Kai Lenny Surfs the Unsurfable

“Few athletes at a high level have much appetite for innovation,” a coach of Lenny’s said.
“But Kai has absolutely no pride or ego when it comes to learning something new.”
Photograph by Brendan George Ko

Watching Kai Lenny surf at Pe‘ahi, a big-wave spot off the north coast of Maui, is slightly heart-stopping. You may have seen it on video, but that doesn’t prepare you for the velocity, the impossible confidence, of a hard braking turn at the top of an enormous wave, often right in the luminous turquoise window of a lip about to pitch—for that abrupt turn back toward the bottom, as if he wanted the weightless drop of the downcarve more than he wanted to make it out in one piece. When I first saw it, from the back of a Jet Ski, in February, I yelped involuntarily. These things aren’t done, or at least they weren’t.

Professional big-wave surfing is a niche activity, practiced by only a handful of brave souls. But millions of video-­content consumers watch their best efforts—or their worst wipeouts, which can drive even more online traffic. Lenny, who is twenty-nine, began to light up big-wave surfing five or six years ago with performances that defied understanding. Whipped into position by a Jet Ski, he would drop the towrope on a rapidly steepening wave with a fifty-foot face and start carving quick little rhythmic turns, then launch a three-hundred-and-sixty-­degree aerial rotation, as if he were enjoying himself. Possibly he was enjoying himself, but if so that was unnatural. Those waves were packed with speeding-truck-crash quantities of violence, and Lenny was going faster, turning harder and more stylishly, than anyone before him.

Where did he come by his poise, and his reaction times, which border on optical illusion? Pe‘ahi is part of the answer. There are few places in the world—some say none—that produce waves of comparable size and beauty, and Lenny was born just up the road. He first surfed Pe‘ahi at sixteen, and he tries to be out there whenever it’s ridable. On that February afternoon, Lenny seemed to be on the biggest wave of every set—fading, hucking airs, downcarving right at the edge of physics, disappearing into foam-choked barrels. He pulled out of one wave with an attempted double rodeo flip and splashed down beside me. His eyes seemed to be starting out of his head. “It’s so fun,” he said, with Pentecostal conviction. “Just wish it was three times this size.”

The surf was in fact huge that day—twenty-five feet or more on the face. But it was not huge by local standards, and the surfers in the water were all locals. A few people got pounded and had to be rescued from the white water by ski drivers. A couple of boards hit the rocks. But the wipeouts were rare and not terrifying.

The wave at Pe‘ahi is known as Jaws. The coast is rugged and rural: tall sea cliffs, tropical forest, a few muddy farm roads. In the mist are the lower slopes of a dormant volcano called Halea­kalā, which rises more than ten thousand feet from the sea. Surfers often make their way to the great wave, which has a deep channel beside it, by boat or ski. I had travelled on Lenny’s support boat, sixteen miles, from Kahului Harbor.

As waves get bigger, they get wildly more powerful. The difference of a few feet in height or thickness can mean the difference between a tough fall and a catastrophic beating. Big waves also move faster, so that just catching them calls for unusual skill and specialized equipment. Above fifteen or so feet, waves require a board known as a gun—longer and faster-paddling than a modern shortboard. Most surfers, including very good ones, make a point of not owning a gun, in the interest of avoiding poor choices.

When the waves reach a certain size, or when the wind gets too strong to paddle against, as it was that day at Pe‘ahi, even a gun becomes inadequate. The few people still interested are towed into place on a short, narrow board built for high speeds. Nobody knows how big a wave might be ridden on a tow board, although Lenny has expressed a determination to find out. Traditionally, those who surf the biggest waves are more concerned with not falling than with style, and people watching them are mostly astonished that they don’t die. What distinguishes Kai Lenny from this lineage is his ability to surf very big waves as if they were small—shredding, dancing, as if fear has somehow left him alone.

As a baby, Kai ran his parents ragged. Once he could walk, he would simply vanish—at the mall, in the neighborhood. His mother, Paula, was often frantic. His father, Martin, told me, “She couldn’t even look at photos or home movies from those first four years. She would just start crying.” Fortunately, the Lennys lived in Paia, a small town with many beaches. Kai could splash around all day in front of the old Zen mission, or at Sugar Cove, in Spreckelsville. The ocean could reciprocate his relentlessness.

That was the mid-nineties. The north coast of Maui, which gets plentiful trade winds, had become the unofficial world capital of windsurfing, and Martin and Paula had moved there from the mainland. She had recently finished medical school. He worked as a busboy at Mama’s Fish House, on the coast east of Paia. They spent as much time as possible in the water, and Kai followed his parents into windsurfing.

But windsurfing was not cool, at least not among Kai’s peers on Maui, or really anyplace where kids surfed. The sport was popular in countries that weren’t known for their ocean coast—dubious places, like Germany. You could do it on a pond, for Christ’s sake. The people who windsurfed were older, mostly, and dorky, and the boards and sails were expensive, bulky contraptions. For most beach kids, surfing was the one true religion of the waves. I grew up in this church myself, in California and Hawaii.

“I used to be terrified of this end of Ho‘okipa,” Kai said, as he eased his truck—a buffed-out Ford F-150 Raptor—down the narrow road into Ho‘okipa Beach Park. Ho‘okipa is the main surf spot near Paia. The east end of the beach, known as Pavilions, is the tough end, commonly reserved for surfers. “You were either in down here or definitely out. And I was one thousand per cent out,” Kai said. “The windsurfers hung out over there.” He pointed to the west. Lenny has the physical confidence—every move intentional, nothing fumbled—of a superior athlete. It’s hard to picture him as a scared kid getting bullied. He’s not a big guy—five-seven, a hundred sixty—but his cheerful composure and direct gaze seem inborn. And yet everyone I talked to about his childhood mentioned the resentment Kai aroused in the little Ho‘okipa surf gang.

Pete Siracusa, a retired businessman whose house looks out on Sugar Cove, remembers watching Kai in those days: “What I saw was a young kid who was unusually comfortable in the ocean.” The boy had uncanny balance and a prodigy’s feel for the wind. New sports kept popping up, and Kai threw himself into each of them. He was windsurfing at six, kitesurfing at nine. His parents tried hydrofoiling, then gave it up as too hard, but Kai jumped on the board and mastered it more or less immediately. He started standup paddling, or sup—another ungainly activity scorned by “core” surfers. He also surfed, tuning out the hecklers.

The local surf punks who scorned windsurfing were, in part, rejecting gentrification. The newcomers, many of them from abroad, were often wealthier than local families. Paia went from being a dusty plantation town for sugarcane workers to a tourist crossroads, full of boutiques, galleries, and restaurants. Property values began a steady ascent that hasn’t yet ended.

Kai pulled his truck into an overlook at the west end of Ho‘okipa. He had already gone kiting, foiling, and windsurfing that day, and was still looking for a sundown session. He scanned the wind-scoured waters and sighed. “You know, Ho‘okipa produces great surfers,” he said. “Or it used to. But now it’s kind of sad. As gnarly as that end of the beach was, this place had meaning.” It sounded like he missed the era of high tension between surfers and windsurfers. That era had turned out to be the heyday of windsurfing. “There were helicopters, all the best photographers, all the new gear, everybody trying to rip, trying to get on the covers of magazines.” Kai laughed. “No wonder the core surfers hated us.”

A few windsurfers were out skittering around today, but the little water war was over. We drove west, and stopped at a grocery, the Kuau Store. Kai had a deli order to fill—hot dog with sauerkraut—for his fiancée, Molly Payne. While he was at the counter, I noticed a familiar-looking surfboard mounted on the wall. It was one of Kai’s. He has all his boards painted royal blue, with a red vertical stripe. It’s probably the best-known board design in surfing. “Kai Lenny gave us that,” the cashier said. “He rode it at Jaws.”

I wandered outside and saw a row of surfboards standing on their tails. The first board had a message, in block letters, on its deck: “foilboarding is a crime.” Maybe the war wasn’t quite over.

The people who pioneered Pe‘ahi travelled far above these sectarian squabbles. They were the big guys, literally: Laird Hamilton, Dave Kalama, Brett Lickle, and others—what became known as the Strapped Crew. In the late eighties, having caught glimpses of Pe‘ahi’s waves from the cliffs, two of them windsurfed down from Ho‘okipa to check out the place. “It felt like we had sailed into the Land of the Lost,” Kalama told me. “You half expected a pterodactyl to come flying out of the forest. The waves were way bigger than anything we’d seen or ridden before.”

To surf such waves, the Strapped Crew basically invented tow surfing, using an inflatable Zodiac dinghy and later Jet Skis. I remember when the first video of Hamilton surfing Pe‘ahi began to circulate in the surfing world. It was incomprehensible. He was riding waves that looked too big to catch, on a board that looked not much longer than a skateboard.

Kai had a friend, Kody Kerbox, whose father, Buzzy, was one of the pioneers. On big days at Pe‘ahi, Kody’s mother took the boys out to the cliff. “We used to climb the trees to get a better view,” Kai said. “Those guys were my heroes.” Eventually, Hamilton and Kalama invited Kai to join them. The Strapped Crew was known for experimentation, and they surprised Kai by suggesting that he ride a foil board—a small board with a hydrofoil attached to the bottom. The hydrofoil acts like an airplane wing, lifting board and rider off the water. Kai rode his first three waves at Pe‘ahi in a state of levitation.

By then, he was being homeschooled, his bottomless energy channelled into twelve-hour training days. Kai’s fitness coach, Scott Sanchez, who has been working with him since he was eleven, told me, “I remember hugging him through his night terrors. But he was already very, very disciplined.” This certainly set him apart from the surfers I grew up with. We surfed constantly, but we had little interest in other forms of exercise. Maybe skateboarding, in a pinch.

Sanchez, an ebullient fellow in his sixties, has an airy gym in the countryside, right next to a dog­-training facility called Sit Means Sit. I noticed a sign near the gym entrance: “Kindly Refrain from Whining.” Sanchez got his start as a ski-racing coach, and he told me that he emphasizes symmetry, working your weaker side. Kai came to him ambidextrous—he skateboarded goofy-foot and surfed regular-foot. Also, wind sports often require the ability to reverse one’s footing. So teacher and student were in synch from the start.

Kai was already beginning an eclectic career. At ten, he had his first sponsor, a company that made windsurfing rigs. He’d made his first magazine cover, on a German publication called Surf. He did standup-paddle racing, sup surfing, and long-distance paddling, and he later competed on the windsurfing and sup pro world tours, where he ultimately won eight world titles. Red Bull, the energy-drink behemoth, staged a kitesurfing contest, called Kings of the Air, on Maui, and Kai’s performance, along with his blinding smile, caught the attention of a talent scout. Kai was invited to meet Dietrich Mateschitz, Red Bull’s owner and the richest man in Austria. “He had such a badass motorcycle,” Martin Lenny recalled. Red Bull was in the market for young daredevils of good character who could promote the brand. At thirteen, Kai became the youngest athlete in the stable. “The only rule was that, if he wanted to do all this stuff, he had to keep up his grades and do his chores,” Martin said.

In the early days, Kai didn’t have agents or managers or assistants. His “team” was his family. As he grew up, Martin rose to become the general manager of Mama’s Fish House, which is a fancier joint than it sounds. Then he went into real estate. But he still seems to work long hours as the de-facto general manager of Kai, Inc. Kai’s frequent sudden travel to chase waves, and his many overlapping projects and commitments—his sponsors now include GoPro, Hurley, Tag Heuer, Cariuma, and, of course, Red Bull, which recently put out a TV series called “Life of Kai”—all require scheduling, logistics, and decisions, much of which falls to Martin.

The Lennys’ younger son, Ridge, also pitches in on occasion. Ridge was born four years after Kai, and did not reduce his mother to despair. “My little Buddhist,” Paula called him. Though a talented surfer, he decided not to pursue a career in the water. Instead, he did something off the wall: he got a degree in accounting. For Team Kai, it helps to have an accountant’s sense that time is, while not precisely money, a finite commodity that can always be better organized.

The newest team member is Molly Payne. “He calls me the velvet hammer,” she told me with a wicked laugh. We were sitting on a deck behind Martin and Paula’s sprawling one-story house in Spreckelsville. Molly and Kai began dating eight years ago. She is an interior designer but was already familiar with the surfing life—her brother Dusty was the first Maui surfer to qualify for the World Championship Tour, the big leagues of competitive surfing. Surfers on the C.T., as it’s called, make most of their money from sponsors, but Molly had never seen anyone as attentive to sponsors as Kai: dutifully showing up for a trade show in Florida, flying to Thailand to test new boards. “He was so accommodating,” she said. “I was, like, ‘This is pathetic.’ ”

Then, there were the schismatic ­issues. “I grew up in a strictly surfing family,” Molly told me. “When my brother heard about us, he said, ‘Oh, you’re dating a super.’ ” Kai was competing in sports that didn’t even require an ocean. “He used to travel to, like, Paris for a sup race. It was so random.”

At Nazaré, Portugal, two swells combine, and on big days they create some of the tallest waves ever surfed.Photograph by Octavio Passos / Getty

Molly, who surfs, gamely tried kiting, foiling, windsurfing. She shrugged. “I still prefer surfing. It’s so simple. You don’t have all this gear—mast, sail, foil, guylines for kites. And I don’t like getting wind-blasted.” Kai’s relationship with big waves made more sense to her. She had watched him get bolder over the years at Pe‘ahi. “I used to tell him, ‘You should be sitting deeper’ ”—hunting waves from a more committed, perilous position. “But that’s just because of the family I come from. He was always going to get to that deep spot in the lineup.”

Molly and Kai had also reached a deep spot in the lineup, I thought. They were living across the street from Martin and Paula, in a smaller house, on the ocean. Molly was eight months pregnant with twins. They were planning to get married on the seawall by their neighbor’s house later that week. A traditional Hawaiian kahuna had been engaged to do the honors. Molly’s father would be bringing a shotgun.

When they got the news that the twins were girls, Kai threw himself into a gender reveal. At sunset, with filmers filming, he had himself whipped into a wave at Pe‘ahi and then somehow lit a pink flare and surfed all the way to the channel with the flare held high. “i’m gonna be a girl dad,” he announced on Instagram, where he has a million followers.

Afew far-flung spots provide the main arenas of big-wave surfing: Pe‘ahi, a spot in Portugal called Nazaré, and a reef break south of San Francisco known as Mavericks. Two Hawaiian pros have drowned at Mavericks, and Shane Dorian, one of the world’s best surfers, suffered a two-wave hold-down there—a near-death experience that inspired the invention of a flotation device with a CO2 cartridge, which nearly all big-wave surfers now tuck under a wetsuit for serious waves. Mavericks is an exceptionally serious wave.

Mavericks had a great season the winter before last, and in December Kai and his fellow Maui big-wave surfer (and Red Bull soldier) Ian Walsh caught it as good as it gets. All the takeoffs were elevator drops, but the faces, some as big as fifty feet, were unusually clean. Kai was taking off extremely deep, chipping in early with crazy paddling power, and then turning hard as the waves spat clouds of trapped air. He caught twenty-plus waves and didn’t fall once. He stayed out from dawn to dark, paddling over to a support boat once or twice for water and a bean burrito but never leaving his board.

There was footage from that day from a GoPro camera mounted on the nose of Kai’s board. There always seems to be GoPro footage from Kai’s paddle sessions. Also his kiteboarding and windsurfing sessions. Sometimes there seem to be multiple point-of-view cameras (one in his mouth?). I remember one of the first times I saw a surfer using a GoPro, probably twenty years ago. As he paddled past, wearing a helmet-mounted cam, he looked at me sheepishly and said, “Full circus act.”

For Kai, being on camera both feeds his mythos and undergirds his business model. New clips appear on his Instagram with Fordist regularity, and he often tags his sponsors. But the selfie footage of Kai in big waves is fascinating. The angle flattens the waves so that they seem small, no matter how big they are. The only time the waves seem to have any heft at all is when the rider gets deeply barrelled. Suddenly, we’re in a blue room with walls of rushing water, and we’re being pursued by a horizontal waterfall and a fire hose of mist.

The most interesting part of the footage is that Kai’s face is almost unrecognizable. The easy smile is gone. His expression is ferocious—his eyes seem twice their normal size. Even inside a triumphant barrel, he is all business. And he doesn’t post only good GoPro days. There was a session at Mavericks, in some of the biggest surf ever seen there, during which Kai got annihilated. Same expression, with a trace more concern.

Paula told me, with a laugh, “I think Kai got his masochistic tendencies from me.” She was a bicycle racer in college, in Oregon, and won a state championship while in medical school. During a road workout, she got hit by a pickup truck and fractured her skull. She healed up and kept racing, training at altitude in the Rockies.

After moving to Maui, “I hung up the bike,” she said. She practices integrative medicine out of a clinic above a café, but she still gets in the water whenever she can. She’s sixty-three now, and her devotion to demanding outdoor sports is not unusual in the Lennys’ corner of Maui, but my impression is that Paula feels like she’s taking it easy.

Kai, meanwhile, works hard to create the impression that he’s just having fun, pursuing an appetite for going fast in the ocean in any way that pre­sents itself. But the reality is that he lifts weights every morning, rarely takes a day off, and does seem to have acquired a masochistic gene from somewhere. No one becomes a big-wave champion—or a long-distance paddling champion—on talent alone.

Kai and his ilk live glued to global forecasts, monitoring the movements of storms. They try to predict where the biggest waves will arrive, and then dash, with mountainous loads of board-shaped luggage, to convene over certain reefs in Europe or Tahiti or central California.

A few weeks after the pink-torch affair, a winter storm in the North Atlantic morphed into a promising blob on the weather map. Kai jumped on a flight to Lisbon. Paula and Ridge went with him. This was not just the usual big-swell chase. There was a World Surf League competition preparing to run at Nazaré, the fearsome break on the Portuguese coast.

Nazaré is an old fishing town eighty miles north of Lisbon. I got there the day before the contest, a sunny Saturday. I walked through narrow, cobbled, crowded streets, then past a perfectly round praça de touros—a bullfighting ring, very old, but freshly painted white. Posters for upcoming fights showed young matadors in traditional suits of lights.

Off the rocky point at the north end of town, the swell was already big and rising. Not far from the point is the end of the largest offshore underwater canyon in Europe, a hundred and forty miles long and as much as three miles deep. Huge refracted swells surge out of the canyon and run into waves arriving from the north and northwest. The two swells combine, and on big days they create some of the tallest waves ever surfed.

The sheer height of the Nazaré waves has captured the fancy of the non-surf press. Could these be the long-awaited hundred-foot waves? Measuring waves at sea is an inexact science, but the Guinness World Rec­ords people have got in on the act, ruling this wave seventy-seven feet and that one seventy-eight. The current Guinness record for Largest Wave Surfed is eighty feet. Occasional claims to a hundred are made, but so far unpersuasively. For old-school, high-church surfers, the search for a hundred-­foot wave can seem like a marketing conceit, not to mention a death trap. But I heard Kai say, more than once, that he’d like to be the first to ride one. He seems to mean it. HBO produced a documentary series called “100 Foot Wave” about Nazaré, starring Garrett McNamara, an American surfer who helped pioneer the spot before he was slowed by injuries. In the last two episodes, Kai steals the show with dazzling, next-gen surfing.

On a ridge above the ocean, a crowd was milling around. Venders were already out in force: food trucks; T-shirt shacks; weathered old women, wearing layered flannel skirts against the sea breeze, shouting about the quality of their roasted chestnuts. This would be the second tow-in contest held at Nazaré. The first one, in 2020, had ended badly when one of the surfers, Alex Botelho, nearly drowned. He was unconscious, face down in the water, throughout a frantic rescue effort, during which he did not breathe for an estimated ten minutes. Another surfer, a Brazilian named Maya Gabeira, was also once carried up the Nazaré beach not breathing. She had returned for this year’s contest. Andrew Cotton, a British big-wave surfer, was in town to compete, too. He had broken his back in a wipeout at Nazaré in 2017.

Unlike most big waves, the wave at Nazaré has no deep-water channel next to a reef, which means there is often no escape, even after a successful ride. Most surfers go left, riding away from the cliffs on the point, but there is also a shapely, super-dangerous right. The water near the shore turns into an inferno of foam so aerated that Jet Skis choke on it. Rescue drivers looking for surfers have to read a maelstrom of currents. Fallen surfers can be carried underwater a hundred yards—you can’t expect them to pop up anywhere near where they went down. Nazaré, truth be told, sometimes looks more like an ocean-storm-survival course than like surfing. People were flocking here to see an exciting day of ocean sport, but there was also a blood-sport aspect.

Along the road that leads from the old lighthouse on the point to town, L.E.D. displays were showing a promotional video for the next day’s event. One clip jumped off the screens. It was Kai at the first Nazaré tow-in contest. He starts by fading left on an absolutely massive black wall of water, and then reverses direction, driving hard against the grain. The wave is a solid seventy feet by the time he reaches the bottom, but it isn’t the height that stops your eye. It’s the concentrated power of the ocean behind him: probably the hardest-breaking wave ever photographed at Nazaré. Then Kai, turning sharply and slicing cleanly up the face, changes rails and gives it a little downcarve. If you don’t know that he’s surfing straight at a cliff, it probably seems less insane. Still, the nonchalance on a seventy-foot death wave is indelible, which is why they’re playing it over and over in an ad.

I ran into the man himself an hour later, at the Nazaré boat marina. He had just arrived, with Paula and Ridge. The eighteen surfers in the contest were gathered at a warehouse full of surfboards for a safety briefing. Kai and his tow partner, a strapping Brazilian known as Chumbo, had a fierce little reunion. Chumbo, whose real name is Lucas Chianca, had just come in from surfing. He stood under an outdoor shower and peeled off his wetsuit, listening closely as the safety briefing went forward. The subtext for the discussion was the Alex Botelho incident. Botelho, who has still not fully recovered, believed the safety measures were inadequate. There needed to be more rescue skis, more reliable contingency plans.

Contest day dawned sunny and clear, except for a dense fog that lay on the ocean. From my hillside hotel, it looked like a vast snowfield—white and seemingly solid to the horizon. Kai told me later that he and Chumbo had suited up at first light and driven their ski to the point. “You couldn’t see anything,” he said. “You could just hear these big explosions. It was not happening.” As the morning wore on, would-be spectators wandered the ridge path, in brilliant sun. Out at sea, the fog layer didn’t budge.

Surf contests have always been rickety propositions. Besides the inescapable subjectivity of judging surfing performance—critics like to say that it’s like a dance contest—there’s the ocean and its caprices. Flat spells, bad winds, fog: it’s easy to get shut down. For big-wave competitions, the unpredicta­bility of huge surf necessitates a last-­minute alert system, calling in surfers who live all over the world. In 2016 and 2017, when there was still something called the Big Wave World Tour, the organizers had six contests on the slate. Now the list is down to two, at Pe‘ahi and Nazaré—and Pe‘ahi didn’t run last winter. “The big-wave tour is a joke,” Kai says.

Still, for the World Surf League, the organizing body of professional surfing, big-wave surfing may represent the best hope of attracting a mainstream audience. Big waves and their manifest risks captivate far more viewers than the small to medium-sized waves on the World Championship Tour, where, to the untutored eye, all the surfers seem to be doing basically the same things. The stark difference between the two was highlighted in 2012, when a C.T. contest took place at an offshore reef in Fiji. The swell was rising fast during the morning heats, and officials shut down the contest when the waves got scary. A big-wave contingent that had seen the weather maps and flown in—from Hawaii, South America, South Africa, and California—immediately paddled out. Videos from that session are likely the most revered surfing vids of all time.

This befogged Nazaré contest was a strange one, if only because it was tow-in. The surfers traded off driving the ski and were in theory trying to put their partners on the best possible waves. Except that their partners were also their competitors. Faced with this contradiction, the contest directors had emphasized the prize for best team. When Kai won nearly everything in sight for that huge wave in 2020, he graciously noted that Chumbo had put him on it perfectly, and also spoke of his “blind faith” in Chumbo’s ability to rescue him from anywhere, even from a notorious cave in the cliff below the lighthouse.

“It’s a funky format, but I don’t care,” Kai said. “This wave is insane, and you have to tow it. And I love to compete. I surf better in contests.”

We were at a fish restaurant on the main drag in Nazaré, which runs along the town beach. It was nighttime, and the fog was still thick. I was astounded that Kai didn’t seem upset. He and Paula and Ridge had travelled eight thousand miles to be here. By tomorrow, the swell might be gone. I asked Kai how he had spent the day.

“Watching Formula 1,” he said, between bites of a hamburger. “It was such an insane race, I’m almost glad we weren’t out surfing.”

Paula seemed unfazed, too. She had spent the day reading.

There was obviously nothing to say about the fog. Kai started talking instead about a gruesome recent incident at Pe‘ahi. A visiting surfer had shattered his femur in what sounded like a freak accident—his board leash had yanked too hard on his leg. Kai had been nearby. “You could hear the leg break underwater,” he said. “It sounded like a tree splitting.” But it wasn’t a freak accident, he said. “The guy was totally caught inside”—trapped in front of a breaking wave. “He should have ripped off his leash.” Ripping off one’s leash in the face of a life-threatening beating was so counterintuitive that I was sure I wouldn’t have done it, either. But Kai sees these things clearly, even coldly.

Molly had told me something about his discipline around danger: “I know how calculated every decision he makes is, how well prepared he is for what he’s doing. He does so much preventative training.” But his management of risk seems to coincide with a palpable lust for it. Over dinner, the conversation turned to wingsuiting. “They go, like, a hundred eighty miles an hour, don’t they?” Kai said excitedly. “That’s faster than terminal velocity. And some of them go right next to the mountain.” Now he was talking about wingsuit base jumping and “proximity flying”—probably the world’s most dangerous hobby. “They pretty much all die, I think. I heard that when they hit something there’s basically nothing left. It’s just pink mist.” I was losing my appetite. “Pink mist,” Kai said again, with a faraway smile. Ridge and Paula didn’t seem to be listening. Maybe they were used to this kind of ghoulish talk.

“I don’t know if I believe in reincarnation,” Kai said. “I just hope that when you die you get to see what it’s all about, how it all works, like why little fish get eaten by big fish, all of it. That would be cool.”

The next morning, there was still big surf and, to my surprise, no fog. The swell looked crossed up, but that was normal for Nazaré, with its underwater canyon. The waves must have been at least thirty feet on the faces.

In the first heat, Kai put Chumbo on a tall but not particularly powerful left. Chumbo has been based primarily in Nazaré in recent winters, and his knowledge of the place showed, as he delayed his run across the wave just long enough and then went very high on the face, where he knew the top fifteen feet might pitch hard and give him a chance for a quick, safe barrel. The lip did pitch. He disappeared briefly, and then shot out at high speed, still under control. That was how to ride this place this morning.

And yet Kai ended up going right. He later said that he had misjudged the takeoff, and let the left get away from him. But it was breathtaking, seeing him run against the grain of the swell on a very large wave. He accelerated, now low in the face, then hit a stack of small wavelets coming off the cliff. It was like running over speed bumps while going eighty on a highway. His fins began to cavitate. His board flipped in the air, bucking him off, and the whole wave landed on him from a considerable height. He later said that his jersey was pulled over his head, so that he couldn’t get to the rip cords for his inflation vest. He was underwater for quite a while.

I was at the lighthouse, looking down on the action. Chumbo was running the ski behind the wave, and when Kai didn’t appear on his board he swerved left toward the turbulence. Kai’s head finally popped up. Chumbo raced to him, slung him onto the rubber sled that rides behind the ski, and gunned it. The next wave was a foamy mess, and Chumbo hit it sideways. The ski went up on its side, and Chumbo tumbled into the water. Kai hung on to the driverless ski for another second or two, before it flipped over and the whole contraption went over the falls. It was a yard sale, with intensely swirling currents, but the two surfers seemed unruffled. Chumbo was mostly concerned that he had lost his phone. He yelled something to Kai, who turned and swam seaward until he found it. Then they were both thrown on the sand by the shore break, along with their tumbling, eight-hundred-pound vehicle.

That little fiasco was likely the most-played video clip from the contest. When I asked Kai about it later, he laughed. “Welcome to Nazaré,” he said. “At least we didn’t go in the cave.”

In the end, Chumbo came in first in the individual competition, Kai third. The two together won the team trophy. At the awards ceremony, though, Kai showed up late. He had told Ridge that, as soon as the contest ended, he would tow with him. The swell was still twenty feet plus, and the beach break farther north was firing. I sat with Paula on the hillside while she watched her sons surf, peering down through binoculars. “This is the best,” she said.

The conditions were immaculate, and other tow teams had appeared—coming in from the sea on skis, since the inshore white-water zone was still too ferocious to cross. In a lifetime of surfing, I had never seen surfers playing in twenty-foot beach break. Kai and Ridge had lucked into this session, but they had obviously made their own luck, staying ready to jump into anything.

Kai’s unusual virtuosity is also a result of making his own luck. As a kid, when the surf wasn’t good, which is often the case on Maui, he would get in the water on some craft that was not a surfboard. When the trade winds revved up, he would switch to another type of board or sail and go faster. As you move out from shore, the wind gets stronger, which means that everything gets rougher and more challenging—plus, no one will know where you are if your gear breaks or you get hurt. Kai learned not to worry about it, if he was even worried to start with.

The result was that Kai came to big-wave surfing with a deep understanding of going very fast over choppy water. The sheer speed of tow surfing, especially if there is any chop, which there usually is, causes even great surfers to tense up, and the same goes for the intense acceleration of dropping into a big wave on a gun. People naturally assume a survival stance. To Kai, however, this speed and those bumps are familiar. He treats them like a playing field, even with a mountain of water chasing him.

Scott Sanchez, Kai’s coach, confirmed this unoriginal theory and added a key element. “Laird and those guys also windsurfed, really well,” he said. “But they all got exposed to this high-speed stuff at around Kai’s present age, not as children. There’s a magic window for children for learning complex motor skills, and Kai got it all as a young kid—surfing, kiting, windsurfing. The Strapped Crew set the pace for the four-minute mile. Kai’s running it.”

Sanchez went on, “Very few athletes at a high level have much appetite for innovation. But Kai has absolutely no pride or ego when it comes to learning something new. He’s like a toddler. He has that innocence. He keeps falling and getting back up.”

These days, Kai and Sanchez are concentrating on surfing. Sanchez pores over film of Kai’s Pe‘ahi sessions, and they talk about what can be improved. Sanchez is on Kai’s support boat for real-time study and tweaks. On the day I was out at Pe‘ahi, Kai would return to the boat after every couple of waves. He was trying out different sets of fins. They all looked the same to me, but Kai could apparently feel the difference. His tow boards had a set of tiny, sharp permanent fins along the tails. Kai tapped the side of his head and gave me a conspiratorial smirk—this was some kind of secret weapon. Late in the afternoon, he came back to the boat yelling about a set of fins: “Did you see those turns off the bottom? These aren’t even tow fins, and they’re slingshotting me off the bottom.”

Kai keeps his gear in a garage on his parents’ property, a high-ceilinged place. Dozens of surfboards line one wall, from shortboards to full guns. Overhead are foil boards, sups, tow boards, a kayak, sailboards, kiteboards, and the outrigger for a traditional Hawaiian canoe. There are racks of tightly wrapped sails, for kites, wings, and windsurfers, and the masts, booms, carbon struts, inflatable struts, pumps, and other gear that go with them.

When he’s not on the water, Kai spends time with Keith Teboul, his main board-maker. He and Teboul can geek out on design for hours, sitting at a computer, dialling in specs to the millimetre. They make special Pe‘ahi and Nazaré tow boards, tiny and sharp-nosed and super-­weighted with .50-calibre bullets. I saw a new tow board in Teboul’s workshop. It looked like something a fighter jet might fire to destroy a ship.

In Kai’s garage, the boards hang near tidy racks of wetsuits and foils, racing bikes, mountain bikes, helmets of many types, tools. Even the skateboards are carefully stowed on their tails. It’s the cleanest garage ever. The sheer variety of watercraft assumes a breadth of technical knowledge and enthusiasm that I found exhausting just to contemplate.

“I can never get bored,” Kai says.

His eclecticism confounds the culture of surfing not just locally but globally. He’s been described, often, as the world’s greatest “waterman,” which some hear as faint praise. Sam George, a former editor of Surfer, wrote a passionate essay last year denouncing the narrow-mindedness of the surfing world for failing to recognize Kai as “the most progressive surfer in the world today.” He invoked Reinhold Messner, the Tyrolean mountaineer who revolutionized high-altitude climbing, in 1980, by reaching the top of Mt. Everest without bottled oxygen. “Kai Lenny is our Reinhold Messner,” George wrote. Kai’s performances at Pe‘ahi made his peers look “archaic by comparison, and should completely redefine the state of the art.” Perhaps now, he suggested, “myopic surfers” and surf journalists were beginning to forgive him “for all the other areas of expertise he’s mastered.”

George quoted, mockingly, the institutional self-description of the C.T.: “The tour is made up of the most talented surfers on the planet and the surfing done in competition is the most high performance in the world.” That may be overblown and self-serving. Still, the C.T. is the N.B.A. of shortboard surfing, and even Kai likes to say that the myriad wind sports and board sports that have emerged in recent decades all basically come from surfing. When the waves are good, and not mutantly large, shortboarding is the call. And so, when the World Surf League, a few months back, offered Kai a local wild-card spot in a C.T. event on the north shore of Oahu, he didn’t have to weigh it against competing obligations. He said yes.

The event, the Hurley Pro, would take place at Sunset Beach. It’s been years since a C.T.-level contest was held there. A shifty wave that breaks far from shore, Sunset Beach was long considered one of the world’s best big-wave spots, but it’s more complex than it is spine-tingling. Familiarity with its specific reefs and quirks is usually thought to be the key to success.

I asked Kai if he had any Sunset experience. He gave me a sideways look. We were watching the Super Bowl at a house on Oahu. “I won five sup titles there,” he said, with not much scorn in his tone, considering. “I love Sunset.”

Lenny competes in a dizzying range of water sports, from windsurfing to
long-distance paddling.“I can never get bored,” he says.
Photograph by Brendan George Ko

Kai had also done well at surf events one tier below the C.T., but the opportunity to leap directly to the big leagues was huge. The normal route is a dreadful grind of lower-level contests in mediocre waves. But wild cards who exceed expectations have been known to make the tour, simply by winning heats consistently. I had heard people say that Kai wouldn’t want to be on the C.T.—living out of hotels, missing good swells. I had not heard Kai say that. Making the tour would be a stunning accomplishment, settling any arguments that still exist about how good a surfer Kai is. Nothing could be more Reinhold Messner.

The Hurley Pro included thirty-six men and eighteen women, hailing from at least a dozen countries. They were all presumably hanging out in the neighborhood, watching the forecasts. The surf was small at the moment, but that would change soon.

Kai’s shortboard coach, Doug Silva, was pacing in and out of the room. Silva, a tight-wound ex-pro in his fifties, seemed far more nervous than his athlete was. Kai was full of ideas about how to succeed at Sunset. After the Rams sneaked past the Bengals, he regaled me with lineups and strategies. “There are so many different planes out there,” he said. “Depending on the size, swell angle, where you are on the reef, tide, wind, all of that. There’s no point doing sharp little tight-radius turns. You need to go big, draw huge old-school sweeping carves.” Seeing complex waves as planes was kind of brilliant, if your goal was high performance. Then it got more subtle. “When it comes time to smash a closeout lip at Sunset, you need to hit it at a softer-than-usual angle, not straight up and down. Straight up is standard with small boards in small waves, but you’ll get obliterated out there if you try it. If you do a more drawn-out bash, the arc will allow you to float down the broken wave under control and more likely land on your board.”

Kai was acting out these maneuvers when he was interrupted by a ­visiting nurse bearing bags of yellow fluid, some kind of vitamin I.V. drip. Faster recovery was the idea, or maybe strengthened immune systems. Kai, his photographer, even the owner of the house, Monte (no last name), all sat for a dose. I passed, which gave me a chance to look around.

We were in an oceanfront place called Hale Komodo. Hale means “house” in Hawaiian. “Komodo” means Komodo dragon—the world’s lar­gest lizard, which lives in Indonesia. The Komodo is an apex predator with a venomous bite. It is also one of the most unpleasant-looking animals around. Nevertheless, somebody had taken the trouble to place stone and wooden replicas, some of them life-size, around the luxurious grounds of Hale Komodo. There were two big boys perched menacingly above an L-shaped saltwater pool in the middle of the compound. Monte was a smiling, muscle-­bound guy in a trucker hat, perhaps fifty. Kai said he was an asset manager, something like that, with a big house in Honolulu. This was his country place. Kai often stayed here when he was on Oahu.

Kai is discreet about his thing with tycoons. They want to be around him, tech titans especially. Sergey Brin, one of the founders of Google, wants to come out on Kai’s support boat at Mavericks? Sure. “He’s supercool,” Kai says. In 2019, he spent some time on Richard Branson’s private island in the Caribbean, where he taught Sir Richard to kitefoil—we know that mostly because Branson posted video on Facebook of the two of them. But Kai’s most elaborate billionaire bromance has been with Mark Zuckerberg. They went foiling together on Kauai, and the paparazzi caught Zuckerberg looking extra silly. Zuckerberg later described Kai as “magical,” and then introduced his big metaverse gaming play with, among other things, a cringe­worthy virtual-reality skit about foiling with Kai. Even so, Kai has nothing uncharitable to say about him.

As Kai and his team took their supplements, I flipped through a coffee-table book, “Big Wave Surfer: The Greatest Rides of Our Lives.” Author: Kai Lenny. It was three hundred pages of ravishing surf photographs, published in late 2021. Kai had never mentioned it. Most of the photos were of Pe‘ahi. Many featured Kai. But the book also contained brief essays by thirty well-known big-wave riders, women and men, young and not young. A handful of them had established themselves on the World Championship Tour before getting into big waves. But crossing from the top of big-wave surfing to the C.T. has never been done.

That night, Kai and Doug Silva both seemed to have colds. We were at a sushi place in Haleiwa, the only town on the north shore, and Silva was attacking his stuffiness head on with sake. Kai doesn’t drink, but he seemed amused by Silva’s tales of his swashbuckling days on the pro tour in the nineties, when he partied hard—very hard, he assured me—with a couple of high-profile Australians. He had his hair in a topknot of some kind, with the sides of his head shaved in confusing patterns. Martin Lenny had described Silva to me as a philosopher who liked to dress like a Formula 1 driver. He spared us the colored leather that night, but he did give me many penetrating glares and cagey looks, all equally mysterious.

Kai was ready to head back to Hale Komodo. He was in training, as always. From Silva’s perspective, though, the night was young. The visiting I.V. nurse was at another table. The restaurant hostess busy escorting parties to their tables was a stone-cold beauty queen. Haleiwa is pretty dead after dark, but Silva had long experience conjuring excitement in sleepy surf towns. I wondered if his frenetic, pseudo-samurai decadence was refreshing to the kid from Spreckelsville. Not that Kai would ever say so. Maybe he was just a great surf coach.

Overnight, Kai’s cold turned flulike. He flew home to Maui, looking for some last-minute miracle remedy, perhaps from Paula. The next morning, the contest was called on, and Kai was scheduled to be in heat six, surfing against Filipe Toledo, who is currently the world No. 1, and Joao Chianca, Chumbo’s little brother, a red-hot rookie. But, in the early-morning reckoning, Kai figured he was at seventy per cent—not good enough to compete with the world’s best. The decision was made. Kai stayed on Maui. His spot went to an alternate.

I watched the contest for a day or two. Sunset did itself proud. Ten feet plus, wide blue walls, plenty of power. I loved being on the north shore. This was the faith I grew up in, pure thrill surfing, and the north shore in winter has a superabundance of great waves. At Hale Komodo, Kai had pointed out the window and said, “It’s not fair. Oahu has so many good waves.”

I went to Maui. In his parents’ kit­chen, Kai looked and sounded rheumy but otherwise seemed unfazed. He said that he had been horribly disappointed the first day. “After all that prep,” he said. But then, the next day, he had started watching the Webcast of the contest, and got into it. “People are surfing so good,” he said. He was especially excited by a young Australian named Ethan Ewing.

“I put a board on the floor in front of the screen,” he said. He crouched. “And I was doing everything exactly like he was. Legs like this, not like this. You see the difference?” I did, though it was not enormous. “Shoulders turning like this, following your eyes.” Kai was performing, in slow motion, a persuasive set of deep, clean turns, squinting hard with concentration. “I want to surf exactly like Ethan Ewing.” Ewing was not one of the top C.T. names. He had never won a C.T. contest. But Kai was right. Nobody at Sunset looked better.

We took his truck to Ho‘okipa to check the surf. It was piddling, despite the swell that was still pounding Oahu. Kai turned off the engine and pointed west. “We’re blocked by Molokai and west Maui,” he said. The landmasses he indicated were not small. “The swell has to be more north. Half the big winter swells that hit Oahu don’t even get into Pe‘ahi.”

Somebody shouted from a passing truck, and Kai laughed. “I gotta call that guy,” he said, then turned his attention back to the ocean. “This is the ridiculous thing about being a big-wave surfer. You’re a professional at a sport that, in some bad years, you can barely practice. It’s like being a Formula 1 driver and having no track.”

I was disappointed not to see Kai get his shot at the C.T., but he didn’t seem that disappointed. Whatever he needs to prove, he’s pretty much proved it. I thought of something he’d told me: on huge days at Pe‘ahi, when the channel was full of boats and gawkers, and he was surfing his brains out, he sometimes saw guys who had bullied him when he was a kid. He admitted that seeing them humbled, too fearful to surf, gave him a certain rueful satisfaction.

For Kai, big waves still present endless opportunities. One day, we rode in an all-terrain vehicle up to the top of the Pe‘ahi cliffs. We were with Campbell Farrell, a local landowner, coastal-cleanup activist, and big-wave surfer. In the back seat were Kai and his buddy Lyon, Campbell’s son, a professional snowboarder. Kai had decided that Lyon could teach him some aerial tricks to perform on big waves. “It’s the future,” he said. “It’s the only way to go.” I wasn’t sure about that, and neither was Campbell. But Lyon was excited to teach Kai how to throw a corked frontside five-forty, and assured him he could do it without tearing his A.C.L. Kai, looking down at the restless swells ghosting, unbroken, above the long ridge of the reef, was already picturing these moves busted out on a big wave. “You know, I could pull into a huge barrel,” he said. “And, if I was gnarly, I’d just go for the five-forty right in there!” ♦

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