Childhood and Family
James “Jimmy” Winkfield was born in Chilesburg, an African American community east of Lexington, Kentucky. He was the youngest of seventeen children. His father, George, served in the Union army after enlisting at Camp Nelson, in Nicholasville, Kentucky, in 1865.
After the death of both of his parents, Winkfield moved to Lexington and lived with a sister near the Kentucky Association track. Winkfield recalled riding horses bareback starting when he was only seven years old. In 1896, he was working as a carriage driver and on his days off, he went with friends to the race track at Latonia.1
In the spring of 1897, the track offered him a job as an exercise rider. He rode Jockey Joe in his first race at the Hawthorne Race Course in Chicago, Illinois. Winkfield’s was so focused on winning that when he saw space between other horses, he pushed Jockey Joe through and bumped other horses out of the way. The judges suspended him a year for his reckless riding. Though he did not win, his first race revealed natural talent.
Owners W. H. and Bud May had watched Winkfield and decided to put him on Avenstock for the September 13, 1899 race at Harlem track at Chicago. When the starting gate opened, Winkfield charged out and never looked back. He had won his first race! Winkfield signed a three-year contract and established a reputation as a successful jockey.2
The Kentucky Derby and More
Winkfield rode in his first Kentucky Derby in 1900 and placed third. In 1901, not only did he win the Kentucky Derby aboard His Eminence, he also won other high-profile races:
- Latonia Derby
- Tennessee Derby
- Clark Handicap
The next year, Winkfield again won the Kentucky Derby aboard Alan-a-Dale. He rode in the Kentucky Derby one last time in 1903 and placed second. He never rode in the Derby or in any major race in the United States again, due to racism and legal challenges.3
Like many of his contemporaries, Winkfield found a second career abroad. In 1904, he won the Warsaw Derby, and his European career took off.
His victories in Russia included:
- The Russian Oaks (five times)
- The Russian Derby (four times)
- The Czar's Prize, aka as the Emperor’s Purse (three times)
Winkfield enjoyed his fame and fortune while in Russia. To describe his life during this time, Winkfield said: “I was at the top of the tree.”4
The Russian Revolution
Political uprising in Russia disrupted Winkfield’s career. After the Bolshevik Revolution in 1917, Winkfield moved to Odessa, a city on the Black Sea. There, horse racing continued despite economic and societal instability. By the winter of 1919, revolution came to Odessa. Winkfield and others traveled a dangerous and difficult journey on horseback to Warsaw, Poland.5
Life in France
In 1920, Winkfield moved to France to resume his career. Much like his time in Russia, Winkfield’s career in France was successful.
Winkfield’s victories in France included:
- The Prix du Président de la République
- The Grand Prix de Deauville
- The Prix Eugène- Adam
In 1930, at age 48, Winkfield quit riding and switched to training. By this time, his son Robert James was a jockey. Winkfield trained him, his own horses, and other owners’ horses as well.6
Wartime Return to the United States
Political unrest disrupted Winkfield’s career again. In 1941, the Nazis invaded France. Nazi soldiers occupied his home and took over his stables. Winkfield and his family all returned together to the United States in April of 1941. He worked as a groom and assistant trainer in Illinois, South Carolina, and West Virginia.7
Discrimination and Return to France
In 1961, the National Turf Writers’ Association invited Winkfield to a pre-Derby banquet at the Brown Hotel in Louisville. When he arrived with his daughter, they were not permitted to enter through the front door. Instead they were told to enter through the back, due to their race. Winkfield and his daughter stood their ground and were permitted to enter the front door. This incident reminded Winkfield of the prejudice and maltreatment he had previously endured in the United States, and he soon after returned to France.8
Winkfield married three times and was the father of five children. He passed away at the age of 92 at his home in France. In 2004, the National Museum of Racing Hall of Fame inducted him. The Aqueduct Race Track in Queens, New York inaugurated The Jimmy Winkfield Stakes in 2017 to honor this accomplished horseman.9
Drape, Joe. 2006. Black Maestro: The Epic Life of an American Legend. New York: William Morrow.
Ebony. 1974. “The Saga of Jimmy Winkfield,” June 1974.
Hotaling, Ed. 2004. Wink: The Incredible Life and Epic Journey of Jimmy Winkfield. Camden, ME: McGraw-Hill.
Hotaling, Edward. 1999. The Great Black Jockeys: The Lives and Times of the Men Who Dominated America’s First National Sport. Rocklin, Calif.: Forum.
“Jimmy Winkfield.” n.d. National Museum of Racing and Hall of Fame. https://www.racingmuseum.org/.
Mooney, Katherine. 2014. Race Horse Men: How Slavery and Freedom Were Made at the Racetrack. Cambridge, Massachusetts: Harvard University Press.
New York Sun. 1909. “A Gentleman from Kentucky Came Second Class So As Not to Vex the Intolerant,” December 13, 1909. Chronicling America.
“Passenger and Crew Lists of Vessels Arriving at New York, New York, 1897-1957.” 1941. Washington, DC. Records of the U.S. Customs Service, Record Group 36. National Archives, Washington, D.C. Ancestry.com.
Terrell, Roy. 1961. “Around the World in 80 Years: Jimmy Winkfield.” Sports Illustrated, May 8, 1961.
Thoroughbred Record. 1900. “Jockey War At Chicago,” August 18, 1900.
Wall, Maryjean. 2012. “The Racing Life.” Humanities, February 2012.
When citing this article as a source in Chicago Manual of Style use this format: Last name, first name of Author. Chronicle of African Americans in the Horse Industry. n.d. “Title of Profile or Story.” International Museum of the Horse. Accessed date. URL of page cited.