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Source: https://writers.stackexchange.com/a/29346
License name: CC BY-SA 3.0
License URL: https://creativecommons.org/licenses/by-sa/3.0/

Source: https://writers.stackexchange.com/a/29346
License name: CC BY-SA 3.0
License URL: https://creativecommons.org/licenses/by-sa/3.0/

To add to Mikailo's excellent answer, another character you should definitely look at is Sora from _No Game No Life_: he has both the chessmaster intellect _and_ the foolish, goofy personality. In particular, watch the episode with the shiritori game, which combines both those elements to spectacular effect.

Anyway, the two basic traits of this type of character are that a) they possess a genius-level intellect, and b) they are extremely analytical, and can read people's behaviours exceptionally well. There are a few tropes that come into play with this type of character (won't link the TV Tropes pages just yet though):

- Xanatos Gambit: A plan thought out in such a way that no matter what happens, the outcome is to your advantage or can be twisted to your advantage. Named after David Xanatos, the villain of _Gargoyles_, who might also be a good example of a chessmaster (I haven't watched _Gargoyles_ and know nothing about it beyond what I've picked up on TV Tropes, so I can't say for definite).
- Batman Gambit: A plan that hinges on the "reading people's behaviours" part, and relies on someone acting in _exactly_ the right way in order to further your plan.
- Xanatos Speed Chess: The ability to rapidly adapt to any spanners in the works. Because there WILL be spanners in the works. _Code Geass_ (which Mikailo mentioned) is a brilliant example of this: none of Lelouch's plans _ever_ go exactly as he wants them to, but he manages to make them work for him anyway.

Now, the simplest and laziest way to write this sort of character is that whatever their opponent throws at them, they reply, "Aha! I knew you would do that, so I planned accordingly!" But that's bad for two reasons:

1. At best, your character will be a Boring Invincible Hero. At worst, they'll come off as practically omniscient, being able to predict things that they simply should not be able to.
2. This can easily descend into I Know You Know I Know, where characters plan for each other's plans for each other's plans for each other's plans and it all gets very confusing. _Death Note_ is a very good example of this problem.

So how to write a story with this kind of character? Well, the most important tip is: **throw spanners into the works**. Have their carefully-laid plans go spectacularly wrong, forcing them to adapt. This doesn't necessarily mean outsmarting them - there are plenty of other ways of accomplishing this.

- Have someone disrupt their Batman Gambit by not acting how they expected them to.
- Introduce outside elements that they could not possibly have known about. Just be careful that they don't come off as ass-pulls.
- Have their plan go off without a hitch only for them to realize too late that in the process, they've made something else _worse_, and now they have to deal with that. To use an example from _Code Geass_, at one point Lelouch's plans inadvertently result in the death of the father of one of his closest friends, something he doesn't know about until after the fact.
- Just because a chessmaster knows about something, or can anticipate it, that doesn't mean they can counter it easily. They might know, for example, that their enemy has sent an assassin to kill them, but they can't truly plan against that if they don't know who the assassin is or what they look like.
- Have them misinterpret what they know, so that their plan has an intrinsic flaw that they don't know about.
- Have them just plain screw up. It's one thing to come up with a brilliant, intricate plan, it's quite another to carry it out without making a mistake.

Original score: 2