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Skateboarder Heimana Reynolds dreamed of the Olympics years before the sport was added to the Summer Games

In his endless quest to land the perfect trick, skateboarder Heimana Reynolds circles the subterranean bowl like a tornado,

gathering speed on the steep, curved walls until he pops out and launches into the air, where a dazzling and dizzying display of acrobatics ensues.

The 22-year-old Hawaii native makes it look effortless, and as he lands and rolls away on his board, it’s difficult to appreciate the falls and spills that preceded all of this — for Reynolds, who has reached the top of the skateboarding world, but also for his sport, which has burst into the mainstream and finds itself under the Olympic spotlight this summer in Tokyo.

The hospital records are probably as good of a place as any to start. Reynolds’s charts require a strong stomach. Broken bones in both feet and wrists. Multiple concussions. Separated shoulders — probably four or five, actually. Shattered collarbone. Not to mention the daily bruises, scrapes and gashes that come from flinging himself into the air and hoping gravity will be kind.

“It’s all part of the game, you know,” said Reynolds, who is representing the United States at the Tokyo Olympics. “It’s either you get hurt, you cry and you quit, or you want to come back stronger. That’s what skateboarders love to do.”

They get back up because they’re chasing a sensation: twirling in the air, board flipping, Earth spinning, adrenaline pumping. For Reynolds, the sport revolves around tricks, and the tricky part is wowing crowds by making the implausible look easy.

That’s exactly the kind of energy Olympic organizers are trying to inject in their quadrennial affair. To attract a younger audience, they added skateboarding to the Tokyo Games in 2016, a move that surely surprised anyone who still viewed it as a counterculture activity associated with misfits and delinquents. With Tony Hawk largely carrying the torch, skateboarding has gone mainstream over the past three-plus decades, graduating from the streets to skate parks and now to the sports world’s largest stage.

Skateboarding at the Olympics

In Tokyo, Olympic organizers settled on two medal events, and in each, judges are tasked with scoring skaters’ 45-second runs. Competitors will aim to showcase a combination of creativity and athleticism, similar to many other judged Olympic events, from snowboarding to gymnastics.

Street skateboarding involves an obstacle course of sorts that resembles an abandoned urban cityscape. Featuring rails, ledges and stairs, it calls on skaters to string together grinds, board flips and ollies and to take advantage of big-air opportunities along the course.

Reynolds competes in park, and he enters Tokyo as the world’s top-ranked skater. Park features a hollowed-out concrete course — imagine an empty swimming pool that includes multiple bowls. Park skaters have grind opportunities, but the real goal is to string together big-air tricks, launching off the curved walls — one in Tokyo measures more than 9½ feet tall — as well as a pair of concrete structures in the middle of the giant course.


Judges are looking for three elements in both events: speed, power and flow. They want to see skaters barreling fast into obstacles, pulling out dynamic tricks, catching big air and stringing it all together in a smooth, fluid manner, with a focus on the transitions that connect the bigger pieces.

“He knows how to connect the dots — the tricks — and he makes it look good,” Lincoln Ueda, the head of judging for the Olympic park competition, said of Reynolds.

Reynolds has taken countless spills mastering the tricks he will take to Tokyo — he estimates that 80 percent of the sport is falling — but he hopes those bruises and doctor visits help him reach the Olympic podium. The trick many consider his signature is called the frontside invert. It’s a handplant in which Reynolds skates into the wall, places his left hand on the rail and goes upside down. He keeps his left arm stiff as his right hand grips the board. Just as he appears frozen in place atop the wall, he twists his feet and board slightly, a tiny mid-trick wink to the judges.

Frontside invert

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“The hardest part about something like that is trying to stall it and bring it back without tipping over,” he says.

He loves the handplant so much that he memorialized it with a tattoo on his right leg: a cartoon skateboarder performing the trick with his hand buried in a gardening pot — a “hand plant,” get it?

Tricks require skaters to build speed as they head into the wall and, in many cases, use major power as they execute the landing. For the Madonna, invented by Hawk and named for the famous pop singer, Reynolds pulls his front foot off the board and lets it hang low as he rises seven or more feet over the bowl. He grabs the nose of the board with his left hand, and as he comes down, he slams the tail of the board onto the edge of the wall, which is called the coping, hoping for a resounding thwack — anything that might distinguish him from other skaters.

Skaters often save their biggest, baddest offerings for the end of their runs. They call it the banger trick. In Tokyo, Reynolds probably will be the only skater who can land a 360 flip tail grab. It’s a trick in which Reynolds launches through the air while his board rotates on both axes — spinning and flipping at the same time — before Reynolds grabs the tail, pulls it underfoot and somehow lands.

Kickflip frontside air

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“One trick, if it’s done by 10 skateboarders, they all could look different,” Ueda said. “The ones that stand out, it’s the style they do it, the way they can just turn their body or the way they can stall it for a second or two. That’s what judges look for.”

The tricks are years in the making, an evolution of foot placement, balance, rotation and body mechanics.


Reynolds grew up on Oahu’s North Shore. His father was a competitive surfer who put his son on the nose of his surfboard and paddled him around the ocean when he was just a baby.

How did you get started skateboarding?

Heimana Reynolds

When I was first born, he instantly threw me on a surfboard. But growing up … it was cold, windy, wet, and I wasn’t super into it. When I was 7, my dad was like: “All right, here’s a skateboard. See what you think about this.” And I instantly fell in love with it. I was like, “This is what I want to do.”

Do you prefer skating street or park?

Heimana Reynolds

I like to skate street, but I’ve always gravitated to park skating because I love going fast. I love going really high in the air. That is what I was raised on, you know what I mean?

What part of skateboarding hooked you?

Heimana Reynolds

I remember as a kid, I just loved the feeling of my board underneath my feet and seeing all the speed I could generate, just pumping around the park. Using no machines, just using my body power and pumping around, going fast.

When you’re in the air learning a complicated trick, what is going through your head?

Heimana Reynolds

Many skaters have an open disdain for organized competition and consider skating to be more of an anti-establishment lifestyle or an artistic form of self-expression, but Reynolds kept his board in both worlds. When he was 10, he told a Hawaiian television station that the Olympics were a goal. Never mind that skateboarding was seven years away from being added to the Summer Games slate.

“I was like, whenever it happens, I want to be there,” he says today.

Ueda has been watching Reynolds compete since the skater was 10. Every year he has seen Reynolds go faster, higher and bigger with his tricks, pushing the sport and himself.

“He has the height; he has the style; he has the tricks,” Ueda said. “It’s just a matter of putting it all together, which he’s been doing.”

Reynolds won the park competition at the 2019 world championships, which gave him a head start on Tokyo qualifying. He also began to realize that if people were going to start accepting skateboarding as a real sport, he needed to train like a real athlete.

He splits his time between Hawaii and Carlsbad, Calif., waking up most days by 7 a.m. and hitting the gym for 60 to 90 minutes of weight work with a personal trainer. After a midmorning surfing break, he spends six-plus hours on his skateboard, honing tricks and practicing runs through the bowl.

The pandemic changed that routine. Skate parks were shuttered, and for months Reynolds couldn’t find a proper place to train. For the first time since he was a grade-schooler, more than a year passed without a single competition. He built a quarter-pipe in his backyard and found himself skating on flat ground rather than inside deep bowls. In retrospect, he calls it a “blessing in disguise.”

“It forced me to remember why I love skateboarding and remember I don’t need to just skate the park, skate a perfect rail or perfect coping,” he said. “I can still have fun skating in my driveway, skating in my living room, over a coffee table, stuff like that. … We took this year off to pretty much go back to our roots and kind of understand and learn why we love our sport so much.”

It also has given him a deeper appreciation for what this summer could bring. The Olympics might very well change skateboarding. But the skaters, with their attitude and artistry, could just as easily change the Olympics.

“For skateboarding to be recognized finally as a real sport — as a top-level Olympic sport — is going to be incredible,” Reynolds said. “It’s like, right now, the general public … they’ll look at skateboarding and go, ‘Oh, that’s for kids who don’t give a crap, who don’t go to school, who just want to do graffiti in the park and smoke weed and vandalize [stuff].’ For it to be recognized as a sport in the Olympics is going to be insane.

“Parents are going to be like, ‘I want my kid to skate now.’ ”

About this story

The on-site production team took 36 GoPros and a custom camera rig to capture Heimana’s signature moves. Our video team rendered the 36 angled video shots to create a interactive moving image of each signature move viewers can expect to see at the Olympics.

Additional development by Lo Benichou and Seth Blanchard. Additional production by Steve Johnson. Editing by Elite Truong, Virginia Singarayar, Ann Gerhart, Matthew Rennie, Chiqui Esteban, Courtney Kan and Monica Ulmanu.

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Rick Maese is a sports features writer for The Washington Post. He has written about the NFL since joining The Post in 2009, including three seasons as beat writer for the Washington Redskins.
Madison Walls is a designer at The Washington Post with a focus on developing innovative and immersive storytelling. She joined The Post in 2018 after graduating from UNC Chapel Hill.
Artur Galocha is a graphics reporter focusing on Sports. Before joining The Washington Post in December 2020, he was a graphics editor at El País (Spain).
Leslie Shapiro has been a Graphics Reporter for The Washington Post since 2016, focusing on data visualization and new media storytelling.
Ashleigh Joplin is an award-winning video journalist for The Washington Post. Her team specializes in live political coverage and breaking news events.