The constraining role of racial, social, and economic stratification on the lives and education of African American males has been argued both theoretically and empirically (Massey, 2007; MacLeod, 1987; Noguera, 2001). Some have argued that one important mechanism is the perception of limited opportunity structures (Noguera, 2004; Ogbu, 1987). This dissertation explored how real and perceived opportunity structures were shaped by political, social, and economic forces in an urban neighborhood. Specifically, this study focused on a core group of Black males in a bounded historical time and geographic locale and explored how life pathways were identified, conveyed, and chosen. This study was historically situated in the period starting with the inception of the Black Panther Party for Self-Defense in 1966, until the time of the death of its co-founder, Huey P. Newton in 1989. This study argued that the complex interplay of competing ideologies that arose during that time period was at the crux of redefining Black life pathways to achieving the American Dream, also conveying the outcomes from that pursuit. This study took place in Oakland, California as this was the birthplace of the Black Panthers and it focused on the Oak Knoll neighborhood. I explored the ways in which the Black Power movement, the burgeoning drug epidemic, and State suppression in post-industrial Oakland informed how a cohort of over 40 Black males made sense of their societal positionality and how that 'sense making' influenced their choice of pathways and life outcomes. I will draw on Critical Race Theory in order to examine the ways in which race and power were central in the choices youth perceived, communicated, and enacted (Crenshaw, 1995; Ladson-Billings & Tate, 1995). Methodologically, I will utilize interviews with members of the cohort, biographical narratives, primary and secondary sources, with the dissertation taking the form of an autoethnography of the block cohort. Primary and secondary sources will be employed to give a historical context to the time period and to contextualize the differing pathways. Interviews with cohort members and the development of autoethnographical narratives will focus on what I am calling 'block pedagogy', which I define as the organic community discourse that reflects the constant negotiation of identity, power and privileged knowledge, informed by the historical context. A focus on 'block pedagogy' (as remembered by informants) will be used to illuminate alternative/oppositional life pathways that were available to this cohort and how those options were developed and conveyed across the cohort through the use of privileged knowledge. Ultimately, this study will contribute to our understanding of the ways in which the multiple spheres of societal contact—with the power structure, Black radicalism, and criminality—resulted in identity-shaping knowledge. In doing so, it will document the ever-changing nature of oppression and community response to it: both in ways that subvert and reproduce existing oppressive social structures.