The volitional model of Machiavellianism emphasizes that the Machiavellian person chooses to be manipulative. The model is critiqued. An alternative model is proposed, which asserts that the Machiavellian is a person who is unconnected to his or her own emotion, that is he or she is alexithymic. This deficit results in an inability to emotionally connect to others with the result that other people are treated as objects to be controlled to meet his or her self-focused goals. The model was tested on a general population sample of university students. Findings indicate that Machiavellianism was highly associated with alexithymia. In particular Machianvellianism was positively associated with externally orientated thinking and difficulty in identifying feelings. In addition Machiavellianism was positively associated with shame proneness but negatively associated with guilt proneness. The findings are discussed in relation to the role of emotion and the formation of interpersonal relationships, and the concept of volitional Machiavellianism. Implications for the concept of “successful psychopathy” are explored.