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The majority of research up to this point that assesses the impact of criminal justice involvement on life outcomes, for both juveniles and adults, looks primarily at aggregated general measures of arrest and incarceration that do not distinguish between arrest types. This general categorization may miss patterns and effects that exist for different types of arrest. Using longitudinal data, this article this study compares the effects of drug, violent, and property arrests on educational attainment (high school dropout and college enrollment), and also looks at racial differences in the effects of juvenile arrests, adjudicating between labeling and propensity theories, which suggest different effects of arrest. The results indicate that drug arrest are significantly more damaging to the educational outcomes of youth, especially Black and Latino youth.