Imagination is considering something differently from how it is currently. Between the COVID-19 pandemic and the resurgence in the movement for Black lives, 2020 has created a space to examine our institutions to see how well they serve us. Through leveraging in-depth interviews and productive methods (where participants produce drawings, poetry, etc.), I am asking young Black people in Chicago high schools to reimagine educational contexts. This project is interested in how schools are implicated in anti-Blackness, and how young Black people are affected by and reproduce/transform/interact with anti-Blackness in narrating their experiences and imagining learning communities otherwise. Articulating the disruptive power of Black imagination connects the dissonance between what schools give Black students and the realities of their anti-Black experiences (ross 2020) to conversations of school abolition and educational freedom.