Black jockey dominance began in the late 18th century and was evident in the inaugural Kentucky Derby in 1875, where 13 of the 15 jockeys were Black — including the winner. Jimmy Winkfield emerged from this powerful lineage. He wasn’t just a jockey — he was a master of his craft, a global champion, and a symbol of Black excellence whose brilliance reshaped the world of horse racing.

Born in Kentucky in the early 1880s, Winkfield rose from the heart of the Bluegrass to become one of the most celebrated riders of his era, winning more than 2,500 races across three continents.
In 1901 and 1902, he made history with back-to-back Kentucky Derby victories, a feat achieved by only one other jockey in the Derby’s long legacy. His talent was undeniable — but as racial barriers tightened in American racing, Winkfield took his gifts abroad, becoming a superstar across Russia, Poland, Germany, Austria, Hungary, and France.
There, he dominated the sport, winning major titles including the Russian Derby, Russian Oaks, Czar’s Prize, Warsaw Derby, and premier races throughout Europe. His mastery transcended borders, languages, and politics.

When revolution swept Russia, Winkfield led a daring 1,000-mile evacuation of hundreds of elite racehorses — a testament not only to his skill, but to his courage and leadership.
He eventually settled in France, where he continued to race, train, and inspire until his passing in 1974. Today, he is honored in the National Museum of Racing and Hall of Fame, and the Jimmy Winkfield Stakes at Aqueduct carries his name forward.