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I want to try writing a character that is able to seemingly be one step ahead of their opposition, and is able to turn all outcomes into an advantage, no matter if it seems disadvantageous, but has a trickster-like behavior and is able to turn any situation to their advantage with 'plans' that always seems to teeter in the edge of failure but actually working, and able to make/simplify plans on the fly, a trickster-chessmaster, for lack of better word.

Said character is supposed to also look really goofy and foolish on the outside, as well.

Is there any tips/tricks to writing this type of character? The story is going to be set in a world similar to the real world, so I cannot use "abilities".

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    Hi and welcome to Writer SE! I am going to add that, writing an all powerful character that can do anything they wanted and always win is going to end up fairly off-putting for a reader. What's the point of reading if their plans always ends up with them winning? It gets boring to read through, especially if you turn it into a series. If you are into anime, this theme is fairly overused. Especially in anime 100+ episodes like Fairy Tail. No matter the odds or setbacks, they always win. After 70+ episodes, it simply gets... boring. I would try to mix it up instead. – ggiaquin16 Jul 24 '17 at 15:45
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    @ggiaquin well one punch man is a show where the protagonist is certain 100% to win all the time and it is hailed as a great show. If you go down the invincible protagonist road you just change the dynamic of the story. There is I believe definite potential for stories with protagonists like that, as long as the story doesnt pretend to be a usual hero story. In which case, if it does, you are 100% right – Mikailo Jul 24 '17 at 17:39
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How exactly your character is going to be, I think heavily depends on what kind of story you are telling but good points to remember for any character but especially this kind of characters are these:

1)They must be flawed. (Unless thats what you are going for)

2)They cant be on top of everything all the time. (Unless thats what you are going for)

1) The most common problem in my opinion with those "chessmaster" as you say, characters is that they usually aren't characters at all, at best they are merely plot solving deus ex machinas(which i dont think is ever fine), or crazy empowerment characters with no actual flaw whatsoever (which could be fine if your story is about exploring this kind of character, which I find rather hard to do it right), leading to a character which is neither relatable nor believable most of the time.

2)This has more to do with the actual story and not the character itself but it is equally important, escpecially in stories where solving conflicts/mysteries is an integral part of the appeal of the show, which from your description is what i guess you are going for. You must make sure that there are NEVER asspulls. Nothing breaks immersion more than having your character do something either practically impossible or "figuring out" things nobody could possibly figure out. Outsmarting the opponents must feel natural and not forced. In that train of thought, you should also make sure that your characters are in danger. They have to ACTUALLY! be in danger and not just seem like it. The best way BY FAR to accomplish this is to have your protaginsts lose. People dont neceserilly have to die when things dont go the way of your protagonists but THERE MUST BE consequences to them losing otherwise its meaningless.

I'd say this sums up the most important pitfalls in these kind of characters.

TL;DR: Flaws , danger and vulnerability.

And for some examples of characters like that: THe very first character that came to mind is this: http://codegeass.wikia.com/wiki/Lelouch_vi_Britannia code geass

The series litteraly starts with the main character playing chess :3 I'd say the series tries and succeeds in making a characters that both feels human with real flaws and ambitions who is also able to out smart his opponents , ussually just in the nick of time. The bad things I'd say is that many times the means he uses often feel like asspulls , but the real issue is that the opponents often feel completely and utterly useless.It can be said that this fact reinforces the theme of the show, that nobility an the aristocratic systam promotes people in power that aren't the right people for the job, but regardless this simply cheapens the encounters and make the main character feel completely over powered and unrealistc.

Lesson to learn: Your adversariers must actually be clever and resourcefull and not simply cannon fodder for your protaginst to beat otherwise it simply cheapens the experience

Other notable characters: Sherlock Holmes ( For a character who doesnt usually lose and is clearly "over powered " but stil delivers great stories) (Any of the Sherlock holmes stories , series, books, movies)

Protagonist of aldnoah zero: https://myanimelist.net/anime/22729/AldnoahZero (For a character similar like sherlock but maybe not done quite as right i.e. omniscient plot device)

Antagonist from Captain America Civil War (Cant eloborate without spoilers)

Francis Underwood from house of cards.

House of cards

I tried to give several examples of varied characters from different shows to both inspire you and also iterate that there are many many ways to write this type of character. Cheers xD (Couldn't think of anyone thats is also goofy and foolish maybe tobi from naruto but i think thats a bit of a stretch)

Edit: I forgot something important, if you want you can completely ignore both what i said and most other common "rules" for writing characters as long as you know what you are doing and you have a reason to do it. It will certainly though make your job of writing a well structured and interesting story much harder I'd say.

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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.
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    Right Sora, he matches the description perfectly! Knew i was missing simehting important. Also important to note while all these ways are amazing ways to "throw spanners into the works" , I'd say it is very important to choose a way that makes sense for your world and your characters.The biggest gripe with these situations is personally losing my suspension of disbelief even if the situation is theoretically possible, so my priority would be delivering a logical and believable "fight" instead of a convoluted one for the sake of being convoluted. – Mikailo Jul 24 '17 at 13:07

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