Youth in the criminal justice system commonly suffer from multiple medical and psychological health problems. Because they likely live in lower socioeconomic environments, the medical care they receive through the justice system might be their only recent medical care and can result in the discovery of health problems or chronic illnesses that must be managed while in the system and beyond. We describe the case of an adolescent diagnosed with a serious chronic disease during his time in an urban detention center to illustrate how health workers and justice staff must use a team approach in caring for this vulnerable population of children. Barriers to appropriate care, including social and systems-level challenges, are discussed. The lessons learned in this case can be applied more broadly to other vulnerable youth populations, including those in foster care and impoverished communities where the primary care pediatrician (or other assigned pediatric specialist) is both the leader of the medical team and an advocate for quality care.