Maui’s Kai Lenny Tackling Massive Surf

Kai Lenny, a born and raised Maui surfer, grew up watching his idols tackle waves thought impossible at Peʻahi. He channels this mindset and draws from his multidisciplinary background to take big-wave surfing to new heights. One of his more recent accomplishments is one that can…...
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Big-wave surfer Kai Lenny considers Peʻahi his backyard. In just one surf session, he will alternate between five to six water sports. Photo credit: Nick Moran

Kai Lenny, a born and raised Maui surfer, grew up watching his idols tackle waves thought impossible at Peʻahi. He channels this mindset and draws from his multidisciplinary background to take big-wave surfing to new heights. 

Lenny, 28, is an eight-time stand-up paddle world champion, distinguished kitesurfer and windsurfer, and recently paddled on his hydrofoil across four major Hawaiian channels. With his creativity and energy in the ocean, Lenny is constantly experimenting with emerging watersports, far ahead of any other athletes. 

He uses his expertise in multiple sports, making him one of the most dynamic and visionary big-wave surfers. When Lenny was 26 years old, he was inducted into the Surfers’ Hall of Fame. In 2019 and 2020, Lenny earned the World Surf League Big Wave award for Men’s Best Overall Performance. He also placed first with his tow partner, Lucas Chumbo, in the 2020 Nazaré Tow Surfing Challenge and won the Men’s cbdMD XXL Biggest Wave Award in 2020 for a 70-foot wave at the same notorious surf break. 

But one of his more recent accomplishments is one that can be enjoyed lying on the couch. Lenny, who struggles to stay out of the water, has compiled epic stories and action shots from some of the world’s elite big-wave surfers, including himself, in an aptly titled book, “Big Wave Surfer: The Greatest Rides of Our Lives,” available this October. It is a remarkable tribute to the athleticism, tenacity, and courage of all big-wave surfers. 

“Big Wave Surfer” is Kai Lenny’s latest project. The book is a compilation of stories from Lenny’s experience chasing monstrous waves as well as tales from other big-wave surfers.
Photo credit: Marc Chambers

Starting with his first ride at four years old at Ukumehame, the book features Lenny’s most memorable waves, followed by stories from pioneers of big-wave surfing, world champions, and local legends. 

Trailblazer of big-wave paddle surfing Shane Dorian clearly recalls his greatest wave. World champions John John Florence and Billy Kemper recount the feeling of dropping the competition mindset to experience the pure joy of surfing. Maui’s Ian Walsh recollects getting destroyed chasing a typhoon swell in Japan. Paʻia Fish Market even gets a shoutout.

“Big Wave Surfer” also reveals the transformative power of big waves. Australian professional surfer Laura Enever took a brutal fall on a 20-foot wave at Peʻahi that resulted in a torn knee ligament. After recovering, she wanted to recreate that adrenaline and excitement found in massive waves. Enever dropped out of the WSL World Tour to surf out of passion rather than competition. 

The most meaningful story that Lenny shares is the day he teamed up with his younger brother, Ridge. After a demoralizing session at Pe‘ahi, Ridge changed the course of the day by towing Lenny into two massive barrels. “We’ve been talking about the dream of riding these big waves our entire lives, so to fulfill it together is really special,” Lenny told MauiTimes.

Woven into these stories are lessons on perseverance, patience, and the ability to make critical decisions in life-or-death situations. Many names are repeated throughout these pages, revealing the camaraderie and experiences these athletes share. Often they are competing, but really they are challenging and supporting each other to continue surfing the biggest waves on the planet. 

Flipping through the pages of “Big Wave Surfer,” there are photos of jaw-dropping rides, gnarly wipeouts, beautiful barrels, and crashing walls of water. World-class photographers in unimaginable angles capture the extraordinary skill of these athletes surfing 20 to 70-foot waves, underscoring the sheer strength of the ocean. The result is enthralling. 

While Lenny believes there is something for everyone in his book, he stressed that there is something for everyone in the ocean. “You don’t have to do what I’m doing. You could be swimming two feet off the shore, and there’s a moment for everyone out there,” he said. “If you’re able to witness, listen, and hear the ocean, it’s the greatest teacher I’ve ever known besides my parents. The ocean has always been there for me but there’s always something to learn.”

Lenny grew up during the surge of innovative watersports on the North Shore of Maui in the ‘90s and early 2000s. There was the birth of tow-surfing, kite-surfing, hydrofoiling, and the revival of stand-up paddling.

“My brother and I were the products of our environment,” said Lenny. “Thanks to our parents, they were taking us down to the beach every chance they had.” He followed his parents’ interest and learned to windsurf when he was six years old. The ocean became his playground as he pursued kitesurfing, stand-up paddling, and hydrofoiling.

When they were not in the ocean, Lenny and Ridge were watching VHS tapes of the “Strapped Crew,” consisting of Laird Hamilton, Dave Kalama, Darrick Doerner, Rush Randle, Buzzy Kerbox, and Brett Lickle as they started chartering Peʻahi. “They redefined what big waves were possible to be ridden,” Lenny said. 

Inspired by real-life heroes and fueled by ceaseless energy, Lenny set ambitious goals in each sport. He secured sponsorships, won world titles, and set world records. 

At 16, Lenny joined the lineup at Peʻahi on a foil-board. “Back then, it wasn’t as accessible and you had to earn a place out there. I respected my elders and mentors of the ‘Strapped Crew’ so much. I waited for the ‘okay’ from my heroes,” Lenny recalled. “I was so amped about knowing everything about the wave from studying it on the cliff. Got out there, realized I didn’t know anything.”

It took 12 years for Lenny to feel comfortable at Peʻahi. “Now, I’m in a place where I let my imagination run wild,” he said.

At Peʻahi, what he now considers his backyard, Lenny draws on his multidisciplinary background, rotating between five to six sports on 20-foot plus waves. It tests his ability to adapt while allowing him creative freedom. “I consider all of them tools to enjoy the ocean. Each one gives a unique experience the other can’t and that’s what’s really fun about it,” he said. “The artform of riding waves is what I love to do.”

Each sport demands agility and dexterity. While windsurfing and kite surfing, Lenny harnesses the wind to propel himself down enormous walls of water. Paddling into these waves requires him to navigate the currents and strategize the take-off. Switching to his tow-in surfboard and grabbing the tow rope, Lenny focuses on performance, like a snowboarder maneuvering down a mountain. 

For Lenny, big-wave surfing proves riskier than other aquatic sports but comes with unparalleled thrills. “If I find myself on a tow board inside a giant 50-foot barrel, it’s the single favorite thing in the world that I can do,” Lenny said. “Anything you have in the back of your head bothering you on land disappears real quick and you get pure euphoria.” 

Take away the accolades and recognition, and Lenny would still be surfing enormous waves. “I’ve always approached big-wave surfing as the more spiritual side of my surfing,” he explained. 

Among sets of monstrous waves, Lenny witnesses not merely the height but the magnitude and force of the wave. “It’s the greatest example of a higher power and way for me to be in touch with Mother Nature at her finest moments.” 

Big-wave surfing has provided Lenny with his most reflective and surreal moments. “When I look at a giant wave—a towering wall of water—it serves as a mirror. I see who I am as a person. Sometimes I’m pleasantly surprised and there are other times where I’ve been a little disappointed in myself. I take those experiences and apply that back on land.”

The surfer has been surrounded by hundreds of dolphins, seen manta rays larger than living-room rugs, and encountered sharks. “The most common thing I see are turtles. Those are the equivalent of seeing a cat on the street. I guess on Maui, it’s more like seeing a chicken,” he joked. 

But with sincerity, Lenny said, “The single most impressive thing I’ve seen in the water is the insane power the ocean can produce in the winter months.”

October marks the start of the big wave season. At any moment, Lenny might get a call to hop on a plane for a big-wave competition. As he put it, “One doesn’t really know when the big waves are coming.”

Grace Maeda

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