In the soft gray dawn of November 26, 2018, off the north coast of Maui, 40-foot waves rolled in off the Pacific Ocean like watery mountainsides half-visible in the mist. By 9 am, as a big-wave surfing contest called the Jaws Challenge at Pe’ahi began, waves nearing 50 feet high broke with such extreme violence that the first surfers in the water fell off their boards on almost every ride. By late morning, 70-footers formed giant aquatic walls topped by foamy cornices that leaped forward and tumbled through space, exploding onto the flat sea with enough force that two surfers were knocked unconscious and had to be rescued. Contest organizers put the event on hold in the interest of keeping athletes safe.
Most of the competitors retreated ashore to rest, but not Kai Lenny, a 26-year-old Maui local—5'8", chipmunk cheerful, with his own support boat in the water and a film crew circling overhead in a helicopter.
Big-wave surfing has two main variants: traditional, or “paddle in,” for which surfers lie on cumbersome 10-foot boards and paddle with their arms to catch waves; and so-called tow-in surfing, for which surfers start out standing on small surfboards, hold ropes connected to Jet Skis, and get towed into the waves.
The 2018 Jaws Challenge, like the rest of the Big Wave World Tour, was strictly traditionalist, driven by a vogue for old-school confrontation between man and nature; the idea was to showcase the insane difficulty and danger of catching a 50-foot wave with muscle power alone. But Lenny was no purist.
That day on Maui, at the surf break known as Jaws, Lenny traded his 10-foot paddle-in board for a tow-board. Then he had a Jet Ski pull him into tsunami-sized walls of water. With that helicopter overhead and contest video cameras livestreaming for a global audience, Lenny seized the spotlight for the next four hours, riding mountainous swells like so many skateboard ramps, launching Cirque du Soleil aerials and spinning pirouettes utterly at odds with the death-or-glory style of the traditionalists.
This wasn’t the only way in which Lenny—“an Energizer Bunny,” in the words of a contest announcer—stood out from his fellow surfers. He had been a sponsored pro athlete since age 9. The Lenny family had structured much of its life around launching him into athletic stardom via a diversified strategy of multiplatform dominance. While Lenny’s ambitious childhood peers on Maui stuck to surfing, favorite sport of the coastal cool kids, he trained as much as 12 hours a day in so many disciplines it was hard to keep track, including some that were severely unfashionable with the Maui-teen beach set, like windsurfing.
Flying around the world to compete in all of the above, Lenny chased professional opportunity wherever he found it: windsurfing when it was the most popular water sport on earth; stand-up paddleboarding, or SUP, when that replaced windsurfing and briefly became the world’s fastest-growing water sport; kitesurfing when it seemed like the Next Big Thing; and then, of course, big-wave surfing. Along the way, Lenny accumulated what has to be the most diverse portfolio of extreme water sport wins: In addition to numerous contest victories in all his disciplines, Lenny was named 2009’s windsurfing rookie of the year and was the 2013 Vice KSP Kiting World Champion, became a world-record holder in the Molokai-to-Oahu prone paddleboarding race, and won eight world titles in SUP, making him the latter sport’s most dominant athlete.
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Lenny also acquired an athletic style unlike any other, fusing elements of all those sports into the idiosyncratic technical fluency that he displayed during that tow-in performance on Maui, chasing hypertechnical tricks of his own invention.
None of that served Lenny particularly well, however, when he reached the final heat of the Jaws Challenge after the contest resumed the next day. Lenny found himself facing off against a childhood rival from Maui named Billy Kemper, a living embodiment of the traditionalist tough-guy ethos. Early in that final heat, lying prone on a 10-foot surfboard, Lenny paddled to catch a 45-foot-tall wave, hopped to his feet, and rode down the watery cliff. Then he lost balance and fell. He landed facedown and skipped like a stone into the impact zone. The wave’s enormous lip landed on Lenny like a truck-sized hammer.
I happened to be on Maui that day and was watching from a nearby cliff as Lenny disappeared deep underwater. It was horrible to witness. (And I’m not particularly squeamish: I’ve been surfing and writing about surfing for 30 years.)
“We call it going to the 12th dimension,” Lenny told me recently, with a chuckle. He seemed to mean that big-wave wipeouts are so violent they transport a fallen surfer to an alternate world, with severity of wipeout corresponding to the number of dimensions in that world. “If it’s the worst possible wipeout, where you’re unsure if someone will live or die, that’s when they get sent to the 13th dimension,” he said. “You have access to the multiverse. You get sent so far out of this realm that you see everything—like it’s a black hole or a wormhole or something.”
Describing that fall at Jaws in 2018, Lenny said, “I ended up in a dark part of the water, and it compressed my head so much that it felt like my brain got rewired. I’ve never experienced that, where my personality changed when I hit the surface. Like, I went from the super-confident monster that I had kind of forged myself into, then all of a sudden I felt very emotional.”
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Badly concussed and with a broken surfboard, Lenny let a Jet Ski safety driver take him back to his support boat. Grabbing a fresh surfboard and “still seeing cross-eyed,” he caught another monster wave. Lenny rocketed into a whirling tube big enough to fly a small spaceship through, soared back out into sunshine, and finished safely. On his third ride, Lenny slashed a big turn as if that wave were 4 feet high instead of 40—right before his concussion made it impossible to carry on.
“The last 15 minutes I couldn’t even paddle for a wave, because my brain was scrambled, but I knew I had done enough to win,” Lenny said.
At the time, however, judges in traditional big-wave contests placed enormous value on pure risk-taking, encouraging surfers to take off at a wave’s biggest and most dangerous point, and deliberately ride across the most dangerous parts of the face. And Billy Kemper excelled at those kinds of risks. On his second wave, Kemper displayed absolute mastery of his own fear by willfully soaring inside a tube the size of a whirling subway tunnel and frothy enough to dismember a horse. When that tube collapsed on Kemper, burying him under 30 feet of white water, he resurfaced and did exactly the same thing on yet another wave.
When the contest horn sounded, many of us watching assumed that Lenny had won. But judges handed victory to Kemper, who went over to Lenny’s boat, beat on his own chest, and yelled, at Lenny, “This is my wave!”
For Lenny, though, the defeat hardly mattered. His every-sport-at-once approach buffered the sting of any single loss. And by that point he had already begun to craft that approach into a sui generis career as a kind of virtuoso of versatility, with a million-plus Facebook and Instagram followers enjoying Lenny’s magnificent performances in so many different endeavors that his real product appears to be the exploration of human adaptability.
Since that day on Maui, Lenny has won three international big-wave contests, claimed the world’s most prestigious big-wave surfing award two years in a row, has become the youngest person ever inducted into the Surfer’s Hall of Fame, and was the breakout star of the HBO docuseries 100 Foot Wave.
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Along the way, he has also become a kind of secret spirit animal to the world’s tech elite—a sweet, smart, curiosity-driven mascot who has excellent toys and wears his mastery far more lightly than the masters of the universe ever do. Even the most cursory search of the internet easily brings up video of Lenny riding a kiteboard in a drag race against Larry Ellison’s multimillion-dollar America’s Cup catamaran on San Francisco Bay, teaching Richard Branson to ride a so-called foil board, and appearing in digital avatar form during Facebook’s recent rebranding as Meta, in the role of water sports BFF to Mark Zuckerberg himself, who can now safely be called Lenny’s number-one online fanboy.
Skateboarding barefoot—that’s what Lenny was doing last summer when I first caught sight of him on the quiet Maui street where he grew up. Ten minutes from the Maui airport, in an upscale residential district known as Spreckelsville, I turned left onto a dead-end street, and there he was. Trim and tan in board shorts, wearing a fashionably faded T-shirt and surf-branded trucker cap, Lenny carved smooth S-turns across black asphalt, fluffy brown hair bouncing in the breeze.
Sliding to a stop, Lenny, now 29, greeted me with a professionally mellow politeness, then slipped into friendly tour-guide mode.
“It’s funny,” he said, in a soft, high voice, “I’ve only lived in a mile-and-a-half radius my entire life.”
Pointing to the inland side of the street, Lenny drew my attention to the palatial buff-colored beach house where he spent most of his childhood, and where his parents and younger brother, 24-year-old Ridge Lenny, still live. One side of the vast grassy yard held a skateboarding half-pipe with a cable-harness contraption allowing the practice of extreme aerials without injury. Across the street, fronting the ocean, sat a cottage with vast lawns of its own, purchased by Lenny when he finally moved out, which he now shares with his fiancée, Molly Payne.
Our plan for the day included meeting up with a friend of Lenny’s who was busily customizing Lenny’s F-150 pickup—for the third time in four years. From there, Lenny would drive that truck to an auto shop to meet a Red Bull film crew shooting the latest installment of Lenny’s autobiographical video series, Life of Kai.
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First, though, Lenny led me across his parents’ lawn to a barnlike structure. Pulling open double doors, he revealed a high-ceilinged room in which many dozens of surf- and windsurf and kite- and foil and prone-paddle and SUP boards of countless sizes and shapes hung from rafters and stood vertically in racks along the walls, nearly all painted Red Bull blue and emblazoned with logos from Red Bull, Tag Heuer, GoPro, and many other sponsors. The overall effect was not unlike the exquisitely appointed kitchen of an online food influencer, a combination workshop and soundstage.
Walking through this collection, Lenny ran fingers along ultrashort tow-in surfboards and 10-foot paddle-in boards with strangely bulbous front ends.
When I asked about the latter, Lenny said it had to do with aerodynamics, encouraging proper airflow during free-fall plummets down 50-foot walls of water. “If a big wave is going 25 miles an hour,” Lenny said, “and you’re traveling another 30 miles an hour down the face, it’s simulating 65, 70 miles an hour in terms of what your board is experiencing. Add a 20-knot breeze up the face, and the air traveling around your body and your board could be in, like, the 100-mile-per-hour range.”
Point being, apparently, that bad airflow could cause turbulence around the surfboard, and thus catastrophe—for which a bulbous front end was somehow prophylactic, funneling air more smoothly.
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Lenny led me next into a back room where wall racks held the hydrofoils that he’s most famous for now—shiny bladelike contraptions that seem optimized for the efficient decapitation of swimmers. The idea is that a submerged hydrofoil acts like an airplane wing, lifting the surfboard itself up off the water, and thereby eliminating surface friction. The rider generates momentum by pumping up and down with their legs, and riding unbroken waves.
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“Two miles out at sea, and you can’t see your board,” Lenny said, explaining how the shortness of the foil board makes it effectively disappear from peripheral vision as the rider focuses on the water ahead. He described the feeling as somewhere between flying and walking on water. “That’s one of the most liberating things, because you just have endless space.”
I’d seen YouTube videos of Lenny levitating over the ocean this way, as if on a magic carpet. I’d also seen Instagram images posted by Mark Zuckerberg, in August 2019, of Zuckerberg doing the same thing, with the caption “Trying a new sport in Kauai with one of the best, @kai_lenny.”
Hearing Lenny talk about this in person, I could see his appeal to the Zuckerbergs of the world. The nearest cultural antecedent to Lenny—the other obvious choice for a billionaire’s water-sport man crush—was Lenny’s own childhood hero, Maui big-wave surfer Laird Hamilton. But Hamilton was the living archetype of the blond, muscle-bound surfer-god, with giant shoulders and cold green eyes—and therefore too reminiscent of the high school bully who pushes around the budding computer genius before the latter flips the script and becomes richer than God.
Lenny, by contrast, reads more like the protagonist in an extreme-sports version of Revenge of the Nerds, where the dorky kid from a loving family, abused in adolescence by the popular boys, grows up to become a better athlete than any of them, and way better looking.
The loving-family part of this vision begins with Martin Lenny, Kai’s father, a barrel-chested Californian with the menschy vibe of a paterfamilias enjoying early retirement. Kai introduced me to Martin in the spacious living room of their main house, a broad room of white couches and chairs and a big entertainment center cluttered with old surfing DVDs.
Martin, wearing a pressed Hawaiian shirt in pale faded blue, white linen shorts, and deck shoes, led me on yet another gracious tour—first into the dining room, where huge, beautiful wooden surfboards hung from rafters, and where an umbrella-bin thingy bristled with wooden ocean-canoe paddles that Kai had won as race trophies. Then Martin walked me through the Kai Hall of Fame—a hallway lined with framed magazine covers featuring photos of Kai, mostly shirtless and shiny, as if gleaming wet, smiling a harmless smile.
Back in the living room, Kai’s mother, Paula, a physician and former professional cyclist, appeared. Hyper-fit, stealthily muscular with dark brown eyes and bright blond hair, she said a quick hello as Martin directed me to a plush white chair—at which point I sat down and caused an extremely expensive-looking Pinarello road bike (a recent Mother’s Day present for Paula) to crash down and clatter across the hardwood floor.
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After Paula left, Martin told me they’d both grown up on the US mainland and moved to Maui during the 1980s windsurfing boom. The pair met in the north-shore Maui town of Pā’ia—at the time a sort of artist-hippie mecca outside the usual tourist circuit.
Martin and Paula married in 1990 and had Kai two years later, determined not to become casualties of new parenthood. “We made a pact, Paula and I,” he said. “We weren’t going to change our lifestyle. We’re going to the beach, we’re going to surf, and this kid is going everywhere with us. The tail wasn’t going to wag the dog.” The tail ended up wagging the dog anyway, just not in the way they’d been worried about. Lenny started surfing at age 4; by age 6, he had his own windsurfing rig with the Disney character Pluto on the sail; by age 7, teachers routinely ordered him to run laps around the school to calm down. Lenny threw himself at his parents’ pastimes with a physical hyper-intensity that outmatched their own.
He also had a sweet disposition: “When he’s had any criticism from these gnarly surfers, which he did, he would never say, ‘Frick those guys,’ or anything like that,” Martin said, apropos of nothing. “He’d go, ‘Well, they just don’t know how much fun they’re missing.’ He would take it on the chin and keep going.”
The upshot seemed to be that Lenny, while growing up, was the odd one out in local tough-kid surf culture—too nice and privileged, way too bonded with affluent Mom and Dad.
It also can’t have helped that, in a community where success in water sports has the cultural currency that actual currency does in Manhattan, Lenny got noticed early. According to Martin, Lenny was only 9 or 10 years old when a German surfing magazine put him on the cover, and when the Maui-based windsurfing company Naish offered to sponsor him. Two years later, Red Bull offered an endorsement deal lucrative enough to cover Montessori school tuition.
“It turned into a business relationship,” Martin said, of their father-son connection. “With him windsurfing or surfing every day, I go, ‘Look, I’m making a deal. You be good at school, get good grades, do your chores, and I’ll take you to the beach every day.’”
Pā’ia, by that point, had become a kind of water-sports mashup of Telluride and Palo Alto, epicenter of both athletic performance and technological innovation—thanks to a group of locals known as the Strapped Crew, with Laird Hamilton as their most visible member. Back then, in the early 1990s, conventional wisdom considered it physically impossible to paddle a traditional surfboard fast enough to catch a wave taller than about 50 feet on the face. So the Strapped Crew started experimenting with Jet Skis. Right there on Maui, at Jaws, they more or less invented tow surfing, making it possible, for the first time in human history, to ride waves 60 feet and taller.
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The Strapped Crew experimented with early kiteboarding rigs too, launching 60-foot aerials before most people even knew the sport existed; they more or less invented foil-boarding, by cutting a hydrofoil off a weird contraption called an Air Chair; and they were responsible for the revival of the ancient Hawaiian practice of stand-up paddleboarding.
As unusual as the Strapped Crew were—there wasn’t a similar bunch of guys anywhere else on earth—for Lenny they were larger-than-life local heroes, “like the Avengers or the Justice League,” as he puts it.
Lenny’s parents helped him emulate the Strapped Crew by acquiring a family Jet Ski for tow-surf outings, hiring a competitive kitesurfer for family lessons, and buying one of the earliest foil boards.
Martin and Paula did worry that Lenny was missing out on childhood. “He’s talking about fins, board development, sales,” Martin explained, referring to Lenny’s early adolescence. “We thought, ‘God, he’s got to hang out with kids his own age.’ We were going to force him to go to a sleepover one weekend and he was just like, ‘Dad, I really don’t want to go. All those kids do is play Nintendo. I’d rather be windsurfing with you guys.’”
That has to have hurt Lenny’s social status further, as did the fading popularity, in the early 2000s, of the Strapped Crew’s poly-sport approach to life. As windsurfing, in particular, lost cultural cachet, trendy young water kids on Maui mostly dropped the sport.
“All the kids that he learned how to windsurf with,” said Martin, “they all just turned their back on it and they all went to surfing.”
Lenny, who never changed course at all—except insofar as his personal course was all about relentless changes, of gear and competitive focus—started losing surf contests to all those young specialists. Before long, he’d given up on small-wave surfing competitions.
By small-wave surfing, incidentally, I just mean regular old competitive surfing—as in, not big-wave surfing. There’s no hard dividing line between the two disciplines, but regular competitive surfing, of the kind practiced by Kelly Slater and every other superstar surfer, typically happens on waves under about 20 feet on the face. The point is that this kind of competitive surfing was, by the 1990s, fast becoming the main event in wind-and-wave sports. So Lenny’s abandonment of it was not without social cost.
“I’d see him get hazed all the time,” said Martin. “And I go, ‘Kai, you know, do you want to just stick to one sport, maybe just surfing?’ And he looked at me, goes, ‘Why would I do that? Dad, the sports I do are so much fun. I don’t want to give them up.’” The hazing grew even worse, Martin recalled, when Lenny added SUP to his repertoire. “Oh, God,” he said, “that was big backlash.”
For a while, Lenny ducked the negativity through homeschooling, traveling the world to compete in windsurfing and all his other sports, and tow-surfing big waves at Jaws—just like Hamilton, his childhood idol. Lenny was in his late teens, though, in 2010, when other men and women at Jaws figured out how to paddle old-fashioned surfboards into waves bigger than conventional wisdom considered possible. Catching 60-footers with nothing but their own muscle power, that new Maui crew reignited the popularity of traditional big-wave surfing.
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As a new Big Wave World Tour formed around this traditionalist revival, and aspiring big-wave superheroes eschewed the now-unfashionable tow-in game, Lenny took his usual all-of-the-above approach. That’s how he wound up in the 2018 Jaws Challenge at Pe’ahi, badly concussed and watching Billy Kemper—who has now won that event an unparalleled four times—beat his chest in triumph.
“He comes from that surfing culture here on Maui,” Lenny said, speaking of Kemper. “Like, underground ‘fuck you’ attitude. And, funnily enough, I went to his mom’s day care and we grew up together in diapers, but we weren’t friends, because he just didn’t like me. But I actually loved losing because the excuses would be gone, and I would just have to go get better.”
Still thinking about Kemper and Hamilton, Lenny added, “I think the world needs those guys. It’s fun to go to battle against them and then destroy them, and then they take it way harder. Like, if I lost, I would be like, ‘Oh, shoot! I lost! What do I got to do to get back?’ For them? They beat themselves up for a week and go break things. Or hate you, like have animosity toward you. Isn’t that funny?”
Closing up the surfboard barn, Lenny climbed into the passenger seat of my rental sedan. We drove past fallow cane fields, and Lenny directed me through a chain-link fence onto the grounds of a defunct sugar mill, enormous old concrete buildings with rusted tractor-trailers parked outside. We stopped outside a crumbling warehouse that Lenny rents as an auxiliary gear barn, for toys too big to keep at home.
The steel roll-up door was open, and I could see, just inside, Lenny’s four-man outrigger canoe, two Jet Skis, a Polaris four-wheel-drive all-terrain vehicle, and the 25-foot Coast Guard Defender power boat that he uses for support on big-wave outings. Next to the boat was Lenny’s newly tricked-out Ford F-150 Raptor, which had preposterously oversize off-road tires—courtesy of Lenny’s new endorsement deal with BF Goodrich. Lenny then drove this truck to meet up with the Red Bull film team for a shoot in the vehicle, gamely admiring those new Goodrich tires on camera, poking fun at the lavish comedy of his own life as a pro athlete.
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Afterward, back at Lenny’s parents’ house, over gigantic juicy burritos at a patio table with Lenny’s brother, Ridge, I finally asked about Lenny’s tech-billionaire fans. He mostly maintains the omertà code of silence common to those who consort with the world’s richest people. When I asked about a rumor that he’d been kiteboarding with Sergey Brin and Larry Page, Lenny would say only, “Yeah, I’ve met them and they’re super cool. I’ve kited with them, actually. Sergey came out to Mavericks”—the California big-wave surf spot—“on our boat and watched. He’s super cool. They’re all pretty active people. I mean, why wouldn’t you be when you own the world?”
I asked also about a notorious paparazzi photo of Zuckerberg riding a foil board with his face covered in so much white sunscreen that he looked like a circus clown.
“We were there,” Lenny said, referring to his brother and himself. Not only that, he said, they may have inadvertently led the photographer to his prey. As far as Lenny could tell, the paparazzo had trailed Lenny and Ridge as they rode a Jet Ski miles down the coast of Kauai to meet Zuckerberg.
“I could see it being pretty annoying,” Lenny said. “They’re, like, waiting to get you at your worst moment because it will sell.”
By all appearances, Zuckerberg saw the incident differently. Addressing it during an Instagram Live Chat with Instagram CEO Adam Mosseri, on April 27, 2021, Zuckerberg called Lenny “magical” and a key factor in helping him take up foiling. Zuckerberg also confessed that, after seeing the paparazzo in hot pursuit, he’d tried to camouflage himself by covering his face in sunscreen—a total fail that served only to produce that absurd image. Zuckerberg laughed off the outcome with Mosseri, saying, “The delta between how cool you think you look and the worst photo a paparazzi can take is pretty funny.”
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As if recognizing an opportunity to make himself less menacing in the public eye—more goofy novice surfer than misinformation arms merchant—Zuckerberg had a version of that sunscreen photo painted onto his personal foil board. Then, further capitalizing on the image and the warm glow he got from associating himself with Lenny, Zuckerberg folded both into his big metaverse announcement during Facebook Connect 2021 on October 28.
In the elaborate video presentation, a digital avatar of Zuckerberg starts talking about gaming in the metaverse, and suddenly a virtual window appears in the air above his animated shoulder. Right in the middle of that window, Lenny’s own digital avatar says, “Hey Mark, down for a VR foiling sesh?”
Suddenly, Zuckerberg’s avatar is sitting on a foil board in aquamarine surf. Floating to his left, on yet another foil board, Lenny’s avatar watches affectionately as Zuckerberg toggles through a set of virtual outfits that evoke previous outings with Lenny in the real world—including a white-face one called SPF 5000. Both avatars then lie prone on their foil boards, side by side, and paddle with their arms to catch a flawless digital wave. Hopping to stand, Zuckerberg wobbles awkwardly—as if to show the entire world, See, I’m human, too! Just like you! Lenny’s avatar zips past Zuckerberg and, like a friendly mentor, says, “Whoa! Hang in there, Mark!” He then coaches the Meta CEO through a series of foil boarding tricks—“All right, back flip!”—then leads him through the hollow tube of a curling wave and across the virtual finish line, winning handily.
“Kai, you’re out of control,” Zuckerberg says.
“Don’t worry, I’ll let you win next time, all good,” Lenny says.
Back on Maui, I asked the real Lenny how he’d come to know Zuckerberg in the first place. “He was just into hydrofoiling,” Lenny replied. “And he loved …” Lenny caught himself, then said, “He liked what I do. So, I just so happened to be on Kauai once, and I just went foiling with him. He was super nice.”
I struggled to believe that Kai and Zuck really met by coincidentally foiling at the same time in the same waters on the same island, but I figured a nondisclosure agreement probably had something to do with that version of events.
“People have their issues with him, for sure,” Lenny added. “But he was super cool, super into water sport, really active. Super fit. Like … strong, strong strong. Physically strong. It’s crazy. He’s an athlete, for sure. Probably the most athletic of the tech people I’ve ever met.”
Just then, Ridge handed Kai his phone to show him an Instagram Zuckerberg had just posted. Ridge then handed the phone to me. It was still more footage of the real Zuckerberg riding a real foil board on the ocean. The caption: “@kai_lenny am I doing this right?”
The question was obviously about foil boarding, but it might as well have been about Lenny’s approach to life and success, his peculiar combination of nerdy good cheer and emotional flexibility.
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I think I just love being a beginner,” Lenny told me as we walked across his lawn for a look at the ocean. A strong wind had come up, blowing whitecaps across the pale blue sea, so we sat on a weathered wooden bench and I asked about a story that I’d heard recently, about Lenny entering his first small-wave surf contest in many years, with hopes of joining the World Surf League’s Championship Tour.
It bears mentioning that the Championship Tour, or CT, is really the main event in wave riding. Big-wave riding tends to captivate the nonsurfing public more effectively, but it really attracts only borderline-crazies lucky enough to live near one of the world’s few consistent big-wave breaks, or privileged enough to buy international plane tickets on the regular. The CT is more like the NFL or NBA, magnetizing the overwhelming global preponderance of athletic surf talent. It is also hyper-specialized, practiced only by the most preternaturally gifted of all obsessives, born athletes who have been doing and dreaming of nothing else since before they can remember.
Merely to qualify for the CT, moreover, requires good results in numerous contests on a parallel—and utterly unglamorous—tour called the Qualifying Series, often held in obscure places with lousy waves and many dozens of desperately hungry competitors, all of whom would be the absolute best surfers at almost any beach in the world on any given day.
For Lenny to begin the grind of Qualifying Series contests necessary even to be considered for the CT was not unlike Michael Jordan humiliating himself in minor league baseball. And yet, Lenny had done exactly that. After all those years at the pinnacle of so many sports, he’d flown to China in early 2020, right before the outbreak of Covid, to compete in the Corona Open qualifying contest in the city of Wanning.
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“I was like, ‘OK, if you want to fly with the eagles, you got to go to their nest,’” Lenny said. “So I decided I’m going to China to get the experience, and maybe I’ll surprise myself. Well, I didn’t surprise myself.” He chuckled happily, confessing that he lost his very first heat and finished 73rd. Then, right back where he likes to be—at the bottom, with nowhere to go but up—Lenny walked down the beach alone and started practicing the aerial maneuvers he’d need to get better.
He was still up to his usual tricks, of course. Hearing rumors of a giant swell about to hit Portugal, Lenny flew straight there from China and tow-surfed 80-foot waves. Then he caught a plane back to Maui, spent a few weeks surfing at home, flew back to Portugal for a big-wave contest called the Nazaré Tow Surfing Challenge—which he won, earning himself a prominent role in that HBO documentary.
Next Lenny flew to Wyoming, to improve his small-wave contest game by studying the aerial techniques of elite snowboarders. Then he went to Texas to join a group of preteen and adolescent surfers at an artificial wave pool— because the younger set is already doing more progressive aerials than almost anyone else, and Lenny liked the idea of taking inspiration from them, and also because the predictability of a wave pool allows a surfer to practice the same maneuver many times in a row.
“I think most people are afraid, once you get to a certain level and you’re winning things,” Lenny said, “you don’t want to be off that pedestal. I force myself off it.” That may be the one thing that distinguishes Lenny most from his fellow surfers, and from many of the powerful people who admire him, winners who guard their pedestals with grim determination while trying to convince the rest of us that they gamely welcome a wipeout.
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