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This paper examines Black childhood literacies across time, tracing connections between narratives of formerly enslaved people and the contemporary experiences of Isaiah, a seven-year-old Black boy labeled a “struggling reader.” Using ethnographic fabulation—a method blending rigorous observation with imaginative reconstruction—I analyze archival texts from the Federal Writers’ Project alongside ethnographic data from a racially affirming community learning space. Findings reveal how Black learners navigate structural violence while forging literacies grounded in resistance, emotional expression, and creative world-building. This work challenges linear histories of progress, showing that racialized constraints persist in shaping educational experiences. Ultimately, it offers a paradigm for understanding Black literacies as sites of refusal and possibility, contributing to scholarship on educational carcerality, Black childhood studies, and literacy research.