Despite boycotts, hecklers and a dubious society, on Feb. 7, 1969, Crump became the first woman jockey to ride in an American pari-mutuel race at a major thoroughbred track. In 1970, at the age of 21, she became the first woman to ride in the Kentucky Derby.

Crump had grown up horse-crazy. At 13, she discovered thoroughbred racing. “I loved the sport. I loved the power of the horse,” she said. But women couldn’t yet hold jockeys’ licenses. “To come up along that, and not know if you ever could ride in a race, it didn’t diminish the way I felt, it didn’t diminish the love that I had, but it did increase the intensity that I wanted to do it. I guess that’s what happens when you can’t, right?”

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The rules barred Crump from racing but not from racehorses. She exercised horses, groomed them, and ponied them on their way to the starting gate. “I just kept pressing on in the hopes that one day [being a jockey] would become a reality,” she said.

In 1967, United States Equestrian Team rider Kathy Kusner applied for a Maryland jockey’s license, but officials denied her. A year later, a judge citing the Civil Rights Act of 1964 ruled that the Maryland Racing Commission had to certify Kusner. But Kusner broke her tibia before she could ride in a race. In the last months of 1968, Penny Ann Early was scheduled to ride at Churchill Downs, but male jockeys boycotted by backing out of the races. In January of 1969 it was Barbara Jo Rubin’s turn, but jockeys at Tropical Park in Florida threatened a boycott. A male jockey replaced her.

That same month, at Florida’s Hialeah Park, female trainer Mary Keim named Crump to ride a filly named Merr E. Indian. “[Diane is] cool and she’s smart and I think she’ll make as good a rider as any boy,” Keim told reporters. But Merr E. Indian didn’t “draw in,” meaning that her name wasn’t chosen to race. Crump would have to wait.

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Meanwhile, officials grew weary of the tumult over women’s riding. The Florida Racing Commission met the morning of Jan. 31 and said it would stiffen penalties against jockeys who refused to ride. “If [the jockeys] back out now, God help them,” said one Florida State Racing Commission supervisor.

Early in February, Crump learned that her first race would be on a horse named Bridle ‘N Bit, on Feb. 7, in the seventh race at Hialeah at a mile and 1/8. The trainer’s wife, who owned the horse, had insisted, he told reporters. “She said, ‘Put the girl on or I’ll get another trainer.' ”

When the day arrived, some jockeys did drop out, but trainers found replacements right away. Crump put on her red-and-white silks in the Horseman’s Benevolent and Protective Association office, rather than the jockeys’ room. In the paddock, many cheered, while some booed or catcalled. “Why don’t you stay home and do the cooking?” one man said.

Instead of the traditional “Boots and Saddles” call to post, the bugler played “Smile for Me, My Diane.” “Remember, ladies first,” a bystander yelled to jockeys as the horses filed through the tunnel on the way to the track. Next to Crump in the starting gate, jockey Craig Perret reminded her to put her goggles down.

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And they were off.

Bridle ‘N Bit broke from the number-2 post position and was last at the half-mile pole. When they turned into the stretch, Crump asked the horse for more, and Bridle ‘N Bit thundered by two other horses, smothering himself and Crump in mud and finishing 10th out of 12.

“I think I did okay for the first time,” she told waiting reporters.

Nick Jemas, the director of the Jockeys’ Guild, fumed over women riding. He considered Crump “the best of the lot.” But, he believed, she distracted male jockeys. “They’re watching Diane every step of the way to see that she doesn’t get hurt. That’s only natural,” he said. “But it’s a bad thing for racing.”

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Crump kept riding and started winning races. That summer, she worked at Delaware Park alongside her trainer husband, Don Divine. One heckler, Crump said, attacked her every day, saying, “Go home and clean the kitchen, go home and do the laundry.”

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After Crump’s initial ride, more women began to race. By 1970, about 10 women had won races, said Mark Shrager, the author of a biography of Crump. “Barbara Jo Rubin had won three races in a day by that time,” he said. “The women, once they were allowed to ride, proved they could do it. And by 1970 it wasn’t that much of a novelty. Except riding in the Kentucky Derby.”

Crump would do that, too. “A gal in the Derby? Next thing you know they’ll be playing second base for the Dodgers,” wrote one reporter. By then, she said, she had proved her skill as a jockey. Male jockeys didn’t tease her anymore. “I think I’ve got their respect now,” she said at the time.

Crump started Derby Day strong with a win in the first race. Her mount for the big race itself was a chestnut long shot named Fathom, whom she had ridden since he was a yearling. He wasn’t likely to succeed, Crump said, but his owner, a Kentuckian, had always dreamed of seeing his colors in the Derby. She would ride in a 17-horse field against Hall-of-Fame jockeys like Angel Cordero Jr., Bill Shoemaker, and Bill Hartack. (That particular Derby Day became famous as the setting for gonzo journalist Hunter S. Thompson’s article “The Kentucky Derby Is Decadent and Depraved,” which mentions Crump.)

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“The fact that I was in a jocks’ room waiting for the Derby was a great feeling. And the crowd and in the spring — it’s the most awesome feeling you could ever imagine,” she said.

The Derby was on. “I’d never ridden in a field that big,” said Crump, “but it just gave you a good feeling. And [Fathom] actually ran a pretty good race. He was certainly not that caliber, but he was in the thick of things for most of the race. I got him in a good position around the first turn, the fact that I was able to put him in the right place, find racing room, no trouble.”

Dust Commander won; Fathom finished 15th. “I don’t think any of us were disappointed,” Crump said. “The horse did try.”

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Crump has spent her life with horses. She retired from race riding in 1999. “She was able to make this happen for herself in a world that really didn’t want her to be part of it,” Shrager said. “She was a jockey for nearly 40 years and did it because she insisted that she had to do it.”

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A female jockey still has yet to win the Kentucky Derby. Julie Krone became the first to win a Triple Crown race in 1993 when she took the Belmont aboard Colonial Affair. In 2013, Rosie Napravnik rode Mylute to fifth place in the Derby, notching the best finish by a woman jockey. Napravnik is also the only woman to have ridden in all three Triple Crown races: the Kentucky Derby, the Preakness and the Belmont.

“I think there’s still a lot of reluctance to use women jockeys,” Shrager said. “I clearly see that they don’t get the opportunities that they should, and that the numbers of them out there are not what they should be.”

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Today, Crump lives in Linden, Va. She doesn’t ride any longer, but she does own a horse sales company. “I’ve never won the Derby,” she said. “I never made much money. But I always lived my dream.”

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Eliza McGraw is the author of “Here Comes Exterminator!,” which is about the 1918 Kentucky Derby winner. Roda Ferraro at the Keeneland Library provided research assistance.