“Did Brown really desegregate schools?” This is the question that inevitably is asked when we begin our study of Brown v. Board in my graduate level class, “The History of Education in the United States.” Certainly, it is a valid question, but one that is problematic when one tries to reconcile the goals of the landmark case with the large number of segregated schools that exist today. When students compare how many segregated schools exist today with those of 1954, the simple answer, according to them, appears to be that Brown did not desegregate schools. It is the complexity of addressing this issue that makes teaching Brown a challenge. Pedagogically I should welcome the opportunity to teach such an issue that has no easy conclusion. As a result, it has the power to engage and challenge students in complex ways. Yet, there is a part of me that dreads teaching Brown because I fear that I cannot do justice to the enormity of that decision for the United States in 1954, nor to the significance that it has taken on in the ensuing decades. However, even with these challenges, how could I not teach Brown? From the outset I want to make clear that this is a reflective as opposed to directive piece. I certainly do not believe that I have a lock on the best way to teach Brown. Instead, I would like this essay to reflect my own uncertainty about what is pedagogically most effective.