Two years after achieving the best finish by a female jockey in the Derby, she will try to become the first woman to win it. Napravnik's pursuit of the milestone comes a year after she became the first female rider to win the Kentucky Oaks, the second-biggest race on Churchill Downs' marquee weekend.
Mylute is a 15-1 shot to win the Derby on Saturday, but his last win came in December with Napravnik aboard. That performance offered a glimpse into her ability to get the most out of a horse, something she has shown in being the leading rider at four tracks.
Napravnik is confident Mylute will give her a strong ride
"Mylute will definitely come from off the pace because that's his style," said Napravnik, who will start from the No. 6 post position. "That's not a bad style to have when the race is a mile and a quarter. It's very long, so if you can have a horse that can stay relaxed in the first part, that's definitely to your advantage."
For her part, Napravnik has been more relaxed preparing for her second Derby appearance. That hasn't been easy considering the barrage of questions about her attempt to do what six women, including herself, have failed to do in 138 previous Derbys against male jockeys.
Napravnik is well aware of the tectonic impact her victory could have.
Having gone through the Derby experience in 2011 while guiding Pants On Fire to a ninth-place finish, Napravnik feels more like a veteran the second time around.
"It's nice to have the experience of when I was here two years ago," she said. "It's a little less overwhelming and I know what to expect. I've been able to handle it better.
"A lot has happened in my career since I was here two years ago. I think I've been more recognized, it's very flattering and everybody has been very positive. Winning the Kentucky Oaks last year was probably the greatest moment of my career."
As it turned out, Napravnik's breakthrough victory aboard Believe You Can in the Oaks was just the first of several big moments. She rode Shanghai Bobby to five wins including the Breeders' Cup Juvenile at Santa Anita, helping the colt claim the 2-year-old championship.
A couple of months later she climbed aboard Mylute at Fair Grounds Race Course near New Orleans and immediately forged a bond that led to a second mount in the Derby. The horse earned his second career win by nearly 11 lengths on Dec. 26, his best effort in nine starts.
Napravnik went on to be Fair Grounds' top rider for the third straight year, adding similar honors at Laurel, Pimlico and Delaware Park.
"We're lucky to have her," Amoss said. "It may be a bit surprising that she was available for the Kentucky Derby with what I thought about her being very much in demand. But their loss is our gain."
Amoss struggles for an exact description of Napravnik's success but notes that her ability to connect quickly with her mounts. The only other jockey he has seen with that talent is Hall of Famer Pat Day, which is saying something.
At the same time, Amoss notes Napravnik's businesslike demeanor that has helped her deal with a male-dominated sport. Not to mention, all the attention she has gotten.
Napravnik is all smiles when it comes to Mylute. She has been pleased with his breezes this week and is ready for Saturday.
"He feels great, he's acting great and I'm very confident heading into the Derby," she said. "Hopefully, we can make history."