The intergenerational transmission of traumatic memory and its link to violent backlash in communities that have suffered collective trauma is a topic well studied in psychology and the peace-building field. However, the question of how the legacies of mass human rights abuses at the level of the state play out in individual perpetrators is an area that demands investigation. In the post-apartheid era, South Africa has witnessed the emergence of different forms of violence, including crowd violence, xenophobic violence, unspeakable forms of rape, and gang violence. This chapter explores the mechanisms whereby youth who have grown up with the legacies of collective violence are primed to become potential perpetrators of crime themselves. Specifically, we take a closer look at perpetrators of gang and domestic violence in the context of a South African low-income community. Drawing on neuroscientific findings regarding the effects of traumatic stress and emotional deprivation on the developing brain, the chapter reviews the neuropsychological sequelae of growing up in an environment where violence has persisted over time and across generations. Hence, the notion of a “victim-perpetrator cycle” is clarified amidst the complex matrix of interacting factors of historical oppression, a culture of violence, and its intergenerational consequences.