In this paper, we examine the role of educational leadership in promoting and/or challenging racism as an intentional outcome of schooling. We focus on Egypt and South Africa, two countries uniquely framed as both deeply divided by race, religion, and/or class and as models of resistance and conscious activism. We draw upon experiences working as, or with, school principals in South Africa and Egypt to reveal how the context of education is negatively shaped by schooling practices that foster race and class-based inequalities. Using personal narratives of school principals, we situate educational leadership as core to understanding how Western educational reforms are structured, conceived, and enacted within Egyptian and South African contexts. This analysis sheds light on how educational inequalities are reinforced and justified by contexts of educational leadership and how efforts to resist are institutionally silenced.