Over the past two decades, the number of children with parents in prison has increased substantially. Using structural equation modeling with prospective longitudinal data gathered as part of the ongoing Linking the Interests of Families and Teachers (LIFT) trial, the study tests a theoretical model that examines the direct and indirect relationships between four specific domains (parental incarceration, social advantage, parent mental and physical health, effective parenting) as they relate to youth antisocial behavior in the 5th, 8th, and 10th grades. Across all three grades, the relationship between parental incarceration and youth antisocial behaviors was mediated through a complex set of pathways involving social advantage, parent health, and effective parenting. The models explained up to 60% of the variation in youth antisocial behaviors. (Contains 1 figure and 3 tables.)