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Background & Purpose: There is broad agreement that a connection exists between neighborhood disadvantage and adolescents’ justice system involvement, with much scholarship aimed at elucidating that connection. However, there remains a critical need to further conceptualize the measurement of neighborhood disadvantage. This paper offers an initial exploration of how different operationalizations of neighborhood disadvantage may function as predictors of adolescent police contact. Methods: Using data from Wave 1, Cohort 15, of the Project on Human Development in Chicago Neighborhoods, we used multilevel logistic regression to test and compare models with three different codings of a measure of neighborhood disadvantage and key covariates predicting self-reported police contact. Results: No operationalization of neighborhood disadvantage significantly (p<.05) predicted the outcome in any model. Significant predictors included self-reported illegal activity, peer engagement in law-breaking, substance use, gender, ethnicity, and socioeconomic background. In models where illegal activity was the only covariate, neighborhood disadvantage coded dichotomously at the 90th percentile performed the best (OR=1.67, p=.15). Conclusions: There may be some advantage to using a narrow, bifurcated measure of neighborhood disadvantage. These and prior findings also highlight the need to further understand associations between neighborhood disadvantage, police contact, peer lawbreaking, substance use, and family socioeconomic resources.