This paper presents a conceptual analysis of the essay by F.E. Paktovsky dedicated to the works of A.P. Chekhov. The pertinence of this research stems from the significance of the literary figure for the history of Russian criticism of the XIX-XX centuries, the importance of his views on the works of the authors of Russian literature of the XIX-XX centuries, as well as for the history of Belgorod State National Research University, as long as the critic was one of the directors of Belgorod Teachers’ Training Institute. The study of the creative heritage of F.E. Paktovsky was carried out using motivational-figurative, biographical, historical and literary methods. Turning to the works of A.P. Chekhov, the literary scholar, considers his characters as "impotent, pitiful and ridiculous" people who are not capable of opposing their fate. He does not shift the blame from the person in his misfortunes, but calls to fight with them, calling for spiritual transformation. F.E. Paktovsky was one of the first who tried to classify the characters of A.P. Chekhov, and this fact has cultural significance as evidence of a contemporary on the social composition of Russian society at the turn of the XIX-XX centuries.