“There are so many trends he’s been in front of, partially because he does not care,” McMahon says. “And he kind of never has.”

At 13, his mother sent him off to a predominantly white boarding school in East Hampton, New York. As he recalls, the decision was left to him, but his mother’s stance was, “You would be silly to not take this opportunity.” He did his own research, came to the same conclusion, and ended up in a cafeteria with recycled bamboo floors where the quality of the food blew his mind. Despite the East Coast culture shock, he assimilated quickly, did well, made friends — but he was a sensitive, lonely teenager who couldn’t shake an undercurrent of doubt. “Why am I entitled to have this life of promise and all these blessings?” he’d wonder. “And I have friends I’ve left at home who are inevitably going to be in the system.” During those years, he’d take the bus into the city on weekends, stay with his friend Aidan Mackey, and skate with him through Tompkins Square Park. 

Strobeck, the proto–Frederick Wiseman of chronicling modern skateboarding on film, recalls meeting a 15-year-old Elsesser. He was goofy, but he was also utterly obsessed with skateboarding. “That’s all he cared about at that moment,” Strobeck says. “He was young and just so electric. He had that big energy, and he had to put it somewhere.” Elsesser knew all about Strobeck, including the skate videos he’d made. “He texted me every day to meet up” and film together, Strobeck says.

After “cherry” was released, Elsesser just wanted to keep going, Strobeck says. So the pair of them, plus Tyshawn Jones and Sean Pablo, put out another video called “JOYRIDE.” six months later. “We were in a bulletproof bubble” of success, Strobeck recalls. “It almost felt like we could do anything.” 

Strobeck, their elder, watched the three skaters get stronger and better and more sure of themselves. But they also became recognizable. “They walked down the street, and people knew who they were,” he says. “Everyone wanted them. I remember a lot of casting agencies and companies hitting me up like, ‘Hey, can we use those kids?’ As soon as things get hot, everyone wants a piece.” 

For Elsesser, a deal with Converse followed, then a cascade of opportunities. Still, his doubts never went away. Some of the people he was skating with didn’t need to rely on the sport for income, but for him, going pro came with added pressure. It was his one chance to make it big, and who knew how long it would last? 

Skateboarding is not a sport that is kind to the body or the mind. As Elsesser describes it, “we [skaters] all have a little bit of that self-harming vibe to us where we kind of enjoy getting beat up. We’ll be trying a trick for hours and tell ourselves, you know, ‘Just one more. I’m not allowed to have a sip of water until I land it,’ or, ‘I can’t eat.’ Just this kind of ultimatum in our heads.” 

What starts as a harmless mental negotiation with yourself can turn dark very quickly. Despite the meteoric trajectory of his fame, being the constantly photographed face of Supreme, a sense of isolation began to infect Elsesser. He’d always struggled with depression, but this time, “it manifested through my struggles with addiction and substance abuse,” he says. “I’m super grateful to have made good money through something I love to do, you know, I never worked a nine to five. But I look back, and that’s when things started to get strange for me — when I started to disconnect emotionally.” 

“He can be very passive about his own accomplishments,” says his sister, McMahon. “Part of that is because no one has ever given him the fucking credit.” When Supreme blew up with “cherry,” she says, it wasn’t because the Supreme “guys were finding skateboarders and being geniuses. It was Sage saying, ‘Here are my friends. Here’s who I want to put on. Here’s who I like and think is talented.’ And that’s how you get a team that’s basically all brown. 

“A lot of people got credit for how they found those kids,” McMahon adds. “And they didn’t find those kids. They asked one kid who his friends were. And those kids had flair. They had style. They did all these things organically that no one else was doing.” 

Elsesser was a depressed 18-year-old when he began posting his tracks to SoundCloud — without his name attached. “I felt safer just posting it anonymously, so I didn’t have to bear the brunt of saying, ‘Hey, I make music now,’” he explains. “I was also fearful of the judgment of people in skateboarding at that time. I was really public-facing. I was doing a lot of modeling for Supreme. So every couple months there were like 30 images of me online.” 

Elsesser’s one refuge was his music, which he’d been making all his life. Even while filming “cherry,” Strobeck says, Elsesser would text him videos of himself “doing a rhyme, just doing what he does.” He finally started sharing his work with some industry friends, who encouraged him to make more. Matt Martians, one of the founding members of Odd Future, told him he had good ideas. Earl Sweatshirt, Elsesser’s close childhood friend, said, “‘Man, your music is special. You should explore more of that. You should rap more,’” Elsesser recalls.

Elsesser began slowly distancing himself from the sport that made him famous. “I felt like I wasn’t getting the support that maybe I deserved,” he says, and his sheer love for it had started to fade. He was a little older and less willing to risk injury. And even though he’d been pro for 10 years, he still felt like he was failing to honor young Sage, who’d spent hours and hours investing in his dream. 

As Navy Blue, he could stash away a lot of his discomfort. “Every spliff is but a remedy,” Elsesser raps on Sir Render, made when he was emerging from his “emotional and spiritual bottom.” He was battling with his mental health and realizing he needed to get sober, both running refrains through 15 haunting and sonorous tracks. But the record isn’t entirely morose. On the song with his friend and mentor, Ka, his joy is palpable. “I think it’s my best one,” Elsesser says of the album. “It’s a world that I created, that I spent a lot of time in. I really wanted it to feel like a film. I wanted to make something that you could just press play on and have a full experience.” 

Music has served Elsesser well. At the time of our interview, he was just coming off an extended tour across London, Europe, Australia, and New Zealand as the opener for the British hip-hop performer Loyle Carner. Despite being in the limelight since he was a teenager, opening across multiple nights wasn’t an effortless task for Elsesser. “My music is quite emotionally charged, so it’s already tough going out there and being as vulnerable as I am,” he says. “And then imagine the extra layer of being vulnerable with people who don’t know you.” He’s referring to the hierarchy: “The stigma of being an opener is like, you know, your music is lower. People are still coming in. People are getting drinks.” But getting over that self-consciousness was important to him. “Once I just started doing the thing, I felt some relief,” he says. “Going onstage having set an intention, grounding myself, it always gives me that extra push that makes me feel like I’m not performing for an audience.” 

So, Navy Blue is thriving. And Elsesser has gone in new directions, too. He met Adrian Douzmanian, the co-founder of Miami-based skate brand Andrew, through his model sister. The two men bonded over their shared love of soccer, Stone Island, and watches. 

Still, Elsesser hasn’t fully given up on skating. After years of a self-imposed sabbatical, two summers ago, he finally reconnected with the sport in a way that surprised him most of all. A friend was staying with him and one day casually said, “I’m going skating if you want to come.” Elsesser found himself smiling. And his first thought was, “You know what? Why not?”

He’d been so absorbed in music that he’d forgotten how much he loved doing this thing. So he went. And he ollie’d. And it all came back. He remembered the hours and hours he’d invested in skating “when I wasn’t good, when I was a kid and I was learning,” he says. He remembered who he was: the boy who’d found such wonder in daring physics to hold him down. And he found that the wonder was still there. 

He could still live in “that moment when you’re like, ‘I just made the board leave the ground, stay on my feet, and go back down,’” he says. “When you’re a child, you’re watching it happen and thinking, ‘How do you do that?’”