James “Jimmy” Winkfield (April 12, 1882 – March 23, 1974) was a thoroughbred jockey and horse trainer from Kentucky, best remembered as the last African-American to ride a winner in the Kentucky Derby.

Winkfield was born in Chilesburg, Kentucky and began his career as a jockey in 1898 at age sixteen. He was suspended for four years after just one race for his involvement in a four-horse accident at the starting gate. However, he returned in 1900 to ride a horse named Thrive in the Kentucky Derby, finishing third. He rode the race again in 1901 and 1902, winning on His Eminence and Alan-a-Dale respectively – in 1901 alone, he won 220 races. He competed in his final Derby in 1903, finishing second on Early.

Jimmy Winkfield gave up on his country just before the 1903 Kentucky Derby began. The 21-year-old African-American jockey had already won two Derbies and was clearly the nation’s finest rider. Nonetheless, as he guided his mount to the mark, the starter shouted at him, “You little nigger! Who told you that you knew how to ride?”

The insult reminded Winkfield that he was in constant danger at U.S. tracks. The more he won, the more white Americans despised him: Jockeys bumped and whipped him during races, trainers were reluctant to hire him because they feared that an attack on Winkfield could result in an injury for their mounts. And so, after finishing second in his third–and final–Derby, Jimmy Winkfield set sail for Europe.

Winkfield emigrated to Russia where he was greeted as a celebrity and in the name of the Czar Nicholas II competed at racetracks all over Europe. He won the Russian Oaks five times, the Russian Derby four times, the Czar’s Prize on three occasions, and the Warsaw Derby twice. The Russian Revolution caused him to leave the country in 1917 and he moved to France where he resumed racing, scoring numerous wins including the Prix du Président de la République, Grand Prix de Deauville, and the Prix Eugène Adam. He retired as a jockey at age fifty having won more than 2,500 races then began a second successful career as a horse trainer.

Winkfield lived on a farm near the Hippodrome de Maisons-Laffitte (racetrack) in Maisons-Laffitte on the outskirts of Paris. He remained there until fleeing the German occupation of France during World War II. After the war, he eventually returned to the farm at Maisons-Laffitte where he lived until his death 1974.

In 1960, Jimmy Winkfield made an appearance at the Kentucky Derby to celebrate 60 years since his historic victories. In 2004 he was inducted posthumously into the National Museum of Racing and Hall of Fame. The Jimmy Winkfield Stakes at Aqueduct Racetrack is run in his honor.

In 2005, the United States House of Representatives passed a resolution honoring Jimmy Winkfield. The full details can be read here at the National Museum of Racing and Hall of Fame.

Read, learn, and share…Have a Family Meeting!

I must credit my man at the local grocery store, who while he was replenishing the salad bar asked me if I knew who Jimmy Winkfield was…I answered no. After listening to him talk about Winkfield and the need to do more with our history, I explained to him that I would write this post after doing some research on the jockey. Thanks my man!

Information for this post was obtained from Wikepedia and an article written by Charles Hirschberg entitled “Pilloried At The Post.”

This entry was posted in African-American History, Athletics, Black History Month, Conduct and Behavior, Education, History, Motivation and tagged , , . Bookmark the permalink.

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