I don't know why I kept DMing this group, as they've pulled a *LOT* of stupid things in the past. Enough that I have a list that I'm currently working on. That's a story for another day, however, as today's story is legitimately the dumbest thing I've seen the group pull.
On this particular session, the group was busy trying to go from town to town, and had stopped at a bar to unwind, and rest after an encounter with some goblins just outside of town. It's been enough that I don't remember what the other players classes were, but I do remember this guy's. The barbarian of the group, bored out of his mind, decided to get himself absolutely wasted and challenge the first person he saw to a fight. Cue the captain of the town guard showing his face at the bar. What followed was an absolute curb-stomp battle, as the barbarian was level 8, while the captain was I want to say somewhere around level 15. The short brawl ended with the barbarian being thrown in prison. At this point, I, through the Captain, let the party know that the town often sees drunken brawls and has become desensitized to it. Punishments for such offenses have been lightened in recent years to reflect this. As such, the barbarian was only going to be thrown in prison for 3 days, at most.
After two days, the party decided to break the barbarian out of prison. If I could push my palm through my skull, I'm pretty sure I would have that day. Cue adventure through the prison. The party did manage to get to the barbarian's cell, and were about to break him out, when the Town Guard Captain showed up. The party barely lasted a few rounds before they were all thrown in prison for attempted jailbreak, which would have been at least a few years in prison.
Now, they decided to break out of prison, instead of await any further proceedings, which they, from what I can remember, could have lied their way through and gotten out damn near scott-free. They did manage to break out of prison, but their joy was very short lived. Because of their attempts at breaking out of prison, the town had sent notices to every town nearby warning them not to deal with this group of adventurers, and, if possible, to arrest them or kill them on sight. Not only that, but it turns out that later, the guard captain was a major NPC in a quest later. So any information they could have obtained from him was now out of reach. All because this group decided to break out a party member from prison the day before he was set to be released.