2004-01-01 - James “Jimmy” Winkfield: Inducted in 2004 - Horse Racing

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James “Jimmy” Winkfield: Inducted in 2004

Even today, James “Jimmy” Winkfield comes up in the conversation about history’s best jockeys. The Kentucky native took the top prize in the Kentucky Derby in successive years, 1901 and 1902, becoming the second jockey to achieve this feat. After winning over 2,000 races in his storied three-decade career, Winkfield was gifted post-mortem with a race in his name to honor his legacy. It’s no surprise that The First Kentucky Derby makes mention of Winkfield’s incredible run in the book, noting how Winkfield, a.k.a. the “Black Maestro,” would mark the end of the Golden Age of Black jockeys.