The author argues that A. Pushkin chose Kantian philosophy as the social-philosophical, as well as aesthetic, guide for the moral-legal and political tools to solve the burning issues of Russian society. The paper sets out to prove that there is every reason to consider Pugachev’s History [Istoriya Pugacheva] and The Captain’s Daughter [Kapitanskaya dochka] as a unique duology, where the same subject is interpreted by means of the historical apparatus (reliant on documents) and art, with a much wider scope. Kant’s influence manifests itself in Pushkin’s works starting from the ode Liberty [Volnost] to The Captain’s Daughter. It is stated that the poet structured his duology according to Kant’s The Metaphysics of Morals. In Pugachev’s History, Pushkin focuses on the problems of law. He follows Kant in claiming that substitution of natural law with a state of lawlessness was exactly what drove the Yaik Cossacks, and then peasants from the whole of the Volga region, to rebellion. The Captain’s Daughter, on the other hand, focuses on moral issues, in line with the structure of Kant’s most mature work on practical philosophy.