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As key figures in pragmatic philosophy, John Dewey and Oliver Wendell Holmes both deeply engaged in the theoretical development and practical controversies about freedom of speech. However, the connection between their thoughts on this issue has long been overlooked in academic discourse. Dewey’s theory of the “community of inquiry” views free speech as the cognitive foundation of democratic society, emphasizing critical dialogue, inclusive participation, and shared responsibility for the common good. He advocates for cultivating public reason through education. In contrast, Holmes established the “clear and present danger” standard in wartime cases, using the metaphor of the “marketplace of ideas” to defend individual expression rights. Yet, his instrumentalist logic overlooks the long-term impact of speech on public reason. Their divergence highlights a division within pragmatism: Dewey, prioritizing community, calls for institutional reconstruction to rejuvenate democracy; while Holmes, focusing on the individual, defends judicial neutrality to prevent overreach. Historical context partly explains Holmes’ stance, but the fundamental difference between their theories—individual versus collective, market versus institution—remains evident even in peacetime. In the digital age, where information monopolies and algorithmic manipulation are prevalent, the complementarity of their theories becomes more apparent—both Dewey’s ethical framework for rebuilding a “digital community of inquiry” and Holmes’ baseline thinking to guard against the spread of censorship are necessary. The ultimate meaning of free speech lies in the dynamic balance that ensures the intergenerational commitment to democracy.