He lived in tents, had a trademark African hair, collected 100 wins in his amateur surfing career, and switched feet like no one else.
Kaluhiokalani started surfing in Waikiki but soon felt attracted to big waves on the North Shore of Oahu.
Montgomery Kaluhiokalani, nicknamed "Buttons," was also one of the sport's grand innovators.
The Hawaiian was the first to perform a carving 360 on tape.
Later in his life, the Hawaiian wave-riding legend nearly succumbed to heavy drugs but was able to regain control of his life in 2007.
At 51, he was riding giants at Teahupoo.
Three years after taming the Tahitian beast, Montgomery "Buttons" Kaluhiokalani passed away after a long battle against cancer.
The more footage we see of him, the more we admire his gracious spirit.
"I never went to school. I just went there for lunch. All I did was to surf and skate and surf and hitchhike to the North Shore. And there was no one out there," he once revealed.
Kaluhiokalani dedicated the last years of his life to Buttons Surf School, where he taught kids how to surf. He left this world in peace with himself and with others.
And he will never be forgotten. "Buttons" is one of the stars of the iconic movie "Many Classic Moments."
His infectious smile and raw talent are an inspiration to future generations of surfers.