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Black Maestro by Joe Drape

About.com Rating 5 Star Rating


Black Maestro

Black Maestro by Joe Drape

The Bottom Line

Although Laffit Pincay, Bill Shoemaker, and Eddie Arcaro are generally regarded as some of the best American riders in history, there was a rider in the first half of the 20th century who must be considered among these greats. Jimmy Winkfield was the last African-American rider to win the Derby, but his life story goes well beyond his native Kentucky. New York Times writer Joe Drape has written a most fitting tribute to one of racing's forgotten heroes.
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  • A truly amazing story about one of America's greatest horsemen
  • Detailed account of the Maestro's many struggles, both on and off the track
  • Winkfield is an inspiration to people of all ethnic backgrounds


  • No fault was found with this work. A fitting tribute by a top racing writer


  • Winkfield got his start in his native Kentucky as a share cropper.
  • His first experience as a jockey was at Latonia Racetrack, considered the "big time"
  • He traveled around the country to ride, ending up in New York, Chicago, and Louisiana
  • Despite winning 2 straight Kentucky Derbys, losing when trying for his third turned trainers away
  • Unable to get live mounts he joined the exodus of American jockeys to Europe, settling in Russia
  • Here he was admired for his riding and training skills, and was respected by the royal family
  • The rise of the Bolsheviks forced yet another exodus, this time to France via Poland
  • After setting up a successful stable at Maisons-Laffitte, the Nazi invasion shut down French racing
  • His life came full circle when he left France to escape the Nazis, returning to America
  • Finally in 1961 Churchill Downs invited him to the Kentucky Derby as a special guest.

Guide Review - Black Maestro by Joe Drape

Fifteen of the first 28 Kentucky Derbys were won by black jockeys, including the 1901 and 1902 editions with Jimmy Winkfield. The Black Maestro, as he came to be known, was a natural horseman, a sharecropper in his native Kentucky, and made his way to Latonia to start his career first as a groom, then exercise rider and finally as a jockey. He traveled around the country following the circuit through Louisiana, Kentucky, and Chicago, once even getting caught in the middle of the bloody mobster war in the Windy City over control of its tracks.

He won the Derby in 1901 and 1902, but when going for the three-peat in 1903, an apparently bad ride aboard the heavy favorite Early caused a quick downfall in his career. Trainers ceased to give him live mounts, so he crossed the Atlantic to Europe and restarted his career in Czarist Russia. He was a popular figure in Moscow, as both a jockey and a trainer, but with the start of the Russian Revolution, racing in that country was shut down. He fled to Poland then France, and again opened a public stable out of Maisons-Laffitte. World War II and the rise of the Nazi's again forced him to flee, as the German army commissioned French tracks and training centers as barracks as well as stole top French bloodstock, bringing them back to Germany. Winkfield returned to America, but when he died, he was buried in France with a headstone marked "Moscow", in Cyrillic, showing his appreciation for the city that loved him most.

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