Stealing from the players?

[Elric VIII]

I'm looking for tips on making an encounter where the players are betrayed by a party follower who steals their unspent gold and consumables. I want the players to try and find him as a way to introduce an enemy organization. Any tips on not making the player feel like it's a "screw you," from the DM?

[Necroticplague]

Easiest way I can think of is have him try, but get caught partway through. He can escape empty handed and still pique their interest as long as he leaves behind/says something appropriately suitable.

[Barstro]

Any character possessing something of little market value, but great sentimental value? That would be something would not mechanically effect the party if lost, but still provide in-character motivation to seek its recovery.

[TheFurith]

I find the best way to do pretty much anything that might upset players is in character foreshadowing. So that in character they could have prevented it, but they just didn't. Now that does come with the risk of them actually preventing the thing from happening, but only if you make it too blatant. It should be obvious only afterward.

Have the character always be more than happy to carry things for people. Or have them be looking through people's things all the time. Not secretly. So they seem more like they just stick their nose in everything when they shouldn't. So if they get caught digging though something it doesn't seem malicious.

Then when stuff turns up missing they won't blame you, because they'll see you've been dropping hints forever.

[The_Jette]

If your party isn't opposed to theft in general, have him stealing from other NPCs in front of them. It'll probably change their view of it a little, once they have their own stuff taken. And, stay away from major items, like favorite weapons, and spellbooks. There's no way that will end well for you.

[NomGarret]

Consumables and currency is a good choice. It's annoying but replaceable. If you make it clear that you're doing this as a hook toward the next adventure, I as a player would give you the benefit of the doubt that we'd be getting that value back and then some as the adventure unfolds. All this really hinges as much on preexisting trust in the DM as anything else.

[AnimeTheCat]

Introduce a kender into the party. Watch the world burn ;)

[Gildedragon]

What role would the person have? Build then to that role as a secondary. Build them to be sneaky and thievy. Let the dice play things out.

[molten_dragon]

This can go wrong really easily. I've seen parties get really pissed off when a DM does something like this. Especially if it's done with no way for them to stop it. And especially if their gear is being stolen.

I've found the best way to do something like this is to make sure they have a chance to stop it, even if it's a small one, and to have what was stolen be important to the plot, but not important to their characters mechanically.

[Elric VIII]

Thanks for the advice. So, basically the scenario is that they ran into this guy on their way to infiltrate a den of bandits and sort of pressed him into their service. He's definitely got a reasonable motivation. I think what I will do is introduce some plot-important item over the next few sessions, show his major interest in it, and have him abscond with it along with a portion of their wealth along with the hint that he's got a larger stash (maybe in the form of a letter or some such in his personal pack that he was unable to retrieve).

[daremetoidareyo]

Him getting caught halfway through and + limiting it to cash & consumables + foreshadowing is about as fair as you can get. Warning, PCs can still just throw their hands up in the air and press on with whatever they were doing.