From NKAA, Notable Kentucky African Americans Database (main entry)
Winkfield, Jimmy
(born: 1882 - died: 1974)Born in Chilesburg [later Uttingertown] in Fayette County, KY, Jimmy Winkfield was the youngest of 17 children. He was the last African American jockey to win the Kentucky Derby, in 1901 and 1902.
Winkfield left the U.S. after a contract dispute and became a national riding champion in Russia and a trainer in France. He retired from racing in 1930 and died in France in 1974. In 2004 he was inducted into the National Museum of Racing and Hall of Fame.
For more see The Great Black Jockeys and Wink: the incredible life and epic journey of Jimmy Winkfield, both by E. Hotaling; and "The Epic Journey of James "Wink" Winkfield," 4/23/2020, on America's Best Racing website, by Terry Conway (includes photographs and a video).