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?
Tag: Legends
Stars of Yesterday: Looking Back at Best Holy Bull Stakes Winners
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.
How a Dinner Party Begot a Classic: Oden Bowie, Pimlico, and the Preakness
When the gates fly open each May at Pimlico Race Course (or Laurel Park in 2026), 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.
Inside Information: A Hall of Fame Racehorse With Push-Button Brilliance
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.
