Timothy is 12 years old and in the middle of his seventh-grade year. The novel is comprised of fifty-two weeks of his journal entries, which he is required to write as part of his punishment for stealing a wallet to pay for his infant brother Levi’s expensive medicine. In addition to keeping the journal, Timothy attends weekly meetings with his parole officer, James, and his court-appointed psychologist, Mrs. Bainbridge. His movements are also restricted, as he is allowed to leave home only for school and his meetings. 

Initially, his relationships with James and Mrs. Bainbridge are somewhat antagonistic. Timothy’s first few journal entries are terse, and he calls them idiots for asking him what he was thinking when he stole the wallet. Desperation, not rational thought, drove him to steal the wallet. He was caught within a day and a half, the medicine was confiscated, and Timothy was taken to juvenile detention. He realizes in retrospect that he made a bad decision but resents that James and Mrs. Bainbridge fail to understand what motivated him. As he continues to interact with both, however, they come to empathize with his predicament and help him beyond the boundaries of their job descriptions.

Timothy’s father abandoned the family shortly after Levi’s birth, and his mother’s income is not sufficient to cover the high cost of Levi’s complex medical needs.