By Mint Julep

James Winkfield Jockey: Two Kentucky Derby Wins

his eminence kentucky derby winner 1901

Join James Winkfield on an exciting journey through his extraordinary life as a pioneering jockey who made history by winning two iconic Kentucky Derby races. Starting from his modest roots in Kentucky, Winkfield’s incredible talent and determination took him to the heights of success both in Europe and Russia. His inspiring story continues to captivate riders and fans around the world, showcasing his resilience, skill, and groundbreaking accomplishments. Discover how he left a lasting impact with his impressive victories, transition into training post-retirement, and prestigious induction into the National Museum of Racing Hall of Fame.

Early Life and Career Beginnings

James Winkfield, born in Chilesburg, Kentucky around 1880-1882, began his successful career as a jockey at the young age of sixteen in 1898. Despite facing a one-year suspension early on due to an incident at the starting gate, he quickly made a name for himself in the competitive world of horse racing.

With determination and skill, he rapidly advanced within the racing circuit after overcoming initial obstacles. By rising above challenges with unwavering resolve, Winkfield caught the eye of many industry insiders with his talent on horseback. Through perseverance and grit, he established himself as a formidable presence on racetracks across America.

Winkfield’s journey was more than just riding horses; it was about defying odds and showcasing his abilities time and again. His natural connection with these magnificent animals shone through every race he participated in. With each step towards victory, James Winkfield solidified his place in horse racing history.

The young jockey’s early achievements laid a strong foundation for what would later become an inspiring legacy that transcended borders and captivated audiences worldwide. From humble beginnings emerged an exceptional individual whose love for horsemanship knew no limits—a true example of resilience against adversity and unwavering commitment to mastering their craft on tracks near and far.

Historic Kentucky Derby Wins

James Winkfield’s impressive wins at the Kentucky Derby showcase his exceptional talent and determination. His victories riding His Eminence in 1901 and Alan-a-Dale in 1902 not only secured his place in history but also highlighted his unmatched skills on the racetrack. Despite facing racial discrimination and daunting obstacles, Winkfield overcame them all, leaving a lasting impact on horse racing.

Winkfield’s triumphs were more than just moments of glory; they marked significant milestones for African American jockeys during a time when opportunities were limited due to prejudice. By winning one of the most prestigious horse races, he broke barriers and paved the way for future riders from diverse backgrounds. His resilience and expertise inspired many who came after him.

The legacy of James Winkfield goes beyond his Derby victories; it continues through generations of riders drawing inspiration from his story. His ability to excel in a predominantly white sport with finesse earned him respect that transcended boundaries. Winkfield’s influence on horse racing is immeasurable, highlighting not only his outstanding abilities but also the unwavering spirit that defined him throughout his career.

By honoring James “Soup” Winkfield, we celebrate not just an extraordinary athlete but a trailblazer whose contributions resonate through horse racing history. His achievements remind us that talent has no limits, breaking down societal barriers or circumstances imposed by society. With each stride towards victory, he cemented himself as a sports legend—a symbol of perseverance, skill, and enduring passion for the beloved sport he cherished deeply.

The Pros & Cons of Racing Legends


  1. Motivates upcoming racers for the future

  2. Reveals the fascinating past of horse racing

  3. Shines a spotlight on African American athletes' accomplishments in a mostly white sport

  4. Advocates for diversity and inclusivity within the racing sector

  5. Honors James Winkfield's trailblazing legacy in horse racing

  6. Imparts important lessons about persistence, drive, and achievement


  1. Racing history often overlooks many minority groups

  2. We face difficulties in confronting the racial discrimination that happened in the past

  3. Not enough people know about the amazing lesser-known racing legends

  4. We might end up ignoring current achievements if we only focus on historical figures

  5. It's tough to make things right now while dealing with past injustices

  6. There is a risk of continuing stereotypes or misunderstandings about African American athletes.

Success and Controversy

James Winkfield had a thrilling journey filled with both triumphs and controversies. After facing challenges in the U.S., he sought refuge on racing tracks in Russia, where he displayed his exceptional talent by winning prestigious titles like five Russian Oaks and three Czar’s Prizes. Despite being overlooked in his home country, Winkfield’s fame continued to soar abroad.

In Russia, James Winkfield quickly established himself as a dominant force, captivating audiences with his outstanding skills and unwavering determination. His victories showcased a remarkable story of resilience and expertise that transcended boundaries. The issues that haunted him in America seemed to fade away amidst the cheers of international spectators who were amazed by his performance on the track.

Winkfield’s tale is one of perseverance turning into success under foreign skies. Each win not only highlighted his unparalleled horsemanship but also served as a reminder of overcoming obstacles against all odds. As he raced towards victory after victory in Russia, it became clear that nothing could dull the shine of this legendary jockey.

The legacy left behind by James Winkfield goes beyond mere victories; it represents breaking barriers and surpassing expectations even when faced with challenges. His narrative is an inspiration not just for those involved in horse racing but for anyone striving to conquer obstacles on their way to greatness—truly establishing him as an unforgettable figure both within American history and global equestrian lore.

European Racing Triumphs

James Winkfield’s incredible journey across Europe was truly legendary. He won big races like the Prix du Président de la République, Grand Prix de Deauville, and Prix Eugène Adam, establishing himself as a top jockey. Every time he raced, fans in Europe were captivated by his amazing skill and strong determination.

Winkfield stood out in European racing circles like a master at work—every move planned carefully, every race approached strategically. As he navigated tough courses and fierce competition, he showed an unmatched level of expertise that separated him from other riders. His smooth handling of horses not only earned praise but also deep respect from fellow riders and spectators.

In Europe, James Winkfield wasn’t just another good jockey; he represented excellence—a shining example for African American athletes during a time when racial barriers were high. His wins went beyond just victories on the track; they symbolized resilience against challenges and shattered stereotypes with each step towards glory.

The legacy that James Winkfield left behind in European horse racing is now part of history—a testament to his unbreakable spirit and unwavering love for the sport. From Russia to France, his name became linked with success and inspiration for future generations of aspiring jockeys worldwide. By conquering new boundaries and overcoming obstacles, Winkfield blazed a trail that still shines brightly today—an enduring reminder of what it takes to defy odds and achieve greatness against all challenges.

James Winkfield: Legendary Jockey and Racing Icon

Occupation Jockey
Born April 12, c. 1880–1882[1] Chilesburg, Kentucky
Died March 23, 1974 (aged 91)
Spouse Lydia de Minkiwitz
Career wins 2,600+
Major racing wins Clark Handicap (1901)
Tennessee Derby (1901)
Latonia Derby (1901)
Moscow Derby (2)
Russian Derby (3)
Russian Oaks (5)
Warsaw Derby (2)
Grosser Preis von Baden (1909)
Prix Eugène Adam
Prix du Président de la République (1922)
Grand Prix de Deauville (1922)
Critérium de Maisons-Laffitte (1927)
American Classics wins: Kentucky Derby (1901, 1902)
Racing awards Russian Champion Jockey (3 times)
Honours National Museum of Racing and Hall of Fame (2004)
Jimmy Winkfield Stakes at Aqueduct Racetrack
U.S. House of Representatives Resolution 231 honoring the life of Jimmy Winkfield
Significant horses His Eminence, Alan-a-Dale, McChesney

Post-retirement Life and Recognition

After James Winkfield finished his exciting career as a jockey, he smoothly transitioned into training horses. Winning over 2,500 races on the track gave him valuable experience that he used to shape future champion horses. Despite facing racial segregation in America at the time, Winkfield remained dedicated to working with horses. His love for these incredible animals was evident in every race he ran and every horse he trained.

James Winkfield’s exceptional talent and strong commitment to horse racing earned him a spot in the National Museum of Racing and Hall of Fame posthumously in 2004. This prestigious honor confirmed his status among the greatest figures in the sport’s history. It wasn’t just about individual awards but also recognition for breaking barriers when social challenges made it difficult for many others to follow similar paths back then. The tribute paid to him underlined his lasting impact on global horse racing history.

Even after building an unmatched legacy as a jockey and transitioning successfully into training horses, James Winkfield’s influence continued resonating throughout the equestrian world long after retiring from competitive racing at age fifty – setting an example not only through his skillful handling of horses but also by overcoming challenges both on and off the racetrack with unparalleled resilience rarely seen before or since – truly leaving behind footprints across time cherished by enthusiasts worldwide.

Legacy of Resilience

James Winkfield’s incredible journey is a shining example of determination and resilience. Despite facing challenges early in his life, he broke through racial barriers to become one of the top jockeys of his era in the early 1900s. He showed remarkable strength as he tackled prejudice and discrimination, proving that talent can triumph over adversity when given a chance.

Winkfield’s exceptional skills on horseback set him apart, leading to back-to-back wins at the prestigious Kentucky Derby in 1901 and 1902. These victories not only showcased his outstanding riding abilities but also highlighted his strategic brilliance on the track. His name became synonymous with excellence, creating a benchmark for future riders to emulate.

Throughout his career, James Winkfield faced numerous obstacles but never wavered from pursuing greatness. He expanded his horizons beyond America by venturing into Europe where he continued to dominate racetracks and secure victory after victory. His international triumphs not only underscored his talents but also shattered barriers for jockeys of color worldwide.

The impact left by James Winkfield extends far beyond just horse racing; it stands as an inspiring symbol for anyone striving towards big dreams. His groundbreaking accomplishments paved the way for diversity and inclusion within an industry once plagued by segregation. Today, Winkfield’s legacy remains alive as a testament that with determination, skill, and perseverance, anything is achievable – be it on or off the racetrack.

Legendary Tales Surrounding James Winkfield's Derby Victories

  1. James Winkfield's Derby Triumphs: Fascinating Stories That Still Spark Intrigue:

  2. The "Unsung Hero": James Winkfield clinched two Kentucky Derby victories in 1901 and 1902, making him one of the top jockeys at that time. However, his remarkable achievements were dimmed by racial bias prevailing during the early 20th century.

  3. Overcoming Challenges: Winkfield went down in history as the last African American jockey to win the Kentucky Derby until Marlon St. Julien shattered this barrier inThis accomplishment shed light on the obstacles faced by minority riders within the sport.

  4. Innovative Training Techniques: Winkfield stood out for his unique training methods, such as bonding with horses through meditation and visualization exercises to form a strong connection with his mounts.

  5. Unexpected Victory: Seizing victory astride His Eminence in 1901 at odds of 19-5 marked James Winkfield's first triumphant ride at the Derby, surprising many onlookers and solidifying his reputation as a talented and strategic jockey.

  6. Enduring Legacy: Beyond just winning Derbies, James Winkfield continues to inspire future generations of African American jockeys with his story of resilience and determination against all odds – showcasing how perseverance is key when facing challenges head-on.

Continued Recognition Through Stakes Races

The Jimmy Winkfield Stakes at Aqueduct Racetrack honors his incredible influence on American horse racing. This exciting event, held every year, not only celebrates his wins but also showcases the lasting impact he made on the sport over time.

Through this stakes race, we see Winkfield’s legacy shining brightly, reminding everyone of his exceptional skills and strong spirit. His victories in major races continue to inspire jockeys and fans from all generations, displaying a talent that went beyond boundaries within the racing world.

As horses race down the track during the Jimmy Winkfield Stakes, you can feel a sense of history and respect in the air. The echoes of Winkfield’s groundbreaking achievements resonate with each stride these majestic animals take, honoring a man who opened doors for diversity and excellence in horse racing.

Each year as competitors fight for victory in this legendary race named after him, James “Jimmy” Winkfield’s name rings out through time with pride and admiration. His legacy remains firmly rooted in horse racing lore—a symbol of hope for those daring to dream big while overcoming challenges just like he did during his remarkable career.

Through events such as the Jimmy Winkfield Stakes, we remember not only a talented jockey but also a trailblazer whose passion for horseracing knew no bounds. James Winkfield left an indelible mark on American sports history—an eternal flame lighting up racetracks worldwide with stories of resilience, skill, and unwavering determination.

Congressional Honor and Lasting Impact

James Winkfield’s impact reverberates through the annals of history, filled with stories of victory and resilience. His exceptional talent on the racetrack only matched by his unwavering determination drove him to unprecedented success in a predominantly white sport amidst times of deep-rooted racial prejudice.

Winkfield’s journey from modest beginnings in Kentucky to clinching the prestigious Epsom Derby twice is truly extraordinary. Despite facing obstacles due to segregation and discrimination, he overcame all odds with sheer grit and limitless skill. His wins not only displayed his jockey prowess but also broke stereotypes, paving the way for future African American riders.

Exploring Winkfield’s narrative reveals that his influence goes beyond mere numbers or awards. He embodies perseverance against adversity and an unshakeable commitment to his craft—a source of inspiration for budding athletes worldwide. By dismantling racial barriers in horse racing, he has left an enduring mark on the sport that continues to motivate individuals from diverse backgrounds today.

The United States House Resolution 231 stands as proof of James Winkfield’s lasting impact on horse racing—an overdue recognition for this pioneering figure whose accomplishments were once overlooked by mainstream accounts. This acknowledgment not only validates Winkfield’s contributions but also sheds light on a crucial chapter in sports history often obscured by biases and oversights.

By honoring James Winkfield, we pay tribute not just to an outstanding athlete but also to a trailblazer who challenged norms and reshaped perspectives within horse racing circles. His tale serves as a poignant reminder that greatness transcends boundaries—whether geographical, social, or cultural—and true champions rise above their circumstances through courage, persistence, and an unyielding love for their vocation


1. How did James Winkfield's victories at the Kentucky Derby impact the history of horse racing?

James Winkfield won the Kentucky Derby in 1901 and 1902, becoming one of the few African American jockeys to achieve this feat. His back-to-back victories not only secured his place in horse racing history but also helped promote diversity and inclusion in the sport. This significant accomplishment left a lasting impact on the legacy of horse racing.

2. What challenges did James Winkfield face as an African American jockey in a predominantly white sport during his time?

During his time as an African American jockey in a mostly white sport, James Winkfield encountered widespread racism, discrimination, and few chances for success.

3. Can you elaborate on James Winkfield's journey from slavery to becoming a celebrated jockey in the early 20th century?

James Winkfield went from being a slave to becoming a famous jockey in the early 1900s. His amazing talent, strong determination, and historic accomplishments transformed horse racing forever.

4. What were some of the key accomplishments that set James Winkfield apart as a legendary figure in horse racing history?

James Winkfield made history in horse racing by winning the Kentucky Derby two years in a row, in 1901 and 1902. He became the final African American jockey to accomplish this feat, establishing himself as an innovator and leader in the sport.

5. How did James Winkfield's success at the Kentucky Derby pave the way for future generations of African American jockeys and riders in the sport?

James Winkfield made history by winning the Kentucky Derby. His wins not only proved he was an amazing jockey, but also motivated and paved the way for future African American jockeys and riders in horse racing. He broke barriers and left a lasting impact on the sport's history.

6. What is James Winkfield's enduring legacy in the world of horse racing, and how is he remembered today?

James Winkfield left a lasting impact on the horse racing world through his exceptional talent, determination, and trailblazing success. He opened doors for upcoming African American jockeys and made a significant impression on the sport that continues to be honored and respected today.