Acrobatic, no-brakes surfer from the North Shore of Oahu; winner of the 2004 Pipeline Masters, a leading figure among a small but popular group of corporate-paid anti-surf-establishment pros; named by Surfer magazine in 2003 as one of the top five free-surfers in the world.
O'Brien was born (1983) and raised on the North Shore, grew up in a beachfront house at Pipeline, and began surfing at age three under the guidance of his lifeguard father, along with godfather and big-wave rider Darrick Doerner. "When I was a kid I'd surf all day, 'cause my dad made me," O'Brien said later of his father, who became his business manager when Jamie turned pro. "He'd say, 'You're not getting lunch unless you surf.'"
O'Brien began riding Pipeline as a pre-teen, and at 16 the wiry blond regularfooter was introduced in an Australia's Surfing Life article as one of three hard-charging "Pipe Groms," along with fellow haole-Hawaiians Jamie Sterling and Mark Healey. The prodigiously talented O'Brien finished runner-up in the menehune division of the 1995 and 1996 United States Surfing Championships; in the World Junior Championships he placed fourth in 1999 and third in 2000.
O'Brien's reputation was founded, however, on his inventive and fearless approach to Pipeline, where he pulled into virtually any tube section ("I get so many barrels there that I get bored"), and launched aerials where other pros looked for a safe exit. His hard-charging style earned him a broken right leg at Backdoor and a broken left leg at Pipeline. In 2003 he beat Bruce Irons to win the 2003 Hansen's Energy Pipeline Pro, and the following year he beat Irons, Sunny Garcia, and Kalani Robb to win the Pipeline Masters.
Beginning in the late '00s, O'Brien recast himself as a rebellious "freesurfer," with a flamethrowing Twitter account that often took aim at the pro tour, and a Red-Bull-sponsored video in which he burns an ASP rulebook. The new O'Brien at times showed a blunt sense of humor, tapped into a long-standing ambivalence about competition held by many in the sport, and won legions of fans. But there were also detractors. "It is not a spontaneous moment," surf writer Teddy Endo wrote on The Inertia website in 2012, comming on O'Brien's rulebook-burning stunt. "It is not an act of rebellion. It is the recreation of the imitation of a symbolic act, a picture of a facsimile, less than meaningless."