Black Jockeys & The Kentucky Derby: A Book Excerpt

Tomorrow is the 138th Kentucky Derby, dubbed the “Fastest Two minutes in Sports.”   Horse racing faces new challenges: the drugging of horses, the loss of interest in the sport as betting becomes more widespread and fans turn towards football and basketball, and the suggestion that perhaps jockeys aren’t needed and robots will do.

In honor of the Kentucky Derby, I’m sharing a short excerpt about the first jockeys from my book, On the Trail of the Ancestors: A Black Cowboy’s Ride Across America.


Ch. 11: In the Saddle with Jimmy Winkfield (an excerpt)

It’s a cool day in May 1875, the first Kentucky Derby. Ten thousand racing fans watch in anticipation as 15 jockeys (13 of them black) on horseback approach a line drawn in the dirt. As drums tap, the red flag is lowered, timekeepers click their stopwatches, and the race begins. Jockeys, vying for the best position, steer their horses, thundering around the track. Ending only two minutes, 37 and three-quarter seconds later, Oliver Lewis, astride a chestnut mount named Aristides, crosses the finish line and into horse-racing history. Fans roar as Lewis, a garland of red roses adorning his neck, takes a celebratory lap around the track. …


After Lewis’ victory in the first Derby, black jockeys claimed the title 15 times over the next 28 years. William “Billy” Walker, age 17, in 1877, followed by Isaac Murphy, in 1884, 1890, and 1891, then Alonzo “Lonnie” Clayton, at 15 the youngest to win in 1892, followed by James “Soup” Perkins, who began racing at age 11 and won the 1895 Derby. Willie Simms won in 1896 and 1898.

And then there was Jimmy Winkfield. Born the youngest of 17 children in 1882 in Kentucky, Winkfield was smaller than most boys his age. His parents, poor sharecroppers, farmed land owned by someone else. All the children worked. After chores, he would watch thoroughbreds parade between the farms and the racetrack in nearby Lexington, pretending to be a jockey, using a wooden workbench as his horse.

Jimmy Winkfield (

By the 1899 racing season, Winkfield took 14 wins. The next year, 1900, he rode in his first Kentucky Derby. Wearing orange-and-blue silks, Winkfield rode out on his horse, Thrive, and placed third. He went on to win another 160 races in 1901, including the Derby astride His Eminence. In the next year’s Kentucky Derby, 1902, Winkfield rode Alan-a-Dale and won, the only back-to-back Derby wins. He nearly won again in 1903. …


For more about the black jockeys read:

Black Maestro: The Epic Life of an American Legend by Joe Drape

The Great Black Jockeys: The Lies and Times of the Men who Dominated America’s First National Sport by Edward Hotaling

Also: Isaac Murphy: I Dedicate this Ride, Poems by Frank X. Walker

And for children, The Last Black King of the Kentucky Derby: The Story of Jimmy Winkfield by Crystal Hubbard.

Happy Derby Day!

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3 Responses to Black Jockeys & The Kentucky Derby: A Book Excerpt

  1. Thanks for posting this. I loved reading this chapter in the book and your article for the Smithsonian. I has helped me see the Kentucky Derby in a different way.


  2. How interesting! Thank you for sharing this!! 🙂


  3. After watching the Derby yesterday, i realized the importance of this story. Thanks again. The next is the Preakness in Baltimore. It has a long history also. My husband’s uncles worked at the tracks years ago. I also knew some older men who were patients of mine when I lived in Maryland who had worked in the stables.


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