Tags: Jockey (Horse Racer).

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.

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