Chekhov describes the events surrounding Ivan "Vanka" Zhukov, a nine-year old boy, at Christmastime. Vanka is living in Moscow, where he is apprenticed to Alyakhin the shoemaker. While Alyakhin's family is at Christmas Eve Mass, Vanka decides to compose a letter; he retrieves writing materials from a cupboard and, after confirming that he is not being watched, begins to write.
Vanka addresses the letter to his grandfather, Konstantin Makarich. The young boy begins by sending the old man a Christmas blessing, then writes out a little about his family situation: Vanka has neither a mother nor a father, and is reaching out to Konstantin Makarich as his only connection. He then reflects on the figure of Konstantin Makarich himself. As Vanka recalls, his grandfather is a night watchman who works on the Zhivarev estate. The small-figured Konstantin Makarich is himself sixty-five, is energetic and in good physical condition for the most part, and has a tendency to drink.
Konstantin Makarich often keeps company with the Zhivarev kitchen-maids; he also has two canine companions, an old female dog named Kashtanka and a male dog named Eel, who go with him on his nighttime rounds of the Zhivarev estate. Eel has a long black body, and indeed resembles the aquatic animal after which he was named. In terms of personality, Eel often appears to be good-natured and agreeable, yet he is in fact cunning and spiteful. His escapades involve snapping at passersby and stealing food. Despite being punished harshly and frequently, Eel survives such harsh treatments and continues with his normal schemes.
Vanka's thoughts return to Konstantin Makarich. At the moment, the young boy reflects, his grandfather could be looking up at church windows or joking around with the Zhivarev cooks. One of Konstantin Markarich's typical jests involves giving the cooks some of his snuff; he laughs merrily when these women take this ground tobacco and begin to sneeze. He also offers snuff to the dogs, with varying results. Kashtanka does not like the substance, but Eel makes a show of acceptance and obedience.
This memory leads into Vanka's recollection of the splendid weather in his home village. Back home, the night is dark, smoke rises from the chimneys, and the frost and snow create a scene of dramatic beauty. Shining stars and the bright Milky Way can be easily discerned. After these pleasant thoughts run their course, Vanka sighs and returns to his letter.
Now, Vanka records various instances of his rough treatment in Alyakhin's household. Alyakhin beat Vanka because Vanka went to sleep rocking Alykhin's infant child; Alyakhin's wife also scolded Vanka in a harsh manner for gutting a herring improperly. Vanka has also been mistreated by the older apprentices, who mock him and send him for food. His life is characterized by Alyakhin's violence, by an unpleasant diet of bread and gruel, and by consistent sleeplessness. He is desperate for his grandfather to take him away.
Vanka sobs. He continues the letter, explaining to his grandfather that he will be dutiful and hardworking if he is taken away from Alyakhin. Vanka promises that he will grind Konstantin Makarich's snuff, and that he is willing to clean boots or work as a shepherd to prove his worth. Life at Alyakhin's is torture to Vanka, who (as he explains) has only stayed on because he has no boots and is fearful of the cold. Vanka then pledges that, if he is brought back to the village, he will grow up to protect and pray for Konstantin Makarich.
Chekhov's story "Vanka" was written in 1886; for more than a hundred years, this narrative has enchanted its readers with the lucidity and sharpness of the themes that Chekhov has chosen. On the surface, the story seems to be about the terrible plight of a sensitive and agreeable boy who becomes an object of ridicule and beating. At the same time, the story "Vanka" is a statement about the naivety of its title character, who cannot properly address a letter and who innocently assumes that a single small and well-meaning gesture can counteract the cruelty of the adult world. Throughout, Chekhov subtly leads his readers to pair off their more advanced, perhaps more jaded perspectives against the limited, astonishingly earnest perspective of Vanka.
In a further measure that complicates but does not undermine the story's immediacy and clarity, "Vanka" has a rather complex composition. Vanka's letter is interrupted several times with the narrator's remarks, with Vanka's own memories, or with descriptions of the setting. Such movement can be seen early in the narrative, through attention to one part of the objective setting where Vanka sits and writes: "the dark window-pane, in which of the reflection of the candle flickered" (49). Soon after this candle is mentioned, the wistful Vanka turns his thoughts to a scene of rustic coziness involving his grandfather Konstantin Makarich and the two dogs. The candle and the darkness seem to call to mind the grandfather's own wanderings through the dark, or perhaps an image of a lighted church or house. Regardless of the specific associations in Vanka's mind, Chekhov proves adept at pivoting from present detail to backward-looking rumination in this early instance and uses a series of skilled maneuvers of exactly this sort to organize the rest of "Vanka."
Despite these sophisticated turns, Chekhov's story is based on an extremely simple situation. Vanka Zhukov is a nine-year-old orphan. In the village he has only his grandfather, to whom he wrote a letter complaining about his bitter situation as an apprentice to a shoemaker. All of this information about Vanka, his background, and his misfortune is presented with supreme efficiency. As the story progresses—and without distracting from the task of presenting Vanka's letter and Vanka's present conflict—Chekhov continues to filter in new information, including explanations for what may be some of the story's surprising points. For instance, it may seem odd that a lower-class, 19th-century boy such as Vanka can read and write, living as he did in a time of low literacy rates. Only in the second half of "Vanka" does Chekhov explain Vanka's attainment of his skills: he was taught to read and write by a member of the literate aristocracy, Olga Ignatyevna.
"Vanka" deals with a protagonist whose circumstances are unusual in ways such as this, yet the story serves as an expression of its author's conception of childhood. Childhood in Chekhov’s works is a special, lost world that adults cannot re-enter. Though subjected to cruelty and loss, Vanka has not lost his ability to regard the world with refreshing lyricism. In particular, his memories of the village are evidence of the continuing power of his sensitivity and imagination: "The air was still, transparent, fresh. it was a dark night, but the whole village with its white roofs, the smoke rising from the chimneys, the trees, silver with rime, the snow-drifts, could be seen distinctly. The sky was sprinkled with gaily twinkling stars" (50). Vanka is acutely observant of the world around him, capable of holding onto his most vivid memories, and capable—unlike the typical, easily jaded adult—of keeping them unsullied by hardship.
It may seem that Chekhov's characters are clearly divided into adults and children, so that childhood and adulthood are two ever-opposed states. On the one side is the innocent Vanka; on the other are characters such as Konstantin Makarich (a pleasant man who evinces none of his grandson's poetic temperament) and Alyakhin (who seems completely indifferent to his apprentice's pain). Yet these distinctions may not be as clear cut as they at first appear. The world of adults, as represented by Konstantin Makarich and Alyakhin, is not a world of superior maturity. It is a world in which some of the less desirable characteristics of childhood, such as offhand jesting and arbitrary spite, indeed persist, but are not clearly complemented by any new virtues.