Recently, attempts have been made to determine the evolutionary status of psychopathy. However, there is still a gap in empirical literature regarding the connection between psychopathy and fitness. In the present study, we explored the relations between the four-factor model of psychopathy and reproductive success as a fitness indicator in a sample of male convicts (N = 181). Direct relations were analyzed, together with the interaction effects between psychopathy and family risk factors (presence of criminality, substance abuse, and maltreatment in participants’ families). Basic regression models showed that the facet of interpersonal style is positively related to fitness, while other psychopathic characteristics had a negative connection with the criterion measure. Additionally, we found three significant interactions, which further clarified the relation between psychopathy and reproductive success. One of the interactions showed that affective traits can facilitate fertility in unfavorable environmental conditions. Results support a hypothesis of a possible adaptive function of psychopathy, broaden the concept of “successful psychopathy,” and confirm a view of psychopathy as a heterogeneous and complex construct, consisting of facets with distinct content.