Born on October 8, 1992, Lenny’s parent’s dipped him in the Maui shorebreak before his first week on earth was complete. His skills as a waterman exploded soon thereafter. Lenny, whose name is derived from the Hawaiian word for ocean, learned to surf by age five, windsurf at six, stand up paddle at seven and kite surf at nine. He had his first sponsor before age 10. Lenny’s mentors include windsurfing legend Robby Naish and big wave greats Laird Hamilton and Dave Kalama. Lenny is already one of the world’s most accomplished watermen.
A runner-up at the Kite Surf Pro World Championships, Kai is a eight-time winner of the SUP (stand up paddle) world title. In 2014 Lenny finished fourth in the grueling 32-mile Molokai 2 Oahu (M2O) Paddleboard World Championships, the ultimate test of pain and paddling. The following year he came in second. After consulting with Kalama, Kai tweaked his equipment, training and race tactics. He trounced everyone at the 2016 race, setting a new world record in the process.
Following in the path of his pioneering mentors, Lenny has been riding Pe’ahi (Jaws), Maui’s notorious big wave break, since he was 16. On May 2nd of this year, Kai won the WSL Big Wave Awards for Overall Performance and XXL Biggest Wave Award for his revolutionary session at Jaws last November. When the Jaws Challenge was postponed due to its monster waves being too large, the “Kai show” began and he served up one of his best performances to date. Lenny stunned the surfing world when he was towed into an absolutel behemouth then airdropped 20 feet coming off a cutback on the lip and stuck the landing.
Bob Hurley introduced Kai as, “The funnest guy I know. Many sports heroes exhibit machismo. Kai exhibits wonder and curiosity. There’s no operations guy, no entourage. He’s happy to be alive.”
“It’ really amazing to be here,” Lenny said. “There’s so many people to thank. It took a village to get here. When I first started surfing, there was that overwhelming feeling of riding waves. For me, it’s always been about riding the waves.” Kai’s inscription read, “believe in yourself.”