Despite the assertion that due to an Obama presidency America has become a post-racial society, Black males still face a unique social crisis. In this article, we hold that both race and gender continue to work in tandem to produce a certain set of social outcomes for young Black men in America despite this assertion. The educational, economic, and social mobility of young Black men is often limited due to structural constraints that are exacerbated by the intersectional dynamism of race, gender, and social class. As young Black men continue to experience social hardships, they are being pushed further and further away from traditional school contexts. Drawing from qualitative interviews with 24 young Black male participants from EmpowerYouth, a national community-based organization, this study highlights the importance of alternative sites of education and youth development for Black male youth. Findings from this study indicate that flexibility, applied educational and work experience, and positive healthy adult-youth relationships provided by EmpowerYouth, granted solace for young Black males who traversed through difficult circumstances within traditional school contexts. Our findings speak to the need to create new and relevant educational models that address the unique and complex circumstances of young Black men in America. Ultimately, as young Black males are often considered to be social burdens, this study shows how successful community-based programs like EmpowerYouth reframe young Black males as a valued segment of society that deserve support, care, and educational sites that are able to respond to their distinct academic and social needs.