This is the first prospective study to examine the precursors of child externalizing behavior across three generations of African Americans and Puerto Ricans. Participants comprised a community cohort of male and female African Americans and Puerto Ricans (N = 366, X⁻ age = 29.4 years), who are part of an ongoing study of drug use and problem behaviors, and who had a child. Data were collected at four time waves, spanning the participants' adolescence to adulthood. Questionnaires were initially self-administered in schools in East Harlem, NY, USA (time 1). Subsequently, structured interviews were conducted by trained interviewers (times 2 and 3), and self-administered via mail (time 4). The independent variables consisted of the participants' prospective reports of their (a) relationships with their parents during adolescence, (b) depressive mood and drug use (adolescence to adulthood), (c) relationship with their oldest child between the ages of 6-13, and (d) perceptions of neighborhood crime and deterioration (in adulthood). The dependent variable was externalizing behavior in the participant's oldest child (X⁻ age = 9.6 years; SD = 2.0). Structural equation modeling showed that the parent-child relationship during participants' adolescence was linked with the participants' depressive mood and drug use which, in turn, were associated with the participants' relationship with their own child, as well as with neighborhood crime and deterioration when participants were adults. The participants' depressive mood, and relationship with their own child, as well as neighborhood crime and deterioration, each had a direct pathway to externalizing behavior in the participant's child. Findings suggest that intervention programs and public policy should address parental attributes, neighborhood factors, and, especially, parenting skills, to reduce risk factors for the intergenerational transmission of externalizing behavior.