This chapter interrogates how gendered power structures in K–12 education disproportionately impact Black women leaders by examining their underrepresentation in senior leadership roles and the intersecting barriers of racism and sexism. Grounded in historical context, it explores the feminization of the teaching profession and the rise of misogynoir, a term describing the unique discrimination faced by Black women due to the combined forces of race and gender. Through firsthand accounts and case studies, this chapter illustrates how harmful stereotypes, biased expectations, and practices shape Black women’s leadership experiences. It further analyzes the “double bind” they must navigate, wherein they are both hyper-visible and undervalued.