Breaking Barriers: 5 Pioneering Trainers of the Kentucky Derby

The Kentucky Derby, often called “The Most Exciting Two Minutes In Sports,” is not just a platform for the finest three-year-old thoroughbreds to showcase their speed and stamina. It’s also a stage where trainers, with years of dedication, strategize to etch their names into history.

As the 2024 Kentucky Derby nears, let us discuss the five pioneering trainers who have broken barriers and left an indelible mark on Churchill Downs’s storied racetrack.

Kentucky Derby, unknown date Permission to use these Kentucky images is provided, free of charge, with the intent of promoting Kentucky as a travel destination. All published images should be credited, “Courtesy:”.
Kentucky Derby, unknown date Permission to use these Kentucky images is provided, free of charge, with the intent of promoting Kentucky as a travel destination. All published images should be credited, “Courtesy:”.

Bob Baffert

Bob Baffert is a living legend in the horse racing world and one of the renowned trainers of today. Baffert’s family owned a 240-acre cattle ranch near the Mexico border in Nogales, Arizona, where he was raised. 

***Please note.  There are sponsored links in this article.***

His upbringing was deeply intertwined with horses, thanks to his father’s involvement in breeding quarter horses. His mother also served as a teacher and a school principal. 

From age 10, Baffert started engaging with horses by grooming and galloping those owned by his father. His early foray into horse racing saw him as a jockey, achieving his first race victory in 1970 at Flagstaff, Arizona.

Given his achievements in the industry, his fame came as no surprise. Baffert has matched Ben Jones by securing six Kentucky Derby victories and holds the unparalleled record of winning the Preakness eight times.

That’s why Baffert horses are among the most favored KY derby picks each year. However, Baffert has been suspended and is not allowed to participate in the 2024 Kentucky Derby race.  

Ben Jones

Based solely on numerical analysis, Ben Jones deserves a spot on the list of the most successful trainers in Kentucky Derby history.

Ben A. Jones, with six Kentucky Derby wins from 1938 to 1952, set a high watermark for excellence in horse training. His legendary horse, Citation, clinched the 1948 Triple Crown, a feat achieved by only 13 horses in the history of American thoroughbred racing.

Jones’ methodology and success laid the groundwork for future generations, embodying the spirit of perseverance and excellence.

In 1958, Jones was inducted into the National Museum of Racing Hall of Fame to recognize his achievements. His success was tied to the legendary Calumet Farm throughout his illustrious career. Under his guidance, Calumet’s horses claimed victory in five Kentucky Derby races.

Ansel Williamson

When we talk about the pioneering of the Kentucky Derby, the list won’t be complete without Ansel Williamson. Williamson was the first trainer to win the Kentucky Derby with colt Artiside in 1875.

Ansel Williamson, originally born into slavery in Virginia, had a professional trajectory that bridged the era of extensive three-mile heats before the Civil War and the inception of shorter, single “dash” races. His documented career started confidently in the Southern United States around the 1860s.

The same year he won the Kentucky Derby, Williamson also won the Belmont Stakes with his horse Calvin.

Williamson’s stable also housed other distinguished horses, such as Merrill, who clinched victory in the 1866 Travers, Virgil, the mother of Hall of Fame inductee Hindoo, and Aaron Pennington, Chesapeake, and Susan Ann. Furthermore, Williamson achieved success in notable races like the Jerome, Phoenix, and Withers.

Wayne Lukas

Dr. Wayne Lukas, often dubbed the “Trainer Who Revolutionized Racing,” transformed the horse racing landscape in the 1980s and 1990s with bold and innovative techniques.

He holds the record for the most Triple Crown race wins and has secured four Kentucky Derby victories. His relentless pursuit of excellence and adaptability to change has significantly impacted the sport.

Since his early fascination with horses, Lukas embarked on a career training in Quarter Horses during the 1960s. This path led to his induction into the American Quarter Horse Hall of Fame in 2007.

Transitioning to focus solely on Thoroughbreds in the 1970s, Lukas achieved remarkable success, securing 14 Triple Crown races, 20 Breeders’ Cup races, and earning numerous Eclipse Awards alongside recognizing his 26 champion Thoroughbreds.

In 1999, his outstanding contributions were honored with an induction into the Thoroughbred Racing Hall of Fame. Continuing to be an influential figure in the industry, Lukas’s innovative training techniques have significantly shaped training practices and the racing industry.

This exhibit explores the pioneering training methods Lukas introduced and evaluates their lasting influence on trainers and the broader industry.

Herbert J. Thompson

Earning his nickname”Derby Dick,” Herbert J. Thompson made history as the initial trainer to achieve victory in the Kentucky Derby four times during his tenure at the renowned Col. E. R. Bradley’s Idle Hour Stock Farm.

Originating from Detroit in 1881, Thompson initially embarked on a career with trotting horses before transferring his focus to thoroughbreds in 1902. He started with the Santa Anita Stable, owned by Elias J. “Lucky” Baldwin.

By 1909, he had joined forces with Bradley, initially working alongside trainer Cliff Hammon and assuming full control of the stable after Hammon died in 1918.

In 1921, Thompson’s training prowess was on full display at the Derby, where his horses Behave Yourself and Black Servant clinched the top two spots, with the former unexpectedly besting the latter.

He achieved a similar feat in 1926, with Bubbling Over outpacing Bagenbaggage by a significant margin of five lengths. Thompson continued his winning streak, securing Derby victories with Burgoo King in 1932 and Brokers Tip in 1933.

James E. Fitzsimmons

Last but not least is James Fitzsimmons. The nickname “Sunny Jim” was bestowed upon Fitzsimmons by George Dailey of the New York World, inspired by a comic strip character mirroring Fitzsimmons’s amiable demeanor.

Within the racing community, he was honored with various titles that reflected the widespread admiration he garnered—he was known as the “dean of American trainers,” the “Sage of Sheepshead Bay,” and frequently referred to as “Mr. Fitz.” Fitzsimmons won the Kentucky Derby thrice: in 1930, 1935, and 1939.


The Kentucky Derby has been a platform for innovation and excellence in horse racing for over a century. These pioneering trainers have achieved personal success and pushed the boundaries of what’s possible in the sport.

Their contributions have revolutionized training methodologies, broken gender barriers, and leveraged technology to gain a competitive edge.

Get notified of new content, podcasts, and our awesome giveaways!!!!

    We respect your privacy. Unsubscribe at any time.

    Leave a Comment

    Digital $50 gift card to Homefield Apparel