I got permission from everyone involved to send this.
During my very first D&D campaign awhile back the story setting was there were two guard captains that controlled the city, with the evil one controlling the majority of the guards which is why our party was hired by the council of heroes and the good guard captain to mitigate and hopefully stop his influence. The catch was us being hired was a secret until he was brought down. Over the course of the campaign we had several run-ins with the evil captain, and each time he almost killed at least one party member if not more. He actually succeeded in killing two pcs. Throughout the campaign many moronic things happened like the barbarian elf running naked through the streets in an attempt to cause a distraction for the rest of the party and the dragonborn cleric convincing most npcs in the poor districts that he was the second coming of Bahamut because he could use heal spells. By the end of the campaign there was a civil war in the streets of the city with us being trapped in an abandoned shack with the evil captain right outside with a dozen guard-knights threatening to kill a friendly and very helpful to us dwarf npc if we didn’t come out.
Evil Captain: Come on out, or short and stout gets it! I know you’re in there!
My Half-Orc Fighter: Uh…I would like to persuade him to leave? Can I do that?
The DM: Sure. Roll persuasion.
*Rolls Nat 20* Alright what do you say?
Half-Orc: Um…no we’re not!
Evil Captain: If you’re not in there, who’s talking?
Goblin Bard: I would like to persuade him as well.
DM: *sighs* Roll persuasion. *rolls Nat 20 plus 8 points in persuasion* *DM sighs yet again* What do you say?
Goblin Bard: The only person in here is me, your grandmother! And I’m very disappointed in you David! (The evil captains first name)
DM attempts insight check for evil Captain that has an ungodly amount of insight skill points *rolls nat 1* *DM sighs again*
DM: Dave is so distraught he drops his gear and as he walks off you see him taking off his armor as he goes home to rethink his life choices. With no leader the evil guards quickly surrender. Congratulations. *DM sighs*