Olympics or Not, Jimmy Wilkins Is Reaching New Heights
Skateboarding’s appeal typically starts with disbelief. Strangers love to stop skaters on the street to interrogate the ollie. How does the board stay attached to your feet like that? You sure there aren’t magnets in there somewhere?
Thirty-year-old pro skater Jimmy Wilkins gets that kind of reaction from skateboarding legend Tony Hawk.
“He’s unlocked some ancient secret of how to do ollies,” Hawk says. “Before Jimmy came along, the highest you would see anyone do a frontside or backside ollie was maybe five or six feet if you’re lucky, and he’s consistently going eight or nine. Jimmy figured out this way of scooping his board and keeping it on his feet. It’s refreshing, but it’s also confounding because … how?”
Watching him navigate the 13-and-a-half-foot tall, 72-foot-wide vert ramp that takes up most of the square footage inside Hawk’s unmarked stucco office tucked away in a nondescript business park in Vista, California, Wilkins melts the senses.
Skateboarding is most notably a visual medium. That alchemy that keeps the board tethered to the feet, the balance, the air, the speed, style, fashion, danger, and the seemingly impossible intersection of them all. But up close, and most importantly, under your feet, the allure is equally sonic.
Skating is loud on purpose. On a vert ramp — massive U-shaped half-pipes with walls that go fully vertical at the top — the beautifully spastic soundtrack of endless onomatopoeia eases into a calming trance. The back and forth of wheels rumbles like a train forever approaching, interrupted by the clank and slash of grinds, and the pronounced emptiness of air that lingers just long enough to snap you back to reality when the rumble returns.
From the deck of the ramp, it looks like Wilkins is moving in slow motion, but your ears know how fast he’s going. The train always sounds like it’s about to run you over. Those empty voids of gravity defied are longer, more suspenseful, and not empty at all, instead filled with the hum of spinning ball bearings and urethane wheels like a thousand bees stuck inside a snare drum.
In skateboarding, style is not your clothes and haircut, although it is sometimes that too. Style is the way you look on a board. The tricks you decide to do, the way you do them, what you do with your arms and hands, the ability to make it all look effortless. Wilkins flies higher, grinds longer, and grabs his board less. Five-foot-ten and skinny enough that he looks six feet one, with a mop of shoulder-length brown hair always hidden under a hat or a helmet, Wilkins is vert’s most stylish skater. His lanky body contorts in directions that don’t make sense except in their apparent ease. He makes skaters already accustomed to bending the laws of physics question just how far they really flex. Wilkins is water.
“The things I want to do are grind long and go high,” Wilkins says. “My process is basically just brute force. Try it until you’re exhausted enough to forget to bail. That’s how I’ve learned most things.”
Skateboarding will take its second turn in the Olympic spotlight at the 2024 Summer Games in Paris, but Jimmy Wilkins won’t be there. There will be no vert ramp in Paris. Instead, two disciplines — street and park — will highlight the type of skating that we typically see in this era: obstacles like rails, ledges, and stairs built to replicate street spots and transition skateparks made up of oversized concrete ramps modeled after backyard pools.
The Olympic stage has reignited a decades-old discussion about the push and pull between skateboarding’s counterculture roots and establishment appeal. In eras past, that debate was driven by vert. With its easy-to-follow back-and-forth runs, emphasis on big air, and contest-minded, jockish reputation within the skate industry, vert was the discipline that captured mainstream America’s attention in a way typically reserved for the three-letter sports leagues. But with the Olympics bringing the highest level of competition to skateboarding without it, vert’s absence is drawing new focus back to the ramp as a core facet of skating’s rebellious, resilient, and progressive tradition, with Wilkins setting himself apart in every corner of the industry as a torch bearer for the future of vert, no matter its, or his, Olympic fate.
It’s corny in a way that skaters try to avoid at all costs, but the story of vert is comically analogous to the skating itself: the ups, downs, high highs, and low lows. There’s no telling how long it will last, but vert is on an upswing, and, like everything he does, Wilkins is trying to take it a few feet higher.
“What does [the future of vert] look like?” Hawk says. “Watch Jimmy. Watch the tricks he’s learning. That’s what it’s gonna look like.”
Wilkins is the son of a ballet dancer and a symphony conductor; his parents split up when he was young but always remained close and supported his passions in ways that most kids can only dream of. Growing up in and around Columbus, Ohio, Wilkins discovered vert skating the same way many millennials did, through Tony Hawk’s Pro Skater video games and the X Games on ESPN. Wilkins told his parents that he wanted to skate ramps like Hawk and Bob Burnquist, but instead of brushing the kid off like most parents, Jimmy’s mom, Anne Adair, ran with it. After days on end at the local skatepark practicing on smaller ramps and one five-hour round trip drive to the closest vert ramp in Kentucky, Jimmy spent months nagging and eventually persuaded Adair to pour her savings into building a vert ramp in the backyard of their suburban Bexley, Ohio, rental home.
Michael Burnett
Jimmy went door to door collecting signatures from neighbors, they got permits and approval from the landlord, Adair hired a contractor who had never built a ramp before, and they put up a 10-foot tall by 10-foot wide wooden vert ramp with PVC pipe coping in the small yard. Jimmy rode the ramp once, carving a few feet up the walls from the flat bottom before the complaints started. Worried about the noise and undesirable characters they were sure it would attract, Wilkins’ neighbors came together to change their minds before construction finished and brought their disapproval straight to the city. Adair hired a lawyer, there was a hearing at City Hall, the mayor fell asleep, and it was decided that the ramp had to be dismantled. The neighbors threw a party to celebrate. Jimmy remembers the fireworks.
“The language they were using was like, ‘We don’t want these kind of people in our neighborhood,’ ” Wilkins says. “It was fucking terrible.”
Of course, his mom never blamed him, but that didn’t stop Jimmy from internalizing responsibility for the conflict that made them neighborhood pariahs. He quit skating altogether, picked up soccer and lacrosse, and tried to fit in with his middle school peers, but that didn’t work. Always quiet and a bit of a loner, Jimmy struggled in conservative Columbus. He picked up skating again at the beginning of high school, kept his head down in class, and spent as much time as he could at the local indoor skatepark. His only friends were local skaters in their 20s, and they only hung out at the park. In a society dead set on driving unsupervised young people out of public, skateparks are a rare space designed explicitly for teenagers and adults who still remember what it’s like to be teenagers. Fourteen-year-olds and 25-year-olds can be peers at the skatepark. It’s an environment that encourages community building, thick skin, and more viral fist fights than you’d ever care to watch. Jimmy always fit in better with the older crowd, and the better he got at skating, the more they accepted him. “At that time in my life, the only way I could talk to people or relate to people was through skating,” Wilkins says. “I was pretty fucked, socially.”
His fascination with vert turned into obsession after a trip to Woodward summer camp in rural Pennsylvania; another aspirational request that Jimmy’s artist parents turned to reality. A renowned campus full of ramps, street plazas, foam pits, visiting pro instructors, and everything else a young skater could ask for, Woodward is space camp for kids who couldn’t sit still during science class.
Skateboarding is still new enough that many of the figures responsible for its creation and early advancement are not only still around but still skating. When Wilkins showed up at the Woodward ramp, legendary vert skater Mike Frazier was waiting to welcome the next generation. While most of the campers were busy skating ledges, stairs, and rails, Jimmy and a handful of kids climbed to the top of the 13-foot ramp and dropped in. By the time Frazier was teaching Jimmy how to frontside air — to fly above the ramp’s coping, grab the board, and turn with your chest facing the sky before riding back into the ramp — the rest of the kids had gone back to the street parks. Jimmy spent the next day on the vert ramp alone with Frazier, doing frontside airs over and over again until one try came back in wrong, he went to his head, and spent the rest of the week sitting in a cabin with a concussion until it was time to go back to Ohio. From that week on, vert skating was the only thing on his mind, and nothing could shake it loose.
On vert, the pads are mostly for bailing, not slamming. That might sound contradictory, but the difference is commitment. Making the conscious decision to bail — to know in mid-air or grind that this isn’t the one, to kick or throw the board away, and slide down the concave cliff to safety — that’s why vert skaters wear knee pads. Slamming is to commit totally and fail. Slamming is inevitable. No matter how much you practice tucking, rolling, and taking impact, there are simply too many things that can go wrong and eventually something will. Helmets do wonders to protect the head, but Wilkins still can’t remember how many concussions he’s had: “I’ve only been knocked out like once, which is pretty good.”
Today, Wilkins’ helmet and knee pads live in a basket next to the ramp and go on for every session, but he doesn’t bother with elbow pads or wrist guards. At the heights and speeds he goes, if you slam hard enough on your wrist or elbow, the pads won’t stop your bones from breaking, they’ll just move the location of the snap. “It basically creates a lever for you to compound fracture your arm,” Wilkins says. “I’ve seen it plenty of times.” Wilkins has suffered a major injury every few years since he was 16. He’s broken his collarbone, dislocated both shoulders, sprained his ankles more times than he can count, had fingers turned the wrong way, and, in an attempt to skate The Loop — a fully inverted skateboard roller coaster custom built for Hawk — suffered a worst-case-scenario slam, falling upside down from the top of the loop straight to the flat bottom, breaking his hip and both arms at the same time. Hawk hasn’t brought the loop out of storage since.
Wilkins spent his high school years skating vert as much as possible, which still wasn’t nearly as much as he wanted. His mom and dad took turns driving the four- or five-hour round trip to Ollie’s Skatepark in Florence, Kentucky, where he would start every session by mopping the ramp with a mixture of water and Coca-Cola to create any semblance of grip on the old surface. In 2005, Jimmy’s dad, Christopher Wilkins, got a job conducting the Orlando Philharmonic, and in high school he started tagging along on trips to Florida on school breaks to skate the ramp at a local Vans skatepark. There was a vert scene in Florida, and for the first time he met other skaters dead set on dedicating their lives to the ramp. When he turned 16, he got his license and started driving the trip to Ollie’s himself almost every weekend. Most of the time, he was the only one skating the ramp, but he was used to being alone. He found escape on the ramp and happiness in progress. Both of the ramps he grew up skating are now gone.
Jimmy moved from Columbus to the oceanside paradise of Encinitas, California, when he was 17. If you want to skate vert, your best bet is to live in Brazil, Japan, or North County San Diego. That’s where the ramps are. Jimmy chose Encinitas for the YMCA and the warehouses. He finished high school online, blitzing through senior year a semester early in an effort to move west as soon as possible. He didn’t go to the beach until he was 26.
Wilkins moved in with fellow vert skater Pual Luc Ronchetti at his parents’ house and got a job serving food to tourists at nearby Legoland. He had skated a few amateur contests as a high schooler and had brief pro dreams, but no sponsors had materialized and he wasn’t winning. In vert, unlike street skating, contest wins are where the money is.
“I’d given up on being a pro skater,” Wilkins says. “I moved out here because I wanted to skate vert every day … That’s all I’ve wanted to do my whole life — if I can just work a job and do that, that’s fine.”
In the 1980s, Hawk and his polar opposite, rock-star skater Christian Hosoi, were big air superstars until the street-skating boom of the early ‘90s turned vert into a sideshow. The vert industry swung back up right before the turn of the millennium, catapulted to national prominence like never before by the convergence of the X Games, Hawk’s groundbreaking 900, and the Tony Hawk’s Pro Skater video game series that followed shortly after. Going back to the days of Hawk vs. Hosoi, vert has long been seen as the corporate side of skating. That glitzy, sellout image was turbocharged in the early 2000s when heavyweights like Hawk, Bucky Lasek, and Andy Macdonald were all over TV and paying bills with sponsorships from car companies, Bagel Bites, and cellphone carriers. In one interview, Hawk recalls being handed a $4 million royalty check for video game sales alone. When skate videos — the beating heart of the core skate industry — were still videotapes, the fast-forward button on the remote found its own place in the skateboarder’s thesaurus as the “vert button.”
While vert’s reputation within skateboarding had sticking power throughout the 2000s, the deep pockets didn’t last nearly as long. Street skating, accessible to anyone with a board and concrete to roll on and already dominant inside the skate industry, had its own breakout celebrities, with Bam Margera, Ryan Sheckler, and Rob Dyrdek changing the channel from ESPN to MTV. Vert is aspirational, but street skating and teen debauchery are at every kid’s fingertips, and it didn’t take long for the energy drinks, car companies, and deodorant brands to shift their marketing dollars to street skaters. By 2010, the year Wilkins turned 17 and started planning his move to California, L.A. street skater Paul Rodriguez was releasing his fourth signature Nike shoe and inking an endorsement deal with Target.
When the big-name sponsors turned their spotlight away from vert, the contests became fewer and farther between, and in turn, the ramps started disappearing. Construction and upkeep on a full-size vert ramp is expensive — and that’s after you find a place to put it. Sending skaters out with a camera and a filmer to get footage in downtown plazas and schoolyards wasn’t just in fashion, it was financially viable. The glamour was gone, but vert skaters never lost the itch. While Nike, Adidas, Red Bull, and more continued to bring the money and focus to street skateboarding, Wilkins and most of San Diego’s up-and-coming vert scene fit ramp sessions in between day jobs and saved all year so that a contest finish out of the cash wouldn’t leave them too far behind on rent. The reputations stayed the same, but the realities of life as a vert and street skater flipped, with vert skaters still pushing skating’s outcast ethos on obsession alone.
Before he finished his first year in San Diego, Wilkins ditched Legoland and got a job working at the YMCA. North County San Diego is not like other places, and neither are their YMCAs. Opened in 1990 with a push from local vert pro Mike McGill, the skatepark at the Encinitas Y has raised countless pros. The vert ramp there and another just down the coast at the YMCA in Clairemont have been instrumental in vert progression for decades. Through the Y, Hawk’s ramp, the now-demolished DC Shoes ramp in a nearby warehouse, and a few private backyard ramps, Wilkins spent his first few years of adulthood skating as much as possible and soaking up all he could from the legends that now surrounded him. It took a few years, but he finally found the community that had been so desperately missing in his childhood. Watching elder luminaries like Chris Miller, Rune Glifberg, Colin McKay, and Max Schaaf pushed him to think more deeply about how he skated, seeing 2011 Thrasher Skater of the Year Grant Taylor skate DIY concrete parks inspired him to learn frontside airs with no grab, but if there was a lightbulb moment on Wilkins’ path to his current style, he points to vert pro Alex Perelson’s penchant for going faster, higher, and longer.
“[Watching Perelson] shifted my interest from doing anything to be competitive to … the way he’s doing it is pretty close to art and it’s expressive and has this different quality to it and that was a perspective that I didn’t have before,” Wilkins says.
Within vert, contests have always drawn out a maximalist style of skating that can fly in the face of the expressive, artistic side of things. The kind of tendencies that led to the jock reputation; more spins, more flips, and more back-to-back tricks often score well, but those runs can turn circus act to skate purists, sacrificing the taste and style that keep skateboarding hanging in the balance somewhere between sport and art.
He can’t explain how, but at some point, Jimmy’s focus on doing tricks that he liked over tricks designed to impress contest judges started to impress contest judges. His trick selection and style evolved at the same time, with no-grab backside 540s, massive frontside ollies, unreal backside disasters, a focus on long, powerful lip tricks, and a growing ability to put them all together at incredible speeds and heights setting him apart from other young vert skaters. Sponsors started reaching out from inside and outside the skate industry. Creature Skateboards, a longstanding skate brand soaked in horror imagery and slime green, put him on the team, and Rockstar Energy Drink added checks bigger than any core skate company could afford. In 2014, at 20, Wilkins won his first X Games gold medal, becoming what was then the youngest vert skater ever to reach the top of the podium. He was making enough money from Rockstar and contests to quit the YMCA, but in skateboarding you are only professional when someone starts selling boards with your name on them. Creature turned Wilkins pro in 2018. The progression never stopped, and in between filming video parts for his sponsors — a rarity for vert skaters these days — he racked up X Games gold medals in ‘18, ‘19, ‘21, twice in ‘22, and again in ‘23. Wilkins’ seven golds are one shy of Bucky Lasek’s record eight first-place X Games vert finishes.
X Games is vert skating’s premier — and for most of the late 2010s, it’s only — pro contest. Originally the Extreme Games, ESPN introduced the X Games in 1995 to showcase a new generation of counterculture sports. Skate contests had been around since the ‘70s, but the primetime exposure on ESPN was new, and when Hawk landed the first 900 live on air in 1999, it was clear the contest had cemented itself as the pinnacle of vert competition. In 2021, Hawk launched Tony Hawk’s Vert Alert in Salt Lake CIty, an annual vert contest that now serves as an X Games qualifier. World Skate, the governing body that oversees Olympic skateboarding, has incorporated vert into the World Skate Games, which will be held in Italy this fall and also includes events like scootering and inline hockey. You can see a clear path for how the contests could be configured as stepping stones into the Olympics, and there are whispers in the industry about a vert ramp at the Los Angeles Games in 2028, but as of now there are no official plans to expand Olympic skateboarding beyond street and park events.
The Olympic snub is largely due to participation numbers. Skateboarding was announced as an Olympic sport in 2016, and at that time especially, the global reach of street and park were undeniable compared to vert. “The bottom line was there weren’t enough vert facilities throughout the world,” Hawk says. “Skateparks were the common ground because there were parks everywhere.” In the eight years since skating was announced as an Olympic sport, though, new vert ramps have started popping up again, and a fresh crop of preteen prodigies like Japanese nine-year-old Ema Kawakami, who recently went viral for landing three 900s in a row, and 11-year-old Canadian Reese Nelson have made waves in ways that inevitably raise the Olympic question every time they compete.
Wilkins has no doubt he would try to qualify if vert was added to the Olympic roster, but it’s not at the top of his mind. He isn’t motivated by winning, and he doesn’t particularly like contests. Unlike street skaters, though, vert skaters don’t have the luxury to survive as professionals in the industry without competing. Most of Wilkins’ close friends still work nine-to-five jobs between vert sessions.
“The contest aspect of it, I definitely think it’s cool, and watching contests is exciting, and they have great moments,” Wilkins says. “But the things you remember about skating … it’s not who won.”
Just north of San Diego, Encinitas is a sitcom-ready beach suburb of steep hills and receding cliffs falling slowly into world-famous surf breaks. The weather is always perfect, wetsuits hang from side view mirrors of lifted trucks to dry faster on drives home, and flat-brim fitted hats never went out of style. As far as anyone can prove, the first vert ramp ever made was built here, constructed out of plywood in a residential front yard. Driving the half hour from his house to Hawk’s office, where he has his own key and can come and go as he pleases, Wilkins points out landmarks — which hill has been bombed by which skaters, which pros from the early 2000s vert boom live on which scenic overlooks, and which stucco buildings used to house ramps or skate brands until the boom went bust.
When he’s not injured, Willkins wakes up every day looking to skate. The access to Hawk’s ramp has made that easier, but for safety’s sake he doesn’t like to skate alone, so his days start with a half hour of yoga and a series of texts. Wilkins is eternally grateful for the consistency and quality of Hawk’s ramp, but moreso for Hawk himself. The undisputed face of skateboarding, he could’ve taken the video game money and enjoyed a chill celebrity life, but instead, he’s spent decades pushing himself on the board and pouring money and energy into championing skateboarding, and vert in particular, in ways that no one else could and few ever would. “He’s the perfect ambassador; it couldn’t have been any better,” Wilkins says. “People are freaking out about LeBron still playing basketball at 38 or 39, and it’s like, [Tony] was still doing the highest-level shit at 48.”
Today, 25-year-old Shea Donavan meets Wilkins in the empty parking lot at Hawk’s compound. The office clears out on weekends so Jimmy and Shea have the place to themselves. Donavan also moved to Encinitas for the vert ramps, driving from Colorado to sleep in the shed behind Wilkins’ house. He’s long since moved out of the shed and runs a small hat brand and embroidery company with his girlfriend while skating vert as much as possible. Once inside, Donavan walks under a set of stairs to get to the ramp, but Wilkins takes the long way, squeezing between stacks of boxes to go around the steps — the portable staircase is too close to being a ladder, and he’s superstitious.
They both change into shorts for comfort, flexibility, and because pads over pants is just a bad look. They strap on knee pads and helmets, and put on a playlist that pumps through the building, shifting from Meek Mill to the Beatles to Andre Nickatina. Wilkins never got into dance or playing music, but you don’t have to have the same career to end up like your parents, and knowing about the passions he grew up around, it’s hard not to see a bit of ballet and symphony in his skating. He reaches back and touches the top of the ramp with his right hand every time he drops in like a surfer swiping the surface of a wave. He whistles to himself on the deck. He whistles in the car and at home, too. When he’s getting ready for contests, he plans runs loosely but with purpose — a fully thought-out beginning, middle, and end, while making sure to save enough space in between for improvisation depending on his speed and location on the ramp.
“There’s a whole new breed of people out there doing their thing on the ramp, but when I want to watch vert skating, I think of the more powerful [skaters] who carry a lot of weight with their tricks,” pro skater Grant Taylor says. “With Jimmy, he carries that same power, but he’s also light. He floats across it.”
Wilkins left Creature and joined Real Skateboards in 2022. Real, as the name suggests, is a cornerstone of the skater-owned industry. Mostly comprised of street skaters, Schaaf, the Oakland vert luminary whom Wilkins considers a role model, has skated for Real for decades, and Perelson, Wilkins’ foremost vert inspiration, rode for Real for years. For Wilkins, it’s a dream sponsor. He and Donavan have spent the past six months filming a shared video part for the company, trading roles as cameraman and skater depending on the day or trick. If contest runs are the closest thing to skateboarding’s sporting side, think of video parts as its artistic output. Long released as team projects and now typically uploaded online as individual showcases, skate videos are filmed for as long as it takes to get it right, and edited to music and b-roll to show personal style and expression alongside the tricks. When Wilkins films, he pushes himself to do tricks that have never been done before, to put together lines that stretch his limits, and to document the skating that he wants to watch. The skating that makes him feel the best.
Michael Burnett
“Jimmy is your favorite street skater’s favorite vert skater,” Hawk says. “He’s one of the few where his style alone will draw attention to what he’s doing.”
Producing content that usually ends up on YouTube and Instagram, skaters haven’t grown into influencers, rather the culture at large has normalized the professional model, or lack thereof, that skaters have long navigated. Pro skaters, operating in an industry without structure or regulation, have always been paid to look cool and convince an audience that they are one shirt, pair of shoes, or new board away from looking just as cool. Social media has no doubt bolstered his career and visibility, but Wilkins isn’t a fan of the scroll. He’s happy to post his latest video clips or promo his pro model shoe, recently released by Lakai Footwear, on Instagram, but he deletes the app from his phone between posts.
Vert skaters need contests for exposure, but contests don’t pay the bills — sponsors do. These days, with the cultural stigma of selling out all but gone, the once-shunned global sportswear giants and energy-drink brands now serve as the financial buoy for most of the skate industry, street, park, and vert alike, leveling the playing field of attention and acceptance for vert within skating and reopening doors of excitement outside of the core skate industry. It’s hard to make fun of vert skaters for being jocks when street icons are sewing Monster Energy patches onto their hats, too.
Wilkins wants to skate for as long as possible, but he’s seen enough industry horror stories and is doing his best to put stable ground under his feet. He bought a house in North County with his contest winnings, Rockstar deal, and, in classic millennial fashion, a little help from his parents. His roommate, Chaz, another Colorado transplant who spent time sleeping in the shed before moving into the house, is a surfer and woodworker. He could live alone, but he doesn’t want to. Chaz is a friend, and Jimmy is always down to help out his friends. Besides, their rent arrangement, well below market rate for the neighborhood, is a win-win for both of them. Wilkins wakes up early, goes to sleep early, and caps out his partying at a couple of beers and a like-hate relationship with brightly colored nicotine vapes. He’s more relaxed than ever. He took a workshop to learn how to make picture frames and got into chess during the pandemic, but mostly, Jimmy wants to skate. The ramp has given him passion, peace, community, and a career, but vert is still a small fraction of the skate industry, and his success has created a sense of responsibility for its future.
“At the time that I started my career, it was pretty clear that vert visibility was at an all-time low, and any attention I got felt like everyone was getting it, so it felt important to try and not fuck it up,” Wilkins says. “The main job of a pro skater is to get more people to skate and stoke people out, but you’re kind of removed from that when you’re a pro skater, so hopefully someone has picked up a board or a set of pads because of me, that’d be the best.”
He’s got one more trick in mind for the shared video part with Donavan — a frontside ollie 540 — a Hail Mary of a trick that Hawk says he’s only dreamed of. Wilkins has never done one before — no one has ever done one — but he’s close enough that he won’t stop trying until he rides away. Until he forgets to bail.
For years, it would have been unthinkable that skateboarding would be added as an Olympic event without vert. By the time we reach the 2028 Games in Los Angeles, thanks in no small part to Jimmy Wilkins, it might be unthinkable again.
