The purpose for this article is to explore the juxtaposition of legal expectations, conflicting community cultural values, and the role of the superintendent in these connected but often conflicting issues. The authors explore several issues through the lens of Gay-Straight Alliance clubs, the "Equal Access Act," and the role of the superintendents and boards of education. Legal and leadership perspectives share equal footing in the discussion which is aimed at helping superintendents, and through their decisions, boards and communities, successfully navigate around the legal and cultural shoals found in such situations.