all in Legends

He was on the doorstep of becoming America’s greatest Black race rider. One of just six men to win back-to-back Kentucky Derbys (1901-1902), he barely missed a third victory the following year.

But, the story of James “Wink” Winkfield being a great jockey would just be a slice of his existence. Has any jockey led a more incredible life?

Black History Month offers an important opportunity to reflect on the contributions of Black Americans whose impact has shaped industries across the nation, including horse racing. While modern racing often lacks visible diversity, Black horsemen were foundational to the sport’s early success. One of the most influential among them was Ed Brown, a formerly enslaved man who became one of the leading trainers of the 19th century.

Gulfstream Park’s road to the 2026 Kentucky Derby Presented by Woodford Reserve begins this Saturday with the Grade 3 Holy Bull Stakes. The race will offer 20 qualifying points to the winner as top 3-year-olds compete to accumulate points and earn a place in the Derby starting gate.

When the gates fly open each May at Pimlico Race Course, racing fans celebrate more than just the Preakness Stakes — they honor a legacy rooted in the vision of one man: Oden Bowie. As governor and a sportsman, Bowie recognized the potential for Maryland to become a national leader in Thoroughbred racing.

Rain has been known to dampen the spirits of many a person.

But not trainer Shug McGaughey, especially on a gray October afternoon in 1995.

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