The delicate dynamics, frustrating as they may have been, made it easy for a young Caldwell to set her goals.
"Since the very beginning, I wanted to be just as good as the boys," she says.
It was a challenge that required pushing her coaches, pushing herself and pushing her sport to places no women had ever been before. Caldwell, 24, will enter next month's PyeongChang Games in South Korea not content simply to chase the podium or prove she's the top female aerialist in the world. She wants to show she can jump with the best, and that potential can't be viewed strictly through the prism of gender.
She'll enter her third Olympics armed with a daring trick that's usually reserved for the men: a triple somersault that no other woman has landed in competition. Perhaps not surprisingly, it's called the Daddy.
Caldwell knows risky jumps tend to invite calamitous landings. One small slip-up could be costly, and an easier trick would almost certainly provide a more dependable path to the podium. But that's not really the point.
"This has always been my mentality: Why win with less when you can win with more?" she says. "I don't want to go out there and show the world my easiest trick. I want to show the world my best trick, me putting everything on the line to be the best."
Viewed in real time, aerials can amount to a dizzying blur — imagine a Swiss army knife spinning through the air. But slowed down, studying a skier flipping and twisting high above the earth, the grace and beauty is apparent — but so is each critical detail, a collection of tiny, essential movements. Caldwell has spent years perfecting each one, training her body to execute a whirlwind of three flips, four twists and, with any luck, one safe landing.
She'll enter the Olympics as the sport's reigning world champion, but it was a process to get to this point, albeit an accelerated one. She discovered aerials as a 12-year-old watching the 2006 Turin Games. By 14, she'd moved out of her parents' Ashburn, Va., home to train full-time in Lake Placid, N.Y. And at 16, she was the youngest member of the 2010 U.S. Olympic team.
She was just happy to be in Vancouver, but four years later, she had the talent to be competitive at the Sochi Games. Coming off a string of injuries, she fell short, and now in PyeongChang, with a world title and a deadly trick in her back pocket, her goals have never felt more attainable. But she's intent on bypassing the easy route to the Olympic podium.
"I've had everyone say: 'You don't have to go so big. You don't have to do these tricks in order to win or be successful.' But I didn't really listen to them," she says. "I wanted to push myself. I wanted to see how good I could be."
'She was always pushing'
In those early days, a young Caldwell would land a jump and refuse to even catch her breath before sprinting back to try something bigger and tougher.
"She was never really satisfied with the status quo in training," said Emily Cook, a three-time Olympic aerialist who trained alongside Caldwell and is now an assistant coach with the U.S. team. "She was always pushing, for sure, always looking to do bigger tricks — incredibly talented but also incredibly eager."
Mac Bohonnon, a PyeongChang-bound aerialist for the American men's team, was at that first camp more than a decade ago. Caldwell's talent stood out, but so did her determination.
"I don't care if that was good for the girls," he recalled her saying. "I don't. I just want to do good jumps compared to everyone in the sport."
Before long, she was trying the tougher tricks more common on the men's program. Bigger risks carried bigger consequences. She tore the anterior cruciate ligaments in each knee in back-to-back years, essentially knocking her out of competition for two full seasons heading into Sochi. She felt healthy enough for the 2014 Games but missed the prep time and feels she might have been more cautious than usual.
Still, only two days after landing a new trick in training, she pulled it out in the opening round of Olympic competition. The jump — called full-full-full — requires three somersaults, each incorporating a full twist. No other female Olympian was close to attempting one in Sochi, and Caldwell nailed it, giving her a huge lead. She had landed the toughest trick of the Olympic competition but somehow faced a tougher task: spending a couple of hours considering her precarious position before her next jump.
"It became surreal, like an out-of-body experience," she said recently. "The event just happened in front of me. I just wasn't prepared. My mind wasn't ready to be in that position."
The ensuing rounds were single elimination, and Caldwell failed to land one of her easier jumps smoothly, over-rotating and hitting her backside on the snow. The miscue knocked her down the leader board and out of the competition before the finals. For a second straight Olympics, Caldwell finished in 10th place.
"My immediate reaction after Sochi was, 'Wow, I totally could have won this, and I blew it,' " she said. " . . . To feel that letdown was dramatic, and it stuck around for a while after that. But it fuels my fire now."
She returned to the ramp intent on honing the triple somersault and ramping up the difficulty, adding a second twist on the middle flip — the Daddy.
At the world championships last year in Spain, Caldwell was trailing heading into the finals. There was no better time, she figured. No woman had ever landed the trick in competition, but Caldwell felt she had no choice. "I really had nothing to lose," she said.
She hit the ramp, went through a dizzying array of spins and twists, and wowed the crowd with a clean landing. The degree of difficulty and her execution vaulted her to the top of the leader board, and Caldwell became the first American woman to win a world title in more than two decades.
"I think I was more excited that I landed the trick," she said.
It's still the only time Caldwell has landed the Daddy in competition. Entering PyeongChang, only a handful of women even attempt triple flips, and Caldwell figured she has four more years under her belt of hitting them in practice and in competition.
"I'm extremely more comfortable doing triples. It's still a triple back-flip on skis going 60 feet in the air," she says, "so it's still terrifying and scary and thrilling."
For her next trick . . .
She calls the trick "the epitome" of her career. Every jump, every competition, every time she has strapped on skis — it has all led to this.
"I think about it all the time," she says. "I definitely dream about it. . . . I lay in bed and think about what it would be like. How fast am I spinning? What am I looking for? What's my coach telling me? How great does it feel when I land? Sometimes it doesn't help me fall asleep."
Every trick is an evolution, years of work going into each movement. Over the course of a winter, the busiest aerialist might only attempt 300 jumps on the snow, but they'll use water ramps year-round to squeeze in more training — 1,000 or more jumps strapped into skis and splashing into a pool.
Before she even hits the water, though, Caldwell will visit the U.S. team's trampoline in Park City, where she lives and trains. The trick is too big to attempt on the trampoline — she needs to go 60 feet in the air; the trampoline only allows 30 to 40 feet — but Caldwell can perfect each element.
On the snow, the trick starts at the top of the ramp. Caldwell tries to stand as tall as possible, lifting both arms to the sky as she races to the bottom. Her speed shoots her into the air, her momentum propelling her through all three flips.
She counts nearly a dozen midair movements before she returns to earth. All the while, she's trying to keep her feet together and squeeze her core to keep the whole package as tight as possible.
All of this happens in three seconds.
"If I land, it's almost unbeatable," she says.
Landing cleanly is no foregone conclusion, and Caldwell wants near-perfect conditions — no wind, good visibility — to even attempt it. Following last year's title, she has struggled this season with consistency, finding the podium just once — a third-place finish last month in China. Conditions have hindered some of her jumps, and the toughest trick she has attempted is the full-full-full — one twist shy of the Daddy.
"Of course, not having the competition results has shaken my confidence slightly," she said earlier this week. ". . . Long term, I've had these big goals and I trust the plan."
In PyeongChang, she'll probably find three other competitors capable of completing triples. But only Caldwell and the male aerialists can pull off the Daddy.
"It takes a lot of different dynamics, which she balances very well," said Cook, her teammate turned coach. "It takes that daredevil courage, that grace, that power and strength. She's the strongest athlete in the gym on any day, and she's in there with the bobsledders pushing huge amounts of weights around. But she's also graceful in the air. She combines those things really nicely."
No U.S. female aerialist has won an Olympic title since Nikki Stone in 1998. Stone took gold in Nagano with a trick that was one flip and two twists shy of what Caldwell intends to unleash in PyeongChang.
As her skills grew and her repertoire expanded, Caldwell's thinking also evolved. She's no longer a tireless teenager chasing the boys. Breaking down gender walls isn't enough, and she's not content to allow gender to serve as a measuring stick.
"I think that my career and how I was raised has definitely changed my view on gender," she says. "I realize that it doesn't matter if you're a girl or a boy. You should push yourself individually, and you should demand that everyone around you does the same."
Coaches don't limit her. She sets the goals, and they work together to make them happen.
"Now they go out there and they go: 'What can Ashley do? What can we do to push her?' Not necessarily because I'm a boy or a girl or because I want to be treated like a boy," Caldwell says. "I realize that mentality was kind of wrong of me.
"I shouldn't have said I want to be like the boys. I should've said I want to be the best."