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Between the early twentieth century, the model of educational vision Black teachers fostered and were deeply committed to greatly mirrored what we today regard as anti-racist systems of knowledge and educational practices. This paper draws our attention to the understudied educational activism, pedagogies, and praxes of local Black teachers during the Early Black History Movement through a biographical analysis of the life and times of Jane Dabney Shackelford, a Black female educator from Terre Haute, Indiana who was most active during the era of Jim Crow segregation. The educational trajectory and systems of teaching Shackelford and her peers embodied serve as a useful tool for conceptualizing the significant ways in which local schoolteachers cultivated an intentional educational and intellectual practice that challenged the anti-Black knowledge systems undergirding American education during the early twentieth century.