Friday Encounter: To Catch a Pickpocket

Aladdin

This encounter is best suited for an urban setting - specifically, an outdoor area where there will be dense crowds of people. A marketplace is probably the most obvious, but it could just as easily work for any other open-air setting where people congregate, such as a theater or a square where an important figure is making a speech. Some setting-specific options include a Cantonal Assembly in the Freikantons or a royal election in Togarmah. All that's really important is that there are enough people to bump into and block sight lines. Certain details may need to be adjusted accordingly for a different setting - as with any encounter, don't be afraid to tweak things to best suit your table or campaign.

While the PCs are amidst the crowds, one of them notices someone has picked their pocket. Ideally, this should be the PC that seems the most outwardly wealthy, such as someone wearing heavy armor or exquisite clothes. This encounter is really more aimed at creating amusing chaos that could set up hooks for further adventures, so it's probably best if the item stolen is fairly inconsequential, like a coin purse - something that would set the party back enough that they'd want to retrieve it, but not something the party would be screwed over without.

At any rate, when the PC looks over, they see a halfling dart through the crowd and disappear into the distance with the stolen item in tow. Now, the PCs will likely want to pursue the thief - but in such a tightly-packed crowd, disaster is bound to happen!

Enter Action Time. Mechanically, the encounter is mapped abstractly to represent the commotion of a busy square bursting into a squabble, so as the DM, you should note how many moves away the thief is from the PCs and in which direction. It will probably be easiest if you plot the positions of each PC and the thief on a grid - you shouldn't show this grid to the players. The thief moves at the beginning of every round. To handle this movement, roll a d8: on a 1, he moves north; a 2, northeast; 3, east; 4, southeast; 5, south; 6, southwest; 7, west; 8, northwest. If he would move in a direction that would cause him to run into a PC, reroll the direction. Don't tell the players what direction the thief moves yet; see below.

At the start of each PC's turn, they must make a Perception check. The difficulty starts at 5, and increases by 2 for each move the thief is away from the PC. For instance, if the thief moved north from the starting point and the PC hasn't moved, the DC to spot him is 7. If, however, the thief moved north, the PC moved south, and then the thief moved north again, the DC to spot him on the next round is 11, as the PC is three moves away from the thief. If a PC spots the thief, they know which direction he is running in that round.

After determining if the PC spots the thief or not, the player chooses a cardinal direction to run in. Roll a d10 to determine what happens in the commotion:

1-2. Nothing unusual happens this turn. The PC moves as normal.

3. The PC moves as normal, but in the commotion, a merchant's stall gets knocked over, spilling the contents everywhere. This creates a diversion; the DC to spot the thief increases by 2 for the next PC.

4. The PC bumps into someone, knocking them to the ground. If they stop to get them back on their feet, they skip movement on this turn. If they keep running, the bystander will alert the guards (see 4 below).

5. The PC bumps into a town guard, knocking them to the ground. Now the guard wishes to have them arrested for causing a disturbance. If the PC stops to explain, they skip movement on this turn. If they keep running, the guard starts pursuing them. This doesn't affect any rolls, but after the chase, the PC will be cornered by the guard and have to explain themselves.

6. The PC runs into a barricade or other obstacle. They must make a DC 10 Acrobatics or Athletics check to clear it, or they skip movement on this turn as they waste time going around.

7. In the commotion, an animal breaks loose and starts charging through the crowd. The PC must make a DC 10 Animal Handling check to calm it down, or they skip movement on this turn as they waste time avoiding the beast.

8. The PC moves as normal, but runs into a wall or other impassible obstacle. They may not go the same direction on their next turn.

9. The PC moves as normal, but it turns out they didn't actually see a halfling moving in this direction, just a child they mistook for the thief. Reroll what direction the thief moved in this round; all subsequent PCs that spot the thief this round see him moving the new direction.

10. The PC moves as normal, but then gets swept up in a throng of people moving a different direction. They move an additional space in that direction - roll the direction as for the thief, but reroll any results that were the same direction the PC moved in.

The chase lasts for five rounds. At the end of the five rounds, if any PCs are within three moves of the thief, they manage to apprehend him. He will give back the stolen item if met with a show of force, unwilling to risk his head - but, optionally, he might have connections to other criminals, who now know the PCs are in town. If no PCs are within three moves of the thief, he is nowhere to be found. Either way, though, the PCs might have more problems to deal with...

Note that those using 5e rules (as I do) may note that there's an obvious interaction between these mechanics and the City Secrets feature of a character with the Urchin background, which allows them to move through crowds twice as quickly. If you wish to represent this, allow a PC with the Urchin background to make two moves per turn. Note that this may lead to them catching up to the thief, which is not supposed to be possible before the five rounds are up under the way the mechanics are designed - it's supposed to simulate the kinds of chase scenes we see in movies, not so much a realistic chase. I would personally treat a PC and the thief occupying the same space to mean that the thief moves on his next turn, and the DC for that PC to spot him on their turn is 5, but if you wish you can also end the chase if the PC and the thief occupy the same space - though this might lead to short and uninteresting chases.