This study examined two theoretical models on the interaction between psychopathy, traumatic exposure, and lifetime posttraumatic stress in a sample of 81 male detainees. In Model1, the interpersonal and affective features of psychopathy were assumed to protect against posttraumatic stress. In Model 2, the lifestyle and antisocial traits of psychopathy were assumed to lead to a lifestyle that increases the risk of traumatic exposure and subsequent posttraumatic stress. The authors found significant negative bivariate associations between Psychopathy Checklist–Revised (PCL-R) total, Interpersonal and Affective facet scores, and posttraumatic stress. Model 1 was confirmed, as they found the interaction between the Affective facet and traumatic exposure had a significant negative effect on posttraumatic stress. Model 2 was rejected. The authors’ findings confirm that the interpersonal and affective features of psychopathy are associated with an emotional deficit and that the affective features of psychopathy are crucial for understanding the relationship between psychopathy and anxiety.