I have a character that escapes from a dungeon and another character helps him. the escape happens off the page... as in, by the time my MC gets there, the person has already escaped, but he sees the aftermath of the escape. The person who helps him escape is someone who works at the castle. is it plausible for him to poison the guards to get the character out? are there any other plausible ways to facilitate an escape, especially if the person imprisoned is heavily guarded?
How important is this person? Are they wealthy or very popular? Mary, Queen of Scots was imprisoned on an island castle, escaped with the help of the brother of the castle's owner, and raised an army of 6,000 supporters. But she might not have been guarded 24/7 and was probably not imprisoned in your typical dungeon.
this person is the villain and is awaiting death. he's not wealthy but has a lot of sway. think of him like a cult leader. One of his followers is the one that gets him out (somehow)
How many layers of guards are around this guy? Is it just one, at the door of his cell? Is there another at the end of the hall? How about at the castle gates? And how far does he have to go to be out of danger of immediate re-arrest? Does he have a safe house or a getaway carriage right across the street? Or does he have to run for miles through a moonlit swamp, baying hounds at his heels etc.? If he's going to have to physically take out (either by fighting or poisoning or whatever) a whole bunch of guards, it starts to become increasingly implausible, to me. Especially if they're starting from the bowels of the castle and working their way outward. Somewhere they're going to miss one, who will raise an alarm and summon a bunch more. It would be easier if he were in some other location, or even better, being transited between locations. On the other hand, if you can compromise the guards at a high level you might not need to fight. Maybe a well-placed bribe to their shift supervisor, who at a pre-arranged moment tells all the guards on duty "Go ahead and take a smoke break out back" and all the lazy, underpaid guards are happy to do so and don't ask why. Then it's just a matter of unlocking the door and letting him walk out. But this depends on establishing whatever organization the guards work for as pretty corrupt or illegitimate.
the villain is familiar with the castle. once he's out of the dungeon, he doesnt leave the premises, but knows of various passages to hide himself. so the person basically just has to unlock his chains and somehow incapacitate the guards. Compromising a guard might work! he's like a cult leader, after all. he could negatively influence the guard into helping the other character free him and cover their tracks
Hide him somewhere in the dungeon (somewhere ingenious, like under a false floor stone) while the guards are distracted (Dancing girls? Spiked grog? Poison their food?), then, when the guards are either searching for him (outside of the dungeon) or being upbraided by their superior, sneak him out. Perhaps rolled up in a tapestry over the shoulders of 2 men. Ok, maybe not the last part, unless it's a comedy. But of course it all depends on a number of things, such as how serious the story is, the layout of the dungeon and any weird quirks it might have that allow for better hiding, and how gung-ho the guards are etc. Maybe mere bribery would work?
I was thinking of, um, a dancing girl or reasonable facsimile thereof. Entice, distract, engage, slip the guard a roofie, and give an accomplice time to spring the villain.
I saw an Irish version of an oubliette during a castle tour. I cannot describe the terror a simple glimpse of the entrance funnel brought me. I backed out of the area PDQ and did not take time to apologize to any toes upon which I trod. No one swore at me; perhaps the look on my face just made them glad I was getting the hell out of their presence. Horrible, horrible, horrible.
It could make for a really powerful scene. The guy really really doesn't want to be lowered into the oubliette. "No, no, it's fine, really! We'll come back in 20 minutes and drop a rope and lift you out." "Ummm... unless any of a thousand possible things goes wrong, then I'm stuck in there..."
I just noticed another person responded about an oubliette. Wow you might have your answer there!! LOL