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In 1999, two students, Eric Harris and Dylan Kleobold, armed with guns and explosives killed 12 peers, one teacher and wounded more than 20 others before taking their own lives. Since that date, society has sought to understand what drove these young men to commit such an act of hate and violence as well as the copycat school shootings, cult fascination and fandom associated with the perpetrators. In this paper, I discuss an offender on licence in the community who developed an obsession with the perpetrators and narrative of the Columbine Massacre alongside expressing an interest in participating in violent Islamist extremism – the use of violent tactics for achieving perceived Islamic goals. Furthermore, I explore my counter-transference as a psychotherapist conducting a risk-focused therapeutic intervention with this personality-disordered man. This paper will highlight the importance of using a psychoanalytic perspective to explore the link between an individual’s psychopathology and their fascination with the Columbine Massacre. It will also provide useful reflections for understanding the unconscious appeal of violent extremist narratives and ideologies.