As the most unionized segment of the public sector workforce in the USA, teachers and their bargaining representatives wield significant power in the world of educational labour relations and beyond. Yet, just as the First Amendment's freedom of association clause affords unions the right to exist, its concomitant recognition that employees are free to refrain from having to join labour organizations engenders a potential conflict with its freedom of speech clause when unions attempt to collect so-called fair share or agency shop fees. In the light of the major role that unions play in the educational marketplace, both in the USA and England, this article is divided into three parts. The first section briefly reviews the history of educational unions in the USA, while the second examines Supreme Court litigation on fair share fees, culminating in its opinion in "Davenport v. Washington Education Association (Davenport)," a case that involved fair share fees. The final part of the article reflects on what educational leaders, acting in conjunction with their lawyers, can do to mitigate labour conflicts while protecting the rights of non-union members and dissenters who must pay fair share fees. (Contains 21 notes.)