The Oakley Wave of the Winter award is given to the surfer who “catches and successfully rides the single best wave of the contest period on the North Shore.” Sunday morning, fellow TOOLS team rider Kalani Chapman surprised Jamie O’Brien with a check for $25,000 for taking top honors with a near-impossible Pipeline wave from December 21st.

“I knew it was a real walled up wave,” O’Brien said. “At Pipe, when you know you’re deep, you usually don’t make the wave. I was so amazed I made the wave. It’s really humbling [to win].”

Gerry Lopez, Pancho Sullivan, Ross Williams, and Shawn Briley judged the event by watching hundreds of submissions over the past four months. “We went back and forth, and finally, after more consideration than ever in years past, we agreed that Jamie’s ride had a bit more time in the tube than Mason’s, and that’s what ultimately tipped the scales,” Lopez said.

Photo: Tyler Rock

“Jamie’s wave just stood out, and even though some of those other waves were 10s, I could look at it and go, ‘Alright, now there’s the Wave of the Winter,’” said WOTW judge Shawn Briley.