- Kelly M. Jordan
jockey and trainer, was born in Chilesburg, Kentucky, the youngest of seventeen children in a family of sharecroppers. He first worked at the racetrack shining shoes and made his way to stable hand, then exercise rider, and finally jockey. At the age of sixteen he was riding in races. Nicknamed “Wink,” he secured a place in racing history by age twenty-two for winning the Kentucky Derby back-to-back: in 1901 on His Eminence and in 1902 on Alan-A-Dale. During his career he won an amazing twenty-six hundred races. He also was a talented horse trainer in his later years.
In 1904 Winkfield fled the United States rumor had it that he had a falling out with a racehorse owner and raced in Russia There he continued his winning career taking the Russian and Moscow derbies more than once He scored victories in other races in Germany Russia and Poland ...
A version of this article originally appeared in African American National Biography.