“Big mystery what you have,” snorted my opponent.
I was playing in a private poker game in Detroit and all the chips were in the middle. He was, in fact, right: I had pocket aces, the best possible starting hand. But he hadn’t managed to deduce this in time to act on it. We were all-in: in terms of decision-making, the hand was over.
Many people think the goal of poker is to trick your opponent, but it’s not. The goal of poker is to make money. Deception is a means to an end. It can be valuable if you can transform it into a strategic advantage - for example, if your opponent puts in too much money because you had a hand they didn’t think you could have - but that doesn’t happen automatically.
Poker is a game with defined rules, and those rules imply that some strategies are better than others. That’s what Jungleman means when he says poker is about the truth. It’s about following strategies that make sense given the rules.
A simple example in poker is that the rules say that high card wins. If I have a higher pair (or straight, or flush) than you, I win the hand. So it follows directly from the rules of poker that high cards are better than low cards. This means you can gain an element of surprise by playing low cards, but you pay a price for it: If neither of us folds, you’ll end up winning the hand less often. The value of surprise is real, but you have to balance it against the downside of making the best hand less often. The trap many people fall into is believing that poker is about tricking your opponent, so low cards are actually better than high cards.
It’s sort of like if we were playing basketball and you flipped into a handstand and drove towards the basket upside-down. Will you surprise me? Yes. Will you score a basket? Probably not. Because no matter how disoriented I might be, it’s really hard to shoot a ball into the basket upside down. You’re fighting against not only the defender but also the rules of basketball and physics.
This is the crux of when surprise works and when it doesn’t. If you’re going against the current fashion or metagame, surprise can be a very effective strategy, but if you’re going against the internal logic of the game, you’ll always lose. The trick is telling the two apart.
In chess, lots of newer players talk about how much they hate facing 1. d4, and it’s no mystery why. At lower levels, 1. e4 is far more common, so you get way more experience against it and develop a higher comfort level. But at the master level, e4 and d4 are considered more or less equally good moves. That suggests you could gain an edge by playing d4 at lower levels: it’s an equally good move, but far less popular, so you gain surprise value without sacrificing on the objective quality of the move.

(Whether you want to win games with opening surprises is a different story. If your goal is improvement, maybe you’d rather take your opponent’s best shot? But anyway…)
But now compare 1. d4 with 1. f3. Whereas d4 is a good move that follows standard opening principles - controlling the center and opening lines to bring out the pieces - f3 is just a garbage move that has nothing going for it. That means that even if you surprise your opponent, which you almost certainly will (who has prep against f3?!), you won’t gain anything from it, since the move just fundamentally just doesn’t work. And indeed f3 scores very poorly.
Another example in chess is the value of material. One of the first things many people learn is the point value of the pieces, and beginner’s understanding of the game tends to be very materialistic. But as you get better, you realize there are other factors to the game - space, initiative, etc. - and maybe material doesn’t count for as much as you thought. It’s possible to take this too far though. There’s a line of thinking that goes, “If everyone else is obsessed with material, I’ll get an edge by not caring about material!” This doesn’t work because, all things being equal, it really is better to have more pieces. I’ve run into players who seem more interested in sacrificing their own pieces than taking mine, and it’s like we’re conspiring together for me to win the game.
Strategies that are as good as the most popular strategies but under the radar can be good surprise weapons. Strategies that are justifiably unpopular because they’re terrible usually won’t work, even if they’re surprising. The dream, of course, is to find a diamond in the rough, an unknown strategy that is not only on par with but better than the most popular approach. Such strategies are extremely valuable, but hard to find.
Next time you’re tempted to go against the grain, ask yourself, “Am I going against fashion? Or against the logic of the game?” If the answer is fashion, it may well be a good strategy. But never fight against the logic of the game itself, because that’s a fight you can’t win.
I broke out laughing when I read the part about the opponent conspiring with you so that you would win, imagining a guy staring menacingly as he sacrifices a piece for absolutely no compensation.
And the hits keep coming. Am loving all of your columns, Nate. Using poker and basketball examples: highly entertaining and didactic. Keep up the great work!