Winston Loathington III is the main enemy of Blake and Beef. He is a transfer student from the Harvard Boys Academy, and moves to OceanRug after his parents decide to re-locate to the West Coast. He is the head of the debate team, and loves to ruin everything for Beef and Blake. He manages to steal Laura from Blake, as she is instantly attracted to his attitude and money. He is best friends with his roomate Xavier Rutherford IV and is constantly demanding things from his personal butler, Jeeves.