Jamie O’Brien is about as seasoned as a Pipeline veteran can be. John John Florence once said O’Brien was the best guy out there, which is saying a lot. Every winter, almost without fail, J.O.B. is on some of the best waves—if not the best—of the season. He’s won two Wave of the Winter awards, so Red Bull sat down with him to do a little side-by-side comparison of the two waves that netted him a cool $50,000 in total.