Chaotic neutral semi-antagonist motivations

I'm trying to come up with a third-party trouble-maker to get between a party of Lawful Good types and the main Lawful Evil organization they're opposing. The good guys are, as usual, reactive. The bad guys are trying to conquer the good guy land.

So what should the third-party guy be, and what motivates him to get involved and cause trouble with both sides? Basically I'd like him to be someone the good guys could get as an ally if they wrangle him right, but who usually just shows up to harass them, then leaves. And occasionally they'll cross paths with bad guys who complain about this guy too, about how he's always messing with their plans.

My first thought is a chaotic neutral druid, someone who is just, I dunno, a 'playa hata.' He doesn't like people in authority, and he wants to cause a ruckus. But he can be pointed in a direction and set to go cause havoc, if you make it sound fun for him.

But what are some other ideas for character concepts and motivations that work here? Basically I need ideas for why an NPC would mess with both the good guys and the evil guys.
 

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Maybe someone who is super-smart, and mistakenly believes they have got it " all figured out " . They are kind of amoral, thinking that they have figured out morality is a sham, but are nevertheless empathetic, so are not given to hurting people willy-nilly the way a chaotic evil person might. That, or they believe in good and evil, but are extreme solipsists, so that they discount reality as being a product of their own mind. They feel that the good guys and the bad guys are both trying to become authoritative within the characters perception of reality, and are thus to be resisted as one might attempt to resist insanity or having one's mind changed.
 

The first thing that comes to mind is some sort of rogue character who is trying to play both sides of the fence amassing his power, wealth, and notoriety. He could be bought off by either side for the right amount of coin and the right kind of bump in his reputation. He could be the guy who turns the tide of battle if he is on one side or the other in support of them, perhaps he's the leader of an organization and has his own minions...
 

What about a secessionist or a rebel? She wants her province to leave the good guy kingdom and form its own country. At the same time, she doesn't want the evil empire to conquer her province.

Maybe she's the direct descendant of the old bloodline of local kings, before the province was conquered in the distance past. The natives of the province, while not completely sure about becoming independent or outright warfare, are loyal to her and her family, and will help her escape from the military or the law.

You could model her after someone like Robin Hood, or the Scarlet Pimpernel. Guerrilla attacks, fading back into the forests, robbing the wealthy landowners and helping the poor.

The evil empire is contacting her and offering aid, in order to stir the pot and weaken the good kingdom. But she is basically Good, so while she accepts some help, she resists advice to go too far. But perhaps the evil empire is willing to commit atrocities in her name.
 


What do the good guys want? What do the bad guys want?

How are those alike?

What is a third way that highlights the similarities between the two? "You are both two sides of the same coin."
 

A gambler, or a gambling group - some sort of travelling casino or betting den. Run by someone like Quark from DS9 (with maybe a bit less jerk with a heart of latinum).

Opposed both groups for the overbearing (?) regulations/authority, but a potential source of info, and well, risky bets are some of the best kinds.
 

I'm trying to come up with a third-party trouble-maker to get between a party of Lawful Good types and the main Lawful Evil organization they're opposing. The good guys are, as usual, reactive. The bad guys are trying to conquer the good guy land.

So what should the third-party guy be, and what motivates him to get involved and cause trouble with both sides? Basically I'd like him to be someone the good guys could get as an ally if they wrangle him right, but who usually just shows up to harass them, then leaves. And occasionally they'll cross paths with bad guys who complain about this guy too, about how he's always messing with their plans.

My first thought is a chaotic neutral druid, someone who is just, I dunno, a 'playa hata.' He doesn't like people in authority, and he wants to cause a ruckus. But he can be pointed in a direction and set to go cause havoc, if you make it sound fun for him.

But what are some other ideas for character concepts and motivations that work here? Basically I need ideas for why an NPC would mess with both the good guys and the evil guys.


I think you just described Kramer from Seinfeld.
 

I have had a few characters and neutral parties engage in such behavior. I've had a long recurring group of chaotic individuals who believe entropy is the only path to societal improvement. Essentially they are organized anarchists, as strange as that sounds. Their leader is a millennia old construct who possesses powerful magic and powerful political influence. They are staunchly neutral, believing that all political and national organizations are entirely selfish and are only looking out for their own interests.

They will often help and hinder parties, trying to encourage the party to do something chaotic and destroy themselves in the process. For example, they destroy sources of great wealth or disseminate knowledge. In the main campaign they disintegrated thousands of tons of gold, and donated powerful magical items to small splinter groups such as druids and goblin war parties.

Eventually they were persuaded to help the party stop the big bad evil. It was quite entertaining and the party was very glad to have their chaotic power on their side.
 

In the internet age, the first possibility which springs to my mind is:

For the lols.

See, the problem with high-power pranks in D&D is that so much of the population just can't deal with them. PCs, and their opponents, have the advantage of massive resources and durability. So, if you don't really want blood on your hands, but you think that putting people in terrible situations is hilarious ("Ha! That treasure map actually just points out in the middle of the desert!", or "We've replaced Roger's spell component pouch with a bag of infinite gerbils. Let's see how he reacts."), PC-grade folks are the ideal targets. Makes a better story if it's a famous or powerful target, and the extra risk is exciting.
 

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