This chapter traces the arc of American education, describing how the tension between liberty and equality has shaped education law and policy every step of the way. The chapter begins by exploring the origins of American education, including the equality-minded adoption of compulsory education and common schools and the liberty-minded desire for parents to control elements of their children’s education. Next, the chapter expands to consideration of equality and liberty in the education of groups. This includes the equality revolutions of the 1960s and 1970s during which schooling became more inclusive of multiple groups of students, and also the liberty-based backlash to those revolutions pursuing greater local control and self-determination. The chapter then highlights the liberty and equality-based tensions impacting contemporary education reform, such as the standards and choice movements. Finally, the chapter looks to the future, arguing that advances in technology, increasing student diversity, and unprecedented flux in the structure of American education will force continued balancing of the values of liberty and equality. Ultimately, the chapter argues that these core democratic impulses—liberty and equality—form a double helix at the core of many of the conflicts in American education law and policy and that management of the relationship between them will continue to drive how Americans respond to educational challenges of the future.