Chasing Kai | The Next Laird is Solidly Hinged on Sup

Posted 8-19-17

By AJ Messier
Featured Image Caption: AJ MESSIER One of many for Kai during the swell of swells, January 15th, 2016. TOM SERVAIS (Inset) True legends, Tom Carroll and Kelly Slater: The company Kai keeps is a strong indicator of his desire to be accepted as a surfer first. Editor’s Note: Hats off to Standup Journal’s graphic artist Adam Champagne for crafting the most dazzling opening spread in our publication’s history.

Kai Lenny drops into yet another giant wave. He skips off the 45-foot lip, lands 10 feet below and starts racing to the bottom, hoping to make it before the water crashes over him. Like the 10 times prior to that launch, Kai makes it.

It’s no different than the hundreds of others I’ve already witnessed this winter. This time it’s with a paddle, other times it’s without, sometimes it’s as a windsurfer. But whatever the means, he does it with the utmost confidence. And how can he not, when his first session out at the infamous Jaws surfbreak was with legendary big-wave chargers Laird Hamilton and Dave Kalama? How can he not, when his safety team consists of the likes of Victor Lopez, brother of Hawaiian surfing royalty, and Milton Martinson watching over every rip? How can he not charge every wave that comes his way, knowing that legendary surf shooter Tom Servais is photographing every move he makes?

Kai doesn’t want to be pigeonholed. Whether it be laying down, standing up, holding a windsurf boom, a kite line or a tow rope, he will determine his tool of choice and the path he will take on the wave face; all he asks is to give him the opportunity to choose. And at 23, with his life ahead of him and the skills to do whatever he likes, he might just be the next cross-over face in the overall surfing world.

Chasing Kai 1

MESSIER (Top left) Looking to the horizon from atop Mount Haleakala. (Bottom left) Dave Kalama (center) has been a steady, strong influence. (Here) Kai groovin’ in the slot.

I spent the winter with Kai as he hopped back and forth from island to Hawaiian island. This is his story, which—for me—began January 6, 2016, at 8:15 am with this text message from Martin Lenny:

“Aloha AJ, Kai is on his way to Oahu’s North Shore with Johnny, Jace, and Tom for a sup competition later today. Do you want to join them for a couple of days?”

Uh…yes! By 11 am I was wheels up and headed from Maui to Oahu. By noon I was driving along Oahu’s North Shore, or what the surfing world calls the “Seven Mile Miracle.” It’s named for the 7.2-mile stretch that boasts 36 surf breaks, beginning in Haleiwa in the south and ending at Sunset Beach in the north. We would be staying on the North Shore as guests of the Ginella family, who are friends of the Lennys. My education had begun, and I was going to learn to surf without actually even paddling out into a lineup.

“Hey AJ, so do you know Drake or the Biebs?” Kai asked me as we drove by Waimea Beach, the Holy Grail of Oahu’s North Shore. I replied with a smile, “Of course I do, we hang all the time when they’re back in the Six.” He laughed as we pulled into Ted’s Bakery for the third time in less than four hours. Ted’s has been a mainstay since 1956 as the North Shore’s answer to a fast food greasy spoon. While waiting in line for a famous coconut pie, you’re likely to hear things like “wanna roll back to the compound?” and “are you here for a midday session?”

While we waited our turn to order, we continued to chat about whatever two people who hardly know each other chat about, ranging from Kai’s hope to have a hydrogen truck to never having to use a water bottle again. There was, of course, the occasional surf jargon, like “Alligators is going off,” and “Leftovers is too sharky,” or how to defend oneself from a shark while underwater (tuck your arm in and punch with your lats).

“Kai finished his ham, cheese ‘n egg sandwich and short rib plate before I even had a chance to unwrap mine. ‘Let’s go find some more surf’ he said to me as I grabbed mine to go.”

Then it was Kai’s turn to order: he went with a ham, cheese ‘n egg sandwich with a side of short rib plate lunch. He finished both his plates before I even had a chance to unwrap mine. “Let’s go find some more surf,” he said to me as I grabbed mine to go. Within minutes, we were back staring at a packed lineup at Off the Wall.


It is often said that in surf shooting, “It only has to look good for 1/1000th of a second.” And so, Kai told me, “Off the Wall is all about moments—95 percent of the time it closes out. You really have to look at a wave like a cinematographer rather than a photographer; it’s not just one frame but a series of frames that show the surfer, the wave, and the ride.” That being said, we turned around and headed back to his truck. “Pupekea, Off the Wall, and Backdoor are too slammed. Let’s try Rock Pile, AJ! It’s like trying to find the skate park, but the skate park moves every day!”

What brings a Canadian sports photojournalist used to shooting hockey and baseball games across this blue planet to pair up with a quickly rising surf star on the shores of paradise? Opportunity.

Kai takes time to give back

RICHARD HALLMAN While indelibly inscribing himself into sup history, Kai takes time to give back to a future generation of paddlers with his Positively Kai event held each August during the Naish Gorge Challenge, hosted by the Big Winds Shop, Hood River, Oregon.

I’ve traded in my winter boots for flip flops, my winter jacket for a pair of board shorts, my for, my daily yahoo fantasy NHL roster changes for daily buoy reports, snow for sand, ice for surf, and my studio in downtown Toronto for a writer’s cabin on the side of a volcano. Why? Easy: for a journey where the unbelievable becomes a reality right before my very eyes. To literally go where the waves take you. To live out of the back of a car. To island hop. To live the life of a professional waterman, if only for a few months. Or at least live the life of a photographer just trying to keep up with one.

No story of Kai Waterman Lenny (yes, his middle name is actually Waterman) would be complete without knowing where he came from. Martin Lenny moved from Santa Barbara to the North Shore of Maui during the windsurfing crazed early ’80s with a girlfriend and $3,000. He quickly found a home and, more importantly, a community around the small surf/hippie town of Paia. Before long, the girl was gone, the money was gone, and all he had to show for it was an AMC Rambler that couldn’t reverse. Like all great transcendental stories, he shared a room with a mate and had just enough money to pay rent and put gas in the Rambler to get to the beach so he could ride some waves.

Kai Lenny and Molly Payne

Home turf with girlfriend Molly Payne, a waterwoman in her own right.

Then boy met girl, they fell in love, called Maui their home, got married, had kids and now live a life on the water as much as on land. That woman, the matriarch, is Dr. Paula Lenny, who recently retired after a successful 25-year career as a physician on Maui. She’s the daughter of a Navy fighter pilot, and she moved around a lot during her childhood. She studied medicine at the University of Oregon before taking a vacation to Maui to surf, when fate intervened and a random meeting at the post office forever changed her life. That was in 1988. She and Martin were married in 1990, and the rest is history.

Kai was born in 1992, and his brother, Ridge—who will be a sophomore this coming fall at the University of Southern California—came along five years later. For much of their childhood, Martin managed a popular, exquisite restaurant in Paia called Mama’s Fish House. He’s now in real estate, and he is often seen on his laptop wherever there is wifi and a table to work on. Recently retired Dr. Paula Lenny was in Occupational Medicine on Maui for the past 25 years.

“You have to do what others are not willing to do to succeed” -Robby Naish’s words to Kai when Lenny was just 14 years old

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MESSIER Stoked at where he’s already been: Kai is not so focused on the future that he can’t occasionally glance back.

From the 1930s wooden longboards that hang from their ceiling to the many paintings and photographs that adorn their walls, one can’t help but feel the surfing mana that is present and watching over those who inhabit the Lennys’ Spreckelsville beach home. Mana is a Hawaiian word of supernatural origin that is said to have influence and/or authority over all. There are two ways to achieve mana: through birth or warfare. Kai gets his from both—from the love and strength of his parents and from the epic battle he wages out at Peahi.

Kai began surfing at 4 years old when most other kids were in preschool. He was windsurfing at six, sup’ing at seven, and foiling, towing and kiting before his 10th birthday. When most kids were sneaking into a matinee double bill, Kai had already competed in the M20 (the 32-mile race across open water between Molokai and Oahu) on prone and then on standup, and he was charging out at Jaws when most of the other kids were just getting driver’s licenses.

The night before we went for my first Jaws session, I spent a few hours with Kai as he prepped his quiver of boards for the next morning. We made our way to Matt Smith’s (Captain of the Alexandria, Kai’s safety boat) house to load the boards on the boat, and it was then that I was introduced to Robby Naish. Robby made a joke about my being there, and Kai quickly responded with a quote that Robby told him back when he was 14: “You have to do what others are not willing to do to succeed.”

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Kai got his first pro deal with Naish boards at age 9. By 12, he was part of the Red Bull team. At 17, fate sent him in another life-altering direction. While in Sylt, Germany, for a windsurfing competition forecasted to have no wind (meaning no competition), Kai decided to travel half way across the world to enter the biggest event in the sup world: his first BOP California (otherwise known as the Rainbow Sandals Gerry Lopez Battle of the Paddle). He finished fifth, racing against older and more experienced competitors. It was a new beginning.

That is why Kai is a modern-day renaissance waterman. He is smart, talented, determined and incredibly humble for someone who has achieved such great success at the young age of 23. His success also has come on the shoulders of others, and as Kai put it on his Instagram, he has “a supporting cast of superheroes” that help pick him up when he is down and push him to heights never imagined.

To think that I was allowed to be part of that cast, to be invited inside their home within 24 hours of my arrival, is one thing—but to be in the water at Jaws over eight different sessions this past January is something that most will never get the opportunity to do. As a photographer, I was given unlimited access to a dream studio in a flawless setting, and as a journalist I was given a cast of characters to bring it to life.

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A few days before I left to reflect upon our past 10 weeks together, I sat down with Kai in his apartment above his parent’s garage. Kai couldn’t be more comfortable. He’s sitting on his couch resting his new Naish square board on his legs running his fingers over the fins or the rail of the board—for two hours he doesn’t stop caressing the board is in his lap—the AC wall unit is running on high, and Radiohead plays in the background.

AJ: When we were on Oahu together, I couldn’t help but notice that music plays an important part of your life.

Kai: I love all music, and it changes with my mood. Like this Radiohead song: sometimes I find their music too quiet; I like to get pumped up to music. If it pumps me up, I can visualize with it. Right now I am listening to the new Rihanna album; I think “Desperado” would be a song for Jaws. It starts out slow and then builds, just like riding Jaws.

AJ: When you left the truck to go check out Off the Wall, I had a look at your Jaws Spotify playlist.

Kai: (laughing) So you were creeping on my phone? That’s all right! Yeah I have a lot of Nirvana, Foo Fighters, Smashing Pumpkins, and gangster rap on it. I like music that pumps me up.

AJ: What’s the best song on that playlist?

Kai: I love them all, but how good is “Gimme Shelter”? It’s such a great song because it doesn’t even sound like your typical rock song; it could cross over into a few different music genres.

Chasing Kai 4


  • “Tongues” Joywave ft. KOPPS
  • “Fly Away” Lenny Kravitz
  • “Kings Never Die” Eminem
  • “Life” Big Krit
  • “Gimme Shelter” The Rolling Stones
  • “Still Breathing” Dig the Kid
  • “Lithium” Nirvana
  • “My Hero” Foo Fighters
  • “I’ll Stick Around” Foo Fighters
  • “Ambition” Wale
  • “4-3-2-1” Manafest
  • “Truth Is” Ambitious Zoo Music
  • “Can’t Go To Hell” Sin Shake Sin
  • “Monster” Meek Mill

AJ: What was it like growing up in the surfing tribe on Maui?

Kai: I never actually felt like I fit in with the surfing tribe on Maui. I always surfed, but…it was only in the past few years when I started to surf out at Jaws that I slowly became part of the tribe. It was pretty cool when I was out at Mavericks a few weeks ago with Albee (Layer) and Tyler (Larronde) and they called us the “Maui boys.” A few years ago, I probably wouldn’t have been called one of the Maui boys.


AJ: What is with you and all the other Maui boys and this obsession with Jaws? I mean, you cancelled a trip to stay on Richard Branson’s island in the Caribbean because there might be a Jaws swell.

Kai: It’s my favorite wave in the world. Surfing Jaws is fun to me. It’s a beautiful wave, isn’t it? The ehukai is what I love about it. There is a spiritual side to being out at Jaws that I don’t feel exists anywhere else in the world. It only occurs a handful of times a year, and it just happens to be in my off-season, so I want to be out there for every swell.

“Kai decided to leave Germany, travel half way across the world and enter his first BOP, finishing 5th against older, more experienced competitors. It was a new beginning.” -AJ on how, at age 17, a windless windsurfing competition triggered a new direction: sup racing

AJ: You first hydrofoiled out at Jaws at the age of 16, and was it by chance or plan that Laird was with you?

Kai: When I got the call to go to Peahi when I was 16, it was because of Laird Hamilton and Dave Kalama that I was able to go out there on the hydrofoil. The only way my parents would let me go was with their permission—and even better if I went with them.

AJ: How did you develop your approach to surfing out at Jaws? You usually have a safety boat with at least a crew of two, a few video and stills guys tagging along, two or three jet skis, and a spotter up on the cliff every time you go out there…that can’t be cheap.


GLENN DUBOCK: They use to ride on the heels of Danny Ching and Jamie Mitchell. Now the wolves are chasing the cubs.

Kai: Especially this winter—but why not invest in something that you love? I have always been the most prepared in everything I do. So from day one I wanted to make sure that if I went out there, I had the right support staff. I also have Don Sheer [helicopter] on call every time we go out, so he can be there within 20 minutes of anything occurring. I also carry extra boards, paddles, leashes, cartridges, food [mostly Taco Bell burritos] and drink [Red Bull], so there is no reason that I, (or anyone who’s with me) can’t stay out as long the waves and light allow. I don’t gamble unless I know I have an opportunity to win.

AJ: It’s almost like a triangular safety net: Victor Lopez on the jetski as the point, the safety boat in the channel, and your father on the radio up on the cliff—with you in the middle of it all. Does it help you, knowing that you have that team around you at all times?

Kai: Jaws is the gnarliest, most dangerous wave in the world, but in the same breath it’s almost the safest because of what we have created out there for support. So yeah, the fear factor usually doesn’t play into it, but I don’t know if it ever did.

AJ: What do you think of all the traffic out at Jaws these past few sessions? Boats were complaining about the other boats, the photographers were complaining about all the jet-skis, and the surfers were complaining about all the surfers. One day there were well over 60 surfers in the water with 10 boats and 20 jet skis. Does that bother you?


HALLMAN (Below) Positively Kai Day with Gerry Lopez at the Gorge Challenge.

Kai: No, not really. I mean, I only worry about the surfers and getting my waves and not poaching on someone else’s. Every wave I take, my intentions are to make that wave. Some surfers out there have no idea how it’s going to end up, good or bad, so they are attempting waves that they shouldn’t and won’t be able to catch, and other guys are passing them up because they don’t want to snake their wave. And then no one rides the wave.

AJ: What is it like having Surf Royalty as part of your team?

Kai: Sometimes I forget just how lucky I am to have all these people in my life. I’ve got the best guys on the planet watching my back. Victor [Lopez] is great: he’s easy to talk to and he gives me little tips here and there. He tells me to go outside or to get my standup and go out and catch the biggest wave. He motivates me. Dave [Kalama] knows what I am trying to do out there, and there isn’t one person on this planet who can give me better advice on surfing Jaws. He has told me things that it will take others a lifetime to figure out on their own. I only know because Dave told me personally.


FRED POMPERMAYER Eyes wide open during the Day of Days, January 15th, 2016. SERVAIS (Right) Finding sanctuary with Molly on the North Shore prior to his next heat at last year’s Sunset Pro Standup World Tour stop.

AJ: Have you intentionally followed in Laird’s footsteps of being an all-around waterman, or was it something that just happened?

Kai: I definitely took inspiration from Laird growing up and always dreamed of becoming an ultimate waterman. I can’t imagine giving up one sport—only because they’re all so different in the approaches to riding waves.

AJ: Laird has said that the day they surfed 100-foot waves off Maui he was glad no one was there to record it. With the entourage that you have following you these days, do you ever feel the same as Laird?

Kai: In 2006, Laird rode a 100-foot wave known as Egypt’s that was actually right outside of my house. They call it that because when the wave gets that big it looks like pyramids in the ocean: perfect A-frame peaks. I wish someone recorded those waves that he rode because I remember watching it from shore, and they just looked like they were on another level. But for me personally, I like my waves to be recorded any which way.

Then I can relive those experiences and see what I could do to improve. Truth be told, not everybody would really believe you if you said you rode a 100-foot wave unless you have proof, which doesn’t really matter but is kind of like the classic saying: “If a tree falls in the woods and no one’s there to hear it, did it really happen?”

AJ: That being said, was Aaron Gold’s wave on January 15th, 2016, the biggest you have ever seen surfed? And how does it compare to those that Double D [Darrick Doerner] and Laird made famous at Jaws back in the day?

Kai: January 15, 2016, was by far the biggest day in paddle surfing history—bar none. Aaron Gold’s wave was so big and so gnarly that a few years ago it would have been considered impossible and a tow wave only. Just like life, big-wave surfing is constantly evolving, and limits and boundaries that I thought were once impossible are becoming normal. I can’t imagine that anyone ever thought we’d be paddling into the waves we are now when I first started surfing the place.

AJ: Do you find it difficult to surf smaller waves after the past month out at Jaws, Waimea and Mavericks?

Kai: Not at all. I love all waves, especially little waves. I am fortunate to have all these different boards and a skill set to match any wave anywhere in any condition, and that’s what I love about where I am in my life and my career right now.

AJ: You have been a runner-up at the world championship in kiteboarding and a world champion in sup—but you started your professional career in windsurfing, and now it looks like you are transitioning into the world of professional surf. If you had to choose, which one do you prefer?


SERVAIS Physically, mentally, emotionally, it’s all about maintaining speed. (Right) Photo composite by AJ Messier, with illustration by Joe Paonesa.

Kai: Why do I have to choose? If I get my way, I will never have to choose. The actual definition of surfing is riding ocean waves on a special board. Nowhere does it say one board or another. I just want to ride waves, however that may be.

AJ: Do you feel pressure to try your luck on the pro surfing tour?

Kai: No, not in the least. I put pressure on myself to be the best at whatever I do, and in order to do some things I need to train or I cannot be my best [in others]. For example, I cannot be the best in sup races if I don’t train; and if I am training, then I don’t have time to do anything else. Surfing is the core to everything I do. Surfing helps me get better in all my sports.

AJ: How do your sponsors feel about you surfing Jaws?

Kai: There is no contractual obligation to surf Jaws. It’s something I love, something I look forward to doing in the winter during my off-season. It’s only during the past two years that I have gotten so much attention surfing out at Jaws. Now the sponsors are all on board and love the fact that even in my off-season I’m still out there charging and getting noticed.

AJ: You said to me that once you knew how to win, what it took to win, that it was largely up to you to do it again.

Kai: The greatest challenge to winning anything is doing it for the first time. Once you do it, you have this formula in your head on how to approach things. Winning the first time gives you confidence, and confidence allows you to win. Without it there’s no way you can be a great champion because you have to push yourself mentally and physically.

AJ: Where do you see yourself in a year, or in five?

Kai: Hopefully doing the exact same thing, but maybe I’ll have a house up in Kula as well. Kelly Slater can do whatever he wants for the rest of his life: that’s sick! That’s what I would like to be able to do, but who wouldn’t?
AJ: That being said, you made The SUP Movie last year with Poor Boyz Productions. How did that come about?

Kai: I had the initial idea to do a progressive film based on the current state of standup paddling. Johnny and my dad helped me reel it into what it is now. The premise of the film was to keep it light and simply to motivate you to go sup.

AJ: Do you ever just chill out, sit down and actually watch a movie?

Kai: I can’t really sit still for long. I tried to learn to play the guitar, but I couldn’t sit still long enough. I like the challenge, but the static nature of the process was not for me. I love to draw, and I love to design.

AJ: I remember your father telling me a story about when you were a kid and you would draw all of your windsurfing sails. Do you still have that passion?

MESSIER Letting Go: You’ve got to know where you are at all times at Jaws, otherwise you’ll jump for joy after the ride of your life, only to land in front of a west-shifting set and a two-wave hold down

Kai: I have the passion, just not the time. I have a great relationship with Naish boards that allows me to work with them on designing my boards. I would love to have my own board-shaping space one day where I can relax and just get away and design.

Maybe one day. I think I would find it therapeutic when I am out of the water; it would keep me connected to the water in some way. Sometimes I like to feel the rail of the board and imagine how it would cut through the water.

AJ: You check your heart rate every day when waking up. What have you learned from that?

Kai: Two days after I surf Jaws, my body crashes. I can surf it or anywhere the next day without feeling it, but on day three my body wants to shut down and I have to listen. Jaws isn’t as much physical as it is mental. A full day out at Jaws is like reading the four Lord of the Rings books back to back. I compare it to being in survival mode all day. Whereas, sup racing is a much more vigorous workout on your body.

AJ: When do you find time to do the mundane aspects of life, like grocery shopping?

Kai: I don’t. That’s why I live above my parent’s garage. If you have a look in my fridge, it’s empty. If I had to, I would eat out all the time, or I would go and buy prepared foods. Kinda like we did when we were on the North Shore. I’d go to Ted’s all the time. All I want to do is surf from dawn until dusk, and then eat when I am done. I don’t have time to cook; that’s an hour I could be surfing.

AJ: You seem to be someone who really embraces everything you do, like you’re actually living in the moment and loving every second of it. Is that true?

Kai: I almost feel that I do live in the moment so much that it’s actually bad. When I’m racing sup, there is nothing else that I think about. Right now it’s big waves, and that is all I am thinking about. I have dreams about surfing Jaws. People say they are living in the moment, but I don’t think are actually, because it’s way more stressful. It makes it hard to have a rest day; if it’s good outside, it’s gotta be good for something! -Kai

As I got back into my seaweed-smelling rental car, something came over me. All of a sudden, I understood what it was all about. Something about it had gotten a hold of me: I knew that I just couldn’t leave in two days with another Jaws swell expected that same day. I wanted to be up at 4 am to go down to the harbor still in the dead of night. I wanted to be on the Alexandria as it approached Jaws just as the sun crested over Haleakala. I wanted to hear about buoy readings and swell direction.

There was something spiritual about the whole experience with this thing called Peahi that made me want to do anything and everything I could for just one more session. Without even thinking when I got into my car after the interview, I called and changed my flight by one day—just for another 24 hours with the possibility of one more chance at seeing the beauty of the wave they call Peahi.

Martin had told me in one of our earliest conversations that he and Paula had done their best to give Kai every opportunity to make the most of his passions and his opportunities—however it is Kai’s skillset, his determination, and his charisma that can make him the next face of whichever sport chooses. Whether it be prone surfing, suping, tow-in, kiting or windsurfing, Kai will determine his path on the wave; all he asks is the opportunity to choose.

As each day begins, Kai wakes up, makes his bed, checks his heart rate and figures out which board in his arsenal will be ridden that day. He’s at an incredibly beautiful place in his life, and it’s because he deserves it; he’s earned the right to do whatever he wants to do.

No matter what board he chooses to grab, no matter if it’s at Jaws, Waimea, Mavericks, Cortez or his home surf break of Hookipa, he’s afforded himself the option to do all, or to do none. From the start of this story, there was one underlying theme to Kai’s career and the direction it has taken: it has grown organically and will continue to do so. His sponsors have always been supportive, and why shouldn’t they be? Kai has found his greenroom, and success continues to follow him wherever the wind blows.

But there will always be one thing constant in his life, and that is his love affair with what many know as the most ferocious wave in the world: Jaws. Some say Peahi is like a mistress who could stop by at any time. You can follow the swell and buoy reports all you want, but until she’s actually knocking on the door, you can never really count on her. But when she finally does arrive, you always answer….

Willie Nelson, a long-time resident of Maui and neighbor of the Lenny family has said: “A friend of mine from Austin, Texas, once said, ‘Find something you like, and let it kill you!’” I think there is some poetic beauty in dying for something you love, but it is much more beautiful to love something you live. Kai is doing that every day. Just don’t ask him to get the groceries. –AJ Messier

(c) 2017