Milford woman was first female jockey to race in U.S.

Diane Crump was the oldest of four children growing up on Usher Street in Woodmont in the late 1940s and early 1950s, three houses from Long Island Sound. She had a passion for animals, and there could often be found a rescued duck or seagull, even a pelican once, recuperating in the unfinished basement, which Diane turned into her own wildlife sanctuary.

While she loved all animals, it was horses she was most drawn to, and following horseback riding lessons in Milford and then her move to Florida when she was about 12, Crump went on to make history in the world of horseracing. She was the first female jockey to ride in a pari-mutuel (money betting) race, and she was the first woman to ride a horse in the Kentucky Derby.

Growing up in Milford she may not have had a horse, but she developed her love of them here.

She remembers that her first encounter with horses was at a carnival in Milford, where she got to ride a pony.

“From that day on I fell in love with them,” she said.

She grew up in Woodmont along with twin brothers, Bert and Ben, a year and a half younger than she, and her sister, Linda, the “baby,” who was six years younger than Diane. Diane remembers walking down the hill from home, climbing over the rocks and being at the water.

As a child, Diane attended the former Woodmont School, and later she attended the former Seabreeze School.

“I loved it, loved growing up in Connecticut,” Crump said. “It was awesome. You could run on the beach; you were free.”

Living in Woodmont, there wasn’t much chance of her parents, Jean and Walter Crump, buying her a horse because there wasn’t room for one, but for her seventh birthday they paid for riding lessons at Cadley Farm in Milford.

With plans of moving south, her parents told her that if she saved enough money, she could buy her own horse when they got to Florida. And so Diane delivered papers and did whatever work she could do from the time she was 8 years old, and by the time they arrived in Florida, she’d saved about $140.

“My parents moved to Florida because my dad loved boats and the water,” Diane said. “He had a dream to build a marina in Florida. They just loaded us kids in the station wagon and headed south. They were Florida bound, with no idea where, what or when. They drove down the east coast and came up the west coast. They said they’d know what felt right when they got there.”

What felt right was the Tampa Bay area.

When they settled in Florida, Diane continued to save money and in about a year she bought a horse, which she boarded on the outskirts of town. Not long after, her father bought a piece of land, and with that purchase came two horses for Diane. She boarded them at a stable at the corner of Hillsboro Avenue and Racetrack Road.

“I wasn’t thinking of what that meant,” she said, referring to Racetrack Road, which would become the area where she spent her time as she headed into her teen years. She was 13 years old when she rode down Racetrack Road, came across the horse racetrack and saw all it had to offer. “Something went off inside of me,” she said.

And life continued on this path that eventually led her to become a jockey.

She and her friends would ride horses into the night, she on one of her two mares, Patches and Lulu. She started a riding club, and one of the members was learning to be a blacksmith and knew of a farm nearby looking to hire a kid to work a couple of days a week.

“He took me there and introduced me, and they hired me,” she said. “It was a racehorse farm. One side was a dairy and the other side was racehorses.”

Working on the thoroughbred farm she learned skills that would feed into her riding career. She learned to halter break horses. “Nobody was telling me how. If I got kicked or bitten, I figured out how to make it work.”

One day someone said they needed somebody to break the yearlings, and Diane said, “I’ll do it.”

She didn’t know how, but with someone on the ground telling her what to do, she learned.

She wasn’t 16 yet so she couldn’t go to the racetrack, but the horse trainer at the farm used to smuggle her in.

When she turned 16 she got her license to gallop horses, and when she was a senior in high school, against her parents’ initial wishes, she went to night school to complete her high school diploma early so she could go to Miami, where the horses she had worked with on the farm were to race. “I loved them, and I had done all that work with them,” she said.

The owner of the farm talked to her parents, and explained that he knew a woman in the Miami area who would take Diane in and look after her. Her parents agreed, so long as she finished high school first.
Making history
Back then women could not get a jockey’s license. In 1968, Kathy Kusner successfully sued the Maryland Racing Commission for a jockey’s license under the Civil Rights Act, according to Then in November 1968 Penny Ann Early became the first female to be named to ride in a race in the United States. But the male jockeys boycotted the races at Churchill Downs, refusing to race against a woman, according to

Crump said that another woman, Barbara Jo Rubin, tried next to be the first female jockey to ride in the United States. While Kusner had won the legal battle to ride in Maryland, the fight had to go to Florida, where Rubin hoped to race, and Crump said Rubin took the case there and easily won.

According to, “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.”

In February another woman got a chance to make female jockey history, and it was Crump. On Feb. 7, 1969, Crump was named to ride a horse at the Hialeah Park Race Track in Florida at the urging of the horse owner’s wife, who had heard about Crump. Riding Bridle ’n Bit, she became the first licensed woman rider to ride in a pari-mutuel thoroughbred race in the United States.

According to an LA Times article written in 1989, “It was never planned that Crump would become the first woman to ride in a race. The legal battle over the licensing of a woman jockey had been fought — and won — in the fall of 1968 by Kathy Kusner, who was a member of the American Olympic equestrian team.

“Kusner, who probably would have made the historic first ride in Maryland, broke her leg in a horse show at Madison Square Garden and was recuperating when Crump beat her to the post at Hialeah,” the LA Times wrote.

Kusner and one of Crump’s favorite authors — Walter Farley, author of the Black Stallion series — actually showed up at her history-making race at Hialeah to wish her luck. notes, “Although she didn’t win that race, Crump showed that female jockeys could handle the track and the thoroughbreds as well as the male jockey.”

According to, “Crump faced such vitriol at her first race that [she] required a full police escort.”

“The first professional female jockey in the U.S. still remembers the mayhem that surrounded her as she took to the Hialeah Park Race Track in Florida in 1969,” CNN wrote. “The petite teenager with curly brown locks was forced to fight her way through the flashing cameras and jeering crowd to a small office — the only available space for a female to change.”

Crump said she wasn’t afraid or intimidated; she was just thinking about the ride.

The scene is recounted on her own website with these words: “With flashbulbs popping and surrounded by a police escort, Diane was ushered into the bright sunshine (and spotlight!) at Hialeah Racetrack on a day in February, 1969. A day she’ll never forget. Midst both boos and cheers from the crowds lining the pathway to the paddock, she was about to become the first woman to ever ride in a pari-mutuel race in the U.S.”

But on her website, which Diane’s mother, Jean Crump, created, Jean pointed out that making history was not foremost on her daughter’s mind. She was going to be given an opportunity to do what she knew she could do and was determined to give it her best shot. She didn’t win, but the future was getting started. Invitations started pouring in — to ride in Puerto Rico, Venezuela, the Fairgrounds at New Orleans, and more.

In Puerto Rico, “she was matched against this tough little Puerto Rican guy,” according to Crump’s website. “Puerto Rico is not known to particularly abide by any stringent rules, meaning anything goes. When they came flying out of the starting gate, this little jockey pulled up alongside her horse, jerking the reins and doing whatever he could to unseat her. “Sportsmanship being what it was in that little part of the world, she did the first thing that came to mind. She cracked him over the head with her riding whip. The women booed their own country’s jockey, tossing rotten tomatoes and threatening bodily harm to him after the race. Diane was greeted by cheering enthusiastic women who loved it!”

From there she logged wins and failures as she followed the racing circuit. During that first year, she had 40 wins, some of them quite impressive.

Then came the 1970 Kentucky Derby.

She and her husband were training horses for an elderly man who had a dream of entering one of his horses in the Kentucky Derby. One morning he went to the barn to ask Diane’s husband if he would be embarrassed to run his horse Fathom in the derby, knowing he was a long shot. Her husband answered, “I'll run Fathom down that road there if you want me to!”

So Fathom was nominated for the derby, and the owner asked Diane to ride him.

According to, “Crump came in 15th in a 17-horse race, but, most notably, became the first woman to ride at the Kentucky Derby. A derby win may have eluded her, but she scored more than 230 victories on track before retiring in 1985.”

Today Diane owns Diane Crump, Equine Sales, in Virginia, combining her knowledge and her love for horses. While she doesn’t own a horse today, or ride anymore, through her company she helps match people to their ideal horse.

Crump doesn’t consider herself a hero, or a warrior for the women’s liberation movement.

“I just loved to ride,” she said.