Kant clearly valued freedom in his moral philosophy, but he also seemed to distance the moral realm from the activities of rhetoric. This article challenges the long-standing concept of Kant as anti-rhetoric, complicating the view that rhetoric had no place in Kant’s philosophy. After examining the centrality of freedom as autonomy in Kant’s moral and political philosophy, this article carefully dissects Kant’s pronouncements on rhetoric in his various works. The conclusion reached is that Kant advances a bifurcated notion of rhetoric, with some uses of communicative means being characterized by freedom-restricting features and other employments foregrounding autonomy-enhancing aspects. This latter sense of communication is what can be identified as Kant’s educative rhetoric given its focus on preserving and promoting the freedom of both rhetor and audience.

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