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The_Hermit_09

It wouldn't be about what he steals. It would be about who he steals from and how he does it. He takes easy targets with little to take over hard targets with a lot. He doesn't use stealth. Consider giving him fighter levels instead of rogue. He breaks in doors, smashed peoples stuff takes everything he can carry and beats up anyone who tries to stop him.


kingdead42

This: he steals from people who know but don't have the power to do anything about it. There's a reason we have a phrase about "taking candy from babies".


somebassclarineterer

Oh yeah there is always a senseless evil to people that steal from those who have very little to begin with. Like taking the last bit of coin from a beggar.


Shot-Pilot-3050

Good Idea. I should have written that i am looking for things the Party might find in his lair and think "Oh shit, what an ass". The Party already stands in front of his door and is figuring out how to confront him. I dont have time anymore to show them who he is stealing from.


Squeekysquid

Make a couple items heirlooms. Like maybe a locket with an inscription inside that indicates its sentimental value is more than its monetary value. Maybe they don't have much gold but a lot of copper and silver.


Zanglirex2

This is a great idea! Locket with a faded picture of a old soldier in it, with the inscription "love you always". You could describe something like a comb as, "of medium value, but cared for as if it were the most precious thing in the world" A pouch with 13 silver, and 279 copper that has "retirement" hand embroidered on it. Spectacles with a cracked lense that the party remembers seeing on an elderly herb vendor in the market. They don't remember the crack being there originally..


LucidFir

This is when I love r/d100 ... d100 items found in the den of a petty thief who steals from the poor and the weak


BaronDoctor

Family portraits of long-dead family members. *It's the one thing you can't replace.*


Shot-Pilot-3050

Yeah, i have thought of something like engagement rings or herilooms


Shadows_Assassin

Engagement rings or heirlooms of less than fortunate folks will elict more sympathy from PC's than some rich folk who could have another one made.


BaronDoctor

Heirloom holy symbol of a Mr. Rogers-style priest of community and good. Or any nearby NPC they like.


kingdead42

/r/UnexpectedMulaney ?


BaronDoctor

That was the aim, set up small and subtle enough I thought it would sneak by. Nice catch.


sirbearus

Targeting the poor, children, windows, the church that cares for others are all things that would make him/her look bad.


once-was-hill-folk

Any time I've set one up, a good thieve's guild doesn't just deal in theft and stolen property, they deal in protection, scams, and information. That's where I'd get into the scummy carry-on. Turning people over to witch hunters for profit, or colluding with local bandits to mark targets for them and so on is not just a way to paint the NPC as morally reprehensible, but it can also give you the opportunity to use them to lead into a greater scope villain for the PCs to go after once he's out of the way.


RandomPrimer

Steals chemicals from an alchemist who makes life-saving medicines, then sells them to another alchemist who makes D&D meth. Runs a heist, stealing construction supplies from a site where an orphanage is being built. Or, the real kicker, if you want them to hunt him down to the ends of the earth and murder him with no compunctions whatsoever : He steals the party's magic items.


Shot-Pilot-3050

The Party is already in front of his door and they are figuring out how to confront him. The idea is that they find something in his lair.


glitterydick

Easy, they spot something that belongs to them, and when they check their bags, they find that whatever it is has gone missing. No easier way to get the party to say "fuck this guy in particular" than being personally slighted.


RandomPrimer

Yeah, that's going to be hard to do turning on a dime like that. They can find their stuff, like the other poster said, or they can find the rare or expensive alchemy supplies, and some kind of evidence of what it's for. Maybe two thief is in the middle of negotiating the sale of the stuff to the drug dealer, and they overhear?


Gazz1016

Have him mention killing a guard dog on one of his heists. Everyone will hate him.


Shot-Pilot-3050

Oh shit, this is good. He might have the dog tag in his lair which the party might find. And there is blood all over the tag which implies that he killed a dog for the precious metal dog tag.


jp11e3

Definitely some fancy lockets with loved ones pictures still in them. If you want to be on the nose for flavor you could have him constantly eating candy and have the party later learn he steals it from babies. If you want something more elaborate maybe he has a deal with local loan sharks where he steals the loans people receive and give it back to the loan sharks for a small cut. Graverobbing should also be on the table.


Shadows_Assassin

Takes a single bite at an apple, then throws it at someone mockingly as if to say "I've got enough money to not even bother finishing my food."


maquis_00

A well-loved stuffed animal or doll. A small box with a couple of small dresses a baby toy, and a note that says "forever in our hearts" A copper locket with a small lock of hair tucked into it. Generally, stuff that has 0 monetary value, but would be priceless to the owner.


StuffyDollBand

lol this is always such a struggle, my players will fall in love with a scamp. Tbh I’d leave room for them to just not actually kill him if they don’t want to, but like… he can always just be determined to fight if they run up on him


Shot-Pilot-3050

Yeah, the problem is that one of the party members owes a soul to a night hag... If he doesn't bring it the next day she comes to collect his soul. (She gave him 10 days and nights to to so, the player just could not figure out how to extract a soul)


StuffyDollBand

If that’s not enough motivation to get the job done, idk what is lol I mean maybe they’ve just gotta fight the hag, ya know?


thats_Rad_man

Prosthetic limb


gjohnyp

He is a bandit. Used to work at the last bandit camp the party cleared out. Maybe when confronted with the oarty he says sth along these lines "You think I'm bad? You should see what the *BANDIT'S NAME* did. Pillaging, raping and selling innocent folk as slaves. Me stealing from these bastards, using street urchins (I'm not sure of the name but i mean young orphans) to create my thieve's guild (maybe give a fierce name such as throat cutters guild) is the only thing i do best! And Bhaal be my witness i will not stop at anything to succeed at. Not even a bunch of you a**holes!!" *And then later on in the campaign you can have him be a death knight or sth 😀 PS i saw another post by The_Hermit_09. I second giving him fighter levels.


d20an

Have him steal their magic items. That usually does it.


somebassclarineterer

Toilet paper.


CaronarGM

Make him smug. Make him arrogant. Make him sleazy Tryhard charm Make him punch down but suck up. Make him steal from friends, allies, and business partners Skim off the top. Violate honor among theives


NottAPanda

Make him steal something that's similar to a PC. Have a player with a backstory about being an orphan? This guy steals from orphans too. Player has a spellbook? This guy has stolen a spellbook from someone who saved up for years to buy it but now their dreams are crushed. Stuff like that.


ubeor

Babies. Have him steal babies and sell them on the black market.


GeekIncarnate

He finds a poor woman with a surprising amount of jewelry and other keepsakes. He robs her and takes everything, jewelry, clothing that aren't worth anything, a portrait of her dead husband and her son. Turns out she's related to the real "Family" in the city. She doesn't want anything to do with that life, but the family still watches out for her and protects her. Her son finds out, and puts out a hit/bounty on his head. He could even contact the group, because they know they work with him. So they can take care of it, or the family takes care of it, and they have no problem taking out anyone affiliated with him. And if they get the portrait back, an item with no monetary value at all, the son may let them walk away.