Racial disparities are evident in both educational outcomes and incarceration rates when comparing African American and white youth. It is essential to understand the school-to-prison pipeline and the ways in which school discipline practices and other factors disproportionately affect African American students, limit educational attainment, and increase risk for future incarceration in order to improve students' educational and life outcomes. This study explores how marijuana, anxiety and locus of control interact with school disciplinary practices in pushing students out of schools and into the criminal justice system. Analyses utilizing data from the Woodlawn Study, a longitudinal study of African Americans followed from first grade through adolescence, young adulthood, and midlife (n = 1,242), reveal that suspension or expulsion, frequent marijuana use, and locus of control (males only) all predict criminal justice system involvement above and beyond not graduating from high school, but do not interact significantly. This study offers avenues for intervention to reduce disparities.