This study examines links between the Dark Triad of personality types (Machiavellianism, psychopathy, and narcissism) and workplace behaviors. The research objective seeks to confirm the relationship between the Dark Triad and several negative behaviors while investigating positive externalities that have not been previously explored. A literature review covers the background of the Dark Triad, instruments that have been used to measure it, and ongoing research streams in the field. The Short Dark Triad (SD3) survey was administered to 142 working professionals and data collected were quantitatively examined using a variety of statistical tools in SPSS. Corresponding results provide additional evidence that the Dark Triad personalities are positively related to risk taking. Additional findings support a previously theorized link between these personalities and a distaste for workplace training programs and, notably, could not confirm other previously supported linkages associating this phenomenon with negative behaviors. By better understanding the strengths and weaknesses of individuals with Dark Triad characteristics, organizations are provided with appropriate guidance to ensure the most beneficial relationship possible for all constituents.