As histories within art education expand to cover topics outside of the majoritarian narrative, historians need to take into consideration the ways in which their positionality influences their relationship with their historical subjects. This paper is a meditation on the experience of a White female researcher studying the life of Margaret Burroughs, a Black art education and institution-builder from Chicago. By focusing on positionality in both theoretical positionality and researcher positionality, a case is built for historians to interrogate the relationship between researcher and subject, even when living participants are not involved in the study.