The purpose of this study is to analyze the relationship between Dark Triad of Personality, risk-taking and counterproductive work behaviort. The study involved 200 people aged between 18 and 51 years, M = 27.69, SD = 9.83, of which 35 are males (17.5%) and 165 are females (82.5%). The instruments used were The Dirty Dozen: A Concise Measure of the Dark Triad (Jonason & Webster, 2010), Counterproductive Work Behavior Checklist - CWBC (Spector, Bauer & Fox, 2010) and RISK-TAKING [JPI: Risk Taking [Rkt] (Goldberg et. al, 2006). The results showed that people who work in non-profit organizations (volunteers), those who have a low seniority in work or who hold a leadership position tend to take more risks than others. Low seniority at work also correlates with counterproductive behaviors. In contrast, no significant difference was observed as far as the other two demographic characteristics are concerned. Moreover, the results show that Machiavellianism is responsible for 16% of the variation of counterproductive work behavior, and risk-taking mediates this relatonship. Narcissism and psychopathy are responsible for 10% and 13% respectively of the variation of this behavior, the mediation percentage of risk taking being 19.2% concerning the first one and 22.4% concerning psychopathy. Given these results, the study can be useful in the organizational field, providing employers with more data that they can take into account when recruiting staff. It can also be helpful when it comes to better employee management, as well as a deeper understanding behind counterproductive behaviors, thus leading more easily to diminishing them.