There aren't too many folk other than historians who know that there was a time when African Americans ruled horse racing. Black jockeys won at least 13 or 14 of the first 25 Kentucky Derby events, and 12 of the 15 jockeys in the first Kentucky Derby were black. Jimmy Winkfield grew up during that era, and in 1901 and 1902 he won back-to-back Kentucky Derbies, a feat equaled only by three others. Ed Hotaling unveils Winkfield's rise and the disgraceful reaction it provoked in his wonderful book Wink: The Incredible Life and Epic Journey of Jimmy Winkfield.
Hotaling starts with Winkfield's early years as a shoeshine boy in Lexington, Kentucky, then details Winkfield's rise to superstar status at 22 and his highly confident and combative personality that eventually caused him to be blackballed by stable owners in 1903. Undeterred, Winkfield left America and embraced the European racing circuit. He became the "black maestro" in Moscow, and was later highly celebrated in France. He eventually left France and returned to America to become a construction worker for the Works Progress Administration. Winkfield once again emerged as a winner, this time training horses and owning a stable in France despite being in his 70s. He finally died in Paris at 94. Hotaling doesn't sanitize Winkfield or minimize his flaws. Alongside the biographical details, Hotaling shows how racism and economic pressure combined to displace black jockeys and turn horse racing into an all-white sport before the first decade of the 20th century ended.