Napravnik has been on horses since before she went to kindergarten and began her career as a jockey a few days after completing her junior year in high school. She won her first start.
Although beset by a series of serious injuries, she has become a very successful rider and one of the sport's most accomplished female jockeys. She had a breakout year in 2011 when she became the first woman to lead the jockey standings at Fair Grounds in New Orleans. It was no contest; she finished with 34 more wins than the runner-up, James Graham. One of those winners was a history-making victory aboard Pants On Fire as the first female rider to capture the Louisiana Derby. She became the sixth woman to ride in the Kentucky Derby and her ninth-place finish on Pants On Fire was the best by a female jockey in America's biggest race. Her fine season was interrupted on July 6 by a broken left arm suffered in a spill at Delaware Park. She underwent four surgeries to correct the damage and was able to begin exercising horses again on September 22 and resume riding.
In 2012 Napravnik recorded another milestone for a female rider when she became the first woman to win the Kentucky Oaks, guiding the appropriately named Believe You Can to victory. After riding Mylute in the 2013 Kentucky Derby, Rosie was chosen as the pilot of Unlimited Budget for the Belmont, a fitting combination as the Repole colorbearer is the only filly to run in the race.