A very intelligent person, Caswell believes that everything can be planned out and executed as planned, only to be corrected by Mr. Kay saying that not everything goes according to plan. He has a habit (in the original) of saying "to summarize" whenever he makes a final statement on a subject. In the dub, he says "In the end".

Initially, Caswell had pride in being the class rep as he was greatly saddened and disappointed when Yuma was made the class rep instead of him. As a result, he was willing to accept Carlyle Chesterton's offer of becoming the chief disciplinarian just so he can referred to by position name like he did when he was class rep. After a conversation with Yuma while the latter was Dueling Carlyle, Caswell accepts that it doesn't matter what someone is called, but how good someone is at a position.