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Improving graduation rates among African American male students remains elusive. Prominent strategies include career pathways, small schools, and positive climate. This analysis offers a fresh perspective, exploring the pathways and experiences of urban students beating the odds—entering high school with a suspension and low credits, but catching-up to graduate on-time. Utilizing qualitative focus groups with 28 seniors, the paper maps the pathways and experiences of “recovery students” since 8th grade. Findings identify key stages of the journey, “choice” opportunities, and critical supports, namely resetting peer relationships, personal reinvention via school choice, mentor “nagging”, and credit recovery. The student journey—academic and psychosocial—reinforces a holistic approach in school design and resources, with sensitivity to individual tipping points.