Studies of the association between psychopathic traits and prosocial behavior are limited, with explanatory mechanisms of such dynamics being similarly scant within the empirical literature. Using a large sample of people in leadership roles, we explore the associations between the three facets of psychopathy (TriPM, Patrick CJ (2010) Operationalizing the triarchic conceptualization of psychopathy: preliminary description of brief scales for assessment of boldness, meanness, and disinhibition. Unpublished test manual, Florida State University, pp. 1110–1131), and organizational citizenship behavior (OCB, Smith et (...) al (1983) J Appl Psychol 68:653–663). We examine the mediating role of individualizing and binding moral foundations (MFQ, Graham et al. (2013) Adv Exp Soc Psychol 47:55–130) within these relationships. Correlation analysis revealed that boldness was positively correlated with OCB, while both meanness and disinhibition were negatively correlated with OCB. Mediation analysis demonstrated that only individualizing moral foundations (IMF) mediated the relationship between meanness and OCB, such that meanness led to lower IMF and reduced levels of OCB. Our findings signal that lower IMF enables the nefarious behavior of people with darker psychopathic traits, while moral foundations as a whole play no role in advancing the prosocial behavior of people with so-called adaptive psychopathic traits. The contributions of these findings to the literature are discussed. (shrink)