The Art of Storytelling

I recently had a conversation with a friend who was growing bored with poker. He felt it had become too robotic and wanted to pursue something more creative.

While I encouraged him to pursue whatever brought him fulfillment, I couldn't help but think his characterization of poker as formulaic and lacking creativity was off base.

In fact, there are strong similarities and lessons between poker and the creative arts – even in the solver era.

This week’s lesson comes from an unusual place: The world of 19th-century playwriting.

Chekhov’s Gun

Anton Chekhov was a famous Russian playwright and author. Over 120 years after his death, you still see his most famous maxims in almost every work of fiction – from novels to TV shows and films.

​Chekhov’s Gun​ is a narrative principle stating that every element in a story must be relevant and necessary.

If you see a gun on the shelf in the background of a TV show scene, even if it's never mentioned, that gun will be featured prominently at some point in the story. No time should be wasted on irrelevant details — everything you see or hear has a purpose.

I know what you’re thinking: How can a simple piece of story-telling advice from the late 19th century possibly help with my poker game?

Know the Story You’re Telling

More times than I can count, someone has asked me for advice on a poker hand they played, and they start with:

"So I’m on the river in this hand, and the river brings a 3rd heart, and my opponent shoves for 2x pot…”

“But how did we get there?” I ask. “What happened pre-flop, on the flop and on the turn?”

“Umm, let's see… I think he opened from MP, or wait, maybe there was a limper and he raised, and on the flop he led into me, or maybe he check-called?"

They are focusing on the street where they became unsure of what the correct decision was, and couldn't clearly recall what had happened from the beginning of the hand.

If you don't know the details of the story, how can you judge its credibility?

The Setup

Some time ago, I was playing in a live game. I was in the small blind, and I noticed that when the player to my right first looked at his hand, he didn’t seem interested in playing it.

Normally, he would pay close attention to the action before him when he wanted to play, but now, he didn't seem to care what the action was. It seemed like he was getting ready to fold, but when it was his turn, he realized that no one else had entered the pot, and he was the button. So, he came in for a raise. I 3-bet, and he gave up the pot without resistance.

When you play a hand of poker, you need to be laser-focused on every detail (action) from your opponent(s). You never know when a small detail that at first feels irrelevant may play a crucial role in your decision-making. Had I not paid attention from the very start of the hand, I would have missed that crucial detail.

Everything is important.

Had I not made that observation, I would’ve just folded. While this read didn't end up winning me a million-dollar pot, it won me four big blinds (a decent winrate for the hour!), and it led to me playing a dialed-in, confident session.

The Confrontation

Let’s look at a hand example to see how else we might use our observations to gain more EV.

$2/$5 PLO

CO raises to $17, BTN 3-bets the pot to $58. The blinds fold, CO calls.

Flop: 9❤️8♠️7❤️ ($123)
Check, BTN instantly bets the pot. CO calls.

Turn: 2❤️ ($369)
Check, BTN instantly pots it again. CO calls.

River: 9♣️ ($1,107)
Check, BTN instantly pots…

The board texture has changed dramatically on every street, yet the button is seemingly unfazed by the changed circumstances. This is a story that doesn’t make much sense. The betting itself is confusing, but the speed at which the button played their hand makes it even more puzzling.

If you only read the 1st chapter (pre-flop), or any of the other chapters (streets) for that matter, nothing would seem out of line. But when you take in the entire narrative, it’s easy to see why it’s nonsensical.

More often than not, when a story doesn’t make sense, it’s because the author hasn’t thought things through. And when that happens, they’re usually bluffing.

When I look back at my career, I’ve found myself on the river facing a large bet, holding a pure bluff-catcher, more times than I could dream of counting. Early in my career, I would fold, as I couldn't beat much.

But as I learned to reconstruct the hand, from the very first page to the final sentence, I got quite good at noticing when a story didn’t add up. When that happened, I’d make the call – and the majority of the time, I was right.

Note that this is an important lesson not just as a hand reader, but also as the storyteller: When you’re playing poker, you’ll need to tell stories at the table, and you’ll need to dissect them.

The Resolution

Let’s look at another hand example:

$1/$2 NL

UTG raises to $8, everybody else folds, and you defend your big blind with Ac5c.

Flop: Q♣️3♦️2♠️ ($17)

You check. UTG bets $12. You decide to tell a story. You can’t pretend to have two pair, as you’d fold all those hands preflop, but you have 22 and 33 in your range, and you know this UTG opponent doesn’t.

You raise to $40. UTG calls.

Turn: 2❤️ ($97)

You decide to keep firing, as you would if you actually had a full house or quads. You’re fully prepared to empty the clip on the river, and are pretty confident that your opponent can fold even an overpair. Your story checks out.

You bet $80, and UTG calls.

River: 3❤️ ($257)

Before you confidently jam your stack in, now would be a good time to pause and check your story.

How often do you have the hands you’re representing now?

When you were representing those sets on the flop, there were three combinations of each available.

3♣️3❤️

3♠️3♣️

3♠️3❤️

2♣️2❤️

2♣️2♦️

2♦️2❤️

With the second deuce and second trey landing on the board, you’re down to just two:

3♠️3♣️

2♣️2♦️

Suddenly, it’s become very unlikely for you to have the hands you've been trying to represent. And you’ve still got all the gutshots and other semi-bluffs you would have played this way.

Does your story make sense?

Sure, technically. But it’s become pretty far-fetched.

Sometimes, the only way to end the story that you’ve been telling is by surrendering. Going against Chekhov’s advice and blasting away when you can’t represent much isn’t heroic – it’s just reckless.

You may not find the rest of the table screaming at you in frustration when your story makes no sense – but they will happily take your money.

When you find yourself on the river telling a story, look back at all of the narrative elements you’ve introduced throughout the hand. Consider them carefully, and then piece them together for your happy ending.