all in Legends

Everyone has an opinion in horse racing. It’s one of the most alluring aspects of the sport. Debates rage about which horse was better, which performance was greater, or which rivalry was the most memorable.

Handicappers, racing writers, and fans rarely — in fact, almost never — agree.

But there is one performance that stands out as unequivocally one of the best races a horse has ever delivered on the Triple Crown stage: Afleet Alex’s Preakness Stakes victory in 2005.

The Maryland Jockey Club mourns the passing of legendary Hall of Fame trainer King Leatherbury, who died at his home Tuesday morning. He was 92.

“He’s one of a kind,” said one of his twin sons, Taylor Leatherbury. “There’s never been a man more appropriately named than my father.”

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.

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