The present research investigates the relationship between Machiavellianism, emotional manipulation, and counterproductive work behaviors (CWBs) using a construct replication approach. Sample 1 and Sample 2 were recruited through Amazon Mechanical Turk and utilized different measures to test the hypotheses. Results indicated a positive relationship between Machiavellianism and CWBs, emotional manipulation and CWBs, and an indirect effect of Machiavellianism on CWBs through emotional manipulation. Furthermore, individual differences in personality (agreeableness, conscientiousness, emotional stability, and emotional intelligence) and emotional control attenuated the indirect effect of Machiavellianism on CWBs through emotional manipulation, while self-reported political skill enhanced this relationship. These findings suggest that emotional manipulation is a mechanism through which Machiavellianism is related to negative workplace outcomes, and that personality traits and skills can attenuate or enhance this relationship.