Penny Ann Early (May 30, 1943 – June 23, 2023) was an American athlete who broke barriers in two male-dominated sports during the late 1960s. She became one of the first women licensed as a professional jockey to ride in parimutuel races in the United States and the first woman to appear in a professional men’s basketball league game. Standing just 5 feet 3 inches and weighing around 112–114 pounds, she was also the smallest player ever to suit up in a major professional basketball league.
Born and raised in Chicago, Illinois, Early attended Senn High School and graduated in 1961. She entered the world of horse racing early, working as a trainer and with racehorses. By 1968, at age 25, she obtained a jockey’s license from the Kentucky Racing Commission, positioning herself among the pioneering women seeking to compete in thoroughbred racing at a time when the sport was almost exclusively male.
Her attempt to ride at Churchill Downs in Louisville, Kentucky, that November triggered intense resistance. Male jockeys refused to participate in the races for which she was scheduled—reportedly three mounts—effectively boycotting to keep her out of competition. One of her mounts was scratched due to a muddy track amid the threats. The episode drew national attention and highlighted the deep institutional and cultural barriers facing women in racing. While Early was licensed and scheduled, other women such as Diane Crump would soon become the first to actually complete races in the United States. The boycott left Early without those early opportunities at one of America’s most famous tracks.
The controversy created an opening for an unlikely crossover into basketball. The Kentucky Colonels of the American Basketball Association (ABA), looking for publicity, signed Early to a short-term contract. She had never played organized basketball at any level. Team owners Joseph and Mamie Gregory directed coach Gene Rhodes to put her in a game despite his protests. On November 27, 1968, against the Los Angeles Stars at the Louisville Convention Center (also referred to as Louisville Gardens), Early made history.
She appeared in a miniskirt and turtleneck sweater bearing the number 3—symbolizing the three boycotted races at Churchill Downs. Early warmed up with the team and sat on the bench. During a timeout in the first half, with the Colonels leading, Rhodes sent her to the scorer’s table. She checked in, took the ball out of bounds in the backcourt, and inbounded it to teammate Bobby Rascoe. Rascoe immediately called timeout, and Early was removed from the game. The crowd of about 5,345 gave her a standing ovation (accounts note mixed cheers and some booing). She later signed autographs. Officially, she played one game with zero minutes, points, rebounds, or assists recorded—yet the moment secured her place as the first woman to appear in a men’s professional basketball league game in the United States.
After the basketball interlude, Early returned to racing. On April 19, 1969, she won the $10,000 Lady Godiva Handicap at Suffolk Downs in Massachusetts, an all-female race featuring seven women riders. She finished ahead of Diane Crump and Tuesdee Testa among others. That year she competed in 12 races. She rode none in 1970 and only one in 1971. Her overall competitive record as a jockey remained limited, and she faced ongoing difficulties securing mounts and maintaining the extreme low body weight required for the profession. Critics sometimes accused her of seeking publicity more than sustained racing opportunities.
Frustrated by the physical demands and limited chances, Early shifted to training. In 1974, at age 30, she attempted a riding comeback after rigorous dieting to reduce her weight, but a spill ended it: she broke her arm, ankle, wrist, and several ribs. She then focused on training. From 1976 to 1988 she trained at Caliente Racetrack in Tijuana, Mexico (just south of San Diego), where her horses won 56 races from 666 starters. She later advocated to keep the track open in the early 1990s before its closure in 1992.
In later years Early continued working with horses as an exercise rider, trainer, and instructor. She eventually settled in Shelbyville, Tennessee. She died there on June 23, 2023, at age 80; reports from friends indicated an apparent suicide. She was also known later in life as Penny Ann Hill.
Early’s significance lies less in statistical dominance than in the barriers she challenged. In 1968 the idea of a woman riding competitively against men in thoroughbred racing or stepping onto a professional men’s basketball court was radical. Male jockeys’ collective refusal to ride illustrated the hostility women encountered. The Colonels’ signing, while clearly a publicity stunt, still placed a woman on the court in a major professional league during an era when opportunities for female athletes were severely restricted. Title IX, which would transform women’s sports in educational settings, was still four years away when she checked into that ABA game.
Her career reflected both progress and its limits. She gained a license and a historic victory in an all-female race, yet struggled for regular mounts and sustained competitive success. The basketball appearance lasted mere seconds and produced no box-score contribution, yet it remains unique. Later decades saw women make far greater inroads in both racing and basketball, but Early’s brief, high-profile efforts in 1968–1969 helped force conversations about gender exclusion in professional sports.
She recorded two songs around the time of the controversy and had earlier appeared on the television show What’s My Line (with Barbra Streisand as the mystery guest on one episode). These details underscore how her story intersected with popular culture of the late 1960s. For most of her adult life, however, horses remained the constant—training, riding, teaching, and advocating for tracks and the sport itself.
Penny Ann Early’s life illustrates the uneven path of pioneering. Licensing and a few high-visibility moments did not guarantee acceptance or longevity in the saddle. A fleeting basketball appearance generated headlines and a place in record books without establishing a playing career. Yet by refusing to accept the closed doors of her era, she contributed to the slow expansion of opportunities for women in two sports long defined by male participation. Her story, spanning Chicago roots, the Churchill Downs boycott, an ABA inbound pass, a Suffolk Downs victory, years of training in Mexico, and a final chapter in Tennessee, remains a distinctive footnote in American sports history.