The article, based on the analysis of Chekhov’s The Duel [Duеl], offers a new interpretation of Chekhov’s oeuvre. Modern Chekhov studies often imply that the writer lived in the era of the end of ideologies and therefore refrained from offering any ideological recipes. In fact, nearly each of Chekhov’s longer novellas debunked the nascent ideologies of the time. He warned of the perils of submission to an ideology, even though he could not predict which one would eventually dominate. Therefore, he critiqued each and every one of them. This is how ideology is tackled in his story The Black Monk [Chyorniy monakh] (an anticipation of detrimental Modernist ideas); in A Dreary Story [Skuchnaya istoria], these days often compared to the story of Faust; and in Ward No. 6 [Palata nomer shest], showing descent of normal people into insanity. Similarly, in The Duel, he depicted a proto-Nazi and Bolshevik, no less, in the character of Von Koren, who embraces Nietzsche’s worldview and will not hesitate to destroy an intellectual who crossed his path.