Given the persistence of systemic anti-Blackness, access to quality education for Black youth requires additional resources and opportunities beyond the traditional classroom and school environment. Community-based educational spaces offer a liberatory alternative to anti-Black academic environments. The COVID-19 pandemic and ongoing political polarization exacerbate the inherent racialized inequities in schools. As a result, additional research and theorization of Black male adolescent experiences in community programs are necessary to develop pedagogical strategies that attend to the endemicity of racial trauma and Black suffering in American education and society. This qualitative case study examines The Blue Heart Foundation, a local community-based organization, to explore the processes of individual and collective healing and empowerment among Black male youth. Data collection included an extensive artifact analysis, participant-observations over a two-year period, and semi-structured interviews with 21 participants, comprising 11 Blue Heart alumni, three mentors, two program staff, four instructors, and one guest speaker. The findings indicate that Blue Heart’s programming incorporates high-leverage system characteristics such as paradigms, structures, elements, and feedback loops, which cultivate environments conducive to Black male youth development. Key findings highlight the importance of fulfilling relationships, community engagement, and cultural affirmation in the healing and empowerment processes of Black male youth. A central contribution of this research is the development of the FRESH HEART framework, which serves as a model for culturally sustaining programs that are relationship-based and developmental in focus. This study affirms the importance of community engagement in shaping bespoke models deeply rooted in local realities and contexts. By working closely with communities, organizations and educators can co-create frameworks tailored to their unique needs. These transformative frameworks are key to actualizing both personal and collective thriving by providing actionable strategies that advance racial progress and contribute to the broader struggle for Black liberation.