As a consequence of their multiple identities, underrepresented leaders often navigate both racialized and gendered pathways to leadership in the U.S. education industry. Nevertheless, relatively little is known about the impact of their intersecting identities and the structural barriers in this sector. To deepen our collective understanding of this phenomenon, the author reviews existing theories and research related to the intersection of race and gender within the educational leadership sphere. More specifically, the author highlights the individual and compounding effects of gender and race on the professional realities of current and aspiring leaders in education at the Central Office (i.e., the Ivory Tower). This chapter concludes by proffering future research propositions, theory development, and policy in this arena.