Through oral histories, this article reconstructs the history of a segregated school in the eastern Kentucky coalfields during the 1950s–1960s. Student alumni (also referred to in this article as narrators) (re)construct the school through memory, providing information about both the physical and cultural interiority of this space. Their stories recount the physical manifestations of separate and unequal juxtaposed against memories of their teachers’ care and high expectations, as well as the various extracurricular activities that not only reinforced these expectations but affirmed their humanity and identities as Black youth in a predominantly white town. Created out of the context of Jim Crow unfreedom, the segregated school was a paradoxical space that, in many ways, also represented Black freedom.