Athletes

Kai Lenny: The New Generation of Well-Rounded Watermen

From the Summer 2009 Issue: The Wave Riders

Written by TB Mott

The way I like to ride any sort of wave is to not think about what to do but to do just what the wave says to do. Like if there is a lip there,” Kai’s hands are again rising and falling with the break of the wave and his past perspective, ‘and there’s the possibility of the biggest aerial of my life, I’m going to hit that, and do an aerial. It’s never “I’m going to take off and look for an aerial’, because when you do that you miss three other turns that could lead up to and aerial.” – Kai Lenny

Laird and Dave were yelling at me to get into the channel,” sixteen-year-old Kai Lenny remembers about that day at Jaws…

“I kept thinking I wasn’t deep enough. But Jaws just feels like it lures you in deeper.”

Yes, Kai was out there at that Jaws – the famous big wave on Maui.

Yes, he was with that Dave and that Laird.

And yes he’s good enough at sixteen to have earned the tutelage he’s receiving from them both.

Kai Lenny By TV Mott

Laird Hamilton calls Kai “The Renaissance Kid.” He says, “He’s at a time and place when it’s what you do. He’s the first of the group to be multi-disciplined.” “He reminds me of myself,” explains his mentor, Dave Kalama. “I wasn’t the most naturally-gifted kid out there, but no one was going to outwork me. Kai may not be the most naturally gifted kid in the water right now. But by far he’s the hardest working. He has the best attitude. He’s a great kid.”

The scraggly-haired 10th grader tells me the story of that Jaws day while sitting on his parent’s couch. “Dave and Laird wanted to go foilboarding and I was just kind of tagging along.”

Kai Lenny by Darrell Wong

DARRELL WONG (Top) Lenny at the stick, blazing a trail near his Maui home base. PEPPE D’URSO (Below left) Displaying style beyond his years. OXBOW (Below middle) Waterman Laird Hamilton and his protégé. SERGIORIO (Below right) At 16, he is an exuberant old soul expressively charting his course.

Lenny’s hands are moving like a fighter pilot simulating two airplanes in a dogfight. He’s intently recounting yesterday’s Jaws tow-in surf session with “a couple of his friends.” It was much more than that… Kai had just received an invaluable tutorial on the powers of the ocean from two of the world’s greatest-living watermen.

Kai is animatedly maneuvering on the couch as if one hand is on the foilboard and one on the wave face. He had ridden a wave that – up until then – he’d only dreamed of riding, but he humbly downplays the experience. “It’s such an honor to say that I launched a jet-ski at Jaws with Laird and Dave.”

Kai’s middle name could be Humility. But the truth is even more interesting… “My middle name is Waterman,” he told me with a proud giggle. “And ‘Kai’ in the Hawaiian language translates to ‘Ocean’.”

He’s as closely related to both the definition and lineage of “Waterman” as anyone his age could possibly be. “He’s on the water all day every day,” legendary waterman Robby Naish told us. “He wakes up in the morning and he’ll usually do all three sports we do in one day… And then go back and do it again. He’s 100% stoked on all of them.”


Kai started out in the ocean on a surfboard at age three.


He was watching Paula and Martin Lenny (his mom and dad) windsurfing Maui’s famous winds and waves. By age nine Kai was windsurfing with Robby Naish—the most famous windsurfer ever.

Today, Robby Naish sponsors him. “I’m still ‘schooling’ him…” Robby says. “But not for long I’m sure. I support him in whatever he wants to do, so he can go for whatever he wants.”

Kai says, “I definitely want to become a world champion in windsurfing and right now. That’s my main goal—to really pursue the world championship in windsurfing.” “But I also want to continue doing all of my sports.

I just want to keep doing it all every day—whatever the conditions call for.” Yesterday was a perfect example…

Kai Lenny by Laurent Masurel

LAURENT MASUREL: On the way home from January’s annual Cabo Verde wavesailing championships Kai joined his family for an sup session on the Moroccan coast.

“I went shortboarding earlier. Then I grabbed my standup and went out for a long time. I just worked the shore break until the sun was almost down. And then it got really good for shortboarding. So I did a quick five-wave sesh right out front. Those are the best sessions for me… where I can just go out and do whatever sport the ocean calls for. I like that little routine where I can go Pop! Pop! Pop!”

You can feel the passion sitting next to Kai… His enthusiasm and exuberance are electric when detailing the water events of even an average surf day. You feel his delight.

Kai Lenny by Darrell WongFor standup paddling, he says, “I think by far it’s going to turn into one of the next big things.” His hands leave his lap and begin animating again. “You can do it anywhere in the world: on a lake, down rivers, flat water, little waves, you can do it in big waves; and I think its just going to get more progressive. I think also it’s going to take a lot from windsurfing, surfing, longboarding, all of that will come together, and it will become more progressive in big waves.” “Kai is a really smart kid,” Laird Hamilton asserts. “He’s not going to put himself in any position he’s not capable of. He has a lot of respect for the ocean. When that is your basis, you don’t have to worry about the rest. Kai, he’s just super stoked. He’s having fun.

“He’s the first of what I call ‘My Group,’” Hamilton explains, “to kind of come in at the very beginning of what’s happening now. The first to be into kiteboarding, standup, tow-in, foiling; all the disciplines of what we call a ‘Waterman’. The rest of us, we were already grown up before standup surfing and foiling came along. But Kai, he’s the first to come about when that’s what you’re supposed to do.”

Kai Lenny by Darrell Wong

WONG (Above) Kai’s travel quiver includes kites, sailboards/sails, and now sup boards. Whether kiting the trades or taking on the challenging Konas (the opposite tack from the normal tradewind direction) at Hookipa, Lenny’s ambidextrous talent has the regular foot surfer flying down the line and banking hard on the tool of the day, his sailboard gear.

“I appreciate being able to see the next generation of Waterman,” Laird says. “Twenty years ago, it didn’t exist.” On the wall in his bedroom, next to the computer, across from the surf poster personalized to him from, “Uncle Laird,” is tacked one sheet of paper: a prioritized list of Kai’s goals.

His friend Dave Kalama says: “Nine out of ten times it’s not the most naturally gifted athlete, it’s the hardest working athlete that becomes successful. If you do it for the love like Kai does, then the rest will come. When you love what you do, in the end, the rest will work itself out.” If what Dave says is true, then there should be no doubt that this talented young man will someday soon notch off that goal on his goal sheet that says: “World Champion.” He may just have to fend off his little brother… Twelve-year-old Ridge also inherited the Lenny family waterman gene.

Kai Lenny By Erik Aeder

ERIK AEDER: Kai had the rush of his young life during this Thanksgiving ’08 outer reef Specks’ day, pointing out that “what you don’t see in this shot is that the wave is about to hit the reef and it just jacks up really big. I made this wave, but barely. It took me 45 minutes to paddle back out because of the size.” BOB BANGERTER (Below left) He’s spent enough time on the rocks to learn where to paddle his standup board out without a pounding. MASUREL (Below right) Family time with mom, Paula, little bro Ridge and dad, Martin Lenny, a former general manager at the exquisite Mama’s Fish House. Martin is now the go-to realtor on Maui.

“Ridge is actually really good at all the sports too,” Kai confesses. His brother silently sits at a table behind him listening to every word. “He does everything I do. Ridge lights a fire under my butt. I just hopefully will try not to get passed up by him.”

Kai Lenny by TV MottKai looks over his shoulder and gives a silent brotherly glance across the room at Ridge. Ridge smiles and respectfully dismisses him with a humble and silent nod (though there is a little unspoken “bring it on bro” in there).

At home, Kai loves making videos, and he hates to have a dirty room. He listens to U2, the Red-Hot Chili Peppers, Placebo, and David Bowie. His favorite surf breaks?

Hookipa on Maui, one down in Morocco, he definitely loves Honolua Bay on Maui, Swimming Pools down in Fiji, Rincon in Santa Barbara, and, well, any break he can find at home on Maui!

Kai Lenny by TV MottLenny is clearly having fun doing what he loves, and he wouldn’t want it any other way. “I just want to continuously keep evolving each sport. I want to invent new moves in each sport. In 100 years, I want to be known as one of the greatest waterman, world-champions, and human beings in the whole world.”

Now those are some lofty goals!

With guys like Laird Hamilton, Dave Kalama, and Robby Naish looking after him, if anyone has a chance at achieving those goals, it’s Kai Waterman Lenny.

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Kai Lenny: The New Generation of Well-Rounded Watermen
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