In its Dec. 13, 1968 issue LIFE wrote about Penny Ann Early and her battle to break the gender barrier in horse racing. At age 25 she was one of the first women to become a licensed jockey in the U.S. (The first was 1968 Olympic equestrian star Kathryn Kusner, who sued for that right but then suffered a broken leg before she could attempt to race). Early’s battle to get on the track was chronicled for LIFE by photographer Bob Gomel.

When Penny Ann Early attempted to compete at Churchill Downs, male jockeys were so opposed that they boycotted the races she was set to appear in. One male jockey cast the boycott as defending his livelihood. “If you let one woman ride one race, we are all dead,” he told LIFE.

Early told LIFE, “I have nothing against men. Next to horses I like men best. All I want is a chance to race against them. Is that so bad?”

Apparently it was. That issue of LIFE included a startlingly brazen guest editorial from Hall of Fame jockey Bill Hartack. He acknowledged that women had a legal right to ride and criticized the boycotts of Early as a misguided tactic. But Hartack also predicted that once women had the chance to compete, they would fail.

Hartack wrote:

“They’ll find out how tough it is and they’ll give it up. The tracks won’t have to worry about being flooded with women because a female cannot compete against a male doing anything….They might weigh the same as male jockeys, but they aren’t as strong. And as a group, I don’t think their brains are as capable of making fast decisions. Women are also more likely to panic. It’s their nature.”

Hartrack also dreamed up a scenario where women might use sex to get male jockeys to take it easy on them in a race. “If she was sharp enough I might take advantage of the situation myself,” Hartack wrote. “I wouldn’t ease up in the race, but I wouldn’t put it past me to con her into thinking that I would.”

While Early was ultimately unsuccessful in her attempts to break the gender barrier at the track, she did compete against men in another professional sport: basketball. Her battles at Churchill Downs caught the attention of the Kentucky Colonels of the fledging American Basketball Association, and the Colonels signed her to a one-day contract. She checked into a game long enough to receive an inbounds pass while wearing a sweater with the number 3, representing the number of times that male jockeys had boycotted her races.

But it didn’t take long until the gender barrier was broken—by Diane Crump, racing at another track. On February 7, 1969, became the first women to compete in a pari-mutuel race, at Hialeah Park Race Track in Florida, with LIFE photographer George Silk on hand. Her appearance was controversial enough that she needed police protection from the crowd before the race.

Crump finished ninth at Hialeah. Two weeks later she won her first race, and in 1970 she competed in the Kentucky Derby. And she and Early helped clear the path for other groundbreaking jockeys such as Julie Krone, who in 1993 became the first woman to win a Triple Crown race, atop Colonial Affair in the Belmont Stakes.

In an interview with CNN in 2012, Crump modestly said, “I like to think I was a little inroad on the path to equality.” She died of brain cancer on January 1, 2026, and the Churchill Downs racetrack issued a statement declaring that Crump “will forever be respected and fondly remembered in horse racing lore.”

Jockey Penny Ann Early with her horse Randy in Louisville, Kentucky, 1968.

Bob Gomel/Life Picture Collection/Shutterstock

Penny Ann Early, whose attempts to become to first female competitive jockey were met with boycotts, 1968.

Bob Gomel/Life Picture Collection/Shutterstock

Penny Ann Early, whose attempts to become to first female competitive jockey were met with boycotts, 1968.

Bob Gomel/Life Picture Collection/Shutterstock

Penny Ann Early, whose attempts to become to first female competitive jockey were met with boycotts, 1968.

Bob Gomel/Life Picture Collection/Shutterstock

Penny Ann Early, whose attempts to become to first female competitive jockey were met with boycotts, 1968.

Bob Gomel/Life Picture Collection/Shutterstock

Penny Ann Early, whose attempts to become to first female competitive jockey were met with boycotts, 1968.

Bob Gomel/Life Picture Collection/Shutterstock

Penny Ann Early, whose attempts to become to first female competitive jockey were met with boycotts, 1968.

Bob Gomel/Life Picture Collection/Shutterstock

Diane Crump, the first female jockey to compete in a pari-mutuel race, Hialeah, Florida, 1969.

George Silk/Life Picture Collection/Shutterstock

Diane Crump, the first female jockey to compete in a pari-mutuel race, Hialeah, Florida, 1969.

George Silk/Life Picture Collection/Shutterstock

Diane Crump, the first female jockey to compete against men, Hialeah, Florida, 1969.

George Silk/Life Picture Collection/Shutterstock

Diane Crump readies to become the first female jockey to race against men, Hialeah, Florida, 1969

George Silk/Life Picture Collection/Shutterstock

Diane Crump races against men for the first time in Hialeah, Florida, 1969.

George Silk/Life Picture Collection/Shutterstock

The post Diane Crump and the Jockeys Who Broke Down Barriers appeared first on LIFE.

As LIFE magazine put it in a May 1952 issue:

When wizened 42-year-old jockey Johnny Longden booted home his 3,999th winner, the routine of horse racing at California’s Hollywood Park was completely upset. Fans suddenly stopped playing form and, anxious to help Longden get his 400th win, began playing his horses for sentimental reasons. Officials who had planned a big ceremony fidgeted: Longden himself acted coy. “I never give it no thought,” he said. “I know it’s come, just like night and day.” It came seven races later hen, next day, he won No. 4,000, about 1,000 more than any other U.S. jockey.

Famous for getting his horses off to a fast start and keeping them out in front, little (4 ft. 11 in.) Johnny Longden has at one time or another won almost every big race in the country. Despite his age and a fat bank account, he is still the most industrious jockey going, riding six or seven races every day of the week and occasionally flying down to Agua Caliente, Mexico to ride on Sunday. Rising horses, says Longden, is the one thing he really enjoys. And he expects to win 5,000 before he is 50.

In fact, he ended his career with more than 6,000 wins including his very last race, the 1966 San Juan Capistrano Invitational Handicap at Santa Anita Park, where Longden had enjoyed so many of his greatest triumphs.

But Longden wasn’t merely a Hall of Fame rider who competed as a jockey until he was 59; he is also the only man to ride to victory in the Kentucky Derby, and then train a horse that won the Derby, as well, in 1969 with Majestic Prince. 

Johnny Longden was, in many ways, one of the major figures in horse racing for decades. He should be remembered, and celebrated, for even longer. This is a start.

Liz Ronk edited this gallery for LIFE.com. Follow her on Twitter @lizabethronk.

Johnny Longden, 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden, 1945.

Martha Holmes Time & Life Pictures/Shutterstock

Johnny Longden, 1945.

Martha Holmes Time & Life Pictures/Shutterstock

Johnny Longden (second from right) with fellow jockeys, Hollywood Park, 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden (second from right) with fellow jockeys, Laurel Park, Maryland, 1952.

Mark Kauffman Time & Life Pictures/Shutterstock

Johnny Longden (second from right) with fellow jockeys, Laurel Park, Maryland, 1952.

Mark Kauffman Time & Life Pictures/Shutterstock

Johnny Longden (left) and fellow jockey, California, 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden, Hollywood Park, 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden wins at Hollywood Park, 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden at Hollywood Park in 1945.

Martha Holmes Time & Life Pictures/Shutterstock

Johnny Longden poses after his 4,000th career win in 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden and son at the track, 1945.

Martha Holmes Time & Life Pictures/Shutterstock

Johnny Longden and family, 1945.

Martha Holmes Time & Life Pictures/Shutterstock

Johnny Longden with his pet cockateil, 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden and family, 1945.

Martha Holmes Time & Life Pictures/Shutterstock

Johnny Longden, 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden, 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden (hands in pockets) in 1952.

George Silk Time & Life Pictures/Shutterstock

Johnny Longden and friend, 1952.

George Silk Time & Life Pictures/Shutterstock

The post Johnny Longden: Giant in the Saddle appeared first on LIFE.

But in late July of that year, at Tijuana’s Agua Caliente racetrack, Van “achieved new fame. Wearing borrowed silks and a pair of borrowed jockey pants (two sizes too large), she mounted a cheap claiming horse named Drum Music and rode him to victory by a nose in a revival of Agua Caliente’s famous Powder Puff Derby. Behind her as also-rans struggled six other girl jockeys on six other old nags.”

Today, at least some of the language used in that brief little feature in LIFE would be utter gibberish to the ears of the vast majority of readers. Silks? What silks? And what on earth is a “cheap claiming horse,” anyway? But in 1940, when thoroughbred horse racing was still an incredibly popular sport in the U.S., it’s a safe bet that many, and perhaps even most, of the magazine’s readers would know exactly what those phrases meant.

Here, LIFE’s Peter Stackpole offers a lighthearted look at racing back in the day, through the lens of a single race, the “Powder Puff Derby,” and half-a-dozen women jockeys, on a scorching summer afternoon at a track in Baja California, Mexico.

Oh, and by the way: “Silks” are the racing outfits worn by jockeys, featuring colors and patterns associated with a horse’s stable or owners; a “claiming horse” is a horse that can be bought or “claimed” until shortly before a race.

Liz Ronk edited this gallery for LIFE.com. Follow her on Twitter @lizabethronk.

Original caption: “Weighing in before the race the girls are understandably nervous. Alice Van (third from left) is wondering whether Drum Music, the horse she will ride is any good. Because the girls generally refuse to diet and because they average about 10 lbs. more than men jockeys, their races are usually scheduled at the high weight of 130 lbs.”

Peter Stackpole Time & Life Pictures/Shutterstock

Women jockeys in Baja California, Mexico, 1940.

Peter Stackpole Time & Life Pictures/Shutterstock

Original caption: “From balcony of jockeys’ quarters the girls and two regular jockeys watch an early program race. Most of the girls are rodeo performers, enter for the fun of it.”

Peter Stackpole Time & Life Pictures/Shutterstock

Weighing in for the Powder Puff Derby, Agua Caliente Racetrack, Mexico, 1940.

Peter Stackpole Time & Life Pictures/Shutterstock

Original caption: “Scales read 119 as Alice steps on them as jockey Martin Fallon, smoking a big cigar, leers up at her. She is a former Cheyenne ‘Frontier Days’ champion rider.”

Peter Stackpole Time & Life Pictures/Shutterstock

Alice Van and her husband/manager place bets at the track in Baja California, Mexico, 1940.

Peter Stackpole Time & Life Pictures/Shutterstock

Women jockeys in Baja California, Mexico, 1940.

Peter Stackpole Time & Life Pictures/Shutterstock

Alice’s horse, Drum Music, won the race.

Peter Stackpole Time & Life Pictures/Shutterstock

Original caption: “After race Alice poses for picture with Drum Music and Drum Music’s owner Tom Hunt, a horseman from San Ysidro, California. Hunt won $500. Alice won a wrist watch.”

Peter Stackpole Time & Life Pictures/Shutterstock

The post In Praise of the ‘Powder Puff Derby’ appeared first on LIFE.