Tony Banout, the inaugural executive director of the Forum on Free Inquiry at the University of Chicago, and Tom Ginsburg, a distinguished international law professor, discuss the university’s dedication to free speech. They explore the origins and importance of free expression within academia, referencing key historical documents that guide these principles. The conversation also highlights the challenges of maintaining institutional neutrality amid modern pressures. Ultimately, they underscore the vital role of discomfort in education for fostering genuine inquiry and diverse viewpoints.