Terrence Cutler is a Principal at a middle school in Shelby, NC. He also was engaged to April Buchanon. He is outwardly very outgoing, kind, and friendly. Initially, he seems excited to have a former Major League baseball player like Kenny Powers to be working for him. Even though he is aware of Kenny and April's former high school relationship, he is very trusting, and thus doesn't suspect that Kenny would try to win April back. He is newly into fitness, despite having an average physique, and is seen training for a triathlon. This prompts Kenny to comment that he (Kenny) is a "real athlete", because he plays a sport, and doesn't "train to be the best at exercising". This comment is typical of the bulk Kenny's interactions with Cutler throughout the series. He basically plays the role of unwitting antagonist for the show's first season. While nice and trusting, Cutler isn't above insults and bad behavior himself; as shown when he's in the presence of women while intoxicated; and the fact that he basically gives Kenny a verbal beatdown at the same party. This may indicate that Cutler isn't quite as innocent and naïve as he first appears; he is merely polite and prefers to avoid confrontation, as befits his station as a middle school principal.