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This paper presents a study of the relationship between type of neighborhood socioeconomic context, individual characteristics (individuals are classified by a set of selected key measures of individual dispositions and social situation) and serious male juvenile offending (prevalence and early and late onsets) in the city of Pittsburgh. The analytical strategy may best be described as holistic and epidemiological. The key research question is whether onset and prevalence of juvenile serious offending is invariant by neighborhood socioeconomic context when controlling for individual sets of risk and protective characteristics. The results do not support the notion that neighborhood socioeconomic context has any greater direct impact on the early onset of serious offending. However, neighborhood socioeconomic context appears to have a direct impact on the late onset of offending for those juveniles who score high on protective factors, or who have a balanced mix of risk and protective factors. No support was found for the notion that individual risk characteristics and neighborhood risk are additive. Children and adolescents with high scores on risk characteristics offend in serious crime at a similar high rate regardless of the socioeconomic context of their neighborhood.