How do you make a super villain's plan smart enough to outwit genuinely intelligent heroes but still have the heroes win?

Question

Even if they are not super-geniuses, many villains are portrayed as cunning, charismatic, and manipulative, staying three steps ahead of the heroes at every turn.

But creating a good villain plan is difficult for both the villain and the writer. If the plan is flawless, the heroes need an ingenious strategy too or their win will feel cheap. A win gained through luck, plot armor, or a deus ex machina usually feels unearned.

A stupid plan is much worse, especially if the writer tries to paint it as brilliant despite a million holes in its logic. Take the classic puppet master of most "monster of the week" shows. A good example would be most versions of Power Rangers. The main bad guy will sit in the dark for ages, spam a single main monster, and maybe a few grunts too. Then, the heroes beat the creature after one or two episodes, and the villain does it all again learning little if anything from their defeats.

So here's my question:

How do you make a villain plan that is smart enough to fool genuinely smart protagonists, yet flawed enough that the heroes still win, not by luck or plot contrivance, but rather by their own wit, merits, and courage?

Answer 1

So first of all, as the writer, you have the advantage of crafting a story in any direction and you should focus on the villain's plan from the end and develop it towards the beginning. Figure out what success looks like for the heroes... then figure out how the heroes find him. Reverse the process of the story so that the villain gets all the key steps to the climax but leaves vulnerabilities for the heroes.

If the villain is acting in an episodic fashion, then a great method to keeping him deadly but letting the heroes win is what TV Tropes calls "The Xanatos Gambit." The strategy was named after a villain from Disney's "Gargoyles" series, who was known by the fans, and eventually the heroes, to run schemes that were often designed to distract the heroes from his real goals. Often his schemes were done in such a way that if he won, he got to both defeat the heroes and get the real objective of his plot of the week. If he lost, he still won because he was able to distract the heroes long enough to accomplish his real goals.

An example of this is how, in one episode, he stages a successful prison break of a character... by letting her know not to escape jail with the rest of the villainous team. While they escaped and the Gargoyles spend the bulk of the episode recapturing them, the person he wants out remains in her cell... in doing so, she impresses the parole board enough to give her an early release. Her fellow villains and the Gargoyles' fight against them were all for naught because the villain already won whether or not the action of the story went in his favor or didn't.

The writer of the series (Greg Weisman) loves these types of villains and almost any work of his will have similar villains that have different motives than the obvious.

Answer 2

I see a few options that can work.

1. Specialized information

Have the flaws in the plan rely on specialized information/knowledge/skills that are rather rare. Make sure that this specialized information is brought up before with the hero (so it is not out of the blue) and is hinted at with the villain.

Ex: The villain is worried that they will forget the shutdown steps of their super weapon in case something unforseen goes wrong and so writes down notes on how to do that. But since they know there is a risk that someone might find the notes they write them in an obscure language they studied previously, like old norse. Unbeknownst to them the hero is a linguist or is really into the old norse sagas and has learned to read old norse as a result. So now a weakness that isn't really very weak can be taken advantage of. In this case the foreshadowing for the hero can be them comparing troubles with events from the norse myths and for the villain maybe they use runes on their flag (which the hero can translate).

2. Previous cooperation and/or exploitable character flaws

The villain and hero previously worked together either knowingly or unknowingly. This means the hero might be aware of certain faults of the villain (ex: usually overlooks attacks from above or doesn't trust others so will have no backup systems others could take advantage of - resulting in a single point of failure the heroes can take advantage of). The villain might try to adapt to avoid those faults but they slip up or they overcompensate.

Realistically these small faults could also just be discovered as a pattern over the course of the plot by heroes who never worked with the villains before.

3. Non-sequitur approach

The hero and villain approach problems from fundamentally different perspectives. This gives each sides weaknesses against the other (but also strengths).

Ex1: The villain expects to deal with government investigation style opposition so everything is hidden behind layers of misdirects and careful arrangement of situations to deflect investigators (with a few simple non-lethal traps to deflect police from key infrastructure). The hero dislikes distractions and sleight of hand and subterfuge and so just grabs some big weapons and mounts a frontal assault (blowing past the knowledge & legality based defenses)

Ex2: The villain expects to be attacked directly and prepares for that situation with layer after layer of strong physical defenses. But this is all expensive so salaries are not kept as high for non-military positions. The hero is used to a life of poverty and so ends up drinking with a disgruntled janitor who accidentally tells them the security code to the base and complain that the ventilation system has been on the fritz with no idea how to fix it. The hero can now infiltrate the base and can even take advantage of the ventilation system to incapacitate most of the villains thugs without firing a shot or throwing a punch until the final room that has a separate ventilation system because the computers need extra cooling (or something).

Conclusion

The key of all these approaches is a difference in information and assumptions between the hero and villain. These differences are not inherently mistakes or random chances but are just differences that come from them being different people with different opinions and perspectives and life histories.

Answer 3

The heroes are persistent.

When constructing an evil scheme, no matter how good, you have to stop at some point. Sure, you've compromised or subsumed all world governments, but are you going to get the local councils too? Your Fortress of Doom has a lava moat, laser sharks, and self-targetting flamethrower machine gun turrets on every wall; are you going to put buckets of liquid helium over the doors too, just in case one of the heroes is fire-, laser-, shark- and bullet-proof (and manages to find the Fortress of Doom)?

Your Doomsday Machine is near-impregnable. Are you going to put the leftover budget into titanium-shielded foundations, a backup generator, a decoy installation on the other side of the world, or armed guards? It's not like you have infinite resources, after all; everything spent on unnecessary precautions is just wasted, when you could be using it to further your True Goals.

The heroes, meanwhile, don't have trade-offs to make. Their goal is to stop you, and they don't care how long it takes. If one of their plans fails, so long as enough of them are still alive, they can try another one. They can adapt to your plans, but – unless they happen to be your only opposition – you can't adapt to theirs in any meaningful capacity until they're a sufficiently large threat that you have to.

A smart plan is not a straight line; it's a web, with more contingencies than happy-paths, and with plenty of room for error, modification and (depending on the context) retreat. No matter how hard you try, you're not going to be able to make all your contingencies independent of each other, you're not going to be able to cover all bases, and you're not always going to know what branch of the plan you're currently on. With your resources spread thin, you're vulnerable to to a focused attack; with your resources concentrated, you're vulnerable to attack from an unprotected direction. Everyone who is not you can make mistakes,¹ and you can't do everything yourself. All this can lead to your downfall.

Plan around it.

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A good plan has countermeasures and contingencies. Don't artificially limit how many of these the supervillain can deploy; if you can think of it without outside-context knowledge, and your villain has had more than a month to plan, your villain thought of it too.² Your heroes can win by:

• getting to an unlikely branch of the master plan³ through sheer grit and determination, and then doing something that the villain didn't have the time or resources to defend against in advance, forcing heavy improvisation from the villain;
• doing something nobody could have predicted – or, at least, not the villain;
• or simply by being better than the villain to such a degree that they didn't stand a chance to begin with.

No matter how smart, competent or powerful, nobody can guarantee survival against an enemy who just won't give up. Offence is easier than defence, after all.

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¹: No supervillain survives for long if their character flaws are large weaknesses. If they're sufficiently strong in another area, such that the flaws are only weaknesses in specific and unusual situations, they might be able to get away with having some. Personal growth is hard, and often unpleasant, and takes time away from machiavellian plots.

²: A good tip for writing intelligent characters: give yourself more time to think of answers, strategies and tricks than you give the characters in-story. Apart from in-character ignorance or egregious character flaws, don't restrict what your characters are allowed to consider: if you don't find it hard to outwit your villain, your villain isn't very bright.

³: Don't try to actually describe the supervillain's complete plan, contingencies and all, in great detail. Even skipping the laser shark R&D, that'll take you so long. Focus on the bits that your viewpoint characters will know about / be up against; while you should be aware of the parts that won't make it into the story, they only matter to the extent they affect the parts that are.

Answer 4

Exploit the villain's blind points

Let the villain have one or more blind points that he refuses to reconsider. That the heroes are only doing this for the fame and fortune that comes with it, and if he manages to hide their deeds, they will give it up. That teams will break down on enough temptation. That he knows what this hero's moral weakness is.

A classic version is that a prisoner or a henchman turns out to be less in awe of him that he thought, and he falls to treachery.

Answer 5

No plan survives first contact with the enemy

Villains always seem to have nefarious plans, carefully crafted. Heros always seem to have well intentioned plans, carefully crafted. What is the common thread? They always go awry.

A plan rarely accounts for everything. There is always a certain amount of adaptation required. This is almost tautological -- we tend to plan for things complicated enough that planning was necessary in the first place. Everyone who plans knows that the subsequent adaptation is essential. It is also where the nature of the villain starts to become visible. They must necessarily inject themselves into the system and, potentially, gum up the works.

It is here that the crafty hero can show their mettle. They don't defeat the plan, they defeat the implementation of the plan as implemented by the villain. The crafty hero understands the phrase "know thy enemy," and seeks to understand how the villain is bobbing and weaving and adapting to keep the plan on its wheels. Then they can turn things towards a blind spot.

Perhaps the epitome of this can be seen on a chess board in the play of two grandmasters. When grandmasters play, they typically plan... and plan... and plan. They pour over their opponent's past games, studying how their opponent moves and thinks. They'll formulate opening plans trying to drive their opponent into paths they think they are good at and the opponent is bad.

And then it all starts with a single pawn move, and the press of a clock. The game is on. The enemy is in sight. Now, practically speaking, their plans work for a while. They're no fools at this planning game. They're going to go down one of the paths they studied before the match. Both sides know it. They're just sort of agreeing on which one to go down.

And yet, often they take their time. Some of that is weighing the mind of the human sitting before them. How are they feeling today? Do they look like they're in the mood for a kingside attack or a queenside attack? Grandmasters often talk as if they aren't playing the board at all -- they're playing the mind of their opponent from the first move. Their job is to navigate an opponent into a blindspot.

This can be done by skill, but never underestimate dumb luck. One of the most famous moves in Chess history is 36. axb5!, played by Deep Blue in the rematch of Kasparov v. Deep Blue. This was the match which officially put computers in the driving seat as the true masters of Chess. Humans were left behind. Kasparov, oft considered one of the most brilliant chess minds of all time, had won the first match in 1996 4 games to 2. Deep blue would win the rematch in 1997 3.5 to 2.5 and sunder the human chess community.

Typically we like to view this from Kasparov's perspective, as the human, and make Deep Blue the enemy. Thinking from the perspective of a computer is not all that enjoyable, but for purposes of this narrative, let's treat Kasparov as the enemy. Deep Blue is the plucky hero, with its racks and racks of specialized hardware.

Move 36, taking one pawn with another, is not all that impressive on its own. Especially if you don't play chess. However, it had alternatives. In particular, 36. Qb6 would have won two pawns "free and clear." But Kasparov is no fool. It was a trap. In trade for those "free and clear" pawns, Kasparov would lay the groundworks for a very powerful attack. Kasparov is known for his attacking play. This is where he wants to be. This is his plan. And Kasparov knows his enemy. Computers generally prefer material advantages, such as two free pawns, and undervalue subtle things like attacks.

But that's not what deep blue played. Deep blue played 36 axb5!, which turns out to be a very subtle and nuanced move with profound impacts. It's the kind of thing you'd expect a human grandmaster to play. And it rocked Kasparov's plans. It got under his skin. He truly did not believe a computer could make such a play. And in one move, our hero uprooted the villainous Kasparov's plans.

This was just the start, of course. Deep blue still had to play out the game. And it had to play 4 more games after that. But a chink in Kasparov's armor was exposed, and Deep Blue circled around it. Kasparov claimed the Deep Blue team must be cheating, for no computer could ever see that move, but with the help of a mere intermediate player with a button saying "stop looking at this line" could have found it alongside Deep Blue. Surely the team had cheated, feeding Deep Blue a tiny hint!

His calm resolve was shook, and Deep Blue took advantage of it. Brick by brick, Deep Blue dismantled Kasparov's mind. In a later game in the match, it was commented that Kasparov had lost the game before he even played the first move, he was so shook up.

Sure, 36 axb5 came due to the skill of the computer. It is currently believed by most people that Deep Blue did not cheat. It was programmed to weigh these sort of situations (specifically because Kasparov is so known for his attacking game). It was a skillful move. But it was luck that it was so darn effective. And Deep Blue capitalized on it, never flinching. That is how it took down Kasparov's plans.

Answer 6

Suspension of disbelief

Ideally, an author would like to create a wholly original and logical plot which sees both protagonists and antagonists doing their best. However, I can not think of any definite recipe for doing that. A second-rate recipe that showrunners mostly use is "suspension of disbelief".

First, a villain(s) is trying to do something that, objectively thinking, may or may not be conceivable for them to do. Then, hero(es) may or may not notice them doing that. And finally, hero(es) do something to overcome the evil plan - something that villain(s) may or may not have seen coming.

In all 3 steps above, authors rely on certain level of suspension of disbelief, so the audience would (if grudgingly) agree that villain has had the capacity, heroes were blindsided, and villain could not see the turnaround coming.

For an author, it is important to always keep this level of suspension of disbelief below the level set for the show. Different series have different levels. "Realistic" shows like "Game of Thrones" have very high demands for plot consistency; things like magic can give only a little wiggle room to showrunners. General comic books/Marvel/DC tolerate a greater suspension of disbelief. And children shows (like "Sailor Moon" mentioned in the comments) allow for high suspension of disbelief used repeatedly. If Tuxedo Mask is coming at the end of virtually every episode to save the day - so what? We like to see him in action, and he's so handsome, by the way! :)

Answer 7

I don't like one of the options in the highly-voted answer, namely "Specialized information". Having the hero happen to know something as obscure as what the villain used is nothing more than a lucky break, which you explicitly said you don't want.

I also find the other alternatives in other answers not too satisfying. In particular, a truly intelligent villain would get other equally intelligent villains to find and fix loopholes in his/her plans, so the only way the heros can outwit the villain is simply to be more intelligent.

This is possible; you simply have to be more intelligent than the average person, or spend lots of time thinking through possible scenarios! That way, you can come up with brilliant villain plans and make sure that ordinary people (your test-readers) cannot find loopholes but that there are actually loopholes that can be found by really difficult thinking. Sometimes, mathematics or science can be helpful here, as there are various non-intuitive aspects of the real world that even very intelligent people fail to understand.

Now, if you don't need the hero to outwit the villain, then there are many other options, such as the classic idea that morally virtuous intentions can overpower or override malicious intentions. Another idea that is somewhere in-between is that the world has some kind of magic flow that always tries to restore harmony, so it's easy for heroes to cooperate with it once they quiet themselves and listen to other beings and nature itself. In this way, the heroes can stop the villains not by sheer strength or by sheer intelligence but by doing the right things at the right times and right places. Depending on your tastes, you could have anything from a passive magic flow to a sentient world that can actively assist the heroes in small ways to outwit the villains.

Answer 8

Maybe you might want to read a bit of history.

Maybe history of various wars and battles. Maybe find a battle, campaign, or war were both sides had intelligent and competent leaders, but one side won big and the other side lost badly.

As part of a diplomatic mission to Syria the great Roman general Scipo Africanus met the great Carthaginaian general Hannibal and it was claimed they discussed who was the greatest general of all times.

One version says:

“Africanus asked who, in Hannibal’s opinion, was the greatest general of all time. Hannibal replied: ‘Alexander, King of the Macedonians, because with a small force he routed armies of countless numbers, and because he traversed the remotest lands. Merely to visit such lands transcended human expectation.’ Asked whom he would place second, Hannibal said: ‘Pyrrhus. He was the first to teach the art of laying out a camp. Besides that, no one has ever shown nicer judgement in choosing his ground, or in disposing his forces. He also had the art of winning men to his side; so that the Italian peoples preferred the overlordship of a foreign king to that of the Roman people, who for so long had been the chief power in that country.’ When Africanus followed up by asking whom he ranked third, Hannibal unhesitatingly chose himself. Scipio burst out laughing at this, and said: ‘What would you have said if you had defeated me?’ ‘In that case’, replied Hannibal, ‘I should certainly put myself before Alexander and before Pyrrhus – in fact, before all other generals!’ This reply, with its elaborate Punic subtlety, and this unexpected kind of flattery…affected Scipio deeply, because Hannibal had set him (Scipio) apart from the general run of commanders, as one whose worth was beyond calculation. Livy, The History of Rome from its Foundation XXXV.14″

Appian, in his history of Rome says:

” It is said that at one of their meetings in the gymnasium Scipio and Hannibal had a conversation on the subject of generalship, in the presence of a number of bystanders, and that Scipio asked Hannibal whom he considered the greatest general, to which the latter replied, “Alexander of Macedonia.” To this Scipio assented since he also yielded the first place to Alexander. Then he asked Hannibal whom he placed next, and he replied, “Pyrrhus of Epirus,” because he considered boldness the first qualification of a general; “for it would not be possible,” he said, “to find two kings more enterprising than these.”

Scipio was rather nettled by this, but nevertheless he asked Hannibal to whom he would give the third place, expecting that at least the third would be assigned to him; but Hannibal replied, “To myself; for when I was a young man I conquered Spain and crossed the Alps with an army, the first after Hercules. I invaded Italy and struck terror into all of you, laid waste 400 of your towns, and often put your city in extreme peril, all this time receiving neither money nor reinforcements from Carthage.”

As Scipio saw that he was likely to prolong his self-laudation he said, laughing, “Where would you place yourself, Hannibal, if you had not been defeated by me?” Hannibal, now perceiving his jealousy, replied, “In that case I should have put myself before Alexander.” Thus Hannibal continued his self-laudation, but flattered Scipio in a delicate manner by suggesting that he had conquered one who was the superior of Alexander.”

So anyway, Scipio and Hannibal might not have agreed on their relative ranking, but they did seem to put each other in the top four generals that they knew of.

Even the most brilliant leader can be defeated if the other side has too many advantages. Brilliant leaders on the other side are one such advantage, but not the only one possible, so even less intelligent leaders can sometimes defeat a more intelligent leader if they have enough advantages. And of course finding the advantages which one side has that nobody noticed before is one sign of a good leader.

And of course there are many different varities of good leaership and intelligent decision making. I have often noted that the qualities necessary to rise to an important and powerful leadership position may not be the same as, and often seem to be quite different from, the qualities necessary to be successful in that position.

Answer 9

Maybe the hero does something the villain rejects out of hand as a possibility because of important differences in their worldviews.

And far away, as Frodo put on the Ring and claimed it for his own, even in Sammath Naur the very heart of his realm, the Power in Barad-dûr was shaken, and the Tower trembled from its foundations to its proud and bitter crown. The Dark Lord was suddenly aware of him, and his Eye piercing all shadows looked across the plain to the door that he had made; and the magnitude of his own folly was revealed to him in a blinding flash, and all the devices of his enemies were at last laid bare. Then his wrath blazed in consuming flame, but his fear rose like a vast black smoke to choke him. For he knew his deadly peril and the thread upon which his doom now hung.

From all his policies and webs of fear and treachery, from all his stratagems and wars his mind shook free; and throughout his realm a tremor ran, his slaves quailed, and his armies halted, and his captains suddenly steerless, bereft of will, wavered and despaired. For they were forgotten. The whole mind and purpose of the Power that wielded them was now bent with overwhelming force upon the Mountain. At his summons, wheeling with a rending cry, in a last desperate race there flew, faster than the winds, the Nazgûl, the Ringwraiths, and with a storm of wings they hurtled southwards to Mount Doom.

Another possibility is getting help from unexpected sources -- building alliances and coalitions that the villain didn't expect -- helping opposing sides overcome longstanding enmity to unite against a common threat.

Answer 10

The villain is smart and is doing things that would work 99% of the time, taking lot of variables into account. Ex: he has a lot of competent and smart goons, he used bribe, blackmail to set things up nicely, have escape routes and planned for failure.

Then the hero is stronger/smarter than expected : he finds a way to beat the goons, he refuses the bribe, endure the blackmail or predict the possibility of an ambush (and takes measures against it). He manages in the end to prevent the bad guy from achieving his goal.

But, and this is one of my main points, the hero needs to lose too. If he fought, then he's really hurt. The hero family that was taken hostage is killed. While he survived because he predicted the ambush, one of his friends still died. In this way, it doesn't feels cheap. Here, there's no luck involved.

Also, the bad guy anticipated "normal" cases but the hero is just a little bit better, not by much but enough. And it doesn't even mean than the hero needs to be smarter than the bad guy, you just need to be unexpected.

As people say, No Plan Survives First Contact With the Enemy. What makes plan fail aren't necessarily a better plan, you just need something that wasn't planned.

tl;dr:

• The plan is sound and would work in 99% cases but the hero is an unexpected variable (he's a little bit tougher, smart or righteous than most people).
• The heroes needs to suffer and lose to, because nobody's perfect.

Answer 11

The Villain Could Make the Heroes Help

Xanatos, from Gargoyles, is the classic example. Many of his plans involve convincing the heroes that they need to do what he wants, whether or not they like it.

Thus, the heroes win and the villain’s plan is brilliant.

Heads I Win, Tails You Lose

The villain is so clever that, even when the heroes stop his plan, he still wins. Maybe they successfully saved the thing they and the audience cared about (their home, their loved ones, etc.) but find out that this made the villain achieve his goal in some other way. Possibly one that the audience will approve of or think is funny.

The Villain Could Have a Backup Plan

Maybe it did occur to the villain that something might stop him, even if he didn’t foresee precisely what, but he planned for that contingency too. He was hoping the heroes wouldn’t be able to, but by maximizing the upside and minimizing the downside, the villain made it a good gamble. That’s still impressively clever.

There’s More to Life than Cleverness

Being smarter than the villain isn’t the only legitimate way to beat him. Maybe the hero earns the victory through some other virtue. For example, if the story is about the hero learning to understand the value of integrity, maybe her life story up to that point would have made the villain reasonably predict she’d try to hide something, but at the climax, she surprises him (and us) by coming clean, proving she’s changed. Maybe the perseverance (or empathy, or teamwork, or creativity, etc.) needed to defeat the villain’s plan is what teaches the hero a lesson.

If the story isn’t about the hero becoming a better person, you might reasonably ask, why did the villain underestimate the hero? A classic answer is that the villain’s tragic flaw was not understanding what other people would do for love (friendship, honor, or something else).

Answer 12

The hero is lucky and/or gets help

Harry Potter falls into this category. Harry was a mediocre wizard and student, and was generally struggling in his personal life due to his rough childhood and upbringing. But he had a lot of help, both in terms of actually getting things done and staying motivated.

Frodo was very similar in Lord of the Rings.

The villain doesn't have to be clever, and/or the hero can be more clever

What if the villain isn't particularly clever, but just mediocre, without being a bumbling idiot?

Perhaps the villain is a demon. Maybe in some worlds demons have to earn their power, but usually demons are "just there", and have been for all time. There's no meritocracy in the demon world. Why does the demon have to be particularly smart?

Or perhaps the villain has inherited or otherwise lucked into the wealth, power, etc. that enables them to do whatever villainous thing they intend to do. The might be right in the middle of the bell curve of intelligence, and there's no particular reason that they should be smarter than average.

Plenty of good storylines have been crafted around a protagonist who is smarter than everyone else in the room, if only by just a little bit. Columbo, the first 3 seasons of The X-Files, The Princess Bride, et alia.

The drama and tension can come from sources other than masterful cleverness. Maybe the villain is tremendously powerful, or maybe a lot of people like the villain's plan and don't want it to be stopped. Or maybe the hero is an anti-hero, and despite whatever skills or intelligence they might have, they are their own greatest adversary.

The villain and hero are equally clever; it's a razor-edge battle that the hero might lose

Look at any professional sport or game of skill. At high levels of play, very often you have equally-matched players going up against each other. Maybe the final outcome comes down to an outright error; after all, nobody is perfect, not even a criminal genius.

Perhaps the villain and the hero are evenly matched. Consider Sherlock Holmes and James Moriarity. In that situation, the outcome of the final confrontation was more or less a draw. But the story could have easily been written as a very close shave in which Holmes narrowly prevailed through some tiny advantage in footing, or through a tiny miscalculation by Moriarity, or whatever.

This could also tie in with the "character flaws" angle mentioned in other answers.

Answer 13

The Villain is Playing the Long Game:

The villain is clever, and has abundant resources. He is in no rush to win. So he defers the attack planning to underlings being groomed for future success. Failure is a learning tool, or a filter to get rid of idiots. They don't learn because they are rotating new underlings into the job on a regular basis. Their new tank or armored suit needs testing, and the heroes provide a chance to work out the bugs.

The villain may be too busy developing bigger plans to care much about the heroes. The villain's attacks are half-hearted because he just doesn't care that much if he wins or loses a side-hustle.

The villain may have no intention of killing or defeating the hero. The hero features in their long-term plans as a successor, a tool to use at a critical time, or as a consistent distraction to keep bigger, badder heroes away. Is Captain Godlike going to take an interest in the villain that keeps getting defeated by the Amazing Newby?

Or the villain has an entirely different plan in mind. Perhaps the villain really IS a misunderstood hero. They may be secretly supporting the hero, training them and testing them for greater deeds (think Mr. Glass in Unbreakable). The villain always seems to fail at the end because to succeed would be like Hannibal Lecter killing Clarice Starling. Or the villain genuinely thinks they will eventually get the hero to come over to their way of thinking. Darth Vader doesn't WANT Luke Skywalker to fail, even if they are technically on opposite sides.

Answer 14

"How do you make a villain plan that is smart enough to fool genuinely smart protagonists, yet flawed enough that the heroes still win, not by luck or plot contrivance, but rather by their own wit, merits, and courage?"

I feel like there's an inherent contradiction in this question. It kinda sounds like you're asking "how do you make a villain plan that is A, yet Not-A?" If the heroes win by their own wits, then the villain's plan was not smart enough to fool them. If the heroes don't win by their own wits (if they just bumble along and succeed due to courage and other merits like brute strength and audacity), then the villain plan didn't fool genuinely smart protagonists. I think the first step to answering this question for the purposes of your own story is to decide whether you want the heroes to be...

1. outsmarted and defeated (it doesn't sound like this is what you want)
2. outsmarted, but still win (which would mean they're not as smart as the villain, but they have some other good qualities that make up for it), or
3. not outsmarted, but the villain came pretty close (which would mean the villain didn't ever actually fool them, but did at least give them a good run for their money).

I don't think there's any real solution where the heroes win by their wits and also are outsmarted. Every solution is actually just gonna be varying degrees of one or the other.

Answer 15

Develop the "perfect plan" with different heroes in mind.

If the villain's plan would work on James Bond, Austin Powers and Maxwell Smart, well, then that's a pretty good plan. It's too bad he's actually up against Johnny English, but how could he have known that in advance.

By building the plan around a different expected opposition, you can create a well thought-out and thorough plan, that nevertheless leaves openings for the actual heroes. Because your heroes will have different strengths and weaknesses from the "simulation heroes" the villain took into account.

So, pick (say) three heroes from books in the same genre. Have the villain mock-fight them in your mind, and think of ways to beat them. And then check to what extent those strategies would work against your own heroes, because ultimately you need to make sure you have some wiggle room to actually win.

So for my villainous anti-spy strategy, I'm only going to hire hench-women that aren't susceptible to the charms of men.
Wait, what do you mean your hero is an attractive lady. I didn't plan for that!

Answer 16

Exploitable vulnerabilities of very intelligent villains' arrogance overlook the simple solution that's obvious to lesser minds. In Vacuum Flowers (by Michael Swanwick) the hero created a villain with a mind superior to his own. There is a tense dialog scene where the villain thinks in circles around the hero. The hero defeats the villain as follows:

Hero: I built backdoor vulnerability into your mind.
Villain: you're lying.
Hero: I can prove it, but your minions would kill me.
Villain: we'll meet in private, no minions.

They meet. Hero breaks villain's neck.

Hero (to girlfriend): Ego was the vulnerability. The villain just had to prove his superiority, and was so hyperintelligent that he overlooked the crude solution.

Answer 17

The heroes uses other equally powerful supervillains against the one that has the big plan in operations. The heroes have the advantage of being able to cooperate whereas the supervillain all hate each and are using all means to cut each other down. So the heroes easily have another supervillain's spies in active one's plan (the plan basically requires the supervillain to use more resources in offence than defense so he can't defend against the other baddies).

Answer 18

Have something outside of the villain's control go wrong. One example: the first two Golden Sun games. At the end of "The Lost Age" when all four elemental lighthouses have been lit and the last boss defeated, we see the greater-scope villain Alex atop Mt. Aleph awaiting the arrival of the "Golden Sun" which will bestow unlimited power; he outwitted everyone, including his allies, so that they would light the beacons for him and he would simply await his prize on Mt Aleph. But instead, the Wise One appears and reveals that he basically changed the rules of how that worked simply because he didn't want Alex to receive the Golden Sun - Alex is instead sent to his death as Mt Aleph implodes.

Alex outsmarted the heroes but was himself outsmarted by a greater power completely outside his control.

Answer 19

Other answers have good points. Let me add a few more:

Nakama power

A classic from shonen manga and anime. Heroes cooperate and together they bring down the villain. [Tough luck if you have a lonely hero.]

Sacrifice

The villain(s) carry out their plan to gain something, right? In general, they expect to fully enjoy the results of their plan. On the other hand, heroes are prepared (and many times do) to sacrifice "everything" for the greater good: an easy life, having friends, their health, some times their teammates die, and even their life.

Realism

How realistic is your villain? World domination is not realistic. Power is (e.g. someone very very rich). Similarly, perhaps the conflict between villain and hero can be resolved in a realistic (and probably tragic) way. E.g. the plan does not succeed completely but many people die. Or some lakes end up toxic. Or heroes keep the villain in check (neither let win nor defeat). Or the world ends up with anthropogenic climate change.

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As an aside, I am sure I would not be able to think up a plan without loopholes. Perhaps you too. So, ask one or two other very intelligent people to think together with you! Same as pair-programming and code review. :-)