Exclusionary discipline policies (Casella, 2003; Christle, Jolivette & Nelson, 2005; Tuzzolo & Hewitt, 2007), academic failure and school dropout are some of the most salient factors in the school to prison pipeline (Christle, Jolivette & Nelson, 2005). While previous research has explored the variability in existing exclusionary discipline policies and identified numerous factors associated with expulsion or criminal justice outcomes among youth, there has been little effort to bring these individual and school level factors together into a single predictive model that is informed by existing criminological theories. In this context, the proposed study will use multiple waves of data from the National Longitudinal Study of Adolescent Health to consider how school discipline policies, demographics, and competing criminological explanations affect the risk of expulsion and then future contact with the criminal justice system. Findings reveal that school-level factors such as severe disciplinary policies, school size, and school type are weak predictors of expulsion and adult arrest. Conversely, measures of social bonding, low self-control, learning, and strain theories show promise in predicting expulsion and arrest outcomes. A history of school disciplinary actions and self-reported delinquency present themselves as the strongest predictors of expulsion and subsequent arrest. Theoretical and policy implications are considered.