D&D General How do you do smart chaotic evil?

That's not right. Just because something is CE, doesn't mean they are no longer capable of understanding consequences.
While this is true in the abstract, a pattern of behavior can still indicate that consequences are being ignored so often, it would be unlikely that the perpetrator understood them. I'll get to an example just below.

Now, if I'm strong enough that doing whatever in the daytime doesn't matter and it's easier for me? Then sure, do it in the daylight. I'm probably going to take the easiest path to my goal. But, again, the evil cult that is gaslighting victims into thinking they are doing right, only to reveal at the last minute that they were doing evil all the way along? That's about as chaotic evil as it gets.
Perhaps. I would say the most chaotic evil thing someone can do is maintaining that kind of double life over a long time, two faces so diametrically opposed that there is no reconciling them. The loving, doting father, volunteer, churchgoer, PTA member, etc. etc., who is also a serial r∆π¡§& and murderer. The community grandma who bakes cookies and tortures victims. Etc. Basically the people who become part of a system, but only so they can corrupt, pervert, and destroy more while staying hidden. That's pure CE to me.

Being chaotic means the individual is number one. You don't care about others. That's where the evil part comes in. Leaving my minions to die while I get away? That's pretty chaotic evil. You have no real loyalty to anyone else and distrust anyone who proclaims loyalty to you.
And this is the example I wanted to get to. This is, generally speaking, an instance of stupid evil. Minions' deaths because of your negligence or outright cruelty/malicious deeds? Yeah that has consequences. Big ones. It means fewer people are going to be loyal to you in the future. It means those who do work for you will understand that even if they obey, it's no guarantee that they're going to be treated better than your enemies; even if they perform well, they'll always be one boss bad mood, one head honcho unpleasant day, one "chosen to deliver bad news" moment away from gruesome, brutal death.

Doing that once or twice, especially when the minion really really does deserve a painful lesson for disobedience or horrendous, avoidable failure, sure. Even LG bosses occasionally make a lesson out of a bad employee. But to do so regularly/frequently? No, that is clear evidence of either not caring about consequences, or being too foolish/deficient to understand them. And there's an argument to be made that if you work real damn hard to make your goals happen, only to then sabotage yourself several times without need, that you're either crazy or stupid anyway!

It's all about domination. The others aren't loyal to you because they believe in your cause. They are loyal to YOU personally. It's all about the cult of personality. The "cause" is just a tool for dominating others. It doesn't actually matter all that much. If it wasn't this "cause" it would just be something else. Whatever lets you dominate others to do what you want.
Some CEs will certainly think this way.

Others can differ over nearly every point. Perhaps they pride themselves in truly earning the loyalty of their underlings, because they see that as "owning" the body, mind, or even soul of such loyal soldiers, or because they have mastered arts of turning "good" people into fanatic loyalists. Maybe they really truly do care about the cause above all else, and as a result truly value those who also care about it, loving them in a twisted way, sparing them from truly unnecessary sacrifice so they can be sacrificed in the most beautiful and cause-serving ways, shaping each adherent to become the kind of person who would want to die for the cause. Maybe they actually despise cults of personality, but don't realize that that is exactly what they have, and think the people loyal only to them are actually loyal to the thing they believe in (wouldn't be the first time a naive person in leadership ended up causing horrible problems).

This is what I meant when I said we have to articulate a Chaos, and an Evil, which is compatible with being extremely smart.

Smart people care about long-term consequences and, generally, about efficiency and efficacy, desiring victory not at "any" cost, but rather at any reasonable cost. Even those who are reckless are usually not so to the degree that they throw away their resources.
Smart people leverage the resources at their disposal, they don't squander them nor invest them frivolously. The cavalier, lackadaisical attitude you describe is one of the things we expect smart people to NOT do.
Smart people keep their petty and/or whimsical impulses under control. That doesn't mean they never indulge in pettiness or whimsy; it means they do so with good reason, or at appropriate times, or when the costs (both direct and opportunity) are minimized, etc.
Smart people adjust their basic/ordinary beliefs in response to new data. They don't need to be having no commitments at all to higher beliefs, they just need to recognize when a situation has changed and to try to adapt to those changes reasonably.
Smart people re-evaluate their own methods and approaches. That doesn't mean they have to be right nor that they can't choose wrongly. It means that they are at least somewhat self-reflective when they face challenges, especially if they lose or only win after struggle.
Smart people understand that the emotions of others can be useful in some circumstances. That's a cold and kind of off-putting way to say it, but it's true. Emotions, beliefs, desires, all of these things can let you manipulate or convince others, even if you personally have no special interest in them.
Smart people understand that increasing your available resources is always better than decreasing them if you have a choice, all else being equal. Victory at cost is always worse than victory with extra gain.

I could go on. The point is, genuinely, scarily smart villains need to meet some high standards. They aren't allowed to act in the cavalier way you describe here. Not because someone is forbidding them, but because the actions you describe are among those which mark a villain as not very smart.

Hence, I constructed notions of both Evil and Chaos such that they were fully compatible with someone who evinces the above smart-person behavior most of the time. Without that (any such construction, not just mine), you're going to constantly be fighting against yourself, weakening your "smart" villain with foolish actions because you believe a villain has to do those foolish things.
 

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Q in some episodes of Star Trek Next Generation.
Empress Sato in the Star Trek Enterprise episodes "Through the Mirror Darkly".

IMO - a CE critter doesn't think of itself as CE. It is just doing what it thinks is best at the time or as part of a longer term plan. The side effects of its plans on others don't really bother it one way or the other. Some of those effects may help others. Other effects may harm others. In its mind, so what? As long as its plan or status is improved. Or it just has fun.
I've been reading a lot of Planescape lately, so I'd like to look at your "a CE critter doesn't think of itself as CE" in the context of Tanar'ri Demons. As exemplars, they do think of themselves as Chaotic Evil, and they think of that as the best way to be. What your saying does reflect on a difference between soft alignment and hard alignment. Some beings just happen to be their alignment, while other beings know and actively support their alignment, and I think that's a useful realization to make the alignment system both firmer and softer at the same time.

As for my answer to the OP, the way I conceptualize alignment I call "the warm fuzzies" model. Your personal alignment reflects what actions make you feel good about yourself and what actions make you feel bad about yourself. If X action is good, and doing it makes you feel good about yourself, then you're Good. As a Good person, doing evil would make you feel bad. If circumstances pressure a Good person into doing evil, they feel bad about it and seek to atone. If circumstances continually make a Good person do evil, then they could grow numb to it, representing their player changing their alignment to Neutral; worse, they could hard switch to Evil and suddenly like doing evil.

A Lawful person feels good when they follow the rules and feels bad when they break the rules, while a Chaotic person enjoys breaking rules and doesn't like following rules or patterns.

I'm purposefully avoiding defining what actions are what alignment, as that's where the actual debate happens.

So, to me, a smart chaotic evil person is someone who enjoys being chaotic and doing evil, and they do that smartly. Since chaotic and evil things are often, or definitionally, against the law, then they're smart about concealing their actions. Where as a Lawful Evil person often uses the law to do evil lawfully, a chaotic evil person would prefer to simply not get caught and might even be compelled to find a way to do it flagrantly while not pinning it on them (or better yet, pinning it on someone else). A neutral evil person probably just seeks to not get caught, where as the chaotic evil person likes to cause chaos in the process.

Another idea I had was also inspired by something in Planescape saying that every outer plane is a utopia to somebody. That made me think about alignment from the perspective of "what kind of world do you think is best?" That lead me to make this chart about what each alignment sees as the best guiding principal for society. I'm still working on it, it's subject to change, but it's been helping me to reconsider alignment.

Alignment​
Law​
Neutral​
Chaos​
Good​
Justice​
Charity​
Liberty​
Neutral​
Order​
Peace​
Freedom​
Evil​
Control​
Selfishness​
Anarchy​
 

Robert Howard Bruce (aka “Ether Man”) was a RW serial rapist who got caught after 20 years of crimes in at least 5 states. The detectives talking to him were very frustrated with him by the end of their interview.

One said to him (paraphrasing), “You’re smart, you’re good looking…you could have done anything you wanted!”

He laughed and replied, “I did!”

THAT is messed up. It illustrates an interesting thing about the idea of Alignment: your alignment reflects what you want to do.

I'm reminded of when people question people following the rules and helping people in open world games. What if my power fantasy is helping people and making the world a better place?
 

Imagine a Revolutionary.

They have a specific goal: Overthrowing an Oppressive Regime.

They are willing to do WHATEVER IT TAKES to overthrow that oppressive regime.

We're talking the whole gamut of evil. Torturing the servants of the state for information, killing civilians and children en masse to force people into action. Planting bombs in ambulances so people will let it through, or at least get it deep enough into the checkpoint to get lots of casualties and wreck inroads to the city. Betray their own allies to the police so the cops are busy killing the bad guy's second in command while the bad guy is poisoning the water supply.

They want to do it so they can destroy the people who hurt them and the people they care about. They will do -anything- to achieve their goal, and then leave everything in ruins or take over and be just as oppressive but in their own specific way.

Now. Have that revolutionary be smart. Make smart plays. Use their assets to the best of their horrifically cruel ability.

You now have smart CE.
 

From my perspective, smart CE, is someone who does his evil stuff without regard for other people, but recognizes that he has to cover his tracks. Otherwise his evil activities might be curtailed by others.
Once he does that, though, he's no longer acting on whim and/or driven by his emotions, two major hallmarks of CE.
 

That's not right. Just because something is CE, doesn't mean they are no longer capable of understanding consequences. Now, if I'm strong enough that doing whatever in the daytime doesn't matter and it's easier for me? Then sure, do it in the daylight. I'm probably going to take the easiest path to my goal. But, again, the evil cult that is gaslighting victims into thinking they are doing right, only to reveal at the last minute that they were doing evil all the way along? That's about as chaotic evil as it gets.

Being chaotic means the individual is number one. You don't care about others. That's where the evil part comes in. Leaving my minions to die while I get away? That's pretty chaotic evil. You have no real loyalty to anyone else and distrust anyone who proclaims loyalty to you. It's all about domination. The others aren't loyal to you because they believe in your cause. They are loyal to YOU personally. It's all about the cult of personality. The "cause" is just a tool for dominating others. It doesn't actually matter all that much. If it wasn't this "cause" it would just be something else. Whatever lets you dominate others to do what you want.
I quoted 4 of the 5 editions where the CE write-ups refute that interpretation. The 5th might also, but 4e was kind of an oddball and I don't know what it said about CE.
 

These aren't religious text or contract law. The amount of hair splitting in this thread is getting excessive.

Remember all this started when the PC's main concern was, "these guys are our enemies, but we don't like our odds of survival in a fight, so if we can make a deal with them instead of fighting, can we trust them to keep it?" If the enemy was LE, you could trust them to keep the deal, if they were NE, you could trust them to break the deal as soon as it was advantageous to do so, and if they were CE, you have no idea when or under what circumstances they are going to break the deal, but at some point, they are going to break the deal.

When you think of it that way, smart CE comes out pretty naturally. You don't pick the obvious moment like those predictable NE guys who think they are way smarter than they are, you pick the most interesting (and terrible) moment to break the deal when whoever you made the agreement with isn't even thinking of the deal.

I know with CN and CG, "chaotic" ended up meaning "flakey", but it was pretty rare for CE to be that way.
 

When you think of it that way, smart CE comes out pretty naturally. You don't pick the obvious moment like those predictable NE guys who think they are way smarter than they are, you pick the most interesting (and terrible) moment to break the deal when whoever you made the agreement with isn't even thinking of the deal.
This is in direct contradiction to every edition's alignment description of CE except maybe 4e. What you're describing is the opposite of acting on whims and/or driven by emotion.

What keeps CE in check is being stronger than the CE individual and the CE individual is aware that he is weaker.
 


This is in direct contradiction to every edition's alignment description of CE except maybe 4e. What you're describing is the opposite of acting on whims and/or driven by emotion.

What keeps CE in check is being stronger than the CE individual and the CE individual is aware that he is weaker.
I just see this as a needlessly stupefying take on Chaos.

Chaos does not need to be so utterly enslaved to whim that it cannot organize; it just needs that organization to be one that always justifies its legitimacy to the individual. So you can have an organized group of freedom fighters (aka terrorists, as @Steampunkette noted--which one you see as "evil" vs "desperate" is a matter of perspective), and they can be chaotic without that conflicting with them acting as a group. It's just a group where you cannot rely on hierarchy to justify your actions. You always have to persuade, and if someone wants to leave, then they just leave, there is nothing holding the group together except mutual consent.

Yes, SOME Chaotic Evil--indeed, possibly most Chaotic Evil--beings will be exactly as you describe. But being absolutely RULED by your whims and driven EXCLUSIVELY by your emotions? That's literally one of the characteristic traits of being a stupid person. Allowing foolish and dangerous restrictions to not only hobble you, but outright eliminate the possibility of victory. That's what that is. And it's just as stupid when it's a Lawful person pixelb!%@#ing about needless details (it's me, hi, I'm the problem, it's me; at tea time everyone agrees), or a Good person getting so hung up on personal moral purity that they allow horrible harm to come to others, or whatever else.

There should be some Chaotic Evil people who are not absolute slaves to whim and emotion, but instead express Chaos in any of the myriad other ways that that idea can exist--and who can, therefore, potentially be frighteningly smart, dangerously good at achieving their goals.
 

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