The struggle to raise White’s profile has deepened the family’s appreciation of not just her talents, but her father’s: Raymond Sr. began his career as a horse trainer in 1927, and persisted over the course of an era when many bleachers and backstretches were segregated. In 1932 as a trainer, he entered a horse in the Derby — his first of two.
“Black folks back then were able to clean up horse crap and walk horses and do the menial tasks. You weren’t in charge of somebody’s investment,” said Nikki White, who is married to one of Cheryl’s nephews, Raymond III. “And he had horses in the Derby and he had horses in the Preakness — that takes a level of respect that people of color didn’t get back then.”
The career path was often fraught. Married to a white woman, Raymond Sr. often listed his wife as the owner of his horses to avoid controversy. When Cheryl was born in 1953, her parents agreed her father would not join her mother at the hospital so no one would know she was married to a Black man. On her child’s birth certificate, under race, she wrote “white” in an effort to protect her daughter, her son Raymond Jr. said. After her death, White scattered her mother’s ashes at each leg of the Triple Crown.
As she grew up, Cheryl faced both internalized racism — she loathed that she was the one sibling with “bad,” or textured hair, her brother said — and external: When she rode, sometimes she heard slurs as her horses galloped by.
At the start of her career, despite her talent, she had trouble finding mounts. Her first big breaks came, by necessity, on her father’s own horses. “They can’t really say it’s experience,” White said to a reporter in 1971, expressing frustration at the lack of rides available to her after she’d earned her license. “It has to be either the fact that I’m a girl or the fact I’m black.”
Yet as her star rose, White seemed at pains to assert that, even in the era of the women’s liberation movement and growing Black political and social prominence, she was not trying to make a statement. She was there to ride.
“First black woman jockey waves no Banners — just rides,” reads a 1972 headline in The Los Angeles Times.