The consequences of legal offending and involvement in the criminal justice system are significant and well-established. Research published to date has important implications for understanding the underlying causes behind the perpetration of criminal activity; however, the current body of research is inconclusive and suffers from a lack of integration. For example, though childhood adversity and personality pathology have both been linked to legal offending in numerous studies, there is little research examining these three domains in conjunction. In this study, I investigated the relations among childhood adversity, personality pathology, and adult antisocial behavior to attempt to elucidate the complex pathways that lead to antisocial behavior and legal offending. The study included a wide range of adverse childhood experiences and antisocial behaviors and also used a trait-based dimensional framework of personality pathology, which has many advantages over the categorical models that have been used in most previous studies.ACEs and antisocial behavior were generally associated, but individual experiences and domains of antisocial behavior evidenced patterns that were not apparent when they were characterized as single constructs. Similarly, personality dimensions showed differential relations with antisocial behavior and ACEs. Personality pathology partially mediated the relation between ACEs and antisocial behavior, but personality did not mediate the relation between most pairs of specific variables. Although most of the proposed mediation models were not significant, the results have important clinical implications and suggest directions for future research.