Villain Creation - Flaws

[Hobbo Jim]

TLDR: What kind of flaw(s) would a kingpin villain have?

I'm playing a villain for my brother, and the idea behind him is that I am a spymaster Kingpin. With a ring of spies, I have several spymasters who run various operations of my activities - drugs, weapons, assassination, all the way to slavery. Bad dude. He is a fiend that has come to the material plane for his own gain (doesn't serve anyone but himself), and makes money and gains power as an end, not a means to an end. He has a few quirks, being overly serious with the exception of telling a really lame joke whenever you first meet him. I have been asked to give him a flaw that could be exploited by the adventuring group to bring eventually bring him down, and meet the inevitable as most DnD villains do. What makes for a good flaw for villains that is exploitable but not character ruining?


Edit for those who wanted more info: He is a Yugoloth, specifically an Ultroloth. From what I have gathered, if a yugoloth decides to engage in something that isn't the blood war, then they are usually trying to gain power, and make money and just simply hoard it. They don't spend it on anything in particular, just hoard it. Regarding power, there is a specific ritual that can be undergone with the help of a powerful Hag, but that's pretty far down the line if he survives. His current plans involve taking over the border between a desert country and a large empire that is suffering from famine. He is capable of talking to his subjects over long distances, assuming they are on the same plane, he is a skilled swordfighter, has truesight, and can fly. For the most part, it is standard yugoloth powers, plus some stealth and insight.

[Laserlight]

Pick a couple of flaws that the characters can detect--they may need some investigation but should not, for example, be "secretly in love with X but never mentions it in any way". You don't need to figure out how to exploit it--that's the job of the PCs.
Some possibilities: Hot tempered. Always uses the same pattern in combat (such as "opens with his biggest spell" or "opens with a cantrip" or "moves into melee with the biggest enemy"). Stingy at paying his troops / doesn't have the money. Focused on his plan and does not pay enough attention to resolving side problems (such as the heroes).

[Unoriginal]

What more can you tell us of the character? Appearance? Powers? Which kind of Fiend it is ?

Imagine it was a movie, and this character, with all the traits you got so far, needed to be established for the audience. How would the scene go?

[Trustypeaches]

Here are a couple flaws that could work!

Emotional Attachment: There is something or someone that the villain values to the point it impacts their judgement and reasoning. This could be a possession, it could be another character or a pet, or it could even be an ambition or goal they prioritize above their own self interests or what the logical thing to

Arrogance: The villain underestimates threats due to his enormous power (or enormous ego) and as a result does not properly assess the danger of situations. This is pretty straightforward.

Distrustful: This villain is so notoriously distrustful and backstabbing that none of his peers nor his underlings really trust him. He lacks close or loyal allies as a result.

[Thorgrim]

Here are a couple flaws that could work!

Emotional Attachment: There is something or someone that the villain values to the point it impacts their judgement and reasoning. This could be a possession, it could be another character or a pet, or it could even be an ambition or goal they prioritize above their own self interests or what the logical thing to

Arrogance: The villain underestimates threats due to his enormous power (or enormous ego) and as a result does not properly assess the danger of situations. This is pretty straightforward.

Distrustful: This villain is so notoriously distrustful and backstabbing that none of his peers nor his underlings really trust him. He lacks close or loyal allies as a result.

I think Arrogance is a really tough one. It's definitely the most likely for a character like this and I think it's an easy choice, but I also think it's really easy for Arrogance to turn into Stupidity in practice.

The other two are excellent, though. I think Distrustful is particularly good for a fiend type character.

[dragoeniex]

Want a fun one? Have the fiend chronically overestimate the party.

This doesn't have to be hugely overblown, and it can actually work against the PCs at times. Just as thieves fear being stolen from and liars suspect they're being lied to, this top dog of several overlapping intelligence rings has a skewed idea of what underprepared is. He expects people trying to interfere with him to have done the bare minimum of homework and plans to counter that.

This means leaked "weak points" are the most well-guarded or warded. It means he may let slip what he assumes is a small detail the party must know already while going on. It also means he may overprepare for an encounter with them and use way more resources than should be required to keep the heroes at bay. It's not like this happens with every small opposition; the party has just demonstrated the minimum amount of competency to be considered a threat.

This could lead to interesting encounters like mini game skill challenge segments to get away from or out of overblown traps or ambushes. Let players panic and laugh a little at how seriously he's taking them.

Then let them figure out if they can use that. Maybe they guess he's putting too many resources into this and figure out how to keep him throwing focus and $$$ at areas he doesn't need to. Or maybe they come up with some fantastic bluff he'll likely fall for because he imagines them pulling off their own elaborate schemes anyway. Or, just maybe, they decide terrible decision-making is the one thing he won't have prepared for and charge headlong through all the seemingly riskiest parts of his base.

Whatever they go for and whatever the villain's reaction is... Being overprepared is a flaw that's not used nearly enough.

[ThePlanarDM]

Vain. Greedy. Paranoid.

The villain could be addicted to something.

Indebted to a third party, needing to pay back a loan as fast as possible.

[Unoriginal]

A fun thing could be to take one of the PCs' Flaw and put it up to eleven.

[J-H]

For a classic list that will resonate, consider drawing from The Seven Deadly Sins (not actually Biblical, but a short-list of vices derived from such):

https://factualfacts.com/7-deadly-sins/

Determine his vice or vices, and you'll have one of his main drives, what he fears losing, and a possible weak point the party can use when scheming against him. He even might be a "Fiend of X" devoted to that vice. Lust is covered by succubi/incubi, so I would consider greed, envy (of mortal freedom & wealth?), gluttony, wrath (a hot & violent temper), or pride (he's going to out-wit thousands of mortals at once and...yada yada). Maybe even pick a combo.

[Imbalance]

A subconscious desire to get caught. As a spymaster, part of the ambition is always getting away with it, always keeping secrets, always subverting without notice...or credit. Deep down, though, this fiend's one conceit is infamy. When other bad actors have taken blame or received notoriety for his organization's evil deeds, he can't stand it. Rather than using them as patsies, he destroys them, then misdirects investigations into that violence until such a time when he reveals himself as the one who was behind everything all along.

[darkrose50]

TLDR: What kind of flaw(s) would a kingpin villain have?

I'm playing a villain for my brother, and the idea behind him is that I am a spymaster Kingpin. With a ring of spies, I have several spymasters who run various operations of my activities - drugs, weapons, assassination, all the way to slavery. Bad dude. He is a fiend that has come to the material plane for his own gain (doesn't serve anyone but himself), and makes money and gains power as an end, not a means to an end. He has a few quirks, being overly serious with the exception of telling a really lame joke whenever you first meet him. I have been asked to give him a flaw that could be exploited by the adventuring group to bring eventually bring him down, and meet the inevitable as most DnD villains do. What makes for a good flaw for villains that is exploitable but not character ruining?

Boredom - beating everyone and everything gets boring. He enjoyed the risk, but he is so good that there is no more risk, and he craves it. I think that boredom would be a major factor in a great deal of villains plans. Old creatures will want to try new things for entertainment.

Disappointment - power and wealth is often disappointing. There is a saying that the poor want food, the middle-class want wealth, and the upper-class want prestige. The upper-class folk want things that impress the other upper-class folk. The desire to get his underachieving child into the best wizard academy on the continent could be a good example. Give a homeless man $100 and he would be thrilled with the economic possibilities, give a billionaire $100 and it will not change his buying power at all . . . money used to open possibilities for some people, but at a point money no longer opens more possibilities . . . that gets booring.

Disappointment - having the thing is often less fun than wanting the thing. Perhaps he can be convinced that a new, harder, goal would be rewarding.

Seeks a chance to be mundane - he just wants to go play some cards, and have a few beers at the tavern once in a while. Perhaps he wants to meet a woman who likes him for him, and not his power and wealth. Perhaps he also seeks to meet a woman who is of equal or greater wealth or power.

Basically games are fun, until they are no longer fun. Some games require a prerequisite food -> money -> power and/or prestige. What does this guy need to have fun? Sometimes very odd and/or silly things are fun. Some guy might be an extremely powerful wizard, but really enjoys bird watching. Gold may not get his attention, but an old bird watching log from 100-years ago might be very tempting (migration changes, where rare birds could be possibly found, etcetera). Or just talking about bird watching could be fun, and build a friendship.

[Dr. Cliché]

A subconscious desire to get caught. As a spymaster, part of the ambition is always getting away with it, always keeping secrets, always subverting without notice...or credit. Deep down, though, this fiend's one conceit is infamy. When other bad actors have taken blame or received notoriety for his organization's evil deeds, he can't stand it. Rather than using them as patsies, he destroys them, then misdirects investigations into that violence until such a time when he reveals himself as the one who was behind everything all along.

I would suggest a variant of this - 'a desire to make sure his enemies know who beat them'.

Basically, it's not enough for him to merely win from behind the scenes. He has to leave a message or sign that he was behind their end.

[darkrose50]

I would suggest a variant of this - 'a desire to make sure his enemies know who beat them'.

Basically, it's not enough for him to merely win from behind the scenes. He has to leave a message or sign that he was behind their end.

I even would see this as a game. Someone powerful may be happy to play along and have fun . . . as long as what they are doing is fun. Kill his cat, and he will stop having fun, and go for the kill. I can even see older beings taking turns at who gets to be the good guy and who gets to be the bad guy. Living for hundreds or thousands of years could get boring.

I once had a dream that I was super-strong, and could fly. I was fighting with another super-strong guy who could fly. We were throwing each other though buildings and the like, and really just doing so for fun. We were not really fighting, we were at play.

Seeing powerful beings that are just having fun playing a role sit down for a dinner or get together for a board-game night would be an interesting thing to see from the outside. The city or realm is really just a game board to pass the time.

[R.Shackleford]

Rock Battle.

The answer is alsways rock battle... Demon, kingpin, mob boss... Have their flaw be that they can't say no to a rock off. This could also be a rap battle or whatever else... But yeah.

Fun times.

[Hobbo Jim]

For those who asked, the original post has been updated with more info.

I really like the game idea. I might have it so that he gets bored easily with a splash of overconfidence, and to entertain himself he tries to pit groups of people against each other - e.g. hires a mercenary group or gives a cult a magic item they need, and then tells some adventurers they exist and watch them fight. He would make a decent number of enemies doing this.

I'll consider giving him an extra flaw as well, making it so he wants to take credit but can't. For a currently undetermined reason he has cut off ties from the rest of the lower planes. Sounds reasonable that he already has an enemy and needs some more power before he can reveal himself.

Thanks for your help everyone!

[OmSwaOperations]

A classic flaw for a greedy kingpin type villain, such as a Yugoloth, would be an obsession with a kind of rare and extremely valuable art, substance or artefact. Having such a flaw would mean the kingpin would always seek to track down and claim such art(efacts) that came to his attention, even if it would be a waste of resources, or expose him to discovery. It would also enable the PCs to draw him or his agents out, by using (a rumour about) such an artefact as bait.

[Unoriginal]

Well, reading your description, I think a good flaw would be that he's uncaring. In the sense that he would use people, then drop them without reward when they're not needed anymore, or just have them killed if they know too much, without caring if they could be useful later.

Also, just to bring it up: it's "hoard" money, not "horde". Hording money requires the Tiny Servant spell.

[Hobbo Jim]

A classic flaw for a greedy kingpin type villain, such as a Yugoloth, would be an obsession with a kind of rare and extremely valuable art, substance or artefact. Having such a flaw would mean the kingpin would always seek to track down and claim such art(efacts) that came to his attention, even if it would be a waste of resources, or expose him to discovery. It would also enable the PCs to draw him or his agents out, by using (a rumour about) such an artefact as bait.

Ah that sounds really good as well! Makes sense for him especially since he likes to collect things. If you just like having stuff, art and unique items are definitely a way to go.



Also, just to bring it up: it's "hoard" money, not "horde". Hording money requires the Tiny Servant spell.

Oof, that's embarrassing. Granted, a Horde of a hoard would be hilarious. Fear my tiny mimics.

[Man_Over_Game]

Kingpins often rule by fear. Perhaps the flaw isn't inherently in himself, but the area surrounding him. Maybe people only respect him when he's nearby, and they only obey him because he's the only option available. Maybe evil-doers would be willing to do his bidding, but after he killed any rivals or opposition, what was left are the mundane, fearful and weak, and would be willing to do anything to be spared the terror he has threatened upon them.

[NecessaryWeevil]

Dunno about Yugoloths in particular, but an interesting villain might be one who has a *virtuous* flaw. Honesty, a code of honour, etc.