The photos that are available of James “Jimmy” Winkfield—a thoroughbred jockey and horse trainer from Kentucky, who was the last African American to ride a winner in the Kentucky Derby—show a young man with distinctive features: a lean stature, slight jawline, and kind eyes, the brim of a jockey cap casting a faint shadow.
In his paintings of an early-1900s Winkfield, however, artist Todd Murphy opted for a more abstract treatment: a faceless, featureless jockey to depict Winkfield’s relative obscurity in the history of the sport. While Winkfield was inducted posthumously into the National Museum of Racing and Hall of Fame in 2004, other Black jockeys—like Oliver Lewis, the first winner of the Kentucky Derby—also trained and rode with negligible fanfare or distinction.
The photos that are available of James “Jimmy” Winkfield—a thoroughbred jockey and horse trainer from Kentucky, who was the last African American to ride a winner in the Kentucky Derby—show a young man with distinctive features: a lean stature, slight jawline, and kind eyes, the brim of a jockey cap casting a faint shadow.
In his paintings of an early-1900s Winkfield, however, artist Todd Murphy opted for a more abstract treatment: a faceless, featureless jockey to depict Winkfield’s relative obscurity in the history of the sport. While Winkfield was inducted posthumously into the National Museum of Racing and Hall of Fame in 2004, other Black jockeys—like Oliver Lewis, the first winner of the Kentucky Derby—also trained and rode with negligible fanfare or distinction.
