It has been well established that controversial issue discussions are an integral component to a high-quality civic education. However, as the United States has become increasingly politically polarized, teachers have become more hesitant to engage students in discussions of controversial political issues. Two decades worth of literature on teaching controversial issues has shown that a primary factor in determining whether teachers will engage students in controversial issue discussions is whether they feel supported by their school administrators. Yet, school leaders have rarely been the focus of civic education efforts. This article seeks to bridge that divide by first providing a review of the research showing the importance of engaging with controversy in K-12 education and the influence of school leadership on that process and then ending with implications for school administrators who wish to support teachers who broach controversy in their classrooms.