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Adolescent involvement in the criminal and juvenile justice systems has received widespread attention at national, state, and local levels. Developmental neuroscience has shaped our understanding of adolescence as a distinct period during which young people are at increased risk for a host of problems, especially entrance into the criminal and juvenile justice systems. Overrepresentation of Black and Latino youth, particularly those with disabilities, remains of significant concern. This case study explores the case of a 13-year-old boy, Trey (a fictional name), and his path into the school-to-prison pipeline. The roles of neighborhood, family poverty, parental health, trauma, chronic stress, and attendance to underserved schools are outlined. These factors are connected to Trey’s special needs like trauma, attention deficit hyperactivity disorder, and learning difficulties/disabilities going undiagnosed and untreated within the context of the neurobiological immaturity of adolescence. The extent to which these factors converged to result in neuropsychological impairment is explored. This case analysis focuses attention on implications for research, policy and practice in preventing youth in underserved communities from entering the criminal and juvenile justice systems.