In this historical study of English teaching, Jory Brass adopts a governmentality perspective to highlight the contingency and limits of pedagogical arguments that construct an oppositional relation between power and freedom. In the first part of the essay, Brass historicizes contemporary critiques of transmission pedagogies by comparing them with touchstone pedagogical texts of the 1890s through the 1920s. Next, he revisits two early twentieth-century pedagogical frameworks to identify links among power, freedom, choice, and social norms that are obscured in contemporary pedagogical writing. Finally, Brass examines a popular contemporary text, Deborah Appleman's "Critical Encounters in High School English," to highlight how its strategy to foster adolescents' freedom and empowerment inscribes social patterns of power and regulation. The study denaturalizes oppositional accounts of power and freedom so that scholars and teachers may scrutinize how power circulates when English is positioned to govern how students understand and conduct themselves as free, responsible, and empowered subjects.