A backer on Patreon asked for an encounter based around the idea of gentlemen thieves. As promised, here is an encounter for everyone to steal where a group of thieves tries to be as gentlemanly as possible.
A few miles out from the edge of town, the players see three carts approaching. Each cart has an open top with three feet high sides keeping barrels, crates, and chests from falling out of it.
Each cart has several people in it (the numbers can vary, but I suggest a minimum of two people per cart). Each person wears moderately well-made clothing, though a perceptive player may be able to tell that their clothing is well-used, suggesting they haven’t bought clothes in quite a while.
As the carts approach the players, two of the carts stop, moving to opposite sides of the road. The space between the carts should be large enough for the players to get through if they should pass. Adjust the width so they can fit through whether they are traveling on mounts, in a cart, on foot, etc
The center cart continues moving forward in the center of the road. When it is 30 feet in front of the other two carts, it will stop.
As the players approach, Gravous Starwold, the driver of the front cart, stands and waves at the players. She bears a tired but heartfelt grin as she calls out to the players. She asks the players to stop, but she will continue speaking even if they walk past her.
Gravous Starwold says that she and those in her company are raising money for needy people in a city that is conveniently in the opposite direction of the one the players are going. They are asking for donations, but with a perk for those who donate.
Everything costs about three to five times more than it should, but the money spent will go to a good cause.
For example, Starwold has barrels of wine and ale, expensive clothing, adventurer’s packs, tickets for events in other cities, and an assortment of other things for the players to purchase. In addition, Gravous Starwold knows the mayor of several cities in the area, and a player can pay her in order to get some specific information from the mayor or have Gravous speak well of the character so new advantages can open up for them next time they go to that town.
If the players ask where the things they are selling came from, Gravous Starwold tells them people donated each item. If players want to donate items, Gravous informs them that their carts are full and that people need the money, not barrels of wine and front row tickets for an event in a different city.
The Actual Plan
The gentleman thieves want to make 500-1000 gp (gold pieces) (or different large amount if you’re using a different currency) off of the players. If they do, they will give the player the products and be on their way. If the players paid for Gravous to speak to a mayor, she will, saying whatever it is the player wanted her to say. If the player’s bought information, she will give the information.
If the thieves make less than 500 gp, from the players, then they spring the trap.
If the players walk past Gravous Starwold without engaging or if they spend between 0-499 gp, Gravous will politely wish them a good day and flag her companions to continue on. All three carts will start down the road again, the back two moving quicker to catch up to Gravous.
As the players pass between the two carts, a hidden panel in the sides of the carts open. Rods quickly extend from the front and back of the carts. These rods do not completely pen the players in, but it does make it more difficult to get out, forcing players to climb over them to escape. The moment after the rods appear, a large canvas tarp shoots out and covers the players trapped between the carts. The final piece of the trap hits as vials under the canvas break, releasing a poisonous gas that will render those who breathe it in unconscious or weaken them if they breathe some of it (use saves or system appropriate mechanics for poison).
The first priority of the thieves is to keep the players under the canvas until they are unconscious. The thieves will hold the canvas down, beat on the people trying to escape, and stop non-trapped players from freeing the trapped ones.
The gentlemen thieves all fight with either a bo staff or unarmed attacks (give them the ability to use unarmed strikes. Example: Pathfinder/D&D 3.x Improved Unarmed Strike feat, or the Tavern Brawler feat for Dungeons and Dragons 5e. If you can, give the thieves the ability to deal non-lethal damage. Either way, the thieves’ goal is to gain money and keep everyone alive. They know that a dead person’s family will seek revenge. A robbed person probably will not.
At any point, the gentlemen will stop fighting if all of the active players lay down weapons and give them what they ask.
Whether the player’s surrender or the thieves succeed, the thieves want 1000 gp, either in gold, items, or a combination of the two. If the thieves can’t get enough gp, they might take supplies, kits, alcohol, tickets, scrolls, books, magic items, or anything else that appears worth selling.
The thieves are gentlemen, and they will not take:
– Rations or food of any kind
– Things that believe to be one-of-a-kind
The thieves never want anyone to die as a result of what they took nor do they want to take something that could end up killing a person, such as leaving them defenseless without weapons and armor or having them starve from not having any rations. They also won’t take clothing so the person doesn’t die of exposure or freeze to death. Thus, if a character is clever and hides their gold in their rations or tucks their money inside their common clothes, there is a good chance the thieves will never discover it.
The thieves also will never leave a character without at least one weapon, even if that weapon is the only thing they can steal from the character. The thieves may, however, take the character’s magic weapon if they can replace it with the same kind of weapon they have (though the replacement won’t be magical).
The thieves don’t take one-of-a-kind items or items they think are heirlooms because they do not want someone seeking revenge for stealing such a precious thing.