The setting of the story puts Vanka in a time of misery and almost slavery conditions. He is the apprentice of a shoemaker, but instead is treated like a dog. He is constantly beaten and poorly fed. Lacking appropriate education, as was the case of most poor kids of the time, he still manages to write a plead letter to his grandfather, yet his style is incoherent at times, jumping from moments of sadness to joyful events, triggered by memories of a distant past. His rushed writing is justified by feelings of despair, looking for a prompt solution to his misery. After all he is just a little kid, and at that age his mind is all about fun and games; instead he is even forced to steal. He overcrowded the letter with ideas, fears, promises and hopes. He is also able to transmit, with a limited perception, his visions and interpretations of the surrounding world, as it is described on the impression he has of Moscow. Similarly he is able to picture vivid images of his grandfather, pet animals and remote events, all reminiscent memories of better days. Nonetheless, the letter will not reach his destiny; he cannot understand how to address it properly. His cry for freedom will never reach the objective, but he is ignorant to all this and falls asleep with an intense feeling of hope.
The story is very compelling, but it presents maybe a few flaws. Although Vanka's writing may look childish, and his own analysis of past memories and present conditions are surrounded by a halo of fantasy, the way the story is presented will reflect more the thoughts of an older child. Additionally it is a bit suspicious that he can write at all; taking into consideration the setting, most likely he would be an illiterate kid instead. .
Anton Chekhov, is probably represented by the setting itself, his memories of a brutal time of scarce resources and limitations, a time of dubious morality and trickery. The fact he employs a somewhat limited vision of the events adds additional drama.