The Last Black Jockey to Win the Kentucky Derby:James Winkfield

Between 1900 and 1903, jockey James Winkfield rode in four consecutive Kentucky Derbies. He finished third, first, first, and second. In 1901 alone, he won somewhere between 160 and 220 races (depending on the source). But despite his extraordinary, natural talent as a jockey, Winkfield received little recognition from within or without the horse-racing community.

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