Informed by Galtung (1969), Anderson (2012) and Wacquant (2001), this paper argues that a lifetime of spiraling and everyday state structural violence and overtly racist criminal profiling principally targeted at young Black men living in the Toronto Community Housing Corporation prepares them for prison. Moreover, it contends that interpersonal violence, transmitted from generation to generation and producing a vicious cycle, is a manifestation of institutionalized and systemic inequity. In the context of a hyper-masculine culture, young Black men are both victims and participants in a dialectic of interpersonal-structural violence. Routinely precipitated by powerful state actors and agencies of criminal justice, public policy and assorted ‘moral entrepreneurs’, young Black men have their masculinity weaponized and prisonized by the state’s low-intensity declaration of war against them, and, among others, the poor, LGBTQ, immigrants, and First Nations and other people of colour.