Kai Lenny has tamed waves, wind, and water since he was just a boy.
The son of ocean enthusiasts who moved to Hawaii as newlyweds to be nearer the water, Lenny is the Swiss Army Knife of watersports. “My favorite thing in the world is riding a wave,” says Kenny. “So as long as I’m riding a wave, I’m happy.” He was dipped into the Pacific during his first week of life and learned to surf at three. A natural-born rider, Lenny learned to windsurf at six, stand-up surf at seven and kite surf at nine. One of the world’s most complete watermen, Kenny does not specialize in one discipline. “All of my sports are surfing based,” says the tanned and talented Hawaiian. From kiteboarding to windsurfing, stand-up paddleboarding [SUP] to big wave surfing, the 26-year-old does it all – and does it well.
Is there anything Kai Lenny can’t do? He has completed the grueling Molokai-to-Oahu paddle several times. A veteran of the Professional Windsurfing Association World Wave Tour, Lenny has won the SUP world title eight times [and counting] and was runner-up at the 2013 Kite Surf World Championships. In 2016, he won SUP Awards for Top Male Paddler and Best Performance. The following year, he won the World Surf League Sunset Open in Oahu, one of the most hotly-contested events in surfing.
Molokai to Oahu – better known as M2O – is the most prestigious event in stand-up paddleboard racing. A test of pain as much as paddling skills, M2O is a 32-mile journey across the 2,300-foot deep Kaiwi Channel – the Channel of Bones. One of the world’s most treacherous bodies of water, it connects the islands of Molokai and Oahu. Stand-up paddle racing is a challenging sport made all the more difficult by ever-changing water, current and wind conditions. M2O is one of the most rigorous races in the world. In 2016, Lenny posted his first win there, crossing the Molokai Channel in a world record time of 4:07.41. “This is by far the hardest event I have ever done,” said Lenny after beating his nearest competitor by more than 33 minutes.
Kai Lenny — whose middle name is Waterman — was born October 8, 1992, in Maui. The older of two sons born to Paula, a physician, and Martin, a realtor, Kai has always been around water. “Anything that involves the ocean, I’m game,” says Kenny. Raised on the swell-rich paradise of Maui’s northern shore, Lenny grew up around some of the most famous watermen in history. His “uncles” include Robby Naish, Laird Hamilton, and Dave Kalama. A 24-time world champ who won his first title at 13, Naish taught Lenny to windsurf when the boy was nine. Hamilton and Kalama are legendary big wave veterans who pioneered tow-in surfing, a revolutionary technique that allows surfers to catch giant, fast-moving waves by jet ski or helicopter.
In Hawaiian, Kai means Sea. In the West African country of Sierra Leone, it translates to King of Kings. And in the Frisian language, Kai means warrior.
Kalama and Hamilton have ridden the largest ocean waves in recorded history. Their favorite surf spot is Peahi – better known as Jaws — the most famous big wave on Maui. An angry wall of water that moves faster than a freight train, Jaws is a wave as daunting as Mount Everest. The glassy, sapphire blue barrel has faces that can top 80 feet. Kai Lenny has been riding Jaws since 16, when Hamilton first took him there. While dropping into a wave as tall as a skyscraper, Hamilton offered the teen some valuable advice: “Just don’t fall.”
Laird calls Lenny the Renaissance Kid because he is the first of his group to pursue multiple disciplines. Kalema appreciates the youngster – dubbed Aquaman for his modesty and humility. “Kai may not be the most naturally gifted kid in the water right now,” says the former world surf champion who has served as Lenny’s coach. “But by far he’s the hardest working. He has the best attitude. He’s a great kid.”
A celebrity watersports enthusiast, Lenny approaches his craft with a smooth yet calculated intensity that is unmatched by his peers. Disciplined, organized, reliable, friendly, and positive. Lenny doesn’t drink or smoke, a rarity in the board sports culture. “I’m not anywhere close to where I want to be,” says Aquaman. “I feel like the more you learn, the less you know.”
Kai lives in an apartment above his parents’ garage in Spreckelsville, only a stone’s throw from some of the Pacific’s best surfing breaks. He spends most of each day in the water, never dedicating himself to one activity. “Maui goes from glassy to windy and small to giant so quick. So I’ll start off the day stand-up paddling, then, before it gets too windy, I’ll paddle out for a surf. When the wind picks up, I’ll windsurf. Then, if it dies a little, I’ll go out and kite.”
He currently competes in eight sports and uses on- and off-water training to prepare his body for the waves. He hits the gym for an hour three times a week for high-intensity training and uses one sport to train for another. Lenny has measured his heart rate every morning since 2015 and uses the number to dictate how he will train that day. “A lot of it is mental,” he says. “Your heart rate dictates how your body actually feels versus how your mind feels.” While big waves deliver a pounding to his 5’9”, 154-pound frame, Lenny thinks SUP –especially heavy water races – is the most demanding of the sports he competes in. Under Hamilton’s direction, he sprints up sand hills, where a pull-up bar awaits him. Lenny also works hard on maintaining flexibility through stretching and band work.
Never content to stick with the status quo, Kai Lenny has led a resurgence in hydrofoil surfing. Foil surfing is a bit like controlled aquaplaning. A long and hydrodynamically designed fin with wings is fused to the rear of the board, which sits beneath the surface of the water and creates lift. The board is then above water, mitigating the effects of wind and reducing friction. A blend of steel, aluminum, and fiberglass, foil boards can be used to surf, race or just cruise. Because the bottom surface of the surfboard is above water, foil surfers appear to be flying through the air.
In July 2018, Lenny won the M2O race in the first-ever Hydrofoil Division. Carving across the treacherous Channel of Bones at breakneck speed, Lenny completed the Molokai crossing in a jaw-dropping 2:52.48 – nearly 75 minutes faster than his record-breaking run of 2016.