• Courtney Barkley

Tabletop Thievery: Stealing and Its Many Forms in D&D

Nice things are expensive, both in the real world and in Dungeons and Dragons. While just taking what we want isn’t advisable in real life, it’s a lot more tempting in tabletop RPGs, where it’s just our characters who will be putting their lives and reputations on the line. Isn’t the reason that many of us play to enjoy a little secondhand risk-taking?

If your character isn’t morally opposed to relieving some NPCs of their wares or coin, there are a lot of opportunities out there for your character to pad their pockets.

Those Pesky Alignments

One of the first things many players think about when considering dipping into some fictional crime is their character’s alignment. No good-aligned character would ever consider something as immoral as theft, right?

Not exactly. Of course, there are certainly characters out there who would never steal under any circumstances, and if you’ve decided that’s a trait your character has, that’s valid. However, just being of the ‘good’ alignment doesn’t automatically mean your character can never steal anything. There are plenty of bad people out there in the fictional world, and if your character decides to try a Robin Hood-style scheme, there’s nothing wrong with keeping a percentage for their services.

And honestly, most Dungeon Masters (we call them Quest Masters) aren’t terribly strict about character alignments. Being a good-aligned character doesn’t mean you have to be a shining beacon of morality all the time. So if you’re going to lighten some pockets, what are some of the best ways to go about that?

Starting Small

One of the easiest ways to get a feel for theft is the simple act of pick-pocketing. This is most commonly done by rogues, who are often proficient in sleight of hand, but it can be attempted by anyone. You might gain advantage on the roll (or the NPC might take disadvantage on their perception check) if the character is distracted by something, so be wise about your timing. If you’re working together with other party members, one player could even stage the distraction themselves while the rogue works to pick the character’s pocket.

Stealing from a single NPC instead of a business gives you the opportunity for quick monetary gain without quite as much risk. You stand a better chance of subduing a single person, though you should always ensure their calls for help never reach any guards’ ears.

Bigger Targets

Taking things from single NPCs isn’t the only way to go about theft in the game. If you’re wanting a bigger payoff, you might be better off stealing from a nearby business.

Think about everywhere that money accumulates in the game. Where does the tavern owner keep his day’s take? Does the blacksmith leave her storefront (and cash box) unmanned while she works in the forge? Does the town have a treasury you might be able to gain access to? Does the local store that sells magical goods have some expensive weaponry or enchanted armor you could use or sell for a profit?

As tempting as these targets might be, it is important to keep in mind that the bigger the payoff, the bigger the risk -- and, likely, the greater the chances of getting caught. After all, if a business or person has enough money to make it an especially tempting target, chances are pretty high that the owner has realized this and put deterrents in place, whether those are traps or magical enchantments. That risk makes planning especially important.

Lure Them in With Lies

Outright taking what you want isn’t the only way to steal. Sometimes, in the right situations, a well-placed lie can have people willingly handing over their money. If your character’s skills reside in the charisma realm, you may want to consider cons.

The fun thing about cons is that there is no limit to what you can do. Shine up a rusty old dagger and pass it off to the traveling merchant as a ‘priceless artifact’, convince the merchant that they can easily sell this item in the larger city for far more, but you’re willing to part with it for the paltry sum of a few hundred gold pieces. Convince a shady official that you have some salacious blackmail on him, and watch him throw money at you in exchange for your promise to keep his secrets.

If you wanted to get really fancy, you could even come up with a con playbook with your fellow players so you can be ready to jump into a con at a moment’s notice.

Worth the Risk?

As in real life, stealing in Dungeons and Dragons is not without risks -- you could be captured and jailed, or even end up in a deadly encounter if your attempts at thievery go awry. It’s up to you to decide if your character would consider the payoff worth the risk and to try to play it smart so you can escape with your freedom as well as the gold you’re risking it all for.


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