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Abstract: In the history of Russian chekhovian studies the works by A. B. Derman appear in two points of view that are not equally relevant today. Though Derman repeats the official interpretations of Chekhov’s legacy (for example in his critical biographical essay “A. P. Chekhov” (1939) and “Moscow in the life and work of A. P. Chekhov” (1948) and other newspaper and magazine articles, he is also the author of a curious hypothesis, with the help of which he tried to explain the dominants of Chekhov’s poetics, as well as to give an exhaustive psychological portrait of the writer. Curious hypothesis was formulated in his monograph “The portrait of Chekhov’s creativeness” and partly in its subsequently added alterations. The hypothesis lies in the idea of “disharmony” of Chekhov’s character: the primacy of the rational part over the emotional one. In Derman’s opinion, Chekhov’s mentally evolution was built on the conscious overcoming of the defect, including through creativity, which had reflective and compensatory functions in this process. A comparison of the latter version of “The portrait of Chekhov’s creativeness” with the first edition gives us an interesting facts for characterizing the ideological processes which were typical for soviet criticism and literary studies from 1929s to the 1940s. This article focuses on the following problems: what did literary critics write about the first edition of “The portrait of Chekhov’s creativeness”, and how Derman corrected his work, resulting in the second version of “The portrait of Chekhov’s creativeness” (1944), which he did not publish.