The main theme in Chekhov's story is leniency versus punishment, two opposing philosophies regarding justice.
In the story, Ivan Markovitch (Sasha's maternal uncle) argues for leniency, while Sasha's paternal uncle (the Colonel) argues for capital punishment as the only effective response to criminal conduct. The young juvenile under intense discussion is Sasha Uskov, who is guilty of forging a signature on an IOU.
Ivan argues for leniency because of Sasha's troubled childhood and lack of "good, benevolent influences" in his life. He acknowledges that Sasha is guilty but argues that he deserves the "indulgence and the sympathy of all compassionate souls." Ivan questions whether there is such a thing as free will and presents the argument that Sasha is compelled by inclinations he cannot control.
Meanwhile, the Colonel argues that Sasha needs to be held responsible for his actions. As a military man, he contends that helping the guilty escape punishment is "contrary to law" and represents the height of "civic cowardice." The Colonel worries that compassion will further reinforce Sasha's dissolute ways.
As the story progresses, there is every indication that the Colonel's wishes will hold sway over the small group of Sasha's relatives. However, Ivan Markovitch eventually prevails when he brings Sasha's deceased mother into the discussion. The group becomes powerless under Ivan's masterful and emotional performance. In the end, it is decided that Sasha's debts will be paid for, a sum of fifteen hundred rubles.
However, far from being humbled by the compassion shown him, Sasha is indifferent and cynical. He demands a hundred rubles from Ivan Markovitch. Appalled by his nephew's avarice, Ivan initially refuses. However, Sasha threatens Ivan, claiming that he will either turn himself in to the authorities or make out another false promissory note the next day. Ivan eventually complies, and Sasha walks away satisfied with his ability to manipulate his maternal uncle. He is not at all reformed and is unperturbed by his actions.
The main theme of the story is the conflict between two opposing philosophies regarding justice: leniency versus punishment.