This dissertation traces the development of Alexander Pushkin's sense of the tragic in the context of Russian and European Romanticism. Pushkin was a self-proclaimed skeptic in matters of literature: though deeply influenced by Romantic poets and theorists, he never subscribed to any one school or creed, experimenting in a range of genres to express his changing tragic vision. Many of his works move seamlessly between the closed world of traditional tragedy and the open world of Romantic tragic drama; and yet, they follow neither the cathartic program prescribed by Aristotle nor the redemptive mythologies of the Romantics. My study explains Pushkin's idiosyncratic approach to tragedy by re-situating his works within their literary, historical, and philosophical contexts. In my readings of The Gypsies, Boris Godunov, and The Little Tragedies, I connect Pushkin's works to those of a range of European writers, including Shakespeare, Racine, Rousseau, Goethe, Schiller, the Marquis de Sade, and Hugo; and I examine such topics as tragedy and the tragic, the sublime and the grotesque, the relationship between literature and history, irony and tragic ritual. While I ground my work in traditional Russian philology, I use recent Western scholarship to help frame my study theoretically. In particular, I aim to contribute to the ongoing debate between scholars who claim that Romanticism marked "the death of tragedy" and those who see the change less as a death than as a redefinition.