School engagement has a powerful influence on youth development. Youth who fail in school are at significant risk for a host of subsequent psychosocial outcomes, including substance use, risky sexual behaviors, gang involvement, and increased contact with juvenile justice authorities. Although school engagement is an important determinant of key developmental outcomes, few studies have adequately considered how polyvictimization may not only compromise school engagement but also negatively impact psychological functioning, lead to negative peer affiliations with gangs, thereby subsequently increasing the risk for drug use and subsequent juvenile justice involvement. In addition, no studies have considered how key factors such as age, gender, race/ethnicity and parenting styles may moderate those risk relationships. Based on the existing empirical literature and several unifying theories, we present a conceptual model that documents pathways from polyvictimization to multiple youth problem behaviors, with school engagement as a key mediator. This review is intended to help guide future research in these areas. We conclude with recommendations for school-based interventions and future research based on this innovative model.