Disease features prominently in Chekhov's stories, and his protagonists often suffer tragic and untimely deaths. It is unsurprising that the author seems haunted by the notion of infirmity, since he was plagued by tuberculosis for most of his adult life and died of the disease at the age of forty-four. Often—as in The Black Monk and The Grasshopper—disease acts as a physical representation of a character's psychological turmoil. Osip sickens in The Grasshopper because he is depressed about his wife's infidelity, while Chekhov subtly blends the symptoms of Kovrin's mental illness with those of tuberculosis in The Black Monk. But the author's recurring use of this theme is neither pathological nor self-pitying; Chekhov recognizes man's subservience to forces greater than his or her own will. The author uses the symbolic power of his dying protagonists—such as Kovrin in The Black Monk or Rabin in Ward No. six—to emphasize life's transience as well as humankind's subservience to the whims of fate. Chekhov also examines disease as a reflection of social degeneration. For example, Kovrin's psychosis— which ruins his marriage, kills his father- in-law and wrecks Yegor's prized orchard—seems to symbolize the disintegration of society at large. Chekhov thus focuses on disease to indicate individual frailty as well as the growing conflicts within society.
Chekhov's stories examine many kinds of disappointment and failed ideals. Often the protagonists are disillusioned by events that force them to reevaluate their personal philosophies and understanding of the world, and this disillusionment usually occurs toward the end of stories. Such climaxes range from the mildly pathetic—as when the narrator in The Night Before Easter sees Jerome in daylight and realizes that he is just an ordinary man, to the monumentally tragic—such as Rabin's incarceration in Ward No. six and his subsequent nervous breakdown. The protagonists of The Darling and My Life also tackle frustrated dreams, loneliness, and the breakdown of romantic ties, but they never fundamentally alter their view of the world. Consequently, we see that Chekhov's tales conclude with either a moment of revelation or anti-climax (these endings have been termed "zero" and "surprise" endings, respectively.) His protagonists are either crushed by their sense of disillusionment with the world, or they hold out hope in a better future.
In 1861, when Chekhov was one year old, Tsar Alexander II liberated Russian serfs. This act seemed to herald the dawn of a new age and the collapse of aristocratic privilege, although, in reality, peasants were still impoverished, disempowered, and tied to the land. Many intellectuals began to discuss ideas on liberty and the rights of all social classes to land and education. Although Chekhov did not openly speculate on the fall of the old social order, his writing shows that he was caught up in the debate. Many of his stories examine the effect of change on a prevailing social or familial hierarchy. For example, My Life focuses on a young member of the gentry who defies his father and social convention by working as a laborer. But Chekhov is very subtle in his treatment of change. Most often, the revolutions one witnesses in the stories are neither positive nor negative; they are simply alterations to established systems. In the Ravine deals with a mercenary, Grigori Tsybukin, who is ousted from his position of power when his cunning daughter-in-law takes over the family business. Similarly, Rabin's confinement in Ward No. six shows how professionals as well as peasants can be subjected to social coercion. The only obvious change for the worse occurs in The Black Monk, when Yegor's orchard passes into the hands of a younger generation and is ruined. In most of his stories, therefore, Chekhov deals with the breakdown of an old social order with characteristic moral ambivalence.