monitor late odds movement, as a shortening line may indicate insider confidence from sharp bettors. Understanding these trends can provide valuable insights into an underdog’s true chances.
Additionally, using exotic wagers—such as place, show, exacta, or trifecta bets—can increase the likelihood of a payout without requiring the horse to win outright. Bettors should also compare speed figures and recent form, identifying horses that have posted competitive times despite poor finishes. Sometimes, a bad trip in a previous race can mask a horse’s true ability, making them a valuable betting opportunity.
The Thrill of Betting on the Unexpected
The Kentucky Derby is a race where anything can happen, which makes betting on underdogs so exhilarating. While playing it safe with favorites may seem logical, longshots have a way of defying the odds and delivering massive returns to those who take the risk.