Background Parenting behaviors have been shown to moderate the association between sensation seeking and antisocial behaviors. Methods Data were obtained from the Boricua Youth Study, a longitudinal study of 2,491 Puerto Rican youth living in the South Bronx, New York, and the metropolitan area of San Juan, Puerto Rico. First, we examined the prospective relationship between sensation seeking and antisocial behaviors across 3 yearly waves and whether this relationship varied by sociodemographic factors. Second, we examined the moderating role of parenting behaviors—including parental monitoring, warmth, and coercive discipline—on the prospective relationship between sensation seeking and antisocial behaviors. Results Sensation seeking was a strong predictor of antisocial behaviors for youth across two different sociocultural contexts. High parental monitoring buffered the association between sensation seeking and antisocial behaviors, protecting individuals with this trait. Low parental warmth was associated with high levels of antisocial behaviors, regardless of the sensation seeking level. Among those with high parental warmth, sensation seeking predicted antisocial behaviors, but the levels of antisocial behaviors were never as high as those of youth with low parental warmth. Conclusions Study findings underscore the relevance of person–family context interactions in the development of antisocial behaviors. Future interventions should focus on the interplay between individual vulnerabilities and family context to prevent the unhealthy expression of a trait that is present in many individuals.