The article examines the literary and biographical context of Chekhov's story "Misfortune" (1886). The author poses a hypothesis that the painter I. I. Levitan and S.P. Kuvshinnikova served as prototypes for these characters, and later reprised similar roles in Chekhov's story "The Grasshopper" (1892). To test this hypothesis, a comparison is made between the content of the story and the biographical information drawn from memoir literature, as well as Chekhov and Levitan's correspondence. The story contains two plots: an explicit plot and an implicit one. The implicit plot takes the form of a fabricated trial of the characters superimposed onto the actual travesty trial of Levitan that took place while the artist was staying with the Chekhov family in Babkino during the summer. Moreover, Levitan's ekphrasis serves as an additional evidence to support the supposition that his personality is projected onto the protagonist of the story. It is a verbal description of the painting by Isaac Ilyich "An Autumn Day. Sokolniki". The additional details that refer to the prototypes are the specific features of their nomination. The name of the female character of the story and her prototype are identical - Sof'ya Petrovna. Chekhov took Levitan's patronymic and formed a surname from it: Ilyich Ilyin. A much more significant role in the story than the biographical context is played by the literary context. It is traditionally associated, first of all, with "Anna Karenina" by L. N. Tolstoy. The article reveals the function of a number of other works that remain on the periphery of the attention of researchers, important for understanding the problems of the story. These include the works of Chekhov himself: "On Christmas Night" (1883) and "Big Volodya and Little Volodya" (1893). The female character of "Misfortune" is partially similar to Ranevskaya from "The Cherry Orchard." All of them are united by a similar understanding of love as an element beyond the control of humans, which can ultimately result in trouble or misfortune for a person. Already the first readers of the story noticed that the influence of the doctor's medical profession was noticeable in the story. The second circle of sources is associated with popular -scientific works on the physiology and hygiene of marriage, which were translated from French and were popular among Chekhov's contemporaries. The conducted research allowed the author to conclude that in "Misfortune" Chekhov made the first serious attempt to reveal the personality of his friend in a fictional form. Artistic discourse provided the opportunity for a free creative interpretation of the psychological characteristics of the talented contemporary. Chekhov appears in the story in his two main socio-professional roles: as a writer and as a doctor. As a result, they were based on three types of sources - biographical, literary and medical.