The first Kentucky Derby, in 1875, was won by Aristides. On his back was a black jockey, Oliver Lewis; the man who trained him, Ansel Williamson, was also black. Five years earlier, Kingfisher had won the Belmont Stakes, ridden by Edward Brown, trained by Raleigh Colston, both men who had been born into slavery.

That first Kentucky Derby featured a dozen black riders, young men who had learned about horses from the slaves of a prior generation. Black jockeys won 15 of the first 28 runnings of America’s best-known race.

But since jockey Jimmy Winkfield won his second consecutive Kentucky Derby in 1902, no black rider has won the Run for the Roses, and only a small handful of African-American jockeys have even competed in it, most recently Kevin Krigger on Goldencents in 2013.

The dominance of black riders can be traced directly to the antebellum South, to a system of slavery that saw the white elite entrusting the horses they owned to the humans they owned. Through their horsemanship, generations of slaves earned positions of privilege and an unusual, if restricted, freedom denied field and house slaves.

And while the disappearance of black horsemen from U.S. racing in the early 1900s is well documented, less well known is how the very success of those horsemen served to convince wealthy white people—both north and south—that slavery could be a viable, enduring economic and social model.

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