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The article studies the portrait essay by Genna Sosonko, the eminent chess writ- er in modern Russian literature. A chess theme has a consistent history in Russian literature. Sosonko contributes his essays to this history. His essay Gioconda’s Smile is in focus in the article. The author transformed ‘the material of reality’ into es- thetically organized text. Sosonko chose grandmaster Eduard Gufeld as the central character of his work. For him, a man in the chess game is the best test for his moral and ethical qualities. He uses the elements of chess folklore, rumors, travel stories, speech characteristics to compose a central feature of his essay. The psychological analysis discloses ethically ambivalent character. Nevertheless, Gufeld’s joyfulness, sense of humor and vital energy made him very well known in the chess world. His mother’s epitaph serves as a dominant (Vygotsky) of this essay.