William Douglass Smith is a direct descendant of the legendary racer, Jimmy Winkfield who was a jockey with the best winning average in Derby history during his heyday: two victories, one second, and one third in four starts; he was also the last African-American to win the race. Jimmy “Wink” Winkfield was born on April 12, 1882 in Chilesburg, Kentucky. He rose to fame by winning back-to-back Kentucky Derbies with His Eminence in 1901 and Alan-a-Dale in 1902. He was the last African American to win the world-famous race. Along with the Kentucky Derby, Winkfield won the Clark Handicap, Tennessee Derby, Latonia Derby, and New Orleans Derby that year.
The violent forces of racism deeply impacted him, as he faced death threats from the Ku Klux Klan. In 1905 Wink left America for Europe. He went on to win prestigious races such as the Prix du President de la Republique, the Moscow Derby, and the Grosser Priz Von Baden. Winkfield settled in Russia where he was quite a sensation, marrying into an aristocratic family and living a lavish life until the Russian Revolution in 1917. In 1961, six decades after winning his first Kentucky Derby, Winkfield returned to Kentucky to attend a pre-Derby banquet. When he and his daughter Liliane arrived at Louisville’s historic Brown Hotel, they were denied entry. After a long wait and repeated explanations that they were guests of Sports Illustrated, they were finally admitted.
In 2004, Winkfield was inducted into the National Museum of Racing and Hall of Fame in Saratoga Springs, New York. In 2005 the United States House of Representatives passed a resolution to honor Winkfield , a few days before the 131st Derby. Such accolades came long after his death in 1974 at age 91, March 23, 1974, in Maisons-Laffitte, France; and that same year, the New York Racing Association named a race in his honor that runs each Martin Luther King Holiday at the Aqueduct Race Track. All of this occurred decades after racism forced him and other Black jockeys off American racetracks.