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D&D: Adventure Crime! – Five Side Quests For Criminal Characters

5 Minute Read
Feb 26 2020

It’s adventure crime, come on grab your friends, we’ll go to very distant lands to lie, cheat, steal, win–if all goes according to plan.

Most parties are good. Very few are lawful. The following adventure hooks are aimed at adventurers with larcenous leanings. Because doing fantasy crimes should be more than just a few rolls on the downtime events tables out of Xanathar’s Guide to Everything–though if you’re looking for some inspiration, you should check out the complications tables for some inspiration of how things can go wrong for the characters and make their lives interesting.

At any rate, fantasy crime is an excellent part of D&D. We’ve got a few here as sidequests, for when your players aren’t necessarily lawful–but you don’t want your whole campaign to be about running a thieves guild. These crimes tend to skew a little more towards chaotic good, but we leave that to you and your group.

Steal from a Merchant Prince

Athras Kel is a pompous merchant prince who has made his fortunes off of the backs of others. Thieving and cowardly, Athras Kel has left a trail of betrayed partners and former friends behind him as he made his rise to the top. He started as a metal merchant, and has since expanded his empire to sell all manner of luxury goods and has amassed a fortune that he wastes on lavish statues and gaudy decorations in his manor home.

Athras Kel is a truly unlikable individual, relying on his power and status to shield him from the consequences of his arrogance. He surrounds himself with flunkies who serve as bodyguards and people to reinforce his own high opinion of himself. Athras’ first blush with the party should be to inconvenience them. Whether it’s demanding they move from their favorite table at an inn–and buying it outright in order to ban them from it if they object–or maybe his opulent carriage needs to get somewhere and he tries to hire the adventurers to keep the rabble (including themselves) off the street, offering them 100 gp each to make sure he does not have to look at their wretched poverty.

Whatever the case, the PCs are approached by Xime Tlaruq, a former employee of Athras who sees the PCs disdain for the prince and tells them of the crown jewel of Athras’ collection. A magical jewel that is said to be worth a fortune. It in fact contains a bound devil that has been granting Kel power and fame–but if stolen… well Kel’s fortunes would be reversed.

Frame a Corrupt Guard


Gorth Telgrin is a guard who has swiftly been rising through the ranks of the guard, though he clearly is in it for the power. Gorth and his gang of guards have quickly established themselves as a force to be reckoned with. Extorting money from merchants in order to protect them, while stomping out the local thieves’ guild with brutal efficacy.

That’s where the PCs come in. Realizing that their days are numbered, the thieves’ guild reaches out to the PCs, asking a favor of them. If a player has the Criminal Background this is a great way to spotlight that, having a connection to one of the PCs through their past… but even if they don’t, the Thieves’ Guild mouthpiece, a kenku named Beni, asks the PCs for help. Gorth must go–but he can’t simply be killed, that would raise suspicion and draw a lot of unwanted heat down on them.

Instead, Beni wants to frame Gorth for a crime that not even the captain of the guard can turn a blind eye to. Of course, first they’ll have to commit that crime…

Highway Robbery (the tax man cometh)

When the players rest at an inn along the road, they meet Kleia the Blade, a jovial dragonborn mercenary who regales them with stories of her past deeds, including slaying a manticore with one of its own spikes. Recognizing kindred adventuring spirits, Kleia takes an interest in the player’s accomplishments, asking questions and for stories of their past adventures. As the evening wears on, she commiserates with them about her latest assignment, escorting the local tax collector as he goes on patrol.


“The man takes money and food from those who have none, taking half again what the viceroy demands.” Kleia clearly dislikes her assigned task, and will complain, if the PCs make a DC 12 Persuasion check, that her pay is too low for this. Enterprising PCs might even buy her contract out entirely, leaving the tax collector with one less guard and a chest full of 1250 gold pieces.

Grand Theft Carpet

This one is exactly what it says on the tin. Xivarin Kraalnith, Archwizard of the Seven Spheres, descends upon the party on a pillar of storms–their rival archmage has a new flying carpet. This model has many bells and whistles that Xivarin’s does not. Obviously this is an injustice that must be put right, so Xivarin desires to contract the adventurers to steal the carpet from their rival.

Run The Jewels

Finally, a nice simple side quest to offer your PCs as they’re about to leave whatever town they’re in. Thev, a kobold smuggler with an eyepatch, asks the party to do a favor and carry out a set of jewels past the guards. Thev will meet them on the other side, but trusts that the guards won’t look too closely at a random band of adventurers.

Now at this point, the players might cautiously have said no, to Thev. This is understandable. Thev however does not take for an answer and uses his +17 Sleight of Hand skill to plant the jewels on the adventurers.

Thev is of course, completely wrong. The adventurers find out that the Guards are searching carefully everyone leaving the town, effectively granting themselves advantage on Search checks while the players try and get through. If the jewels are found, the Guards will try and detain the players–at this point, give the players a chance to run and defer to the chase rules in the DMG. If the players make it through, Thev tries to collect the jewels, whether they were aware or not.


Before the happy reunion can happen, a rival gang of thieves show up to try and steal the jewels. This is another great place for a chase ending in a rooftop skirmish, where Thev’s kobold allies show up to “help” the party.

Happy Adventuring!

Author: J.R. Zambrano
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