Contemporary psychoanalytic ideas have been slow to migrate to child and adolescent treatment programs. Meanwhile, thousands of children in the United States whose legal offenses are rooted in emotional difficulties are detained, and often retraumatized, in correctional facilities where they do not receive mental health care. Reluctant to allow this fate to befall a 14-year-old patient who vandalized my office, it became necessary to explore an alternative treatment model for his delinquent behavior. My treatment of Angel, and the contemporary theory behind it, illustrates an alternative mode of treating delinquent behavior in adolescents. This article argues that a more rigorous consideration of, and a more psychologically enlightened response to, the emotional experiences and meaning of adolescents' behaviors increase the likelihood of resuming normal, healthy development in young people who are otherwise often retraumatized in and by more traditional treatment settings centered on behavior modification techniques.