Please rescue my thieves
April 15, 2014 3:38 PM   Subscribe

I’ve gone and written myself into a corner in a story I’m writing. I need to figure out how two thieves can escape from the grounds of a castle.

There are two gates: one at the front, and one at the back. The front gate would be suicidal to attempt – it is brightly lit, overlooked by a gatehouse and only accessible across a wide expanse of gravel which is too noisy to walk on without being heard.

The back gate is a far better prospect. The back gate stands between two guardposts, each of which contains windows looking out over the surrounding area. The angle of the windows means that each of the guardposts is partially overlooked by the other. The gate itself opens using a lever inside one of the guardposts. There are two guards in each guardpost, and they are on alert, since one of their colleagues was killed the previous night by an intruder. The guards are armed with swords and crossbows. The outside of the gate is lit by torches, but the inside (where the thieves are currently stuck) is dark. There are no guards watching the inner courtyard, so unless they make too much noise, they’re safe until they open the doors to the guardposts. I’ve drawn a basic sketch of the plan in case the description is unclear.

The only other possible way out is to scale the wall and rappel down – this being the method they used to get in earlier. They have a one grappling hook and one climbing rope between them. However, one of them is badly injured with a concussion, and anything acrobatic is out of the question. Other equipment they have with them includes two blackjacks, one dagger, a bow with a supply of broadhead and blunt-headed arrows, an assorted collection of shiny valuables they stole from the Castle, and one Maltese toy dog (which belongs to the lady of the castle, but which decided that the thieves were its new best friends after they fed it to keep it quiet and it’s now following them around).

My problem is that given that only one of the thieves is in decent enough physical shape to get into a confrontation, they can only infiltrate one guardpost at a time. If they turn the lights off in one room, the guards in the other will see the light go out and come to investigate. The same goes if they get into any kind of fight in either of the rooms.

Both thieves are experts at sneaking. They would strongly prefer not to kill anyone, but will do so if they have no other choice. The best outcome would be for them to escape without anyone raising the alarm, but they could probably lose a pursuit if they had to.

What would be a reasonable plan for escaping through this gate? Please help me rescue my thieves!
posted by talitha_kumi to Writing & Language (45 answers total) 5 users marked this as a favorite
Hide in a wagon filled with ______ that's already leaving? Though it would have to be leaving before the valuables are discovered missing.
posted by ODiV at 3:41 PM on April 15, 2014

Is the dog too unreliable to use as a decoy to lure the guards away from their posts? Maybe tie it to something in the courtyard somewhere and let it bark when they leave it?
posted by mon-ma-tron at 3:48 PM on April 15, 2014 [1 favorite]

Can you solve this problem with planning earlier in the story? Perhaps they threw/dropped something helpful over the wall on their way in, and now they can retrieve and use it? A sling to carry someone? Something with which they can open the door, perhaps a small explosive charge or a lockpick kit/ bar for leverage?
Get the dog to scratch at one door or somehow otherwise attract someone in the room with the gate lever to come outside. Sap them. Wait for their partner to investigate. Sap them, too. All quiet-like. Then walk in and open the door.
posted by Adridne at 3:48 PM on April 15, 2014

Clearly, the dog needs to be part of a ruse.
posted by jamaro at 3:49 PM on April 15, 2014 [8 favorites]

Every night, a set of nuns who live on the castle grounds bring the court's leftover food to the beggars outside the castle wall. So your thieves could either A, dress as nuns (which would be delightful if the thief with concussion is staggering and moaning a bit and the other thief has to keep him in line: nothing is funnier than a nun with concussion), or B, conceal themselves in a giant cauldron of cabbage soup that the nuns wheel out every night (also delightful, with one thief keeping a small, bright-eyed pup from making happy arf-arf noises from inside the cauldron while struggling to keep his concussed comrade from opening the lid).
posted by mochapickle at 3:50 PM on April 15, 2014 [2 favorites]

Would it be possible for them to slip away in a group of kitchen staff or some other such hands departing the grounds after a day of a hard work? Could they blend in with a found coat or some such thing and just slip out as though they were part of the crew and then hang back while the crew continues to depart?

Did they meet anyone earlier along who may be in the castle and can provide assistance in getting them out and then to whom they owe a debt?

Could it just be that one set of guards is not very bright that they're able to talk their way out?

Could the lady start looking for her dog and then demand a set of guards leave their post regardless of whatever was said earlier to find it? Then they comically chase the dog while your thieves escape? The more disbelief the thieves hold in their luck, the better.
posted by zizzle at 3:51 PM on April 15, 2014

If they turn the lights off in one room, the guards in the other will see the light go out and come to investigate.

How about taking advantage of that?
  • Cause a deliberate ruckus in the right-hand tower - pull the door open and throw something at the torch to dislodge it, and also throw the dog into there so that it causes a ruckus
  • Guards in the left-hand tower run across to see what's happening! Or at least, one of them does
  • Less-concussed sneaky thief dashes in and kills or incapacitates the remaining guard, if one of them has stayed behind
  • The less-concussed thief opens the gate
  • Both run out and try to lose the pursuers
It's not something you'd want to rely on for a real escape, but it kinda works under Heist Fiction Rules.
posted by severalbees at 3:51 PM on April 15, 2014

(The second option could be fun: They'd stink of cabbage for days.)
posted by mochapickle at 3:51 PM on April 15, 2014

Have Concussion Jack walk the Maltese into the guardhouse with the gate lever and complain about Her Ladyship and her unreasonable demands that the dog be walked *outside* the grounds to do its business.

Have Canny John stand by with the cosh outside the guardhouse in case anyone follows.

(Having someone die the previous night is really inconvenient, though. Maybe go with the nuns.)
posted by RedOrGreen at 3:54 PM on April 15, 2014 [3 favorites]

Does the castle have a sewer system?
posted by erst at 3:55 PM on April 15, 2014 [1 favorite]

The garderobe? It includes bonus gross humor potential, if that's a thing you can use.
posted by winna at 3:57 PM on April 15, 2014

RedOrGreen: That was similar to an initial idea i had for getting rid of one of the guards from one of the rooms. I figured that if they used one of their shiny trinkets to play fetch with the dog, it would make enough noise that one of the guards would come to investigate, and could get taken out with a blackjack. But that still leaves the problem of dealing with the second guard without alerting the other guardpost.
posted by talitha_kumi at 3:57 PM on April 15, 2014

I like RedOrGreen's idea! Maybe the other guy could pretend to be the flunky of the first guy -- the poop boy, if you will.
posted by El Sabor Asiatico at 3:57 PM on April 15, 2014

I'm in favor of social engineering here. Have them dress in, say, regular clothes, and then have them brazenly walk out as if they owned the place.
posted by spinifex23 at 3:59 PM on April 15, 2014

The more dramatically interesting thing would be for them to come up with an audacious solution that allows them to escape through the "impossible" front gate.

My first thought is that they disguise themselves in some way that makes being observed unimportant.

Could you leverage the fact that one of them is injured? Maybe load the loot into a cart, have the physically OK thief in the driver's seat, and the injured thief riding in the cargo area as a "plague victim"?
posted by Sara C. at 3:59 PM on April 15, 2014

I was thinking they pretend to be the dog's new groomers or something like that. Dote on the spoiled dog and blah blah blah and walk right out as dog Doters. something.
posted by Michele in California at 4:03 PM on April 15, 2014

It's a castle. It has a secret passage.
posted by aniola at 4:12 PM on April 15, 2014 [4 favorites]

You could backfill a stranger on the castle grounds--someone not well known to the staff, newly arrived as a guest, whom the pair can tie up in his room, steal some clothes, and then impersonate.

Make the guest powerful enough to be obeyed, and perhaps someone who speaks a different native tongue so there is a reason for the concussed one to stay quiet while the other one handles everything. The healthy one can tell the guards that the guest is an incurable pervert and insists on leaving the grounds in the middle of the night to satisfy some unspeakably comic desires.

Of course the noble guest gets his way, right? The pair walk out together, turn the corner, and are gone.
posted by jsturgill at 4:13 PM on April 15, 2014 [1 favorite]

Dammit, I had a whole sketched-out scenario with dialogue in my head as I was reading the other answers, but jsturgill beat me to it. Bluffing is the way to do it, especially if you've established these guys as being all super sneak-thief cat-burglary.

But my idea was to just have one of them, in the middle of a whispered hasty planning session, say, "Right, sod this," and walk right up to the guardhouse and start acting like that. By the time the guards realize they've totally been conned by the most obvious con in the history of conning, the thieves are out of the castle and running like mad through the forest.
posted by Etrigan at 4:28 PM on April 15, 2014

150 years ago, the third earl of bettencourt had a secret passage installed so he could sneak off to the local monastery and discretely join in the midnight revelry. It exits the lowest level (right next to the hatch for the garderobe), travels below the moat, and comes up behind a bush just beyond the guard shack.

The thieves found out about this when the fifth earl got drunk (and a bit mouthy) in the town pub, and was overheard.
posted by jenkinsEar at 4:30 PM on April 15, 2014 [1 favorite]

How many people are in the castle? Couple dozen, maybe?

If so, here is how to get them out of there in ten steps:

1. Acquire civilian-looking clothes if they don't already have them. The non-concussed one will go fetch these.
2. Put the shiny valuables in an inner pocket.
3. Acquire a bottle of liquor.
4. Heavily dilute the liquor and give some to the dog; it will go to sleep and stay that way long enough for them to get away. The dog would be recognized by the guards and raise suspicion.
5. Get rid of the weapons and tools - throw them down a privy or whatever. Someplace they won't be found anytime soon.
6. Put on civilian clothes.
7. Dump out most of the liquor bottle.
8. Have the concussed guy put his arm around the non-concussed guy's shoulder, leaning on him for support as they walk. Either one can have the bottle in his hand.
9. Wait for the guard to change and then count out about ten minutes. If the guard doesn't change, or if they don't know the schedule, proceed to step ten.
10. Walk out the front gate.

If at all possible, they should just sort of slip into a group of drunken revelers leaving the castle at the same time, but circumstances may not allow this.

The concussed guy will appear drunk at a distance; he should probably take a few swigs (but not swallow) so he'll smell like liquor in case he's questioned, but he won't be. Guards will be on high alert and will be looking for people trying to sneak in, not walk out. A cat burglar's biggest liability is overthinking.
posted by FAMOUS MONSTER at 4:47 PM on April 15, 2014 [2 favorites]

Intercept and drug the guards food when it gets delivered from the kitchen.

Or wait in the privy until after they eat and one guard subsequently visits. Take him out, borrow his clothes and use them to take out the second guard inside the shack where no one can see.
posted by fshgrl at 4:59 PM on April 15, 2014 [1 favorite]

Social engineering: bullshitting, bribery and/or exploiting human error. It happens.
posted by scaryblackdeath at 5:16 PM on April 15, 2014 [1 favorite]

Channeling Wes Anderson?
posted by whyareyouatriangle at 5:30 PM on April 15, 2014

Thief with concussion goes coocoo, calls the guards on his accomplice:

"Guards, guards, the thief is here! He's right here!"

The guards peer down from their perch in the guardtower. It's a dark night, and all they can see is a pair of figures shrouded by shadow."

"The thief is here! I've got him!"

The accomplice struggles to shut up his companion.

"Shut up you fool," he hisses through clenched teeth. "They're going to get us!"

He quickly reaches to clamp a hand over his brain-addled companion's mouth.

The concussed thief, in no shape for a struggle, collapses under his accomplice. For a moment there is no sound and no movement below the watch tower. But the accomplice can hear footsteps.

"Help! Help! He's got me! Get him off me! My head! I've been hit! I can't move."

Suddenly, rough hands are hauling the accomplice off of the concussed thief. A burning torch is thrust in his face.

"A thief! Look in his sack! You - help him up. But be gentle."

The concussed thief rubs his head, and thanks his rescuers.

"The dog hit me over the head. Take him away before he hurts anyone else!"

The guards grab him and frogmarch him away.

The concussed thief is left with a grappling hook and some rope.

Using his last ounce of strength he quickly gongs the captors over the head with the hook and collapses on the ground.

The accomplice grabs the rope and ties them up.

And both thieves slip quietly out the back door.
posted by KokuRyu at 5:32 PM on April 15, 2014 [1 favorite]

Well, castles often have side doors, doors within the main doors, waterways, and, well.... garderobes, which depending on the castle can be a fairly modern USA type toilet, or whats basically an outhouse built onto the side of the castle, often over the moat. And, not much should be flammable in a castle, but there is always fire
posted by Jacen at 5:45 PM on April 15, 2014

What are good reasons for someone to be leaving your castle at night (if you want to try subterfuge)? I would guess that a noble/peasant would be less likely to be going out the gate unless an event was happening or an emergency was taking place. Unless your castle is a more modern version, in the middle of a city, where there might be more foot traffic at night.

How big is the castle...would the guards know everyone by sight? Or is there a constant stream of visitors?

Most castles weren't designed to keep people in but to keep them out, so there were often small buildings (craftspeople, storage, stables) built against the walls and of course stairs for defenders to go up and shoot arrows, etc. I think your thieves could manage to get to the top of the wall fairly easily. Your real problem in that case is not being seen and getting Concussion Charlie down with just one rope.

A boring but effective way would involve the healthy thief finding another rope, lowering concussed thief down, and then rappelling down. He would still have to be able to carry/drag him and the loot to get away, though.

Your thieves seem to have not thought this out too well. Are you sure they're pros?
posted by emjaybee at 5:45 PM on April 15, 2014

How does the poop get out of the castle?
posted by oceanjesse at 5:48 PM on April 15, 2014 [2 favorites]

If your story is dramatic and brutal, I'd have them get out by climbing onto a wagon full of dead soldiers/plague victims.
If your story is a comedy, I'd have them get out by climbing onto a wagon full of dead soldiers/plague victims.
Of course, either way, they have to escape from the two guards driving the wagon.
posted by QueerAngel28 at 6:12 PM on April 15, 2014

Something else to consider: The ideal burglary is one in which the victims, and their security detail, never even knew you were there. Any plan which incapacitates or kills any guards is a plan they would treat only as an absolute last resort, because it would give away their presence after the fact.
posted by FAMOUS MONSTER at 6:15 PM on April 15, 2014

What sort of castle doesn't have catapults?
posted by sebastienbailard at 6:18 PM on April 15, 2014 [1 favorite]

That's a terrible thing to do to a toy maltese, sebastienbailard.

If the dog is set loose in one guardhouse, then one of those two guards will have to collect the dog, then return it where it belongs, leaving just one guard in one guardhouse. That simplifies shutting off the light there.

Meanwhile, the other two in the other guardhouse...

No wait. sebastienbailard has the right idea.

Toss the dog over the wall.

The guards will open the gate themselves to retrieve the dog, the healthy thief dashes out drawing as much attention as possible, and after a beat or two, the concussed thief sneaks out during all the commotion.
posted by notyou at 6:30 PM on April 15, 2014

Skip the escape entirely and make it a character quirk.

I'm serious. Fast forward from them thinking they'll never escape this to them having sold their wares the next town over. Make it a story they tell when they're drunk/trying to pick someone up, and have the story change every time. At some point you can reveal what really happened. Maybe it was mundane ("We snuck out through the shit-pipe.") or maybe it was epic ("We faked a dragon attack with just a grappling hook and some shinies!") or maybe it's something sinister ("No, we were caught and given a choice by the lord of the castle. And I'm very sorry to do this, but he wants you dead.") Whatever it is should inform the characters and the story you're trying to tell.
posted by greenland at 7:39 PM on April 15, 2014 [9 favorites]

The Maltese really likes the treats they fed it, right? Ok, so one of the thieves has a slingshot, shoots a piece of food through one of the openings in the portcullis; Yappy McFluff goes wriggling out through the gate after it; guard sees this, goes "oh fuck, we're really boned if Milady's dog gets away!", opens up the gate and runs after it. Theives sneak out behind him in the shadows while second guard is watching the dog, trying to give first guard directions on where it went.
posted by MsMolly at 7:40 PM on April 15, 2014 [1 favorite]

Just realized there are two guards in each guard post. This actually works even better for my plan. Two guards out chasing the dog will make the dog run and dodge even more, and two guards trying to yell instructions will add to the confusion.
posted by MsMolly at 7:43 PM on April 15, 2014

How serious are you about being accurate? Because the general answer is that it takes a long time to get out of a castle.

However, you can always go with the Priest Hole 'round back of the priory, if these folks are Catholic English.
posted by klangklangston at 7:49 PM on April 15, 2014

Would they make passably attractive women?
posted by Hermione Granger at 7:52 PM on April 15, 2014 [1 favorite]

What about fake jewelery do that the robbery isn't noticed until later and they can leave in the morning? The other question, is this going to be published and you can backfill or is it more fan fiction based so you'd be hard pressed to have them go back and change something?
posted by Carillon at 8:10 PM on April 15, 2014

Perhaps the lady of the castle realised the dog is missing and runs outside screaming that someone murdered the dog. Lights go on, people everywhere etc, very scary. The your dudes slip out unnoticed. Phew that was lucky!
posted by Youremyworld at 8:31 PM on April 15, 2014

Why do they have to leave in the middle of the night? How soon until the stolen stuff is missed? Castles are big places, hide them somewhere for the night and have them leave during daytime. For extra subterfuge, leave the rope hanging off the outer side of the castle walls, fooling the guards into thinking they are already gone. This was the original escape plan, right?
posted by Dr Dracator at 11:07 PM on April 15, 2014

This is fun.

Is it windy on the castle wall? They could paraglide out. The healthy one could rig up a tandem harness out of rope and his/her single wing,
posted by overhauser at 11:10 PM on April 15, 2014

So many good ideas – thank you!

To answer a couple of queries:

The castle stands in the middle of a city, which was built much more recently and has since expanded to surround it. So the inside of the castle has a more or less traditional arrangement, but once you get outside the gate then there’s streets and alleys and doorways to hide in and lose a pursuer.

The reason they need to leave as soon as possible is because the City Watch are going to arrive at the castle shortly expecting to arrest a captured thief, and there’s going to be an uproar when there’s no thief waiting to be arrested, which will make it even harder to get out. Additionally, once they’re outside the castle they still need to get across the city back to their hideout. That would be possible during daylight, but it would be a lot harder.

The castle population is big enough that the guards wouldn’t necessarily know all the servants by sight. So impersonating a servant might work.

The thieves haven’t thought this out well at all – which is a large part of their problem. One is a pro, and the other is the apprentice. The apprentice (who is expert at stealth, but not so good at patience or forward planning) tried to pull off the mission solo in order to impress the master, and botched the job badly. The apprentice was the one who killed the guard the previous night thinking he’d be quickly in and out, but got himself trapped in a closet by the toy dog, who growled and barked every time the apprentice tried to come out of the closet. The master broke in to rescue the apprentice and freed him by making friends with the dog. However, when they start escaping over the wall, the toy dog who is now following them starts yapping and whining in protest at being left behind, attracting the guards. Having been sent over the wall first and now out of sight the apprentice avoids capture, but the master is caught and dragged off to a cellar. The guards (not unreasonably) assume they’ve caught the guy who murdered their colleague, and take the opportunity to beat the stuffing out of him before sending someone to notify the City Watch to come and arrest him. The apprentice (and the dog) rescue the master by taking out the guard who was left to watch him. They’ve made it back out to the rear courtyard again, and have to find a way to escape the castle before the Watch arrive.

Plumbing – the castle has more-or-less modern plumbing, which empties into the city sewers below. There could probably be an exit through the sewers, but that feels a bit anticlimactic.

I like the idea of leaving the rope hanging off the wall and leaving by a different route. As long as the rope was in an easy to find spot, it might be enough to convince the Watch that there’s no point in continuing to search. That combined with one of the bluffing strategies at first light might work. It’d be more believable for a pair of servants to need to leave on errands at dawn, rather than in the middle of the night.
posted by talitha_kumi at 1:24 AM on April 16, 2014

The unconcussed thief dons the uniform and keys of the knocked out jail guard, and takes the jewelled collar off the dog and breaks/rips it so that it seems to have come off by accident, then approaches the gate guards, shows them the broken collar and tells them he has been assigned to find the lost dog and richly reward anyone who returns the beloved creature (shows them crazy-expensive stolen shiny thing as reward; gives them each some of the rope and instructs them to tie up the dog should they encounter it). Meanwhile, hidden concussed guy throws food over the wall as far as he can, and lets the dog go. The dog immediately scrambles under the gate or through a small grate to the other side of the wall in search of the treat, uniformed thief shouts and points, and the guards comically rush and tussle with each other to get gate open and reach the dog first in order to claim the reward. Thieves separately escape out of the now-open gate, the uniformed thief pretending to chase the dog and maybe having to stop because of a faked sprained ankle or something (then disappears into a side street), the concussed guy sticking to the shadows and quickly disappearing.

As for the dog, you can either have the guards get him, or he leads them on a merry chase, disappears into the city, and later shows up in another fun plot twist to return to the thieves.
posted by taz at 2:05 AM on April 16, 2014

The master thief knows about the secret passage.
posted by aniola at 7:40 AM on April 16, 2014

But they run into someone while using it. That someone also doesn't want to be caught.
posted by aniola at 7:42 AM on April 16, 2014

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