This essay explores key values of John Lachs's work, especially freedom, diversity, and human flourishing, when applied to the history of the philosophy of education as well as to the practical problems of policy and implementation today in American schools. I consider the importance and tensions involved in these values in the thinking of Plato, Jean-Jacques Rousseau, and John Dewey. Next, I examine necessary and then avoidable challenges of operationalizing freedom and diversity in schools, especially in tensions with recent policy initiatives that threaten freedom and diversity for human flourishing. The aim here is to note the central importance of the values that Lachs has long championed, while attending also to the risks and dangers that misunderstanding and narrow thinking pose about them when applied to American public schools. Ultimately, I argue that while advocacy for liberty sometimes raises profound problems in the sphere of public education, democratic education is enriched immeasurably when it enables and empowers freedom to pursue diverse forms of flourishing. [ABSTRACT FROM AUTHOR]