When Rosie Napravnik, who also goes by her first name Anna at times, enters the 2011 Kentucky Derby starting gate aboard Pants on Fire, she’ll be just the sixth female jockey to ride in the race. All she has to do is finish in the Top 10 — a real possibility since she’s on a live horse in a reasonably weak field — to be the highest finishing female jockey of all time.

Napravnik may be a rookie in the Derby, but the 23 year old has shown that she is the real deal in a short time in the sport. In 2006 she was runner-up for the Eclipse Award for outstanding apprentice jockey behind Julien Leparoux when she won riding titles at both Pimlico and Laurel. She dealt with some injury issues after that, but she was second in the Delaware Park jockey standings in 2009, and she absolutely crushed the competition to win the Fair Grounds standings this year. She’s in good form, and she knows this horse well, so she’s going to be a factor. If you let her lack of experience or her gender be a knock against the horse then you are making a real mistake.

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As we get ready for Napravnik’s shot at history, it seems fitting to look back at the five female Kentucky Derby jockeys who came before her.

Diane Crump — Crump was not only the first female jockey in the Kentucky Derby when she rode Fathom in 1970, but she was the first woman ever to ride in a pari-mutuel race in North America when she rode at Hialeah Park in February of 1969 when she was just 19. The time between her first start and her Derby appearance is remarkably short. Unfortunately, the story didn’t have a happy ending — Fathom was a total non-factor in the race and wound up 15th in the 17-horse field.

Patricia Cooksey — Crump led the way, but it took a long time for anyone to follow her. Cooksey didn’t become the second woman in the race until 1984 on So Vague. Cooksey was a barrier breaker of her own — she was the first woman to ride in the Preakness when she finished sixth in 1985, she was the first woman to win a stakes race at Churchill Downs, and she was the first woman to win a major stakes race in California. Unfortunately, Cooksey didn’t have much of a horse under her in the Derby, and she wound up just 11th after a mild-late rally.

Andrea Seefeldt — Seefeldt picked up the ride on Forty Something in 1991 when his regular rider went elsewhere. She probably wished he’d stayed with the horse. Forty Something locked up with Corporate Report at the front of the field and set a very aggressive pace through the first six furlongs. But then he hit a wall — apparently a really big one — and dropped to dead last in the 16-horse field by the time she reached the wire. It was a rough day, but Seefeldt had her biggest day in racing later that same year when she stunned the crowd to win the Pennsylvania Derby at 78/1.

Julie Krone — The greatest female jockey of all time is also the only woman ever to ride in the Derby twice. She’s also the only woman to win a Triple Crown race — the 1993 Belmont on Colonial Affair — and a Breeders’ Cup race. In short, Krone was the real deal. She didn’t have much luck in the Derby, though. In 1992 Ecstatic Ride never fired and wound up 14th. Three years later Suave Prospect got stuck on a wide trip and finished 11th.

Rosemary Homeister, Jr. — Homeister is still an active jockey, though she is pregnant and on an indefinite leave right now. She was born into the sport — both of her parents were jockeys as well. Homeister win the Eclipse Award for outstanding apprentice in 1992, has won riding titles at three tracks, and is the second leading all-time winning female rider behind Krone, though she is far behind. Her lone Derby appearance was in 2003 on Supah Blitz. He ran into trouble a couple of times and was an unremarkable 13th. Little more was expected from him — he was 43/1.

Doc’s Sports expert Kentucky Derby handicappers will have a full card of Kentucky Derby picks for the Run for the Roses on May 7. Doc’s has been putting in extra work this year handicapping the Kentucky Derby field and we expect a big payday on Saturday. Get all Doc’s Kentucky Derby predictions for just $20! Click Here to purchase.