How a Chaotic Evil BugBear Rogue derailed a one-shot

An online one-shot that was envisioned to be a epic underground dungeon-crawl descended into a hilarious farce due to inexplicable player actions.


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I was volunteering as a DM for my local gaming group, playing an online one-shot for a group of strangers. It was a D&D 5e dungeon-crawl, set in an underground cavern underneath a magic academy that I had written myself. It had custom-made magic items, a massive underground fight, and an epic BBEG. I was stoked to see how my players would interact with my dungeon. The characters were a human warlock, a human monk, an elven spellcaster, whose class I sadly don’t recall and a bugbear rogue. Now as we were playing online due to quarantine I ask my players for basic information to help with the technical setup and gain an understanding of them. This included alignment, in this case, the bugbear rogue was chaotic evil. My players were all adults who all played one-shots from the local gaming group before, so I expected them to play as a team and to have fun. 

The story begins when the party were asked by a tiefling student, at a wizard school, to clear her name in a murder investigation of another student and a teacher. She saw something emerge from a disposal pit where students throw away their magical waste and believed there was something below the school causing it. The party decided to begin their investigation by meeting with the teacher who accused the tiefling student of murder.

They arrived to see the teacher along with an animated armour investigate one of the disposal holes that were in the wizard school. After the initial conversation went badly a fight ensued. Now the teacher was supposed to surrender once he realized he was beaten, admitting to falsely accusing the student and pointing them to descend into the pit to investigate further. Unfortunately, the party was a little tougher than I expected and killed the teacher before he could surrender. Then the bugbear further cemented the teacher’s death by tearing off the teacher’s arms and a leg, keeping the limbs as trophies as it was his character trait. A bit off track, but entirely within the expected boundaries of the adventure.

They brought the tiefling student to the scene of combat, where she vomited and told them they’d just murdered a teacher and if they didn’t find the real culprit, they’d be arrested by the city authorities. With that prompt, the party decided to descend the pit, using a rope tied to the side of the hole. Everyone except the bugbear who decided to stay behind on the surface.

When the three party members reach the bottom, they triggered an encounter with four flying swords. The combat quickly went south for the characters due to some incredibly bad rolls on the characters’ part and some great rolls on the flying swords. The fight was going so badly I was severely tempted to fudge the rolls and/or nerf the swords. Eventually, the monk was reduced to 1 hp, and the other two characters fled down a tunnel into another room bumping into a combat encounter with a wererat. 

The players were calling on the bugbear to help them, and so the bugbear decided to scale down but grabbing their tiefling patron, down with him. I made him roll a contested grapple check against her. He succeeded easily. Then I made him roll a Strength (Athletics) check to see if he could descend the rope with the student in one arm. 

Critical fail.

The bugbear fell down the whole length of the tunnel taking 5d6 points of bludgeoning damage and reduced to1 hp. Amazingly the tiefling also survived, landing on top of the bugbear but badly injured. At this point, the monk, afraid of death, abandoned his comrades and climbed up the rope back to the surface. The bugbear also followed him, leaving their badly injured patron, laying their and whimpering in a room full of hostile magical swords. 

Meanwhile, the two other characters managed to cause the wererat to flee by setting wooden furniture in the room on the fire, causing smoke to fill the rooms and forcing them to make constitution checks to avoid passing out from smoke inhalation. 

The monk, now realizing that they couldn’t let their patron die, shouted for her to grab onto the rope and he would pull her up. She did so and succeeding on his Strength (Athletics) check was swiftly yanking her up to the surface. This was when the bugbear rogue stayed to his alignment and cut the rope. The monk only got to see the tiefling students pale and frightened face emerge from the hole before she fell screaming back down, dying on impact. 

The bugbear rogue and monk human finally started acting as adventurers trying to save their comrades. Though with the only rope now at the bottom of the hill, they tried cutting up the nearby carpets into strips to tie into a makeshift rope. This plan did not work and so they both fled the school. 

At this point, the one-shot was beyond salvaging. So a nothic, curious to see what the commotion and smoke were coming from, found the badly injured warlock and spellcaster, wandering around in the smoke. It easily overpowered them, dragging them back to its lair to put them out of their misery. 

Now in the city, the bugbear decided to head off to a temple for some healing, striding into a temple to a lawful good god. The bugbear covered in blood carrying severed human body parts was quite a shocking sight to the well-armed clerics and paladins of the temple. A failed charisma check later and the bugbear was torn to pieces by divine attacks before he could get a word out. 

Only the monk survived the encounter, overcoming his shame at abandoning his friends, fleeing the city for a new life. 

Now I don’t mind if characters go off script from the intended adventure path, that’s what adventurers do, but I also don’t believe in protecting them from the consequences of their actions. Their actions resulted in a near TPK, their patron killed, and the BBEG blissfully unaware of their hijinks. And I enjoyed every minute of it.


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