This study captures the stories of adult Black men from an urban area plagued by generational poverty and low educational attainment. Narrative semi-structured interviews were employed to examine their stories, the factors that contributed to their identities as students, and their decision to drop out of school. Using the cool pose theory (Major and Billson in Cool pose: the dilemmas of black manhood in America. Lexington Books, 1992), their narratives revealed how a lack of culturally relevant learning experiences, positive relationships, and "loose boundaries," together with implicit biases and stereotypes, influenced their perceptions of themselves and school and ultimately their decision to drop out of high school. Cool pose is also used to reframe young Black boys' narratives by presenting their use of cool pose behaviors as a demonstration of strength, integrity, and source of worth in failure situations. This study presents implications for better understanding and educating young Black men from urban communities as individuals and how illustrating their past educational experiences continues to influence their daily lives as adults. Furthermore, it compels us to answer the fundamental question: what more can we as educators do to empower and create successful schooling experiences for Black boys?