Emphasizing the salience of social and historical contexts in understanding contemporary urban school leadership, this article presents reflections from a subset of African American women principals who came of age during the Civil Rights era and assumed leadership subsequent to the enactment of the Chicago School Reform Act of 1988. The main finding being reported is that the unique race, gender, and generational statuses of these principals made them especially vulnerable to the impact of governance reforms that rearranged long-standing authority relationships between African American principals and parents. Implications for urban school leadership research and policy are discussed.