James Winkfield

Who was James Winkfield?

James "Jimmy" Winkfield 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.

Later that year, 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.