Jimmy Winkfield’s career in horseracing began when he started working in a stable at age 15. He was penalized for causing a four-horse accident at the starting gate of his very first race in 1898, which kept him from racing for a year. In 1901 he won the Kentucky Derby riding His Eminence. He followed that by winning it again the next year on Alan-a-Dale.
In 1903 he finished second on Early. After that he moved to Russia, where he was treated as a celebrity and competed for Czar Nicholas II all across Europe. Having been so closely associated with the Czar, he fled Russia during the 1917 Bolshevik Revolution and moved to France, where he spent most of the remainder of his life, excluding the period of Nazi occupation.
In 2004 he was added into the National Museum of Racing and Hall of Fame. He is remembered as the last African-American rider to win the Kentucky Derby.
Photo courtesy of Hard Road to Glory, Jim Bolus