In 1968, a few women, mockingly labeled "jockettes" by a skeptical press, had begun demanding the right to apply for jockey licenses, citing the Civil Rights Act of 1964, which banned discrimination in hiring based on race, religion, sex, or national origin. Most of their applications were rejected by racing's bureaucracy, which alleged that women were unqualified to participate due to "physical limitations" and "emotional instability." Female jockeys who attempted to ride met with boycotts by male jockeys.

Onto this uneven terrain stepped 20-year-old Diane Crump, who had long since demonstrated her riding proficiency during a thousand workout rides on a thousand difficult Thoroughbreds ("I basically got on all the horses that no one else wanted to ride"). On February 7, 1969, having been granted a permit to ride at Florida's Hialeah Racetrack, Crump, surrounded by a protective phalanx of police officers, walked calmly toward the saddling enclosure as she endured heckles from the crowd. Diane's mount would not earn victory that day, but the young rider had earned a more fundamental prize: the right to compete in her chosen field. Just over a year later, on May 2, 1970, after 95 years and 1,055 all-male entrants, Diane Crump shattered tradition by becoming the first woman to ride in the Kentucky Derby. Over her career she amassed 235 wins.