2025 Kentucky Derby Picks: Experts vs AI

It’s a warm spring day in May, and the world of horse racing tunes in to watch what is widely considered the most exciting two minutes in sports. Every May at Churchill Downs, bettors look for an edge at the Kentucky Derby. This year, we’re putting two powerful forces to the test—seasoned racing experts and ChatGPT’s AI-powered picks.

The Derby is over 100 years old, and throughout its history, bettors have tested methods, theories, and superstitions about who will take home the prize. But now, despite the age of the race and the sport, a new way to analyze Kentucky Derby contenders has emerged: AI.

Will experience beat the algorithm, or will AI prove it’s ready for the Winner’s Circle?

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Meet the Contenders: Who’s Making the Picks?

ChatGPT's Horse Racing Picks:

Our AI Kentucky Derby odds systems were built using analysis of race results, odds patterns, running styles, and historical trends. To generate the results, we specifically looked at:

• Recent prep race results: Performance data from key races like the Santa Anita Derby, Arkansas Derby, and Florida Derby.
• Morning-line odds: Early odds are set by race officials to gauge the projected popularity and perceived strength of each contender.
• Historical trends: Patterns from past Kentucky Derbies, such as how often favorites win, and how international contenders perform.
• Running styles and race dynamics: A look at which horses prefer to set the pace, close late, or stalk from mid-pack—used to build multi-horse bets like exactas and superfectas.
• AI pattern recognition: Using natural language processing, ChatGPT synthesized this data to detect consistent patterns and potential overlays, horses that may outperform their listed odds.

The Kentucky Derby Experts:

Kaitlin Free (Churchill Downs Handicapper)Kaitlin Free serves as a reporter and analyst at Churchill Downs, Turfway Park, and Colonial Downs, bringing sharp insights to each circuit. She also specializes in international racing, such as the UAE Derby, with expertise on the Road to the Kentucky Derby in both Europe and Asia.

James Scully (TwinSpires Analyst)

James Scully is a veteran writer and handicapper, offering in-depth analysis and picks for Brisnet.com, TwinSpires.com, and KentuckyDerby.com.Kevin Kilroy (Fair Grounds & Churchill Racing Analyst)

Kevin Kilroy is a seasoned horse racing and handicapping analyst who provides expert coverage of the action at Churchill Downs, Colonial Downs, Ellis Park, Fair Grounds, and Turfway Park.

Note: All three have published Top 10 rankings for the 2025 Kentucky Derby on KentuckyDerby.com.

Win Picks: Who’s Taking the Roses?

When it comes to betting on the Kentucky Derby, knowing who is at the starting gate as well as knowing about trainers and owners can help you pick a winner. When consulting our ChatGPT analysis and the experts, here are their picks for this year’s Churchill Downs.

ChatGPT: Journalism is the AI’s pick for this year’s win. It’s backed by the algorithm because this horse has remained consistent with its solid 3-1 odds and standout performances in key prep races.

Kaitlin Free: Also selected Journalism as her pick for this year’s derby.

James Scully: Sandman is Scully’s pick in the group. Sandman impressed in the Arkansas Derby with a dominant late move and consistent form, making him a reliable contender to watch heading into Churchill Downs.

Kevin Kilroy: Burnham Square comes in for Kevin Kilroy’s pick. This horse enters the 2025 Kentucky Derby as a formidable contender, having topped the Road to the Kentucky Derby leaderboard with 130 qualifying points. Trained by Ian Wilkes and ridden by Brian Hernandez Jr., this bay gelding boasts a record of 3 wins, 1 second, and 1 third in six starts.

ChatGPT and Kaitlin Free agree on Journalism. Meanwhile, Scully backs the late-running Sandman, and Kilroy goes for value with Burnham Square.

Exacta, Trifecta, and Superfecta Picks

Betting on who will be the winner is a simple and solid choice for bettors not looking to get too heavily invested. However, betting on things like the exacta, trifecta, or super high five can yield a larger payout. If you’re interested in different types of bets, there are some elements to consider. Betting combinations reward deeper analysis, it’s not just about who wins, but who comes right behind them.

Not sure on what type of bet to make? Here are some of the most popular bet types for horse racing:

Exacta (1st and 2nd): The Exacta is a bet that wagers on which two horses will come in first and second in that order. Journalism and Sovereignty are the AI’s top horses for this pick.

Trifecta (1st, 2nd, 3rd): Similar to the Exacta, the trifecta focuses on the top three instead of the top two. The AI favors Journalism, Sovereignty, and Sandman.

Superfecta (1st–4th): Similar to the above, the Superfecta chooses the top 4 horses to finish in that specific order. The AI favors adding Tiztastic for 4th place.

Super High Five (1st–5th): Finally, the Super High Five involves picking who will come in the top five spots in that specific order. The AI recommends adding Luxor Café for this bet.

Side-by-Side Picks

Here’s a direct comparison of how ChatGPT and the experts stack up for key betting types at the 2025 Kentucky Derby:

Where AI and Experts Agree -- and Where They Don’t

Kentucky Derby Contenders from AI and the Experts

ChatGPT and Kaitlin Free both favor Journalism and Sovereignty as top contenders for the 2025 Kentucky Derby, highlighting their consistency and strong prep races. James Scully, however, focuses on Sandman, emphasizing his powerful performance in the Arkansas Derby and potential for early speed.

Kevin Kilroy sees Luxor Café as a major player, ranking him second, citing his solid international form and value at longer odds. Combining these insights, the strategy is clear: anchor with Journalism and Sovereignty, include Sandman for his pace, and consider Luxor Café for a longshot boost in Superfecta or Super High Five.

Where Do the Experts Differ?

James Scully ranks Sandman as his #1 pick, emphasizing early speed, while ChatGPT places him 3rd. Kevin Kilroy ranks Luxor Café second, highlighting his international form, and sees Burnham Square as a strong contender, placing him higher than other analysts. Different strategies shape their Derby outlooks.

How to Bet Smarter Using Both Sides

A good thing to do wouldn’t be to just rely on the AI or the experts, but to combine the two and bet on the best of both. For example, combining the AI favorite with the expert's favorite, or combining Sovereignty with Sandman underneath.

Different horses and different types of bets have different odds, and this means that they also have different payouts. Depending on what you’re comfortable with, betting on some horses has higher or lower odds.

Betting tip: You don’t have to pick a side—you can build hybrid tickets blending expert intuition and AI logic.

Will Experience or AI Reign Supreme?

On the first Saturday in May, only one thing is certain: surprises happen. Whether you trust seasoned experts, AI models, or your own gut, the Kentucky Derby delivers excitement unlike any other.

After the race, we’ll revisit these picks to see who came closest to hitting the board. Stay tuned to see how the experts and models stacked up against the thrilling twists of Derby Day.

Build Your Kentucky Derby Bets on FanDuel

FanDuel is the home of some of the best sports betting and horse racing. The road to the Kentucky Derby includes the Kentucky Oaks, the Japan Road to the Derby, and every race from the Triple Crown.

So start reading up on your favorite horses and create an account today, and place your mark on the 2025 Kentucky Derby.

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