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While determining risk and protective factors for juvenile delinquency and crime has been critical to the development of prevention and intervention strategies, we question the utility of classifying youth as “at-risk” based primarily on arrest and/or conviction record. Much research highlights how minoritized youth, especially Black and Latine boys, are more likely to be labeled “at-risk” if criminal history is used as a factor, because of increased involvement in the criminal-legal system. Using the Pathways and Project on Human Development in Chicago Neighborhoods datasets we compare outcomes for youth, examining whether there are significant differences between those officially classified as “at-risk” and those who are not, controlling for demographics including gender, race, ethnicity, and immigrant status and key covariates of crime and delinquency. We conclude with recommendations regarding the use of labels that tend to differentially impact minority youth.