The Bet by Anton Chekhov

The ultimate wager: life, freedom, and the soul.

At last! This is the kind of absorbing Chekhov short story I’ve been searching for—one that strikes the right balance between existential dread and hopefulness without leaving you buried under a pile of despair. The Bet is thought-provoking, packed with pathos, and a perfect showcase of Chekhov’s mastery of the short-story form. Its compact nature and brevity are a masterclass in storytelling—proof that sometimes less really is more.

If, like me, you occasionally find Chekhov a bit... let’s say, intense (or just plain heavy-handed), this story is a refreshing change of pace. It’s surprisingly accessible and, in my opinion, an ideal starting point for those new to his work. Much like Oysters, this is another exploration of suffering but through a more philosophical lens. 

As the title suggests, this tale revolves around a bet. It all begins with a lively dinner party conversation because, of course, nothing brings people together quite like debating life imprisonment vs. the death penalty. A rich banker and an idealistic young lawyer argue over which is worse, and things escalate quickly: the banker bets two million rubles (presumably an eye-watering sum in 19th-century Russia) that the lawyer couldn’t endure 15 years in solitary confinement. To everyone’s shock, the lawyer agrees. What happens next? I'll leave that up to you to discover on your own, since it will spoil the fun. Suffice it to say, there are some unexpected turns that are delightfully ironic where the penultimate question becomes: who is the true prisoner here?

The most captivating part of the story, for me, was its philosophical discourse, grappling with the big, thorny existential questions about happiness, wealth, and the meaning—or meaninglessness—of human existence. And let’s be real, maybe this relentless focus on suffering is just a 19th-century Russian thing. If you have read Dostoevsky, you know what I mean. Yet, Chekhov's stark honesty somehow makes that sorrow feel profound rather than suffocating. 

Admittedly, I was on the fence about Chekhov's work before, but reading The Bet completely won me over. It is such a polished, terse and memorable story, which has officially turned me into a fan. 

"Think better of it, young man, while there is still time. To me two million is a trifle, but you are losing three or four of the best years of your life. I say three or four, because you won't stay longer. Don't forget either, you unhappy man, that voluntary confinement is a great deal harder to bear than compulsory. The thought that you have the right to step out in liberty at any moment will poison your whole existence in prison. I am sorry for you."