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Despite legal reforms and attempts to reintegrate ex-offenders back into society, considerable social and economic stigma remains for individuals with a criminal record. Notwithstanding the severity of the charge, arrestees continue to experience significant discrimination in the labor market, preventing sufficient reintegration into society and in effect increasing rates of recidivism. Drawing from the seminal findings of Pager (2003) and Western (2002), this current study investigates important factors that can influence ones’ propensity to engage in crime during adolescence, including academic performance in high school, level of self-control, race and gender. Using a structural equation modeling approach and a representative sample 4128 of adolescents in high schools from across the United States with data from the National Longitudinal Study of Adolescent Health, this study found that self-control and academic performance are negatively associated with engagement in property-related and violence-related deviance. Additionally, existing findings about minority-status and gender-status as predictors of a greater propensity to crime were replicated. Assessing these results from a theoretical standpoint, both the self-control theory of crime and the general strain theory of crime were supported for violence-related deviance, while only the self-control theory was supported for property-related deviance and violence-related deviance.