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Sigmund Freud sustained a commitment to his scientific dream for psychoanalysis, but remained more conflicted about his “liberal” dream, his quest for individual emancipation born of truth-seeking discourse. Yet both dreams drew inspiration from an Enlightenment ethos of experimentation, with a quintessentially human ingredient: free speech. The American Founding Fathers, prior to Freud but similarly influenced by Enlightenment roots, also sustained an ethos of experimentation with free speech—the exercise of which was seen as essential to human (individual and collective) liberty. While most arguments defending the special status of speech appeal to the tenets of Enlightenment philosophy, neither psychoanalysis nor democracy has a well-articulated theory of why speech is accorded a privileged status. But both did establish fundamental rules that instantiated a bounded space of ambiguity for the unbounded exercise of free speech and truthful discourse. By so doing, psychoanalysis and democracy, by enabling the primacy of speech, both joined experimental and hermeneutic aspects, scientific and liberal dreams, and empiricist and emancipatory truths; and both remain mutually relevant despite having seldom been treated as such.