The African American man who won the Kentucky Derby twice is Willie Simms. He won the Derby in 1896 and 1898 and was also the first jockey to win a race with an American horse at that time

. Another notable African American jockey who won the Derby twice consecutively was Jimmy Winkfield, who won back-to-back in 1901 and 1902, and is remembered as the last African American to ride a winner in the Kentucky Derby