The first chapter introduced readers to Angela Simpson who is an outreach worker for Fifth Street Center. How did she arrive in this position? In this chapter, we learn more about how the center worked with Angela, who many adults saw as challenging if not presenting more serious behavioral issues. This chapter begins with Angela facing a judge in Juvenile Court who uses her authority to address the teen’s problematic behaviors. The chapter then shifts its focus to how a small team of adults work with Angela and her grandmother to turn around the teen’s situation. Readers witness the dynamics of wraparound in which a team of adults combine their strengths in serving as Angela’s principal educational navigators. With this team in place, the judge is willing to divert Angela from detention providing she works with the team in advancing her education and in addressing her conduct. Charley Hanson, who we discover, is a behavioral health specialist with a doctoral degree. He reaches out through the court to Mrs. Simpson, Angela’s grandmother, and indicates that he is willing to create a support system that Fifth Street will tailor to the needs of both Angela and her grandmother. Embedded in the narrative are issues of vulnerability (of the grandmother), the intrusion of the legal system (Judge Williams), and the need to be sensitive to Angela’s background. The readers can witness Dr. Charley Hanson as an advocate for Angela. The chapter shows how Angela’s conduct is a product of complex interacting factors, such as the incarceration of her mother, and the loss of her grandfather. That Charley Hanson is intervening between the court and the kid is salient. His strategy is to accentuate Angela’s strengths, and to disentangle school and education so Angela can benefit from a team of educators who will work with her. Charley does not want to create a new relationship between Angela and her school. Rather, he wants her to enjoy and progress in her education. Schooling and education are different, as Angela discovers.