Despite many historiographical challenges, in this article I briefly examine two significant school leaders from over a century ago whose lives may seem recognizable to contemporary LGBTQ+ educators in that they both stepped outside traditional gender and sexuality boundaries for their time. They are Ella Flagg Young and George Howland, both of whom served as school superintendent in Chicago. This fast-growing city, much like others of the Progressive Era, opened new social opportunities as well as offered a modestly safe place to navigate shifting gender and sexuality norms. And though these two individuals were greatly admired for their exceptional gifts as educators and leaders, they each represented a demographic in school work that was aggressively marginalized only a few years after their deaths. In the end, their stories tell us much about two remarkable educators. As important, their experiences as recognizably LGBTQ+ educators offer hints of deeper, longer-term efforts by school officials to drive their potential successors away.