The Jockey to Look Out for at the Kentucky Derby

Rosie Napravnik was born to be a jockey. In fact, horses were the family business: Her mother managed a training and boarding facility; her father is a hoof specialist. Eager to compete like her older sister, the New Jersey native, now 26, started racing ponies at age 7. But despite training in more formal equestrian disciplines, Napravnik was most attracted to racing. "It was a hassle to do things so properly," she says. "I just wanted to go fast."

As a kid, Napravnik thought her dreams were within reach. But she soon learned that many jockey rooms were boys' clubs—so much so that she originally rode as A.R. Napravnik to avoid unnecessary attention. "This sport is every man for himself," she says. "I've always tried to blend in. But some owners and trainers simply refused to ride girls. I was very conscious when I raced against their horses—and when I beat them."

Riding professionally since she was 17, Napravnik had her most dominant season in 2012, when she became the first woman ever to win the famed Kentucky Oaks. The almost-too-serendipitous name of the horse she rode: Believe You Can.

In this month's derby, Napravnik is hoping for a chance to top her fifth-place finish last year—the best of any female rider in the race's history. Winning aside, nothing beats the high she gets from racing. "When you're coming down the stretch, in a drive, nose to nose with somebody—it's going to be either you or him."