You can read the whole Playing to Win book free here.
This article is an overview of the basics in case you want a shorter version.
"Playing to Win" is for people who are trying to win at games. It's not for people who aren't. For those people who are trying to win, they should make (tournament-legal) moves that help them win rather than moves that don't.
You wouldn't think that would be even slightly controversial, but somehow it is. Even though playing to win is the most important concept in competitive games, it's also widely misunderstood. Let's untangle that now.
The Scrub Mentality
"Scrub" is not a term I made up. It sounds like kind of a harsh term, but it's the one that was already in common usage in games to describe a certain type of player, and it made more sense to me to explain that rather than to coin a new term.
A scrub is not just a bad player. Everyone needs time to learn a game and get to a point where they know what they're doing. The scrub mentality is to be so shackled by self-imposed handicaps as to never have any hope of being truly good at a game. You can practice forever, but if you can't get over these common hangups, in a sense you've lost before you even started. You've lost before you even picked which game to play. You aren't playing to win.
A scrub would disagree with this though. They'd say they are trying very hard. The problem is they are only trying hard within a construct of fictitious rules that prevent them from ever truly competing.
Scrubs are likely to label a wide variety of moves and tactics as "cheap." For example, performing a throw in fighting games is often called cheap. A throw is a move that grabs an opponent and damages them even while they're defending against all other kinds of attacks. Throws exist specifically to allow you to damage opponents who block and don't attack.
As far as the game is concerned, throwing is an integral part of the design—it's meant to be there—yet scrubs construct their own set of principles that state they should be totally impervious to all attacks while blocking. Scrubs think of blocking as a kind of magic shield which will protect them indefinitely. Throwing violates the rules in their heads even though it doesn't violate any actual game rule.
A scrub would not throw their opponent 5 times in a row. But why not? What if doing so is strategically the sequence of moves that optimize your chances of winning? It's "cheap," though, throwing is cheap. And it's not just throwing, it's also a long list of somewhat arbitrary maneuvers. If you keep a scrub away from you by zoning them with projectile attacks, you'll probably be called cheap. If you do one move over and over, that's cheap. If you get a lead, then do nothing for 30 seconds so that you can win by time-out, that's cheap. Nearly anything you do that ends up making you win is a prime candidate for being called cheap.
Let's specifically consider the case where you do one move over and over. This goes right to the heart of the matter: why can the scrub not defeat something so obvious and telegraphed as a single move done over and over? Are they such a poor player that they can't counter that move? And if the move is, for whatever reason, extremely difficult to counter, then wouldn't you be a fool for not using that move? The first step in becoming a top player is the realization that playing to win means doing whatever most increases your chances of winning. The game knows no rules of "honor" or of "cheapness." The game only knows winning and losing.
"It's Not Fun To Play That Way"
This might be true, or it might not be, depending on the game. The scrub mentality is to make this claim for basically all games though so beware of that.
Some games don't hold up to high-level play. That's sloppy design in my opinion. A solid game holds up to experts playing it as hard as they can against each other. That way, the game can be fun for beginners and experts.
When a game doesn't hold up to expert play, it's degenerate in some way. There's only one good move or one good character, or one good strategy, or something like that. The game offers what appears to be a lot of fun options, but you don't actually get to do those fun options against experts, even if you are an expert too. So for this type of game, playing to win really will make it less fun, but that's not a problem with the players who are doing their best; it's a problem with the game. I wouldn't fault players here or complain to them that they are playing in a boring way. I'd complain to the game developer or play a different game.
There are plenty of games that become more fun as you get better at them, rather than less fun. With a good game, getting better and better at it reveals more and more depth to you, rather than exposing the game's shallowness. Games like Street Fighter or StarCraft are like this. My own games are also all designed for competition.
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Consider two groups of players who play a non-degenerate game: a group of good players and a group of scrubs. The scrubs will play "for fun" and not explore the extremities of the game. They won't find the most effective tactics and abuse them mercilessly. The good players will. The good players will find incredibly overpowering tactics and patterns. As they play the game more, they'll be forced to find counters to those tactics. The majority of tactics that at first appear unbeatable end up having counters, though they are often difficult to discover. The counter tactic prevents the first player from doing the tactic, but the first player can then use a counter to the counter. The second player is now afraid to use the counter and they're again vulnerable to the original overpowering tactic. (See the Yomi Layer chapter of my book on Playing to Win or this more visual summary on yomi layers.)
Notice that the good players are reaching higher and higher levels of play. They found the "cheap stuff" and abused it. They know how to stop the cheap stuff. They know how to stop the other player from stopping it so they can keep doing it. And as is quite common in competitive games, many new tactics will later be discovered that make the original cheap tactic look wholesome and fair. Often in fighting games, one character will have something so good it's unfair. Fine, let him have that. As time goes on, it will be discovered that other characters have even more powerful and unfair tactics. Each player will attempt to steer the game in the direction of their own advantages, much how grandmaster chess players attempt to steer opponents into situations in which their opponents are weak.
The group of scrubs won't know the first thing about all the depth I've been talking about. Their argument is basically that ignorantly mashing buttons with little regard to actual strategy is more "fun." Or to be more charitable, their argument could be that the game becomes less fun if they use tactic X, or character X, or whatever. That might be true temporarily until they figure out how to beat whatever it is, but ultimately the experts are having a more nuanced exchange, more opportunity for expression, for clever plays, for smart strategies, and so on.
The scrubs' games might be more "wet and wild" than games between the experts, which are usually more controlled and refined. But any close examination will reveal that the experts are having a great deal of fun on a higher level than the scrub can imagine. Throwing together some circus act of a win isn't nearly as satisfying as reading your opponent's mind to such a degree that you can counter their every move, even their every counter.
And if the two groups meet, of course the experts will absolutely destroy the scrubs with any number of tactics they've either never seen, or never been truly forced to counter. This is because the scrubs have not been playing the same game. The experts were playing the actual game while the scrubs were playing their own homemade variant with restricting, unwritten rules. The actual game really should be more fun if it's not degenerate.
"That's a No-Skill Way to Play"
Complaining that you don't want to do X in a game because "it doesn't take skill" is a common scrub complaint. The concept of "skill" is yet another excuse to add fictional rules and avoid making the best moves. Curiously, scrubs often talk about how they have skill whereas other players—very much including the ones who beat them flat out—do not have skill. This might be some sort of ego defense mechanism where people define "skill" as whatever subset of the game they're good at and then elevate that above actually trying to win.
For example, in Street Fighter scrubs often cling to combos as a measure of skill. A combo is sequence of moves that are unblockable if the first move hits. Combos can be very elaborate and very difficult to pull off. A scrub might be very good at performing difficult combos, but not good at actually winning. They lost to someone with "no skill."
Single moves can also take "skill," according to the scrub. The "dragon punch" or "uppercut" in Street Fighter is performed by holding the joystick toward the opponent, then down, then diagonally down and toward as the player presses a punch button. This movement must be completed within a fraction of a second, and though there is leeway, it must be executed fairly accurately. Scrubs see a dragon punch as a "skill move."
One time I played a scrub who was pretty good at many aspects of Street Fighter, but he cried cheap as I beat him with "no skill moves" while he performed many difficult dragon punches. He cried cheap when I threw him 5 times in a row asking, "is that all you know how to do? throw?" I told him, "Play to win, not to do 'difficult moves.'" He would never reach the next level of play without shedding those extra rules in his head.
In a tournament, winning the match is what counts. It doesn't matter if you used throws or dragon punches or if you run out the clock while running away, or whatever else. It doesn't matter if you "played in an innovative way" or if you "didn't do anything new." Don't be overly concerned about whether you are playing with "skill," but rather if you are playing to actually win.
If an expert does anything they can to win, then do they exploit bugs in the game? The answer is a huge yes—for most bugs. If you think "no" is a reasonable answer, then you haven't thought this through yet. There is a large class of bugs in video games that players don't even view as bugs; they aren't even aware that they are bugs.
A Tame Example
In Marvel vs. Capcom 2, Iceman can launch his opponent into the air, follow them, do a few hits, then combo into his super move. During the super move he falls down below his opponent, so only about half of his super will connect. The Iceman player can use a trick, though. Just before doing the super, they can do another move—an icebeam—and instantly cancel that move into the super. There's a bug here which causes Iceman to fall slower during his super at the same speed he'd fall during his icebeam, even though the icebeam didn't fully come out. The player actually cancels the icebeam as soon as possible: ideally as soon as 1/60th of a second after it begins. This lets the Iceman player connect with every hit of the super.
Is it a bug? I'm sure it is. Getting the movement property of a move you instantly cancel is a pervasive bug in many Capcom fighting games. Would an expert player use this? Of course. No one would even think twice about this, it would be absurd to ban it, and it would also be absurd to not do it because it's "cheap."
A Substantial Example
In Street Fighter Alpha2, there's a bug in which you can land the most powerful move in the game (a Custom Combo or "CC") on the opponent, even when they should be able to block it. If you weren't blocking low at the moment they activated the CC, you can't crouch in time to block it. A bug? Yes. Does it help you win? Yes.
This technique became the dominant tactic of the game. The gameplay evolved around this, play went on, new strategies were developed. Those who cried cheap were simply left behind to play their own homemade version of the game with made-up rules. The one we all played had unblockable CCs, and it went on to be a great game. How CCs were intended to be doesn't really matter: in the game we have available, they work how they work, and taking advantage of that is necessary to win.
A Bug Too Far
Some bugs are actually too problematic for you to use. This is generally not up to you, the player, to figure out though. A tournament organizer's job is to ban what needs to be banned—ideally as little as possible. If something is banned in a tournament, you shouldn't use it even if it helps you win.
When you play a competitive game, you want to be playing the same game everyone else is playing. When you make up your own scrub rules about not throwing or whatever, you aren't playing the same game as everyone else anymore. Likewise, if you use tournament-banned things to your advantage, you aren't playing the same game as everyone else either. You're just cheating.
When tournament organizers determine what (if anything) is banned, they should choose only bans that are enforceable, discrete, and warranted. To learn more about those concepts, read the chapter of Playing to Win on What Should Be Banned.
One example of bugs you should expect to be banned are bugs that only one player is capable of using. (Not because they picked a certain character, but rather because they are player 1 rather than player 2). In some fighting games, there are bugs that can only be performed by player 1. Even if they aren't that powerful and wouldn't normally be banned, they are candidates for banning purely because both players don't have equal access to the bug.
Bugs that turn the game off, or freeze it indefinitely, or remove one of the characters from the playfield permanently should be banned. These aren't about something being too good, but rather preventing there from being any gameplay at all.
This is the most dangerous category. Scrubs will say practically everything is too good in any game. In my experience, 99% of claims that something should be banned because it's too powerful are just wrong. That said, 1% of the time, there's something that's actually too powerful. Something that is game-breaking in how powerful it is, but if you get rid of it, the rest of the game is fine. We'll hope that tournament organizers have the wisdom to tell the 99% case from the 1% case and only ban the rare thing that seriously deserves it.
The character Akuma in Super Turbo Street Fighter is a great example of that rare case. Akuma is a secret character, requiring a long, annoying code to even pick him. He's a boss character that was clearly not intended to be fair at all.
Akuma is the best character in the game. That alone means nothing as far as banning; every game with characters has a best character. The problem is that Akuma is miles and miles and miles better than all other characters. He has a 9-1 or 10-0 matchup against every single character. It's very likely he's significantly more powerful (maybe by an order of magnitude) than any character in any game you've played. Just to give an example, he can use his red fireball repeatedly in such a way that you're stuck blocking until you die. You can even hold the joystick towards him and you're still stuck blocking it over and over. If you fixed that, he's still be 9-1 or 10-0 against everyone though.
This example is so incredibly extreme, that the entire community immediately realized Akuma needed to be banned when the code to pick him was discovered. This isn't because the entire community was scrubs. It was because Akuma is more similar to a game-breaking bug than he is to an overpowered character. The real bug is that he's pickable at all in multiplayer modes (note: 14 years later I fixed that bug in the online "classic mode" of Street Fighter HD Remix by disallowing him in online matches).
You should use whatever you can to win, but just be aware that the are rare cases where something is so broken that tournament organizers will need to ban to have a functioning game.
Playing For Fun
If you play in such a way as to maximize your chance of winning, it means abusing everything "cheap" that you can. It means frustrating the opponent, using bugs, and anything else you can think of that's legal to do. When all this comes together, it gives you a deeper kind of fun than is possible at lower skill levels.
That said, it's also fun to just mess around. It's fun to explore new characters, new strategies, and to do silly things. This type of stuff is actually really useful even if your ultimate goal is to win. You can read more about that in this chapter of Playing to win.
It's also totally fine to mess around with no intention of ever becoming really good. You don't have to try to be the best at every game you play. I certainly don't try that, it would be exhausting. But when I see someone else trying to be the best, I admire it, rather than condemn it. If that makes the game fall apart, I hold the game developer responsible, not the player.
But if you want to win—if that's your intention—then you need to leave behind whatever mental baggage you have that would prevent you from making the moves that actually help you win. By doing that and practicing and learning, you can walk the path of continuous self-improvement that Playing to Win is really about.