In light of the growing interest in the dark side of organizations in mainstream research, two concepts related to organizational behavior and management literature have received attention in recent years: counterproductive work behaviors (CWBs) and dark triad traits (Machiavellianism, narcissism, psychopathy). It is only natural that current studies have tried to find a relationship between them; however, their findings were not impressive. This paper contends that the reason for the weak relationship found between the dark triad traits and CWBs is perhaps that studies have ignored some important mediators and moderators in this relationship. This conceptual paper presents a model of this relationship, arguing that perceptions of organizational politics and perceived accountability are two mediators of the relationship between the dark triad personalities and CWBs. The model also advances four moderators: first, political skill is expected to moderate the relationship between the two mediators and the dark triad. Second, three organizational moderators (organizational transparency, organizational policies, and organizational culture/climate) are expected to moderate the relationship between the two mediators and CWBs. After presenting the model and the resulting propositions, the paper concludes with suggestions for future research regarding the proposed model.