Kentucky Derby 2025: Finding Winners Through Mental Elasticity

In the podcast "Bet With The Best," handicapper Mike Maloney described the Kentucky Derby as "mayhem" - a perfect characterization of America's most unpredictable horse race. With 20 inexperienced three-year-olds attempting a distance they've never tried before, surrounded by a deafening crowd of 150,000 spectators, the Derby demands a different approach to handicapping.

Traditional handicapping often relies on rigid patterns and familiar frameworks, but the Derby rewards what author Leonard Mlodinow calls "elastic thinking" - the ability to abandon comfortable mental pathways and embrace new perspectives. As Mlodinow explains in his book "Elastic," our brains are "predictability junkies," craving the familiar even when it's no longer effective.

For the 2025 Kentucky Derby, we'll apply the principles of elastic thinking through three proven exercises to identify top contenders and potential tosses. By breaking free from conventional handicapping patterns and embracing productive discomfort, we can find value where others see only chaos.

Exercise 1: Productive Prep Races

Since the Derby points system was introduced in 2013, clear patterns have emerged regarding which final prep races produce the most winners:

• Florida Derby: 4 winners (Mage 2023, Always Dreaming 2017, Nyquist 2016, Orb 2013)

• Santa Anita Derby: 3 winners (Authentic 2020, Justify 2018, California Chrome 2014)

• Arkansas Derby: 2 winners (Mystik Dan 2024, American Pharoah 2015)

• Louisiana Derby: 1 winner (Mandaloun 2021)

• Miscellaneous/Low-Impact: 1 winner (Rich Strike 2022)

💡This data suggests horses exiting the Florida Derby, Santa Anita Derby, and Arkansas Derby deserve extra consideration. For the 2025 Kentucky Derby, this highlights:

Top Prep Race Contenders:

• Santa Anita Derby: Journalism, Citizen Bull

• Florida Derby: Tappan Street, Sovereignty, Madaket Road

• Arkansas Derby: Sandman, Coal Battle, Publisher

💡These eight horses have history on their side, coming from preps that have produced 9 of the last 12 Derby winners.

Exercise 2: Final Fractions Theory

This time-tested approach examines a horse's finishing power in their final prep race, focusing on their ability to maintain energy through the final three furlongs (38 seconds or less) and final eighth of a mile (13 seconds or less). This method identifies horses with the stamina and late speed necessary for the Derby's demanding 1¼ miles.

The theory has correctly identified 31 of the last 36 Derby winners (86% success rate), making it one of the most reliable predictive tools for Derby handicapping.

For the 2025 Derby, the Final Fractions Theory identifies:

Double Qualifiers (met both time criteria):

• Journalism

• Rodriguez

• Tappan Street

• Sovereignty

• Final Gambit

• Flying Mohawk

• Grande

• Luxor Café*

Single Qualifiers (met one time criterion):

• Tiztastic

• American Promise

• Baeza

This significantly narrows our focus to these eleven horses, with particular emphasis on the eight double qualifiers.

🚦To learn more about the details of Final Fractions Theory, just use google search. There are plenty of articles, videos, blogs the do deep dives.

Exercise 3: Jon White Strike System

The Jon White Strike System evaluates Derby contenders across eight proven factors that have historically predicted Derby success. Fewer strikes indicate stronger contenders, with most Derby winners having 2 or fewer strikes.

For the 2025 Kentucky Derby field:

0 Strikes (strongest contenders):

• Sandman

• Journalism

• Admire Daytona

1 Strike:

• Tappan Street

• Rodriguez

• Tiztastic

• Sovereignty

• Final Gambit

• Coal Battle

• Chunk of Gold

• Luxor Café*

2 Strikes:

• Burnham Square

• Citizen Bull

• East Avenue

• American Promise

• Flying Mohawk

3+ Strikes (historical tosses):

• Publisher (3)

• River Thames (3)

• Grande (3)

• Madaket Road (4)

• Baeza (4)

Historically, horses with 3 or more strikes rarely win the Kentucky Derby, suggesting we should focus primarily on the contenders with 0-2 strikes.

🚦To learn more about the details of the Jon White Strike method, just use google search. There are plenty of articles, videos, blogs the do deep dives.

Finding Our Derby Contenders

By applying elastic thinking across these three exercises, we can identify horses that check multiple boxes:

Prep races horses have come from last. This doesn’t mean they won their prior race.

Conclusion: Finding Value Beyond the Favorite

Our analysis reveals three standout contenders who check all boxes:

• Journalism

• Tappan Street

• Sovereignty

While Journalism is likely to be the morning line favorite based on his impressive resume, it's worth remembering that even in the modern points-qualification era (2013-2024), the betting favorite has only won 5 of 12 Kentucky Derbies:

While favorites perform better than historical averages in the points era, they still lose half the time. This reality creates tremendous opportunity for value-seeking bettors willing to look beyond the obvious choice.

For those looking to swing against the likely favorite Journalism, our analysis has identified several compelling alternatives:

• Tappan Street and Sovereignty stand out as three-check contenders who could offer significant value. Both exit the historically productive Florida Derby and satisfy both the final fractions and strike system criteria.

• Several two-check contenders also merit consideration, particularly Sandman (Arkansas Derby, 0 strikes) and Coal Battle (Arkansas Derby, 1 strike) who exit another historically productive prep.

• Rodriguez, Luxor Cafe, and Final Gambit register as double qualifiers on the final fractions theory with just 1 strike each, making them interesting longshot plays.

This approach isn't about confidently predicting the Kentucky Derby winner—that's a fool's errand in a 20-horse field facing unprecedented challenges. Instead, it's about identifying reasonable alternatives that provide value and increase the equity of our tickets.

By applying elastic thinking to look beyond the obvious choice, we position ourselves to capitalize on the inevitable chaos that defines America's most unpredictable race. As Mlodinow would suggest, our goal isn't perfect prediction but rather mental flexibility that allows us to see opportunities others miss.

With most casual bettors likely to pile onto Journalism as the favorite, these alternative contenders may offer significantly higher returns while still checking the key boxes that have historically produced Derby winners. In embracing the Derby's mayhem with an elastic mind, we gain both analytical clarity and betting value—a powerful combination for tackling the sport's greatest handicapping challenge.