Psychopathic traits are typically associated with antisocial and offending outcomes. In contrast, resilience (adaptive functioning despite risks) has been found helpful for pursuing positive outcomes (e.g., desistance). To determine the relationship between psychopathy, resilience, and antisocial or offending outcomes, two studies were conducted using two diverse samples: young-adult university students (N = 488) and youth offenders (N = 1,354). In the student young-adult sample, resilience mediated the relationship between psychopathy and antisocial behaviour. In the criminal youth sample, psychopathy had a stable relationship (i.e., consistent predictive validity) with offending over time; resilience was dynamic, its effect deteriorating over longer periods. Agency-related (internal) resilience was found to be more prevalent in females than males and significantly predicted desistance. This runs counter to relational-cultural theory, given that Social-related (external) resilience did not predict desistance in females. Future research should continue to examine gendered effects of internal and external resilience traits.