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Secure in his reputation and income at the age of thirty, Chekhov sought to cast off this despondency by traveling to Sakhalin, the Russian Devil’s Island, in 1890; the eighty-one-day journey was arduous, for the Trans-Siberian railway had not yet been built. The enterprise may have been inspired by a Tol-stoyan wish to practice altruism or it may have been an ambitious project to write a magnum opus of “medical geography.” In any case, the ensuing documentary study of the penal colony was a model of socially engaged field research, and may have led to prison reforms. On a more personal level, it intensified a new strain of pessimism in Chekhov’s work, for, despite his disclaimers, he began to be bothered by his lack of outlook or mission.

No sooner had Chekhov returned, via Hong Kong, Singapore, and Ceylon, than he made his first excursion to Western Europe, accompanying Suvorin. His initial enthusiasm for Vienna, Venice, and Naples began to wane by the time he visited Nice, Monte Carlo, and Paris, and he was eager to get back to work. In Russia, with the writing routines resumed, the sense of enslavement returned. This mood was modulated by a flirtation with a family friend, Lidiya (Lika) Mizinova, who invested more significance in the relationship than he did. Her subsequent affair and illegitimate child with the married writer Ignaty Potapenko would be exploited by Chekhov in The Seagull (although he hoped his own circle would not spot the similarities).

The steady flow of royalties enabled Chekhov in 1891 to buy a farmstead at Melikhovo, some fifty miles south of Moscow, where he settled his parents and siblings. There he set about “to squeeze the last drop of slave out of his system” (as he wrote to Suvorin on January 7, 1889); “a modern Cincinnatus,” he planted a cherry orchard, installed a flush toilet, and became a lavish host. This rustication had a beneficial effect on both his literary work and his humanitarianism. He threw himself into schemes for building roads and schools and opened a clinic to provide free medical treatment, improving peasants’ minds and bodies. During the cholera epidemic of 1892–1893, he served as an overworked member of the sanitary commission and head of the famine relief board. These experiences found their way into the activities of Dr. Astrov in Uncle Vanya.

During this period, Chekhov composed masterful stories that explored the dead ends of life: “The Duel” (1891), “Ward No. 6” (1892), “The Black Monk,” “A Woman’s Kingdom,” “The Student” (all 1894), “Three Years” (1895), “The House with the Mansard,” “My Life” (both 1896), and “Peasants” (1897), carefully wrought prose pieces of great psychological subtlety. They recurrently dwell on the illusions indispensable to making life bearable, the often frustrated attempts at contact with one’s fellow man, the inexorable pull of inertia preventing people from realizing their potential for honesty and happiness. Chekhov’s attitude is clinically critical, but always with a keen eye for the sympathetic details that lead the reader to a deeper understanding.

For several years, Chekhov abandoned the theater, except for some monologues and one-act farces. Not until January 1894 did he announce that he had again begun a play, only to deny it a year later, in a letter to V. V. Bilibin: “I am not writing a play and, altogether, I have no inclination to write any. I am grown old, and I have lost my burning ardor. I should like to write a novel 100 miles long” (January 18, 1895). Nine months after that he was to break the news to Suvorin, “Can you imagine, I am writing a play which I shall probably not finish before the end of November. I am writing it not without pleasure, though I swear horribly at the conventions of the stage. A comedy, three women’s parts, six men’s, four acts, a landscape (view of a lake); a great deal of conversation about literature, little action, five tons of love” (October 21, 1895).

The comedy was The Seagull, which had a rocky opening night at St. Petersburg’s Alexandra Theatre in 1896: the actors misunderstood it, the audience misapprehended it. Despite protestations of unconcern to Suvorin (“I dosed myself with castor oil, took a cold bath — and now I would not even mind writing another play”; October 22, 1896), Chekhov fled to Melikhovo, where he renounced playwriting. Although The Seagull grew in public favor in subsequent performances, Chekhov disliked submitting his work to the judgment of literary cliques and claques. Yet barely one year after the event, a new drama from his hand appeared in the 1897 collection of his plays: Uncle Vanya, a reworking of the earlier The Wood Goblin. It was widely performed in provincial capitals, where the residents found it reflected their dreary lives.

It was during this year that Chekhov’s illness was definitively diagnosed as tuberculosis, and he was compelled to leave Melikhovo for a milder climate. For the rest of his life, he shuttled between Yalta on the Black Sea and various French and German spas, with occasional business trips to Moscow. He had a house constructed in the Yalta suburb of Autka. To pay for it, and to cover the new expenses his multiple residences created, Chekhov sold all he had written before 1899, excepting the plays, to the publisher Marks for the flat fee of 75,000 rubles (in current purchasing power, approximately $81,000), along with the reprint rights to any future stories. It was an improvident move. Marks had had no idea of the size of Chekhov’s output and had underpaid. The error in calculation may have induced Chekhov to return to playwriting as a more lucrative activity.

The remainder of his dramatic career was bound up with the fortunes of the Moscow Art Theatre, founded in 1897 by his friend Nemirovich-Danchenko and the wealthy dilettante K. S. Alekseev, who acted under the name Konstantin Stanislavsky. Chekhov was one of the original shareholders in the enterprise. He admired his friends’ announced program of ensemble playing, their serious attitude to art, and a repertory of high literary quality. At the opening production, Aleksey Tolstoy’s blank-verse historical drama Tsar Feodor Ioannovich, his eye was caught by Olga Knipper, the young actress who played the tsarina. With only slight misgivings Chekhov allowed the Art Theatre to revive The Seagull at the close of its first season. Stanislavsky, as co-director, had greater misgivings; he did not understand the play. But a heavily atmospheric production won over the audience, and the play was a resounding success. The Moscow Art Theatre adopted an art-nouveau seagull as its insignia and henceforth regarded Chekhov as its house dramatist. When the Imperial Maly Theatre insisted on revisions to Uncle Vanya, which had been playing throughout the provinces for years, Chekhov withdrew the play from them and allowed the Art Theatre to stage its Moscow premiere. Three Sisters (1901) was written with Art Theatre actors in mind.