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Using data from the Children of Immigrants Longitudinal Study (CILS), the present analysis is based on data collected from 1992 to 2001 from a sample of first and second-generation immigrants of Caribbean descent (N = 1,139), who resided in Southern California or South Florida when the first wave of the study was conducted. The main objective of this secondary analysis is to determine what variables are more likely to predict susceptibility to delinquency and crime based on arrest and incarceration information provided by the respondents. Results show that 14% of the respondents have been arrested and 9.7% spent time in reform schools, detention centers, jails, or prisons during the five-year period that preceded the third and final wave of the study. Additional bivariate and multivariate analyses show no significant inter-group differences in suspected criminal or delinquent behavior when first-generation immigrant youth are compared to their second-generation counterparts. Findings also indicate that propensity to delinquency and crime is influenced by one’s gender and by early academic performance, composition of the family of origin, current marital and employment status, involvement in religious activities, experience with victimization, and the arrest/detention history of respondent’s family members.