Anyone who has played Dungeons & Dragons, read fantasy, or even heard of thieves know that it’s tough putting them in groups. We seem to think they’re characters who will always be out for themselves. They’ll steal from their allies, sell people out for the smallest of reasons, and repeatedly do things that prevent them from being fully trusted. Now, some of this would make sense since many adventuring thieves require stealth and that’s not easy to do if you have a group. Still, that isn’t a reason to repeatedly have the thief on the outskirts of the party and always looking for a way to trade them all in for their favorite type of mead.
First, you have to consider the type of thief and what’s important to being a successful criminal. They won’t be exact criminals if they’re on the hero side, but some of the aspects jump over. Most importantly, a talented thief doesn’t ACT like a thief. This is where so many people go wrong in my opinion. Yes, it’s fun to have that character that can’t be trusted, but being seen as dishonest eliminates a lot of tricks that a thief needs. Without stats and dice rolls, it doesn’t matter if they character has a lot of charm if they’re always blatantly plotting something. There needs to be a subtlety to their antics because a real thief tries not to get caught. For example, stealing all of the treasure and hording it results in very heavy pockets and suspicion. Let the rest of the party keep their money and take from them when you need to. This is what Sari does and the others have basically accepted this, but at least they have money to spend when they need it too. No hard feelings there. Heck, it’s oddly endearing in a way.
Since thieves depend a lot on stealth and being unseen in combat, they might have to go it alone in a story. Not all the time, but slip away to scout for danger or use a battle to get in position for something else. Thieves aren’t cowards, but they aren’t normally the types to do a frontal assault. You may find them firing a bow or throwing daggers from the shadows or waiting for an opening to deliver a deathblow. Other times they run off to take care of another problem like a trap or locked door. Is this them using the fighters as distractions or bait? Yes, but they’re working with what they have and, hopefully, still helping. Again, this is an area where the betrayal is commonly used and it ignores the fact that the thief is on the good guy side. Is really smart to get the barbarian and fighter killed, which leaves you to face the thirteen ogres alone? Thieves need to be smart enough to work around all of the problems being in a group brings. They truly are the brains over brawn characters.
Also, not many thieves openly admit to being a thief. If they’re uncovered then they’ll fess up and make an excuse, but most use other terms. Sari calls herself a gypsy, which are a people in Windemere known for having thief skills. Nimby was calling himself a carpentry teacher until he was found out. Some simply claim to be adventurers even when they’re proving to be more interested in treasure than helping others. It’s all about the cover identity even among friends. Sure, the group might know they’re working with a thief, but that doesn’t mean the character should openly talk about it. More importantly, there should be an agreement or something where the rest of the party doesn’t out the thief all the time. I’ve been in games where another character will introduce everyone and say ‘this is so-and-so and he’s a thief’. That’s just rude and a reason why so many thieves probably do go for betrayal.
So, what do you think thieves in groups should do?