Since quitting the 2020 U.S. Olympic team and stepping away from competitive skateboarding, Leo Baker has had no regrets. “I am happier than I’ve ever been in my life, beyond what I could have ever even imagined,” he says, speaking on a hot August day by Zoom from his Brooklyn apartment. He’s wearing a black tank top, exposing tattoos on his chest and arms, and his side-parted blonde hair has just the right amount of bounce to call to mind another Leo’s beloved Nineties style. “Purging all the stuff that was not working for me, like quitting the Olympics and getting rid of all this stuff that was not ‘it,’ created a clearing for things that are it or could be it.”

After rising to fame as a child skater on the competition scene, Baker was considered a sure thing for the sport’s debut at the 2020 Tokyo games. But he felt deep ambivalence. A new documentary, Stay On Board: The Leo Baker Story, which premiered at the Outfest film festival last month and begins streaming Aug. 11 on Netflix, captures his misgivings: In addition to feeling disillusioned by the rigidity of the rules and regulations of the trials leading up to the event — a process Baker repeatedly describes as “bleak” — he was also growing tired of being categorized as a female skater after he had already begun using he/him pronouns in his private life. Baker came out as trans-masculine in late 2019, and in early 2020, he quit Team USA..

Now 30, he’s sponsored by Nike and skates for his own queer-centric skate company Glue, which he runs with his business partner and fellow skater Stephen Ostrowski. “We take our team on trips and do things that we were never able to do because there was not space for trans queer people to be in skating in that way,” he says. “We’re living our childhood dreams of going on skate trips, filming, hanging out with our team and being around people that are queer or are down for us.” 

A guitar player since 14, Baker is also starting to nurture a music career when he isn’t skating. His song “Hold Me Til We’re Home” plays at the end of the documentary. “That’s my first song ever to come out, and it’s under the artist Leo Popstar,” he says. “I just think that’s such a ridiculously funny name for the music. I’m like, no one’s taking this seriously. Please do not.” Baker will release an EP this fall called Crying All the Time

Despite his prominence in the industry, Baker has lately been taking time for himself. “I love to do things alone,” he says. “I write music. I go to the gym. I like to feel anonymous, almost not there at all. Especially now, because I’ve been reading so much Buddhist literature, I’m like, the less of me there is the happier I am. So I’m just going to be quiet in my room, and I’m going to talk to the people I love, and maybe I’ll see somebody for dinner.” 

Baker spoke with Rolling Stone about the new documentary, his approach to music, and life after quitting the Olympics.

When you first started making the documentary, were the filmmakers expecting to tell the story of you going to the Olympics? I’m just wondering how big a change it was when you decided not to go.

They definitely pitched this as like, trans, non-binary athlete going to the Olympics, and Netflix bought that story. So yeah, the plot twist was super authentic and really unexpected. I dropped out of the Olympics in February. Then, in March, the pandemic happened, and the Olympics were postponed another year, and I was like, “Thank God I’m not doing that.” The timing of everything was just really interesting. It wasn’t a matter of, oh, no, the Olympics are postponed so now I’m gonna quit. It was like, I quit, and then it was postponed, and then I was like, great. Don’t care.

You spoke in the documentary about knowing from a young age that you were a boy, but that getting lost in your branding, as this “girl skater.” Could you tell me more about how rising to prominence in the skate world in this gendered way affected you?

The fact that my whole career was contingent upon my gender was really strange. I have memories of being super young and telling people that I’m a boy. And then as things started to progress with skating… I got my first sponsor at 10, and people were like, oh my god, this “girl skater” is amazing. And I just didn’t even think about being trans at all, basically, from age 10 to like, when I was like, 20. And then I [realized], ohhh, that’s still a thing. Ah, fuck! Shit! Now what am I gonna do? Obviously, that caused a lot of turbulence for me, because [for a long time] I was like, well, that’s never gonna happen. I just started transitioning at like, 29. And everybody’s like, ‘Oh, you’re such a rad woman skater.’ And I’m like, “I’ve got some news for you.”

I thought the doc captured some moments like that really well: Like the coach at your former high school congratulating you and saying you’re such a star female athlete. And you just sort of looked like, “Oh no. What do I do?” 

I’m so glad they put that in there. Because that really depicted what it is like when that happens. I used to get called ma’am on the phone, and then I was like, I’m just gonna go up on my T dose, because I just can’t deal with this. And now, none of those things happen. So in recent times, I have become a lot more passing, which — that in itself is problematic, right? Because we’re talking like there’s a specific way you have to be if you want to be a guy, and it’s like, none of that applies. But yeah, passing as he/him, it’s happening more now, so I haven’t been dealing much with being misgendered as of late, so that’s nice. 

Was there a turning point? In the documentary, your girlfriend at the time asked you about your pronouns and it seemed like that gave you the space to consider it, perhaps for the first time.

Yeah, meeting Mel was super helpful. In the relationship I was in previous to that it was like, the opposite. I didn’t talk about this relationship at all in the documentary, but this particular person had dated other trans people and had bad experiences with them and had a lot of trauma around it. So when I would talk about it with her, she would get super, like, unhinged about it. So I was like, OK, cool, I just won’t talk about it with you. Then when I got out of that relationship, I met Mel, and Mel asked those questions. Then it all just came out. And I was like, damn, I’ve really got to deal with this. And then, having that come up, and having freedom to explore led to really intense depression, just because I’m like the fucking mountain I have to climb to like, get to where I need to go is too big.

There was a scene in the documentary where the interviewer asked if you were worried about backlash if you came out, and you just stepped away from the camera. What were you feeling in that moment? 

Yeah, it was just everything. I was just thinking like, fuck, I have to come out. That means a name change. And then from the perspective of it being public in my world of skating, that part was the most overwhelming. Because I had already experienced feeling there was no space for me. I had already gotten [ backlash] just by having my whole dyke era. People were like, you’re not cute or fuckable, so you’re not going to get a sponsor. And then I kept pushing through. And now it’s like, I have to do that again. I don’t want to do that again, but I’m gonna have to. So for all of those thoughts to come up at once as a tornado in my brain when I’m getting asked that question it’s like, unfathomable to even start to talk about it. So I’m like, I’ll just walk away. [laughs] It’s gonna be easier. I’m gonna choose not this.

You came out publicly in an Instagram post in Oct. 2019, where you asked people to call you by the pronouns he/him or they/them. What led you to that moment? 

I don’t know exactly what led me to that moment. Having a split life is so exhausting. And then it just leads to more splits, because it’s like, when I’m this person, there’s all of these things I have to do, and it’s just this whole thing. I wanted to bring it back together. I was like, I just don’t care anymore. I can’t keep doing this. People need to stop calling me she/her. Because it fucking feels horrible. So please respect my pronouns.

The doc portrayed the Olympic trials, you seeking top surgery, and the Covid-19 pandemic all colliding. Could you talk a little bit about how all those experienced played off of each other? 

Yeah, it was a perfect storm. I had been trying to get top surgery for years, and it was just not something I could do because of competing. But then [when the pandemic began] I was like, I don’t have to be anywhere except home, and that’s the perfect situation for what I was going through. Leading up to it, the years and years of trying to figure out when it’s going to make sense, getting a consultation, but then, fuck — I’m traveling. In the doc, it shows me asking for two appointments, because I’m like, one has to work. And then a competition came up and the appointment actually was the day before I had to fly out. I was like, thank God. It was just worlds clashing, like, I can’t do both; I’m gonna have to choose. Also I don’t really care about competitions at all, and I never really have. It’s fun to see my friends there, which is why I liked doing it before. But now that it’s hyper-competitive because of the Olympics, I’m like, this is so bleak. I’m super bored. I don’t want to come here. So it was an obvious no-brainer. If I have the option to not do this, that’s going to be what I choose.

Are you done with competitions forever?

The Olympics was the biggest thing. I mean, there will be other competitions that are not related to that, that will probably be more fun as a result of how bleak that side of it is. But I mean, people still are on my Instagram like, ‘Well, who are you? How are you going to be competing now? Boys or girls?’ I actually just had a situation where I was going to do this video competition. I had filmed clips for it, submitted my stuff on time, but the company that was putting the competition on couldn’t legally get the language to be like, men, women and non-binary, even though there was a category for trans and non-binary. I would have had to sign a document as a woman. So I pulled out, because it was like, I don’t need another fucking target on my back. These people are ruthless. It’s a huge sacrifice because I had the potential to win a good sum of money, but it’s not worth people coming for me about like, being somebody who’s on T skateboarding in a competition with cis women. No amount of money is worth the way people would treat me if I did that. I’m tired of being the example. No more guinea pig. No more envelope pushing for me. Like, thank you all for showing up, but I’m gonna be in my room. So yeah, the competition thing is fucking chaotic still.

As a writer for a publication that’s covered you in the past, I’m curious, is it strange to have so much coverage of you out there from when you were so young and also from before you came out? 

Yeah, it’s bizarre for sure. I did not know the weight of what I was doing at that age, putting out videos of my coming-of-age years, where I’m developing tastes in clothes and having phases and some stuff is really fucking weird and embarrassing, and it’s all just out there, and I’m like, oh my god, can everyone delete anything they’ve ever posted of me pre-2020, please. I’m only just now self-actualized in the last four months, probably, where I’ve reached a big level of being at peace finally, and for all of my life leading up to that to be documented in some way is a wild experience. 

What is your music about? What inspires your songwriting?

Oh my god, it’s more of me just pouring my heart out. I just can’t stop doing it, apparently. I’ve always been super drawn to like really sad music. Sufjan Stevens is one of the best. There’s Novo Amor, who I’ve discovered recently, who, Oh my God — it makes me dissolve when I listen to it. Also Amber Run, James Blake. There’s a song by Fionn Regan called “Dogwood Blossom” that is just like, the best song ever. I always find it really comforting to listen to [that kind of music], and so naturally that’s what started coming out. There’s songs coming out about like, family stuff and my relationships and it’s all feelings. Just being super emotional. I really love love songs. 

Have you heard a lot from other trans people in the skate community since coming out?

Yeah, so many. There wasn’t a person before me, in my specific world, who carved a path for trans people, although obviously, there have been centuries of trans people carving paths for future generations. I’m not the hero, but in my world, people tell me, “because of you, I can now exist in this world, too, and feel comfortable doing it.” It feels like a lot of weight, but not in a bad way. It’s just like, that’s intense. And then if you zoom out, it’s like, it’s only because the world is so unaccepting of trans people that this is significant. But actually, being trans is not the most interesting part about my personality. I’ve been having a lot of conversations about this with people. The thing is, I don’t want to hang out all the time in queer spaces and talk about how I’m queer and the ways things are wrong for us and what we need to do to fix it. Like, I want to just have a joyful fucking day and play music and not, be afraid to go outside or use the bathroom. I don’t need to talk about being fucking trans all the time, but it feels like such a spectacle sometimes. So it’s an interesting paradox. People are like, you’re really important. And I’m like, am I? It’s just interesting.

There are few industries more entrenched in the gender binary than athletics, which skating has been pulled into. How would you like to see the skate world change in the future for trans, queer, and non binary kids?

There’s a couple of things. The first thing is, whether it’s trans kids in more traditional sports or something like skating, I’m not saying I have the exact answer [to what this should look like], but let the fucking kids play. Who gives a shit? Nothing matters. We are floating on a rock in space. Stop tripping. And then the other thing is, I’m hoping that by creating Glue, — and Jeff Cheung, the owner of There Skateboards also has a queer-centric skate thing in Oakland — I’m just hoping that the more momentum there is for us, the more people will decide to start something, and then there’s a queer skate industry where the people at the gates are not straight white cis hets. It would just be cool to see like, more than one trans person being successful at something, and to see more examples of how you can be trans and live a dope life. It doesn’t have to be all fucked up all the time because of the fact that you’re trans. There’s going to be more suffering inherently because of the way the world is, but it doesn’t all have to suck. So that is really what I hope to see happen in skating and also in the fucking world. We need to diversify the people at the top so that the people underneath can be seen.

Lifestyle

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