Thrashed

Jake Phelps has run the bible for skaters for more than two decades. He’s nearly died a few times in the process.

By Willy Staley
Photographs by Andrew Paynter

I had spent only a few minutes with Jake Phelps before someone called him an asshole. It was a balmy October morning in San Francisco, at the tail end of the city’s reliably tardy summer. I found Phelps outside of a corner store at 24th and Valencia at the appointed time, dressed like half of a magazine editor: On top, he wore a crisp white oxford and a gray sweater vest, chunky black glasses, and a few days’ worth of graying stubble. But his pants sagged to mid-ass; his shoes had pentagrams stitched into the tongues. At his side he held his skateboard, which had dried rivulets of blood in the griptape.

On closer inspection, the upper half of his get-up revealed an understated gnarliness. Those thick frames housed lenses so studded with scuff marks they looked useless, though they did a decent job concealing a shiner fading beneath one eye and the fresh, crimson scar above it, burrowing into his eyebrow. Five days earlier, Phelps, who had just turned 53, was skating a few blocks from here when he was struck from behind by a car. The impact sent the left side of his face hurtling streetward, and all of him, subsequently, to General Hospital for nine stitches.

Phelps wanted some coffee and had a place in mind. He threw his board down and I followed suit, heading up Valencia Street northbound in the southbound bike lane. Phelps rides his board with a certain economy of movement — shuffling more than pushing — that initially reads as caution. It’s not: We’d hardly gone a block before a middle-aged cyclist had to swerve to avoid a head-on collision. He cursed at Phelps, who, in response, puffed out his chest and grunted in the cyclist’s face.

“People always call me an asshole,” he said over the dull roar of our wheels as I caught up to him. “That’s because I don’t stop.” As if to punctuate his point, he ran the next red light. I watched from the limit line as a truck driver slammed on the brakes.

An unwillingness, or inability, to stop is perhaps the defining characteristic of Phelps’s career. He’s been the editor of Thrasher since 1993. The magazine occupies such a privileged space in skateboarding’s collective imagination that it’s difficult to know what to compare it to. Skaters call it “the bible,” but we’re prone to hyperbole. Maybe it’s Vogue, but for degenerates, and Phelps is skateboarding’s Anna Wintour. Phelps likes to think of himself as the Thrasher brand personified, and in many ways, from his caustic wit to his encyclopedic knowledge of the sport, that’s true.

He’s also a man out of time. Phelps is an unreconstructed punk rocker in a city that has little need or space for them anymore. He refuses to pay his Muni fare, instead slipping through the rear doors. He bums cigarettes everywhere he goes; he calls kids blood. He barks at strangers and screams at drivers. He sails through lights with an unearned confidence, directing traffic with cryptic hand gestures. He shoplifts candy bars just to see if people are paying attention. (Once, in Copenhagen, they were.) His entire affect is charmingly cartoonish. His ears protrude from low on his head, and his smile cracks his face in half. If you dipped him in yellow paint, he might not seem out of place in Springfield.

Because of skateboarding’s quirks, the media plays an outsize role in the sport — if you can even call it that. Skateboarding probably has more in common with pornography: Talented people are paid to be filmed doing something they’re good at, or at least insane enough to try. Unlike in most other athletic pursuits, you can’t really win or lose, and, even at the professional level, it doesn’t typically happen at taxpayer-subsidized arenas; it happens wherever, whenever. There are contests, but by and large, skateboarders don’t care about them. There are “teams,” but these are just loose arrangements of dudes paid to ride a certain type of board (or truck or wheel or bearing; any one pro might have several sponsors, one for each part of his board — plus, if he’s lucky, clothes and shoes). You don’t root for skaters; you have taste in skaters. And a professional’s job is to go out and get footage for his sponsors, who put out videos that are both marketing for products and the means by which skateboarding progresses. It’s less a sport than an ad hoc media ecosystem run by, well, a bunch of skateboarders.

Magazines are the most independent media in this ecosystem, the one spot where editors, writers, and photographers can put forth an ideal vision of skateboarding and the surrounding culture. And while other skate magazines have grown anemic or shut down, Thrasher has maintained its reputation as the rag of record. The most salient expression of this authority is the “Skater of the Year” award. Its physical form is comical — a bronze statuette of a stoic bro (“Rusty”) in shorts, a Thrasher shirt, and a backward hat, lazily clutching a board by the nose — but its symbolic value can’t be overstated. In a sport with an inborn disdain for authority, this is the one title skateboarders hold in high regard. It’s also one benighted by a mysterious process. Readers get to vote for SOTY, sure; they have elections in North Korea, too. It is widely assumed among skateboarders that Phelps handpicks the winner every year, making him an object of both scorn and fascination: Who is this old guy to tell the world what’s rad and what’s not?

Massachusetts, Phelps is fond of saying, is where he learned to be an asshole. He spent the first 11 years of his life in California, before his parents split up and he went with his mother to live in Marblehead. His mom was a native San Franciscan and a bit of a hippie; she would sometimes send him to school in a dashiki. The move east taught Phelps that the world isn’t so kind. “I learned all about racism, street hockey, just punishing people,” he said.

Phelps still remembers, to the hour, when he first picked up a skateboard: April 13, 1976, at 4 p.m. He was 13 years old, and he soon realized it afforded him that most precious teenage commodity: agency. “Dogs, parents, girls, everybody — they all say no,” he said, but your skateboard doesn’t. “Even in the rain, it’s like, ‘Let’s go skateboarding.’” Soon he answered his board’s call all the time, even late at night, and sometimes on acid, transfixed by the sound his polyurethane wheels made as he carved along the concrete. (Phelps claims to have done so much acid, he would later mistake the 1989 earthquake for a particularly heavy flashback.)

Polyurethane completely changed skateboarding. Until the ’70s, skateboards had clay or steel wheels, which were about as effective at gripping the ground as you might expect. Then this space-age material arrived a couple droughts ago, and surfers took their boards into the empty pools of Southern California, transforming what had been a dangerous toy into a nationwide fad. But skateboarding was still in its infancy. Boards were shaped like Swedish fish and not much bigger. The ollie — the way skateboarders jump with their boards, and the foundation for all that would come — wouldn’t be invented until the end of the decade.

The people building early skate parks had even less idea what they were doing than the skaters. In 1977, Phelps began working at Zero Gravity, a skate park near the old Necco wafer factory in Cambridge, Massachu­setts. The park had been built by a middle-aged businessman who had learned about the opportunity while killing time at a newsstand, leafing through a skate magazine. Phelps said it was an absolute death trap; he was on a first-name basis with the Cambridge paramedics.

Phelps was good, and for a brief period of time, he found a backer in Pepsi, an early corporate interloper. He traveled around skating in demos at schools. “I’d come out with my sunglasses on and my cigarettes wrapped up in my sleeves, and I’d tic-tac around, and I’d fall,” he said. The Pepsi team would emerge, clad in Pepsi gear, and admonish him for not wearing proper safety equipment. He was making $500 a week, and he dropped out of school at the end of the ’70s, just as the skateboarding craze came to an abrupt end. “Everybody quit,” said Phelps — including Pepsi.

When skateboarding crashed, the only people who stuck around were devotees like Phelps. Subtly, this shifted skateboarding into a counterculture, closely associated with punk and hardcore. Thrasher was launched near the end of this brief dark age, in 1981, by Fausto Vitello and Eric Swenson, a pair of businessmen in San Francisco. The two had started manufacturing a brand of skateboard trucks called Independent, and they wanted a venue to advertise their product and create a scene around it. The magazine’s first editor was Kevin Thatcher (who would later go on to found Schwing!, a punk-rock golf magazine). It spoke to skaters in 1981, but today these early issues sound punishingly guileless. In his second editor’s letter, Thatcher writes: “If you feel ‘radical’ when you grind a curb then, by golly, you are radical.”

Skateboarding became trendy once more in the mid-’80s, thanks in part to the VCR. Before its invention, pros had to travel around doing demos and contests to earn their keep; with video, the demo could come to every teenage boy’s living room. Stacy Peralta, a former member of the legendary Z-Boys crew, released The Bones Brigade Video Show in 1984. It made stars of the high-flying, neon-clad Bones Brigade, which included Tony Hawk, Lance Mountain, and Steve Caballero. (I had never noticed how fake all their names sounded until Phelps pointed it out to me. “We used to heckle the fuck out of them,” he said.)

Phelps moved back to San Francisco in the early ’80s and started working at a skate shop in the Haight, where he fell in with Thatcher, who tapped Phelps to write a product review column. Phelps’s debut ran in 1986, and the difficulty of writing such a column in that era is on full display. He occasionally uses the space to admonish manufacturers for not giving him enough information (like price and dimensions) or sending useless samples (“how can we review one wheel?”). He begs his readers for feedback, and when he gets it, he doesn’t seem to like it.

Thatcher soon offered Phelps a job at the magazine’s Hunters Point headquarters in the shipping department, boxing up Thrasher shirts and hats. This was the late ’80s, and by that point the guys upstairs making the magazine were, according to Phelps, “kooky desktop publishing nerds” who wore capes to work. Vitello understood this on some level, and he would bring galleys down to his outspoken shipping manager. “What do you think of this?” Vitello would ask. “That’s a bail,” Phelps would tell him — the trick wasn’t landed; the photo’s worthless. “What do you think of this?” “This sucks.” And so on. Vitello would climb the stairs back to the edit staff and relay Phelps’s complaints. In 1993, Vitello decided to close the loop, and he put Phelps at the top of the masthead.

Around that time, San Francisco was turning into the epicenter of street skating, which was becoming the dominant mode of the sport. Justin Herman Plaza, on the Embarcadero just across from the Ferry Building, was the mecca of this age. Skaters called it EMB, and new tricks were invented there constantly. Phelps never cared much for this brand of highly technical street skating. In the ninth issue he made as Thrasher’s editor, he put a tombstone on the cover, declaring skateboarding dead. He wrote an editor’s letter: “Future generations will never even start because all they see is someone down at the local spot trying to varial heelflip noseslide nollieflip fakie” — an impossible combination of tricks back then — “a hundred times, getting pissed and going home to sulk. How could anyone even comprehend it, much less want to do it?”

Skaters at the South of Market skate park in San Francisco

His magazine was, in other words, more antagonistic than Thatcher’s — and more lively. He began publishing reader-submitted photos, and from that pool the magazine would select a phony, pillorying him as “Poser of the Month.” He’d publish photos of scars and open wounds under a “Hall of Meat” rubric. In the annual “Skater of the Year” issue, he introduced a spread of yearbook-style superlatives, some of them harmless jokes, others outright provocation. In 1995, he gave the “Most Annoying” award to a skateboarder named Billy Pepper. The next year, Thrasher published a “15 Most Hated Skaters” page, ranking Pepper No. 4. Pepper was tipped off about the page before it published, and he paid a visit to Thrasher’s offices. “How can I help you, Bill?” Phelps recalled asking, before he was socked in the face. With that, Pepper joined the ranks of pros banned from appearing in Thrasher’s pages. (There are at least four others.)

Phelps’s taste, though it skews burly, has evolved alongside skateboarding over the years. But the bluntness with which he delivers his judgments continues to make him divisive. This is especially true when it comes to the SOTY. Despite the rumors, the SOTY is determined by committee at Thrasher. Still, Phelps claims to have veto power, and with little nudging he will gleefully discuss his arbitrary, and possibly fictitious, reasons for denying certain skaters the award. Dennis Busenitz? (“He skates in German, dude.”) Jamie Thomas? (“He wore a visor to EMB.”) Guy Mariano? (“He clowned the mag.”) Torey Pudwill? (“Could you write ‘Torey Pudwill’ on a fucking trophy?”) Chad Muska? (“The guy was a dick!”) When I asked Phelps who was on his shortlist for the 2015 SOTY, he named just two guys. Six weeks later, I learned that one of them had won the Rusty.

I grew up skateboarding in San Francisco, and if you do that, you hear stories about Phelps. A new skate park opened up when I was 16, and the word was that Phelps had designed it, which seemed weird; the park was, and still is, awful. (During our time together, Phelps told me the rumor was true. He had sketched the park’s design on a bar napkin, not realizing the contractors would actually use it.) I had my first encounter with him years later, when the city’s third park opened up in the Mission District. I was skating a short, sloped ledge in the corner — the sort of thing that’s nice to do in private, away from the gaze of people who are actually good. Phelps rolled up and directed my attention to the base of the ledge. “See that?” he said, pointing at some stains I hadn’t noticed. “Blood.” People think a little ledge like that is safe, he explained, and then they get served up. This was years ago, and I still haven’t decided whether he was making fun of me or not.

Phelps goes to that park, Potrero del Sol, more or less every day, and his presence will be felt there long after he’s gone; an old pair of his glasses is embedded in the concrete. He lives in a rent-controlled apartment just blocks away, with an on-again-off-again girlfriend of 20 years. Though he has never married or had children, he told me he sees the kids at the park as his own, and around them he acts like a cool, if off-kilter, uncle. He cheers them on, heckles them, shoots dice with them, and cadges cigarettes from them.

Phelps’s Ray-Bans are embedded in the concrete of the Potrero del Sol skate park.

Since he sees it as his job to enforce the rules of a degenerate subculture, he’s an interesting role model. But his antics make a certain sort of sense if you skateboard, because skateboarding is such a totalizing worldview. After all, the most cherished places in skateboarding are infrastructural background noise to most people: parking lots, empty schoolyards, disused plazas. It’s as if two universes exist, identical and coterminous with each other, and all you need is a skateboard in your hand to see the other. Phelps has been looking at the world this way for four decades now, so long that he can’t unsee it. It has instilled in him an active distaste for even the most lenient notions of politesse. In San Francisco, this gives him a magnetic quality: He repels and attracts strangers in roughly equal measure.

This tension was on display during our first day together, when we went to DLX, a skate shop on Market Street. Phelps bought a new board, and as he was setting it up, a young man named Alex walked in, his head tilted back in awe at the boards on the wall. He seemed to be cripplingly stoned. Out of nowhere, he asked Phelps if he knew Van Wastell.

“He’s hella dead,” said Phelps. This is true. Wastell was a rising star on Krooked skateboards, a company started by Mark Gonzales, or “the Gonz,” perhaps the most influential skateboarder of all time. Wastell went pro in 2008 and was found dead in an alleyway behind a Berlin hotel soon after. It was a curious enough story that The New York Times picked it up, but the circumstances of his death — whether it was a suicide or drunken accident or something else — were kept under wraps.

Alex pulled down his shirt collar, revealing a tattoo of a crudely drawn monster on a skateboard, the Krooked mascot. Wastell had inked it, he said. (Actually, he said: “He hella tattooed my chest, though.”)

“That’s tight,” Phelps said, somewhat dismissively. He smelled a mark — a kooky stoned kid from out of town — and it seemed he couldn’t resist. He launched into his version of Wastell’s death. Wastell was on tour with his shoe sponsor, and, Phelps explained, he was an opiate addict. His teammates decided to confiscate his stash, hoping it would help him recover. But that was dumb, Phelps said. Usually, addicts bring just enough dope on the road to get them through. When his buddies took his stash, Wastell couldn’t deal, so he jumped. His teammates were down at the hotel bar talking about how they were going to fix him up when they heard the sirens.

Alex, I later learned, was close with Wastell, who taught him how to kickflip. But if he was upset or even surprised by Phelps’s unsentimental account of his hero’s final minutes, he didn’t show it. All he offered was this: “He was the gnarliest skater, though.”

“He was pretty good,” Phelps said, peering over his glasses, preparing to adjust, in the chiropractic sense of the word, Alex’s understanding of the skateboarding canon. “He’s no Gonz. He’s no Eric Koston. He’s hella dead.”

Phelps freely admits that he isn’t very involved with the day-to-day production of the magazine anymore. At this point in his career, he’s more of a figurehead — a walking, talking case for the magazine’s claims to authenticity. (The current owner, Fausto’s son Tony Vitello, calls him an “ambassador of stoke.”) San Francisco isn’t the skating mecca it once was, either. Over the past decade and a half, most of the revered spots have been torn down or knobbed — affixed with little metal strips, rendering them impossible to skate. Justin Herman Plaza was torn down, rebuilt as another great skate spot — unintentionally — and then was knobbed. Union Square, same story. The tech boom’s well-documented effects on the city’s housing market have only exacerbated the undoing.

The skateboarding industry has been disrupted by technology just like any other media business. Thrasher has been forced to adapt and become a viable multimedia organization — hosting events at soon-to-be demolished skate spots (during which Phelps works the megaphone), co-producing a web show with Vice, and premiering videos on the site. Skateboarding magazines are simply less vital now that you can watch your favorite pros’ footage on YouTube and Instagram. In a way, Phelps is anachronistic two times over — both within his subculture, as a relic of an old order, and outside it, as an avatar of the city’s grit that geeky newcomers are pushing to the side.

On a Friday morning, Phelps and I slipped through the back doors of the 49 Van Ness, one of those accor­dion-jointed buses, easing ourselves into the seats all the way in the rear corner. The bus lurched its way downtown, and Phelps, who is a prolific monologuist, unspooled an impromptu history of San Francisco’s sordid side as the city scrolled by. Phelps used to live in an anarchist house on Mission in the ’80s; lowriders would crawl up and down the drag every weekend, he told me. As we passed City Hall, Phelps said, “This is where the mayor got murdered” — referring, of course, to George Moscone — and when the bus slowed to a halt, he pointed out the other window, at the Herbst Theatre. “I got hit by an elevator right over there.” A what? “An elevator.” (Apparently, there are some submerged in the sidewalk.)

“I’ve been bit by a horse, bit by a camel, fell off a camel, fell off a horse, hit by an elevator, hit by a horse, hit by a bus, hit by a car, hit by a van,” he said. “I’ve been a projectile pretty much forever.”

Of all the remarkable facts about Phelps, perhaps the most impressive is this: He’s not dead. When you talk to him about his career, which he calls “a cavalcade of gnar,” he delivers a lowlight reel: He’s been stabbed in the chest by a meth head in the Haight and nearly killed in a drive-by shooting in Antioch; he almost lost an arm to a spider bite he got while sleeping under a vert ramp in Oakland; he’s had two brushes with death in Australia — one when he rolled a car while barreling through the Outback dressed as a priest (so he could tell customs he was there to distribute skateboards to Aborigines), one after hitting his head on a ramp (when he came to ten days later, he found that his friends, convinced he was a goner, had taken his board and sold the parts). He’s broken both legs, both thumbs, both collarbones, and his pelvis. He has fractured his skull. He’s had seven knee surgeries — three on one, four on the other. He says his medical record is 290 pages long. “I’ve spent more time in the hospital,” he told me once, “than most people spend in jail.”

Later that day, Phelps and I made our way toward the waterfront, walking up Polk Street until it started sloping downhill to the bay. Phelps believes that no matter what happens to San Francisco, the city is too topographically blessed to be completely rid of skateboarders. As he puts it, “You can’t knob the hills.” There was no fog that day, and we had a clear view of Angel Island and the Marin Headlands across the water. As we cruised down the street, our surroundings picked up speed while the hills in the distance did not, rendering us the camera lens in a magnificent Hitchcock zoom. We rode past tourists in banana-yellow motorized tricycles, filming their computer-guided tour of the city. Phelps gave them the finger.

He blew through two red lights and lost me so badly he had to call me on my phone to let me know where he’d gone: Aquatic Park, a crumbling Art Deco amphitheater at the edge of the bay. When I found him, he had shed his coat and taken a seat on the top slat of the concrete bleachers. He wore transition shades, and they’d already darkened against the midday sun. He talked about how he used to come here when he was a kid. Sometimes he’d see Carlos Santana playing guitar. “There were crabs and shit in the water,” he said. “It was beautiful.”

Phelps had recently gotten into trouble with Thrasher’s owners, which put him in the mood to reflect on the open question of his longevity. “My doctors” — he has four — “have all told me, ‘Your job’s killing you, Jake.’ I’m like, ‘I know.’” But skateboarding is rarely what kills skateboarders; the accouterments do.

He had just returned from a trip to South Africa for a Thrasher event, touring the country with pros and playing a show with his hardcore band, Bad Shit. (Phelps is lead guitar and occasional screamer, backed by 2002 Skater of the Year Tony Trujillo and his wife, Ashley “Trixie” Trujillo.) Phelps wrote an article about the trip for the magazine, called “Party’s Over,” and, interspersed with his thoughts on aging and substance abuse, he revealed that he was thrown off of his return flight to the States and put in a South African psych ward. “Thought Virgin Atlantic was the party in the air?” he wrote. “Wrong.” He closed the story with the lyrics to a song called “Recovery,” apparently an allusion to rehab, which begins: “Thirty days in the hole / Had to step back / Rewire my twisted soul.” Phelps told me that many of his friends from the old days are dead. “My generation of people, we used to smoke angel dust, huff paint, everything,” he said. “It was gnarly; it was no joke.”

Thrasher, too, has seen more than its fair share of death. Fausto Vitello died of a heart attack in 2006. He wasn’t yet 60. Five years later, Eric Swenson shot himself in the head outside the Mission District police station, apparently to spare his family the horror of finding his body. A beloved ex-pro named Phil Shao was being groomed to succeed Phelps, but he died in a drunk driving accident in 1998.

Phelps’s minders at Thrasher are concerned about his well-being, to say the least. Tony Vitello sees Phelps’s appeal — his embodiment of the brand — as the very source of his woes. “You look at him, and it’s like: Skate and Destroy, both the good and the bad,” he told me, referring to Thrasher’s motto. “The only thing he really cares about is skateboarding, and he’s Skate and Destroyed his body into oblivion.”

Even Phelps’s contemporaries consider him irrationally dedicated to the lifestyle. Dave Carnie, the editor in chief of the now-shuttered Big Brother — a rollicking, absurdist skate magazine published by Larry Flynt — used to joke that Thrasher’s ethos was “push uphill.” That is, those dudes never get off their skateboards, literally or otherwise, even when it makes sense. Carnie likes to step outside that role. “I like to snuggle with my dog and watch cooking shows sometimes,” he said. Phelps never does, and Carnie believes that’s what makes the magazine work. “The thing that’s so attractive about Thrasher is that it’s so dumb,” he said — which is perfect, because skateboarding is, too. “You roll around, fall down, hurt yourself, get back up, do it again. They don’t fuck with that.”

This punk vision of skate culture occludes an uncomfortable fact about skateboarding: It has so successfully resisted becoming a sport that it is now only a business — a business that loathes business and businesspeople. Phelps is invaluable in this ecosystem because he insists over and over that skateboarding is hideous, irredeemable, and, above all, outside the logic of the rest of the orderly, sanitized world. As he put it to me, staring out at the bay: “I don’t like when people candy-coat skateboarding or make fun and games out of it. It’s sacred to me.”

It was perhaps the most earnest thing I heard him say, and it resonated with me. Society reveres athletes for winning. Skateboarders are losers — they can’t win — so instead they seek perfection of form, expansion of possibility. When they fetishize pain, it’s only because it resides so closely to excellence.

If this sounds like the sort of hokeyness that Phelps would ridicule me for — and maybe he will — you should hear the way he talks about his favorite feeling, bombing the hills of his hometown. “My front wheels break free, and I’m flying, and I can feel it; it’s shaking, just a little shimmy-shimmy,” he said. “I’m just on the verge of losing it, and I’m in it.” He told me it’s nothing short of sublime.


Willy Staley is an editor at The New York Times Magazine.

Andrew Paynter is a photographer based in Oakland. He is finishing up a ten-year project with Los Angeles–based artist Geoff McFetridge.

Originally published at californiasunday.com on March 24, 2016.