In this study, the author focuses on the exclusionary school and societal practices that route American males from schools to juvenile detention and adult prisons. Well documented are the linkages between these practices and dropping out or early school leaving. Leaving school without a diploma sets youth on a trajectory toward incarceration. Moreover, the disproportionate confinement of African American males in secure juvenile detention mirrors their experiences with school discipline. Given the potential influence of teacher and leadership preparation programs on pre- and in-service teacher and school practices, teacher educators must deconstruct and reverse pathways from the schoolhouse to the “Big House.” As an imperative, teacher educators must explicitly prepare school personnel to understand and address the complex factors that shuttle African American males from schools and into juvenile justice and adult correctional systems. Findings are reported from focus groups conducted with African American male adolescents who dropped out of school and were adjudicated. In addition, recommendations are provided for teacher educators to reverse school-to-prison pathways.