Machiavellianism is a psychological construct reflecting individual differences in manipulative and strategic thinking, pragmatic morality, and a cynical outlook on life. A recent stream of research has shown that Machiavellianism and psychopathy seem to be redundant constructs and that measures of Machiavellianism do not correspond well with theoretical expectations. In the present study, I juxtapose multiple measures of Machiavellianism against normal (i.e., the five-factor model and HEXACO) and abnormal (e.g., narcissism, psychopathy, impulsivity, and personality dysfunction) personality traits in an online sample (N = 591). Using Goldberg’s (2006) Bass–Ackwards approach, I investigate whether typical Machiavellian traits can be found anywhere in the construct hierarchy by comparing the levels of the hierarchy with expert-rated five-factor model prototypes of Machiavellianism, narcissism, psychopathy, and external correlates. Our results indicate that measures of Machiavellianism mostly reflect psychopathy and narcissism. The implications of these results are discussed, including what the future may hold for Machiavellianism.