This article presents a holistic conception of psychopathy inspired by phenomenological psychopathology and compares it with the mainstream nosographic diagnosis (Schneider, Cleckley, Hare, and Cooke). The article illustrates how a structural-phenomenological approach enhances the investigation of psychopathy. An epistemological discussion of the concept of emotions reveals that psychopaths are competent at managing emotional stimuli, which bestows a psychological advantage upon them. More specifically, a reflection enlightened by the contributions of phenomenological philosophy on empathy and sympathy clarifies the presentation of “psychopathic being-in-the-world.” Starting with the tension between clinical practice and criticism of the dominant diagnostic scales, this article considers the “essential characteristics” of the psychopathic disorder to be: reification of the alter ego without an ego-related disorder, emotional coldness as it provides adaptive benefits, and empathic skills without sympathy.