This study on the psychoanalytic conceptualisation of psychopathy reviews psychoanalytic considerations of anti-social/psychopathic disorders. The researcher questions whether psychopathy is particular to one psychoanalytic structure (neurosis, psychosis, and perversion), an undiscovered separate structure with an internal logic of its own or a universal symptom that crosses all three possible structures. The aim of the study is to gain a theoretical understanding of psychopathy so that psychoanalysts who direct treatments with psychopathic subjects may be better informed. The researcher screened a population of ex-offenders using the Self-Report Psychopathy Questionnaire – SRP-III (Paulhus, Hemphill & Hare, 2009). High-scoring participants were invited to participate in a psychoanalytically informed interview. Participants were encouraged to speak freely while the researcher listened with a free-floating attention. An adapted thematic analysis was employed for the organisation and management of data which was then subject to a psychoanalytic discourse analysis allowing for the broader assumptions and meanings of Lacanian structural theory to be considered. The study found that the participants who scored greater or equal to 3.375 on the SRP-III scale had psychotic structures evidenced by their discourse and the positions they assume in relation to others. The researcher considers the cases of psychopathy detailed in this study as non-delusional, un-triggered psychoses: ‘ordinary’ (Miller, 1998) psychoses in which subversive and violent acts serve to stabilise a psychotic structure. The findings indicate that psychoanalytic work with psychopaths is viable based on a sinthomatic solution.