At first, Chekhov’s “The Bet” seems to be a stark contrast between life and death and the death penalty and life in prison. However, then it shifts its focus to a life of study, the classics, languages, music, and even the Gospel, which is deemed by the lawyer to be pointless. What then is the point of this very short story?

The question of mortality is related to the initial theme of the value of life. The story begins with a debate between the banker and the lawyer as to which is the more humane method of punishment: life imprisonment or a death sentence. The lawyer opts for the former, and the banker opts for the latter. It is clear from their little debate, and the wager that follows from it, that the two men have a radically different understanding of what makes life worth living.
The banker is a thoroughgoing materialist. He is a wealthy man who places much too high a value on the acquisition of earthly goods. When he says that a death sentence would be more humane than life imprisonment, he is thinking of how he personally would cope with languishing for years in a dark, filthy hole, no longer able to lead the opulent lifestyle to which he has become accustomed.
On the other hand, the lawyer understands that life, even in enforced confinement, can still have a certain goodness to it. It all depends on what you make of it, really. After accepting the banker's wager, he settles down to a rigorous program of fifteen years of reading, study, and contemplation. However, the lawyer still proves himself to be every bit as materialistic as the banker. After all, he has accepted the bet on the condition that he will collect a very large sum of money if he wins.
Chekhov's approach in writing "The Bet" is extremely ambiguous. He presents both characters as being highly complex in both behavior and motive. This militates against any easy resolution to the story or any glib moral messages being proffered. On one hand, the materialist banker breaks down and cries after reading the lawyer's letter in which he renounces his right to the two million rubles. On the other hand, however, he is still keen to make sure that this letter is safely hidden away from prying eyes after the lawyer makes good on his premature escape. Perhaps people would think there had been some kind of collusion between the two men. Has the banker really changed all that much?
So much, then, for the banker's materialist conception of the world. What about the lawyer and his worldview? He has chosen to be held in solitary confinement for fifteen long years. Yet, despite the immense knowledge he has gained in all that time, he escapes from prison less than a day before he was due to be released. Who on earth would do that? In addition to renouncing all earthly knowledge, the lawyer also rejects mortal riches. Far from affirming the quality of life as he did when he made the bet, the lawyer is rejecting life completely.
The complexity of "The Bet" frustrated and enraged many when it was first published. Chekhov's staunch refusal to tie up all the loose ends of the story into a neat ending still makes it difficult to infer any moral as such. Nevertheless, I would suggest that the value of a higher, more transcendent wisdom is something one takes away from having read "The Bet." Neither man has shown much in the way of earthly wisdom, either in agreeing to the bet in the first place or in their subsequent conduct over the following years. However, after the banker reads the lawyer's letter, we sense that both men have achieved a much wiser perspective on life. They both seem to realize that life is richer, more complex, and more meaningful than the restrictive world they have both been living in. However, because both men seem incapable of living such a life, it would seem that their sudden moments of illumination have not made either of them any happier.