The Waterman Eclectic

Surfer, windsurfer, foilboarder, kitesurfer, stand up paddler——Kai Lenny takes to the water any way he can
Story by Beau Flemister. Photos by Mike Coots.

On a wind-whipped morning last November off Maui, as monstrous waves swallowed competitors whole—a swell that surged with such force that the waves moved the boulders beneath the Pe‘ahi lookout—the World Surf League commissioner called the Jaws Challenge off. It was too big for the big-wave contest.

Too windy. Too dangerous. Someone could drown. Jet skis and lifesaving sleds had already been obliterated by rogue sets. The debris of this destruction floated in the whitewater at the base of the cliff—and the swell was still building.

While most competitors caught boats and jet skis back to the safety of the harbor, a couple surfers did not. Kai Lenny, a 26-year-old from Pā‘ia and perhaps the world’s greatest crossover ocean athlete, swapped his ten-foot big-wave paddle-in gun to a smaller tow-in surfboard. Grabbing the towrope, Lenny nodded to his jet ski driver to slingshot him into sixty-foot-tall behemoths. He rode more than a dozen waves, one after another, with inhuman endurance, streaking across the rippled wave faces, dancing beneath peaks falling like guillotines, air-dropping twenty feet down, finishing waves with corkscrewed aerial backflips.

Garage of dreams: Kai Lenny among the tools of his many trades at his home on Maui. Lenny’s incredible drops at Jaws have made him a household name in the big-wave surfing world.

Even though the event was called off, the WSL kept the cameras running for the webcast. Lenny’s performance awed and baffled the commentators, who dubbed it the Kai Lenny Show. One of the commentators was renowned waterman Dave Kalama, who along with Laird Hamilton and a half-dozen surfers collectively known as the Strapped Crew, had pioneered the sport of tow-in surfing twenty-five years before at this very wave. He was witnessing what he’d helped invent, but updated. Evolved. Better. You could practically hear Kalama shaking his head in disbelief at Lenny’s acrobatics. 

The contest resumed the following day in slightly less treacherous conditions, with Lenny placing runner-up behind his childhood friend, three-time Jaws Challenge champion Billy Kemper. “Because Kai was into so many other forms of wave riding growing up,” says Kemper, “I honestly never looked at him as a major threat to me in paddle-in surfing. And now he definitely is. He’s trained so hard and put so much effort into it that he’s now right there with the best in the world. It’s crazy.”

Despite his stellar result, Lenny’s been brooding over placing second, and he’s been improving and training since.

A few months later, on the back half of the 2018-2019 winter big-wave season, Lenny lifts up his garage-cum-watercraft storage door to show me the vehicles of his lifelong pursuit. I ask if I should remove my shoes—it is a garage—before stepping into the temple, and although he doesn’t say no, his pause speaks volumes. Another thing I’ll quickly learn about Lenny: He’s a clean freak, which is evident in the orderliness and quality of his equipment. On one side of the room is a row of two dozen surfboards organized by length in racks, all with the identical royal-blue-and-red racing-stripe paint jobs, sponsor decals in identical places. The floor is as spotless as his surfboards. 

Above us hangs a Moth-class hydrofoiling dinghy, and next to that, more big-wave guns, racing paddleboards, stand up paddle (SUP) boards and outrigger canoe ama, or floats. Below are shelves of tools, tightly rolled kitesurfing and windsurfing sails, life vests, coiled towropes, and on the other side of the wall, a row of identically painted tow-in surf and hydrofoil boards, also in Lenny’s signature paint job. Each craft looks like an aquatic race car—also intentional, explains Lenny, who is a huge fan of Formula One racing and MotoGP (Grand Prix motorcycle racing). He has a fascination with speed, precision and finely tuned … well, everything.

“I know there’s no such thing as perfection because of all the variables, but what I love about the idea of precision is that in order to be at my top, top level and become the best in the world at something, my whole ship needs to be tight before I step into the Thunderdome,” he says. “That, and I hate clutter.”

Lenny’s building a barn up the mountain, a watersports headquarters of sorts to house all of his equipment and serve as an innovation center for new craft. Since he was a kid, he says, he was into designing wave-riding apparatus with a focus on how to make a good thing better. He shows me a surfboard with what look like microfins behind its regular fins, which act like diffusers would on Formula One race cars. According to Lenny they increase a board’s performance by more than 10 percent.

On the way out of the garage, he motions me to “check this out” and excavates a canary-yellow orb from a box filled with packing peanuts, cradling it like a sooth-sayer’s crystal ball. It’s a solar-powered marine buoy. Lenny hopes to get a permit to moor it at a secret wave of his choice so he’ll know precisely when to hit it. 

The precision stuff is cool and all, but beholding his arsenal of watercraft, what strikes me most about Lenny is his breadth of expertise. While most focus on one thing, Lenny’s won multiple races, world titles and mega-events by claiming loyalty to none.

He motions me over to his truck. We’re off to Quatro International to speak with his shaper about a new design, grabbing a bite en route. Rolling into misty Ha‘ikū, every pickup truck seems to have some kind of windsurf or paddleboard hanging precariously from the bed. We order up two “Paniolo Skillets” at the coffee shop, bumping into Ian Walsh, a fellow big-wave champion and Red Bull teammate of Lenny’s. They talk about waves but mostly wind, like watermen often do on Maui.

“My superheroes growing up weren’t from Marvel comics,” says Lenny, seen here kitefoiling,
a fairly new ocean sport that he’s been quick to master. “They were the guys surfing Jaws. The whole Strapped Crew — that was my Justice League.”

The son of California transplants, both of whom moved to the north shore of Maui to surf and windsurf, Lenny caught his first wave by age four, a vivid sensation he admits that he’s been trying to replicate his entire life. By six he was windsurfing and entering prone paddleboard races (he’s currently a three-time Molokai 2 Oahu Championship winner and record holder). By seven he was stand up paddle surfing, and is presently an eight-time world champion in that discipline. By nine he was kitesurfing (becoming world runner-up in 2013). Shortly after that he began tow-in surfing in large waves and then foiling under the tutelage of tow-in godfathers Dave Kalama and Laird Hamilton. From tow-in surfing he’s since joined fellow paddle-in big-wave surfers to place second on the 2017-2018 Big Wave World Tour.

As a jack-of-all-aquatic trades, Lenny wouldn’t limit himself to one sport. This is a major departure from the rest of the young talent pool on Maui, who mostly follow the tried-and-hopefully-true formula of going all-in. Against advice from potential sponsors at the time, Lenny stayed his own course and kept moving among the “tribes” of each discipline, including one in particular that wasn’t always so welcoming.

“I never really felt totally accepted by the surfers,” he admits. “I felt like an out-sider, due to the fact that a lot of surfers didn’t think it was cool or ‘core’ to branch out into other [water] sports. It was like, just surf or don’t surf at all. I’d get hazed, sort of bullied by the old guys. I was actually scared of going to my local break at Ho‘okipa because of getting snapped at for SUP-ing. But what it taught me was that I’m really comfortable being alone and walking my own path. Plus, it keeps life fresh when you can transition between so many different perspectives.”

Lenny started surfing at age four, and by age six he was windsurfing, tearing up waves like those at Ho‘okipa, Maui’s north shore windsurfing mecca.

Some of the surf brands told him he needed to pick a side if he wanted to make a living. “I was like, ‘No, I’m going to prove them wrong, and I’m going to exceed my own expectations.’” Which, eight world titles and some world records later, he has. “He’s one of the true icons of his generation and that entire group on Maui,” says Laird Hamilton. “Honestly, I think his multifaceted philosophy comes out of Maui a lot. The nature of the conditions there, and the community … it’s so wind-driven and influenced, so you see a lot of creativity. Kiting, foiling, windsurfing, all these things were birthed on Maui. It’s just cool to see what he’s been able to do with each one.”

“I think the most impressive thing about Kai is that a lot of people can get burnt out with all of it, starting at such a young age as he did,” says Jamie Mitchell, ten-time Molokai 2 Oahu Paddleboard World Champion and big-wave surfer. “But Kai? He’s lived up to all the hype, if not succeeded the expectations of him. That’s impressive. He was Maui’s ‘wonder kid’ and then took it to another level. He’s a star of crossover water sports.”

I’m not entirely sold that he doesn’t have a favorite child. I ask him if he had to choose one, could he? “No. Taking one away from me would be like taking away a finger. And I like all my fingers,” he laughs. “Each one has a purpose, but I guess my thumb is the most important—which I’d liken to getting barreled in big waves.”

I always knew he was a surfer at heart.

After breakfast we walk next door to the old Pauwela Cannery, which now houses a number of craftsmen and surfboard makers, namely Quatro International, the world’s leading hub for windsurf, kitesurf, SUP and foilboard design. Inside the shop the rows of hanging windsurf boards, sails, deck pads and fresh carbon fiber smell like a newborn robot. 

Above, a fan fist-bumps Lenny as he heads out for a session. “The way Kai transitions so well between each discipline inspires a larger audience,” says Maui boy and 2017 Jaws Challenge champion, Ian Walsh.

I follow Lenny to a room where he has a few other giant racing paddleboards stashed upright, a remote office of sorts where he spent time editing his 2017 biopic, Paradigm Lost. He introduces me to Keith Teboul, his main board maker, and the two look at a monitor in the showroom, tweaking digital dimensions on a new foilboard. It’s Lenny who has often been credited with spearheading the recent resurgence and current popularity of the global foilboarding boom. His accomplishments in the sport have been ground-breaking, namely his 2017 Molokai 2 Oahu Race win, where he hovered the thirty-two miles downwind in a blistering two hours and fifty-two minutes without getting his toes wet. I ask him about that feat and he shrugs. “My career is being a ‘professional ocean athlete,’ which sometimes I feel is an odd concept. Like, I get paid to do what I’d do anyway. Paid to play, really.”

We hop back in his truck and head toward Wailuku for a “training session”—at Ultimate Air Trampoline Park. I’m wondering if he’s got a nephew with a birthday, but no, we’re here to bounce. Kai introduces me to his “Air Awareness Coach,” Matt Christensen, a Red Bull project manager and former head coach of the US Ski Team through three Winter Olympics (and Canada’s national team coach prior to that). There’s not a soul in the building yet, and someone turns up Guns N’ Roses’ “Paradise City.” Lenny hands me a pair of padded jump-socks and hops over to the expert’s mat. A giant foam pit beckons in the distance, and suddenly the phrase “paid to play” is making a lot of sense.

Lenny’s family life was filled with time in the water thanks to his parents, California transplants Martin and Paula, both of whom moved to the north shore of Maui to surf and windsurf.

Christensen counts Lenny down and sets up an iPhone for playback, drilling him on backflips and cork-seven twists, techniques that Lenny’s mastering for maneuvers on his kite, windsurf and foilboards out in the ocean. Much of this training is purely practical, though, calisthenics for the superhuman stamina Lenny needs to perform some of his long-distance feats. A couple years ago, to raise awareness for the global ocean microplastics problem, he foiled to five Hawaiian Islands, kicking off massive coastal beach cleanups on the shorelines of each. Some of these distances, like the ‘Alenuihāhā channel between Hawai‘i Island and Maui, required Lenny to balance on that hydrofoil for fifty miles straight. 

Bounced out and thoroughly winded, Lenny gets a call from Teboul; they’ve got a windsurfing session to try out some new craft in half an hour. We hop out of the park and jump back in the truck, Lenny dropping me off en route, practically foaming at the mouth to get back in the sea. I ask him about this connection. “For me … it’s like the ocean is a battery pack,” he says. “I get energy from being in the water, and when I’m not, I don’t have that same spark. The light in my eye dims, maybe. I think for my soul itself, there’s no better feeling than riding a wave.”

I ask Lenny if there’ll ever be a day he finally switches his efforts to land. Racing cars, perhaps? He’s gushed over his fallen idol, Formula One racer Ayrton Senna, multiple times. “I think what makes me immune to getting burned out is my obsession with variety and all the different craft I ride. When I start to get jaded with one thing, I just go to the next thing I do in the ocean.” Lenny says he has no goals to do anything groundbreaking (and if he does, he says, “I don’t talk about it for fear some-one will beat me to it”) other than to keep pushing himself toward “the most high-performance riding and winning the Big Wave World Tour,” which is more than enough to keep him interested. “I don’t know how you can ever get bored riding a really big wave,” he says. “I think that I’ve positioned myself to never get jaded. To me it’s endless. There’s always some new way to ride water.” HH