The scholarship on political skill documents that it is a social savvy, personal style construct, associated with positive personal and organizational outcomes. However, this study takes a counterintuitive view and demonstrates that despite being a positive resource, political skill also has the potential to be used as a self-serving device to achieve one's personal agendas in the form of self-serving counterproductive work behaviors. Borrowing insights from the trait activation theory, this study demonstrates that a context, high in political perceptions, acts as an incentivized condition for politically skilled people to execute its dark side. The results supported the hypothesis and revealed that under high perceptions of organizational politics, political skill will have a significant, positive relation with self-serving counterproductive work behaviors. The study discusses important theoretical and practical implications of these results and extends the domains of political skill and counterproductive work behaviors.