This study examined the trajectories of delinquency among Puerto Rican children and adolescents in two cultural contexts. Relying on data from the Boricua Youth Study, a longitudinal study of children and youth from Bronx, New York, and San Juan, Puerto Rico, a group-based trajectory procedure estimated the number of delinquency trajectories, whether trajectories differed across contexts, and the relation of risk and protective factors to each. Five trajectories fit the Bronx sample, and four fit the San Juan sample. Differences and similarities were observed. The Bronx sample had a higher rate of delinquency and sensation seeking and violence exposure strongly discriminated offender trajectories. In San Juan, the results were substantively the same. Thus, while the youth lived in different contexts, and the nature and level of delinquency varied across the sites, the effects of most risk factors were more similar than different. (Contains 6 tables, 2 figures, and 8 notes.)