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.