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D&D 5E as a new DM, how do I handle a group of wanna be thieves?

It depends, of course. :D

First, the GM is entitled to have fun, too. Figure out whether you're willing (and able) to run a sandbox game where the PCs are self-motivated and not entirely ethical. If not, that doesn't mean either you or they are wrong; it just means you aren't interested in playing the same game. My friends and I are particularly bloodthirsty in Catan and we've actually offended visitors, but it's just in fun, for us. No big deal, just know who you can sit down with.

If you're up for it, then let them have their fun. It's not my favorite way to play D&D, but I prefer it to just walking through modules. (Self-motivated PCs is my holy grail, but I like heroes -- or, at least, a team.)

Some groups are fine with hand-waving descriptive "fluff" like alignment or priestly codes. Again, you'll have to decide whether you can accept this, assuming your players want to. This is probably the biggest risk of a mismatch, IMO, so you might want to feel them out carefully. It sounds like you'd have a problem with it, though (as would I).

I've learned, over the years, that it's better to react than demand. Put another way, alignment should be descriptive not proscriptive. Get a clear picture in your mind of what Law looks like compared to Chaos and Good vs. Evil*. The GM has final say in matters of morality -- Vampire taught me that -- but it's good to be open about what your criteria are. If the PCs then act like they're CN, tell the player that their character is CN. There's no penalty assigned (beyond certain magic items, priestly vows, etc.), so it's just a description of how they're acting; move on with life.

If they disrupt a town, have the authorities react logically. As has been pointed out, that doesn't always mean the city watch. Don't mess with the mob (would you rather have Murphy or Marcone mad at you, if you've read Dresden?). Taken far enough, you get a kind of reverse dungeon going on, with the PCs trying to stay alive. I've been on that side and it's a blast -- in small doses.


* Sometime in 1E, I settled on Lawful beings having a tendency to think/act in terms of groups, being structured, and have expectations of conformity (of behavior or situations) while Chaotic creatures tend to be flexible, handle exceptions well, and think about individuals. Ethically neutral folks balance the two. Good characters tend to put the well-being of others above their own, with the best having the ability to become martyrs. Evil characters put their own desires first, with the worst having no regard for others or even actively reveling in pain. Morally neutral types are, again, balanced, putting themselves in parity with others, which generally translates to self-interest unless the other person is in worse shape and/or you can help them without too much risk to yourself. Chaotic is not insane and Lawful is not stupid.
 

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* Sometime in 1E, I settled on Lawful beings having a tendency to think/act in terms of groups, being structured, and have expectations of conformity (of behavior or situations) while Chaotic creatures tend to be flexible, handle exceptions well, and think about individuals. Ethically neutral folks balance the two. Good characters tend to put the well-being of others above their own, with the best having the ability to become martyrs. Evil characters put their own desires first, with the worst having no regard for others or even actively reveling in pain. Morally neutral types are, again, balanced, putting themselves in parity with others, which generally translates to self-interest unless the other person is in worse shape and/or you can help them without too much risk to yourself. Chaotic is not insane and Lawful is not stupid.

This is a really good way of describing alignment. (Subject to individual table preferences, of course.)
 

Have a better thief steal all their stuff. Then see how they feel when they can't cast a spell without components or money.

Then have someone offer them what they need with a quest .

Maybe that will remind them.

Or do what everyone else said and actually talk to them
 

Just hit them with reprecussions.
If they get too much out of hand, and it sounds like they did, let some bounty hunters/adventuring party come after them. And I do not mean a normal "war as sport" 20% of the ressources encounter, but one which has the potential of a tpk or at least to be a very hard fight.

After a few party members got killed (killed, not the wussy "you are only knocked out at 0HP") they might hopefully consider changing their behaviour.
 

Put them in a location where you don't mind them thinking of the locals as the "enemy". Design a city with evil merchants and a worse government, where the good people don't have anything worth stealing. Make your local police a worthy (evil) adversary that the players can feel victorious when they outsmart or outfight them. Fill the town with dark temples that Conan wouldn't think twice about burgling.
 

You mentioned threatening them with jail. Would it change things if you went down a more historical route to crime and punishment?

Although there were gaols, they were generally used to hold a prisoner awaiting trial rather than as a means of punishment. Fines, shaming (being placed in stocks), mutilation (cutting off a part of the body) or death were the most common forms of punishment.

(http://www.historyonthenet.com/medieval_life/crimeandpunishment.htm)
 

Have a better thief steal all their stuff. Then see how they feel when they can't cast a spell without components or money.

It's the old story - stray outside the law, and you can't easily involve the help of the law when other criminals come after you. The PCs are going to be easy picking for people who are Worse News than they are. The bad guys in the campaign now become the criminal underworld. Perhaps a local crime boss forces them to work for him - or else. See how they like that! Gives you a campaign villain, and keeps them under reign, to a certain extent. And they still have the local rulers as enemies... There are plenty of possibilities with this type of campaign.

Of course, if you really don't want to run this sort of game, that's your call, so as others have said, chat to your players and see if you can find a playing style you can all enjoy. Personally, I don't like having evil PCs in my game world, and I ask my players not to go down this route, as I think it can easily lead down a darker path than I want to go down. However, I'm a big wuss at heart, and not everyone has the same qualms I do. Hopefully, you can find a style that you and your players all enjoy.
 

Hey, unless the players are doing it deliberately just to derail your adventure, I would roll with it. They're trying to figure out the meta-limits of your world. Players creating their own story is actually kind of awesome!

On the other hand, if it gets too irritating, don't be afraid to kill them all and start again. They piss off the wrong person and that person is wealthy enough to send an Artemis Entreri type after them.
 

While it's kind of been hinted at, something you might want to look at is the way the story responds to heroes vs. villains.

Even if you run a fairly simulationist world (as I do), campaigns tend to have a tone and character to them which dictates what sorts of story events are likely to be introduced. Heroes are expected to win, and generally get a sort of "heroic license" to have success. Whether it be in the form of an occasional deus ex machina, DMs fudging dice rolls that otherwise create TPKs, or just having friendly resources available to assist them in their good quests, the story itself wants them to succeed. It feels right to us, and we generally try to make it happen, providing the players allow us to.

Villains on the other hand, are expected to fail in the end. They might have a crazy run of it, they might have intermittent success, or even a streak when it seems that they can't lose. But eventually, things go sour for them, and their lives reap the consequences of their choices. They can't maintain good relationships, their successes don't bring true happiness, and their evil deeds come back to haunt them. The best hope they have is to have a change of heart at the end and switch sides at the right time, usually dying heroically--but that can be a real challenge to verisimilitude if done poorly.

What I might do in an actual campaign about evil characters is to give them no breaks. If they die, tough. If they get their favorite items stolen, tough. Since players are going to get upset if you intentionally make the story be against them (unless it's understood and agreed upon as part of the experience), I'd do this by maintaining a strict simulationism. While I might make sure there is some way for a character in a heroic campaign to recover his family heirloom sword, in a villain campaign, if it makes more sense that it gets melted down for raw materials or magic, then that's likely what happens. The world should respond to them in a way that naturally makes sense. If you want to, you can even set it up so that they are on the bad-side of a heroic storyline. Maybe their heroic enemies are the ones that do get heroic license and breaks. "Why do things to things always seem to go their way instead of ours?" 'Cause they're the good guys and you aren't. Of course, that sort of approach tends to create an adversarial experience between player and DM, and should be done with care and consent. Works great from a gamist challenge perspective, when the goal is to try to win even though the deck it stacked against you. The easier to do method though, is to not give the heroes any particular advantage and just leave them in a simulationist world that reacts to their choices naturally. That should include them being eventually hunted. When they are a big enough threat and higher level bands of adventurers (of any alignment) come after them, you don't have to give anyone any breaks before they eventually get the short of the stick and their heads on a pike.

Of course, my favored approach, as I mentioned, is to decide before a campaign starts--but these are some considerations that might be worth applying even if you have to adapt things mid-game to accommodate and unexpectedly villainous party.
 

I- The model is based on a diverse group of highly trained specialists who work loosely together but are most often each doing their own thing. Thus a constantly split party. In a modern game the PCs can coordinate via ear buds but in a D&D setting it doesn't work so well.

But it can.

For example, in my 4e campaign, my Hexblade has taken the feat which gives him a Familiar. With the DM's blessing, I took Sitak. Its power is the ability to speak Telepathically with anyone who shares a language with my Hexblade (who, coincidentally, can speak a LOT of language) up to 20 squares/100 feet away and doesn't need Line of Sight or Effect to do so.

There is also a Blue Communicator item from one of the Dragon magazines - it was from an article that had super-high tech items as treasure. Essentially it was a Bluetooth wireless device that allowed people wearing it to communicate with one another from some distance away.

The Leverage model works because it's set in Modern times; the crew can find, purchase, steal, or improvise most equipment they need. Since most Rogue missions are gear-based, make similar gear available to the players.

Also, Leverage steals from the rich/wicked and gives to the poor/wronged party. Stealing for fun is one thing, stealing with a PURPOSE other than pure financial gain is a story.
 

Into the Woods

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