<p>Paternal incarceration history has been linked to a range of negative outcomes in offspring, including an increased risk criminal justice involvement. However, less is known about the mechanisms underlying this association, such as legal cynicism and early delinquency during a critical developmental period. The current longitudinal study examined paternal history of incarceration as a predictor of arrest likelihood in early adulthood, considering adolescent legal cynicism as a mediator. Further, adolescent negative interactions with police was examined as a moderator of the relationship between legal cynicism and subsequent arrest likelihood. Racial and ethnic differences in these relationships were also considered. This three-wave longitudinal study included an analytic sample 4897 individuals who participated in the Future of Families and Child Well-being study, which is a longitudinal birth cohort study. Results indicated that paternal history of incarceration was associated with higher legal cynicism and a heightened likelihood of arrest by Year 22 but was not associated with adolescent negative police interactions. Adolescent legal cynicism and negative police interactions both predicted a higher likelihood of arrest, as well. Indirect effect analyses revealed that paternal incarceration history was associated with later offspring arrest via higher adolescent legal cynicism. Multigroup analyses indicated that the pathways did not differ significantly by race/ethnicity. Overall, the findings highlight the complex relationships between paternal incarceration history, adolescent legal cynicism, teen delinquency, and criminal justice involvement.</p>