This narrative qualitative research study investigates aspects of the life journey of Black male adults in the urban context, Scarborough, Ontario through a Critical Race Theory (CRT) Perspective. Four Black male adults who lived in Scarborough as teenagers with previous incarceration were interviewed. Using the counter-storytelling method through CRT, these Black men discussed their experiences with incarceration, school, life in Scarborough as Black males and displaced anger and mental health issues. This data was analyzed using Composite Narrative analysis. The narratives of these young men affirm that their experiences, including those associated with racism and lateral violence, from their school and family settings to the streets in Scarborough, confused their masculinity, affected mental health experiences, and contributed to suppressed anger which displaced in aggressive or violent ways. These men’s stories also confirm that being incarcerated further exacerbated this displaced anger phenomenon, especially surrounding masculinity and certain mental health concerns and did contribute to feelings of hopelessness when trying to reintegrate back into Scarborough following their release.