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Machiavellianism is characterized by planfulness, the ability to delay gratification, and interpersonal antagonism (i.e., manipulativeness and callousness). Although its theoretically positive relations with facets of Conscientiousness should help distinguish Machiavellianism from psychopathy, current measurements of Machiavellianism are indistinguishable from those of psychopathy in large part because of their assessment of low Conscientiousness. The goal of the present study was to create a measure of Machiavellianism that is more in line with theory using an expert-derived profile based on the 30 facets of the five-factor model (FFM) and then test the validity of that measure by comparing it with relevant constructs. Previously collected expert ratings of the prototypical Machiavellian individual on FFM facets yielded a profile of 13 facets including low Agreeableness and high Conscientiousness. Items were written to represent each facet, resulting in a 201-item Five Factor Machiavellianism Inventory (FFMI). Across 2 studies, with a total of 710 participants recruited via Mechanical Turk, the FFMI was reduced to its final 52-item form and was shown to relate as expected to measures of Big Five personality traits, current Machiavellianism measures, psychopathy, narcissism, ambition, and impulsivity. The FFMI is a promising alternative Machiavellianism measure.