In this article, life history methodology and principles of counterstorytelling are used to examine moments when one Black male preservice social studies teacher and three Black male social studies teachers challenge Black masculinist visions of leadership, and moments when they seem complicit in perpetuating these visions. Findings indicate that these educators' understandings of Blackness, maleness, and the pursuit of Black masculine recognition are fluid, developing and sometimes contradictory. We argue that while necessary across disciplines, interrogations of Black masculinity are uniquely imperative in social studies teacher education due to how assumptions about Blackness and maleness have shaped struggles for Black civic recognition.