In this article, we suggest that communities must explore alternative leadership ideologies, actors, and venues to make meaningful academic and social improvements in our cities. We examine how themes from Paulo Freire's critical ideology can help expand our conceptualizations of educational leadership and facilitate pragmatic responses to complex urban dilemmas. To illustrate our claims, we provide two case examples of urban educational leadership that is guided by Freirean dialogical tenets of love, faith, humility, hope, critical thinking, and solidarity. (Contains 3 tables and 1 note.)