Black Maestro: The Epic Life of an American Legend

The life of Jimmy Winkfield is an exuberant epic: the seventeenth child of Kentucky sharecroppers, he was the last black jockey to win the Kentucky Derby, and survived the Ku Klux Klan, the Bolshevik Revolution in Russia, and the Nazis, and died a wealthy landowner in a French chateau.

Jimmy Winkfield is surely the oddest and most invisible witness to some of the greatest historical events of the 20th century. His life is one of adventure and history, of travels around the world.

Winkfield, a black jockey, won the Kentucky Derby in 1901 and 1902. He was the last African American to win that race, and actually closed out an era in which black jockeys dominated the event. (The legacy had its roots in slavery, when plantation owners left the care, training and racing of horses to their slaves.

In the first Kentucky Derby, in 1875, 13 of the 15 riders were African Americans. So was the winning jockey. And, over the first 28 years the Derby was run, 15 of the winning riders were African American. ) Jimmy Winkfield went from being the youngest of 17 in a family of sharecroppers, to racing for $8 a month, and eventually $1000 per race. But in 1903 Winkfield lost his third attempt, and his racing life faltered. He found himself under tremendous economic pressure–and racial pressure at the same time, from the KKK. Anxious about racial riots and protests, Winkfield accepted an offer to race in Russia, where he found refuge from the KKK and became a star again. A few years later, he became the Tsar’s rider, until the Bolsheviks chased him out along with 200 of the Tsar’s horses. In order to save them, Winkfield drove the horses through a nasty Eastern European winter, eating some of them along the way to stave off starvation. He arrived in France with these beloved horses, became a gentleman, married, rode and made a lot of money. Then came the Nazis, who drove him and his family back to Aitken, S.C., where he resumed a humble life as a $15 a day horse groomer. After the War he returned to France and resumed his position, farm and estate. He came for a visit to Louisville in 1961 as a guest of Sports Illustrated and, ironically, was not allowed in the door of the Brown Hotel.