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This paper explores how Milwaukee Youth Brilliance (MYB), a Black-led community-based educational space, supports youth in conceptualizing activism and advocacy through intergenerational dialogue with former youth activists. Grounded in YouthCrit, a youth-centered extension of Critical Race Theory, this study interrogates how racism and adultism shape youths’ experiences while amplifying their voices as agents of change. Using a critical ethnographic approach, data were collected over 12 months through semi-structured interviews, artifact collection, and observations, analyzed via iterative coding with MAXQDA. Findings highlight how MYB fosters justice-oriented youth leadership by positioning intergenerational knowledge-sharing as a pedagogical tool. This work underscores the transformative role of community-based educational spaces in cultivating agency, equity, and solidarity across generations.