Both popular and scientific definitions of psychopathy are far from neutral and could be seen to promote stereotyping. For example, the psychopath is often described as a social predator or cold-blooded beast. Such metaphors might influence how individuals with psychopathic traits experience emotions and social relations, and how they think about their criminal acts. We argue that the mental and contextual embedding of psychopathic behaviours is frequently neglected. Building on a detailed qualitative investigation of the affective, interpersonal and antisocial life of a male adolescent with clear psychopathic traits this paper aims to describe how he positions himself in relation to others. Based on our case materials we suggest that his antisocial behaviour and his emotional and interpersonal functioning bear witness to specific defensive processes, as well as to a psychotic structure.