Objectives: School truancy, school failure, and dropout are highly correlated with delinquency and criminality. There are also racial inequalities regarding the relationship between education and crime. The current study asks, “What risk do demographic, academic, and behavioral factors contribute to later adult justice system contact for urban youth residing in Louisiana?” Method: Using administrative data from the Louisiana Department of Education, the Louisiana Office of Juvenile Justice, and the Louisiana Department of Public Safety and Corrections (LADOC), hierarchical, mixed-effects logistic regression models (N = 507,613) explored whether youth later encountered the LADOC and were incarcerated, and whether they committed a violent crime leading to their contact. Results: The most significant predictors of any adult contact with the LADOC were being male (p < .01; odds ratio [OR] 4.74), contact with the state Office of Juvenile Justice (p < .01, OR 3.742), and school expulsion (p < .01, OR 2.46). The most significant predictors of adult incarceration were being male (p < .01, OR 9.932), contact with the state Office of Juvenile Justice (p <.01, OR 4.637), and expulsion (p < .01, OR 2.368). The most significant predictors of contact with the LADOC after a violent crime were being male (p < .01, O.R. 7.726), contact with the Louisiana Office of Juvenile Justice (p < .01, OR 3.606), and being African American (p < .01, OR 2.651). Conclusions: Despite its intent, punishment-oriented approaches such as suspension, expulsion, and the juvenile justice system seem to encourage further deviant behavior among youth. Reform is necessary to decrease adult criminality for those engaging in risky behavior during adolescence. Additional considerations must be made for youth from disadvantaged backgrounds.