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“Creative Weirdo” Leo Baker Is the Future of Skateboarding

This week's FRONTPAGE puts the spotlight on maverick skater Leo Baker, who chats with us on abandoning the Olympics for street skating, his own business, and his long-awaited transition.

In the opening scene of wick & spit, a video released this summer by New York skate brand Glue Skateboards, co-founder Leo Baker reclines half-naked in a deckchair, the camera wandering between his tatted-up body and his impish grin. “I’ve never been this okay,” the 30-year-old skateboarder tells me weeks after the video’s release with a smile, surrounded by musical instruments in his New York apartment. “I’m in a really dope spot. I feel this absence of discomfort and anxiety, but I had to do this deep, emotional purge to get here.”

Baker’s journey toward true contentment has been arduous, to say the least. It has also been largely captured on camera.

Six years ago, directors Giovanni Reda and Nicola Marsh came to him with the idea of filming a documentary. “Reda and Leo had been friends for a long time,” the directors tell me in a joint statement. “Reda knew the skate world well as a seminal skate photographer, and Marsh knew the documentary world well as a cinematographer and director working mainly in that field. As the Olympics came into view, we realized Leo was heading into some headwinds navigating his private and professional life, and we felt like this was fertile ground for a feature documentary.”

Filming began in 2018. Initially, the recently released Stay on Board: The Leo Baker Story was pitched as the inspirational tale of a trans, non-binary athlete gearing up to conquer the Tokyo Olympics. This triumph had been a long time coming: Baker started earning cash for skateboarding at just 11 years old, driving with his mom to competitions throughout his teen years. He made it big in 2008, at just 17 years old, winning a $25,000 cash prize at the Maloof Money Cup. Baker rose rapidly through the ranks of women’s skateboarding, earning prestigious co-signs from the likes of his idol Elissa Steamer and the legendary Tony Hawk. By the time the Olympic women’s skateboarding team was being assembled for the first time ever, in 2019, Baker was a shoe-in for a spot on the squad.

This is loosely where the documentary begins. We follow his training sessions, the endless competitions, the external pressure to seize the opportunity and mark his name in Olympic history. “The ‘people pleaser’ side of me and the ‘what’s best for me’ side clash a lot,” he tells me. This inner conflict becomes one of the documentary’s main points of tension. Baker could land a slot on the US Olympic team –– but does he want to?

What starts out as Baker’s doubt about whether he’s good enough for the Olympics turns into a question of whether he wants to skate competitively at all, before he ultimately lands on a more seismic conclusion: The hyper-gendered world of women’s skateboarding is beyond jarring to a trans athlete who’s not yet out. He winces as he’s misgendered, cringes at cries of “Yes, girls!” in a photoshoot as the photographer tells him to “work it.” Baker looks sheepish. “I don’t wanna work it,” he replies, sadly. After months of introspection, Baker’s self-preservation side won out. He pulled out of the team. The decision went against the advice of almost everyone in his life, who couldn’t believe he’d turn down a history-making opportunity to represent his country. “I knew almost nobody would approve of the decision,” he tells me with a shrug, “but I had to follow my intuition.”

Baker’s choice complicates linear narratives of success. It’s motivated, too, by Baker’s self-identification as a street skater through and through, as well as his love of skateboarding’s countercultural roots. One fellow skater who did approve was Stephen Ostrowski, who co-founded Glue Skateboards alongside Baker. In a standout scene, Ostrowski jokes: “Do you know what’s cooler than doing the Olympics? Saying ‘Fuck the Olympics!’”

Yet Baker’s decision to quit the team was about more than just punk values. At the time, he had just begun grappling with the United States’ trans healthcare system. “There were so many fucking hoops to jump through,” he explains with audible frustration. “The longer I waited, the more depressed I got. I spent years trying to get top surgery, and then it wouldn’t work out because I had to skate a contest.”

From a young age, competitive skateboarding had been Baker’s life. His passion for skating can be traced back to his earliest childhood years. He was born and raised in Covina, California, and as a working-class kid, it was one of the few activities accessible to him. “I get asked a lot if I surf or snowboard,” he explains. “No, because I grew up with no money. That’s why I find skating really special. If there’s a piece of concrete and you have a skateboard, you can do it.” His earliest exposure to skating came at three years old, during a brief stint in foster care while his mom was in rehab. According to the documentary, Baker saw his foster brothers practicing kick-flips and became immediately enthralled. When he was returned into his mom’s care, she spotted his flourishing passion and decided to nurture it. “I played Tony Hawk’s Pro Skater when I was eight years old, and was like, ‘I want to be a pro skater,’” he recalls with a laugh. (In a full-circle moment, Baker was included as a playable character in the re-release of Tony Hawk’s Pro Skater 1+2.) “Mom said, ‘That’s great, because I’m busy, so you can go out and skate in the front yard.’”

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Baker’s talent was evident from an early age; at 11 years old, his mom set him up with lessons from his first mentor, Ryan Miller. “I thought Ryan was so fucking cool,” he enthuses. “He gave me paint markers so I could tag up my board. He let me borrow skate videos I’d never heard of, like Listen, and early Girl Skateboards videos, like Mouse.”

The pair quickly bonded over their shared love of skateboarding, allowing Baker respite from petty school bullies who would tease him by singing Avril Lavigne’s “Sk8er Boi” in his direction. He rolls his eyes at the memory. “I was just like, ‘Fucking shut up,’” he laughs. “The skaters I looked up to had their influences deeply rooted in hip-hop. I wanted to wear the baggiest pants and shirts, the puffiest shoes. I wanted to look fucking cool like them.” These style choices earned him nasty remarks, too –– but never from Miller. “I didn’t feel weird for wearing baggy pants when I was with him, but in any other public space I’d be asked if I was a tomboy. I’m like, I’m fucking seven years old, I don’t know! Leave me alone, you guys are being weird.” It’s a point of view he stands by today. “Adult stuff needs to stay separate from children and their pure explorations of art and life,” he muses. “Let them figure it out, because really, as kids, I think we know a lot more than adults give us credit for.”

Baker had a strong sense of self from a young age. His school years were spent juggling exams, regular skateboarding practice, and regular competitions, no easy feat for a pre-teen. It didn’t take long for corporate sponsors to sniff out his marketability –– everything from his name to his long, blonde hair were seen by ad execs as marketing gold — so, at 11 years old, he landed his first sponsorship with Billabong. He knew what he wanted to wear –– and it wasn’t the girls’ collection –– but was expected to remain silent in business meetings. “I was in the room [for a meeting] and they were talking to my mom like, ‘Technically, they skate for Billabong girls, so the point is to market the girls’ stuff.’” Baker shudders at the memory. “I remember hearing that and being like, ‘There’s no fucking way I’m wearing that shit.’”

Money, or lack thereof, complicated these discussions. Baker’s mom became his de facto manager throughout his teen years, giving her the unenviable task of mediating negotiations between sponsors and her increasingly frustrated child. In pursuing his passion, Baker had become the family breadwinner. Consequently, his personal aesthetic and identity were up for debate. Baker speaks of a deep frustration throughout his late teens and early twenties. He describes spending his adolescence being preened, polished, and milked as a proverbial cash cow. Frustrated, he eventually grasped at autonomy by shearing his long, blonde hair. Soon afterwards, sponsors dropped like flies.

Filming for Stay on Board began at a turbulent point in Baker’s life. He hadn’t yet come out publicly as trans, but he had told his then-partner, Melissa Bueno-Woerner, and a handful of fellow queer skateboarders. The industry was changing, too. Skateboarding’s inclusion in the Olympics was lauded as a stamp of credibility, but to Baker, it represented a distancing from the street skate culture and values he’d fallen in love with. “The industry has evolved into such a beast,” he explains. “It’s run by corporations now.”

After years of competing with the sole aim of winning money, he was similarly frustrated by people “breathing down [his] neck” about how to skate. “The way that I skate is not conducive to winning competitions,” he shrugs. “If I really want to win, I have to strategize and master tricks I can land every time. People would tell me all the time: ‘If you just hit the big rail you would win,’” he says, his voice becoming whiny in imitation of his critics. “I don’t want to hit the big rail because that’s not how I fucking skate!”

Stay on Board works well as a portrait of a compelling skater: It’s funny and emotive, and Baker himself is wildly charismatic, plus there are glimpses of some of the most badass corners of street skateboarding history. But it’s also an insight into everyday life as a trans person –– and alongside all the joy, laughter, and community, is a whole lot of bullshit. “All of our stories get told under the pretense that we’re struggling because we are trans,” explains Baker. “[But it’s] because of the system we live in.”

That system can be especially hostile when it comes to the world of trans healthcare in the US; some of the most heart-wrenching scenes are of Baker navigating the countless obstacles laid before trans people seeking life-saving care. In one scene, Baker talks about being denied one of the two doctor’s letters needed in order to be approved for top surgery. “I walked out of that appointment so fucking broken,” he recalls. “I came home, got in bed and stayed there for days. My nervous system was so blown out I would randomly start sobbing. It was really fucking dark.” His mental health deteriorated so badly that Baker says Netflix paid for his healthcare. “I gave an interview where I was really, really bad. The executive producer was like, ‘We need to pay for this person’s therapy, because they don’t have the income.’”

Baker’s mental state raised some ethical concerns for the crew, too. “Leo is an incredibly present and thoughtful person,” the directors tell me, “but it wasn’t always easy filming him at such a tender moment in his life. Sometimes, the process felt a bit extractive.” Ultimately, everyone –– Baker, the co-directors, and editor Sasha Perry –– “feel good about the final product,” but the process was occasionally a struggle.

Throughout this period of deep depression, Baker was “self-medicating by drinking and doing a lot of drugs,” he explains. “I was doing a lot of blow.” Endless waiting lists, intensive gatekeeping, and the struggle of scheduling appointments around his travels weighed heavily, but after a years-long wait, Baker was approved for top surgery by his insurance. A few weeks prior to the procedure, he was called in to the hospital and asked to provide a urine sample. Days passed with no further communication, so he called to check on his surgery appointment. “The receptionist was just like, ‘Oh, you tested positive for cocaine,’” he says, mimicking her dismissive tone.

After his positive test, his insurance denied coverage of the procedure, forcing Baker to pay out of pocket. When he finally did go in for surgery, he asked his surgeon if he would have to be drug-tested again. His surgeon laughed: “Tested for what?’” Baker double-checked with his mom, a medical professional. “I shouldn’t have been doing blow, obviously, but [talking to her] was the kicker. She was like: “They drug-tested you? That’s an insurance thing. They’re looking for any way to not have to pay that money to help you.”

As well as the healthcare system, Baker has transphobic trolls to deal with online. “My fucking Instagram has been flooded,” he tells me. “They’re like, ‘Now what contest are you going to skate in, man or woman? You’re still a girl!’” Baker stands up, frustrated. “I literally quit competitions because of this. Leave me the fuck alone –– I’m not competing, when are you going to pick up on that?” He’s got no plans to compete in the near future, either. “It’s too gendered, I can’t do it,” he says. “I don’t want any more fucking targets on my back. I’m done being the spokesperson.”

Stay on Board features turmoil, but the overwhelming message is one of queer joy and the power of self-actualization. In January of last year, Baker and Ostrowski officially launched Glue Skateboards with a deliciously punk, 20-minute clip entitled SMUT. Premiered on the YouTube page of skateboarding bible Thrasher Magazine, it came with a disclaimer: “scenes of hormone replacement therapy.”

Prior to the release, Baker and Ostrowski had been working behind the scenes for months. “We started skating together and filming a bunch of clips,” he says of SMUT’s conception. “I already had some old clips, and so did Cher [Strauberry], so we just put together a video of what we had and were like, ‘All right, let’s fucking run it!’” Grainy, old-school skate videos inspired the clip. “I looked up to teams of skaters who were like a family, the kind of videos where a group of homies would [skate] and one person in the group would be filming.”

Baker sees Ostrowski as akin to a spiritual sibling. “I’m super grateful for the artist experience I’m having with Stephen, who’s so driven and so deeply intelligent,“ he gushes. “They’re one of the best people I know. I journal about it all the time.” Together, they’ve built a company rooted in accessibility, inclusivity, and a desire to create space for skaters who feel excluded within the juggernaut industry. They’ve also accrued a roster of wildly talented skaters, showcased regularly on the joyous Glue Instagram account. “We’re just a bunch of creative fucking weirdos,” says Baker with a smile.

It’s taken decades, but Baker today is living life on his own terms. “I had a therapy session recently,” he says, “because there were some trips I was going to go on, but I had too much anxiety. I needed to process things post-documentary life, to see what I can do and what is no longer something I can do.” Tired of compromising his autonomy, Baker now claims it proudly. He travels “ideally only to film skate clips or for leisure,” and he recently released his debut single, “hold me til we’re home,” as leo popstar, a tongue-in-cheek moniker he says is “pure camp.” “I’m like, ‘I want to be a pop star,’” he jokes excitedly, “but then I write sad songs. Then I’m like, hmm, what about being a house DJ? I don’t know. I just gravitate towards anything gay, really.”

Mostly though, you’ll find him laid atop his bed, “no phone, no music,” content with silence. “I feel like I know my purpose now, which is to just make stuff and skate in the ways that make sense to me, without any outside input. Now that I’ve been able to manifest that as part of my life, I’m deeply grateful. I’m just going to do everything I can to maintain what I have going for me.”

Experience this story and others in the new issue of Highsnobiety Magazine, available from retailers around the world and our online store.

  • WordsJake Hall
  • PhotographyAdam Powell
  • StylingSam Knoll
  • Creative DirectionMicheal Quinn
  • HairHide Suzuki using R+Co
  • MakeupAndrew D’Angelo
  • Photography AssistantSkyler Dahan
  • Styling AssistantNash Koshiro
  • Production AssistantMolly MacIntosh
  • With Thanks toBowlero Chelsea Piers
  • Production byPerris Cavalier at The Morrison Group
  • Lead Image Fashion CreditsTop LOUIS VUITTON Pants FERRAGAMO Necklaces and bracelets BULGARI Rings on left middle finger, left ring finger, bottom left pinky, and bottom right ring finger THE M JEWELERS Rings on top left pinky and right pinky İTÄ Ring on top right ring finger PANDORA Shoes NIKE
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