First female jockey to win multiple Kentucky Oaks

On May 2, 2014, Rosie Napravnik guided Untapable to a dominant victory in the Kentucky Oaks at Churchill Downs.[4][15][16] Having previously won the Oaks in 2012 on Believe You Can, she became the first female jockey to win multiple editions of the Kentucky Oaks.[1][16]

Untapable, a three‑year‑old filly trained by Steve Asmussen, entered the race as the favorite, and Napravnik delivered a flawless, confident ride. She settled the filly comfortably before unleashing a powerful stretch run that resulted in a decisive win. The performance showcased her capacity to handle heavy expectations and execute a textbook ride on one of the season’s standout fillies.[4]

Historically, repeat victories in the Oaks have marked jockeys as specialists with a particular skill in riding top fillies in high-pressure situations. For a woman rider, holding multiple Oaks titles carried added symbolic weight, further breaking down the notion that women were occasional interlopers in major races rather than consistent, top-tier performers.[11][16]

Napravnik’s second Oaks crown solidified her reputation as the premier female jockey of her era and an elite rider overall. It also provided another entry in the growing list of her barrier-breaking achievements, reinforcing the idea that women could not only reach but repeatedly succeed at the pinnacle of the sport. The 2014 Oaks win set the stage for her later Breeders’ Cup Distaff triumph on Untapable and remains a key landmark in the history of women in American horse racing.