This chapter begins with a provocative statement: teachers should cultivate being anti-intellectuals. Antonio Gramsci once argued that everyone is potentially an intellectual by function in addition to being an intellectual by vocation. The reconfiguration of the intellectual does not vitiate against having expertise, which teachers surely possess by virtue of their training and the state’s investment in their credentialization. The question rests on how they function (i.e., not as experts), help transform the nature of authority, and displace the normalized expectations of knowledge as a form of imposition. There is nothing necessarily problematic with this more or less commonsensical notion and teachers have earned the right to be regarded as experts and intellectuals. In some respects, young people are a strategic place to test Edward Said’s theory of the amateur intellectual, as they enter the practice of philosophy and public life as neophytes.