Toby
Toby is a troubled teen whose mother keeps moving him around the country for get-rich-quick schemes. When she fails, she returns to her long list of old flames and lovers, leaving Toby to roll his eyes at her. She doesn't care when those men hurt Toby, and she doesn't stand up for him when they impose their abusive control over their family. Finally, Toby falls in love with literature and writing, but he is deeply troubled and cannot make art.
Rosemary
Rosemary is not a bad person; she is just troubled. As a highly neurotic woman, she deals with intense suffering privately that she does not show to Toby. Her panic is alleviated when she allows herself to "Fall in love" with men who are not right for her, but in secret, she needs mental health and balance. Instead, she often ignores the reality of the situation, allowing situations to become chronically toxic.
Dwight
Dwight is probably not an evil person, necessarily, but he is close. He is violent, and Toby notices that a long time before it is made obvious to him through real violence. He sees it in Dwight's personality, that he's always ready to a fight. Probably, Dwight was physically abused and is in much the same mental turmoil that Rosemary is in. But, because he is an abuse, condescending jerk, he doesn't make situations better.
Geoffrey
The prized son, whom his father picked over Toby. Toby doesn't hate Geoffrey, but when he lives with his older, esteemed brother, he does secretly try to rob him, and it's not hard to see why. Geoffrey got the life Jack always wanted. Although Jack eventually goes to Hill School, he must wonder how he could compete with Geoffrey, who is successful and established, who goes to Princeton of all places.
