Barbara Jo Rubin

Webb, who was working out of Charles Town, West Virginia, at the time, urged Rubin to apply for a jockey's license. Others were not so supportive. After obtaining her license by the Florida State Racing Commission, Rubin was scheduled to make her professional debut on Webb's horse Stoneland at Tropical Park in January, 1969. But a group of male jockeys protested her presence, and threatened to boycott the track should Rubin be allowed to ride. The pressure forced Rubin's withdrawal, especially after someone threw a brick through the window of a trailer she was using for a changing room. The nineteen-year-old was philosophical about the ruckus: "If I were a boy I'd probably fight this thing too," she told Parade reporter Linda Gutstein. "It's been a man's sport for so long—well, it's traditional. I guess I don't blame them for fighting it."

Instead of provoking further confrontation, Rubin found another way to ride. She left the U.S. for Nassau, Bahamas, where the young woman was welcomed onto the Hobby Horse Hall track. There she posted her first race—and her first win, aboard the heavily favored Fly Away. Following the three-length victory, as George Gipe wrote in his Great American Sports Book, Rubin "galloped triumphantly into the winner's circle, where she was greeted by her parents and a contingent of Miami supporters."