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This qualitative study explores Black fugitivity in the midst of dual pandemics—anti-black racism and COVID-19. Drawing on Black Critical Theory and portraiture, the authors draw on interview data and field notes to paint vivid imagery of elders and children at a Black community-based organization in Chicago’s historic Bronzeville neighborhood. During the COVID-19 pandemic, members of this organization responded to the anti-Blackness in school curriculum by organizing a group of approximately 20 community members to develop a social studies curriculum for Black students to explore their history, community, families, and themselves. This curriculum—Know Your History, Know Yourself—created participatory experiences for Black students in their rapidly gentrifying neighborhood; allowing them to research their lives in relation to the past. Through the portraits in this article, we highlight (a) the emancipatory visions that were created from critical, and intergenerational study of Black life in the past and present, and (b) the interpersonal Black love and Black joy that was central to the educational space created. Implications from this study can support educators of Black children in urban K-12 schools and other educational settings in creating loving and critical learning and civic experiences rooted in intergenerational relationships.