Slack 'n' Hash - Yoink!

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You've Got to Pick a Pocket or Two

Pocket-picking is one of the mainstays of the thieving profession. It's pretty basic; the objective is to get as much money as you can out of people's pockets without their noticing. There are two ways in which this larcenous course of action can go.

Appear to have no interest in your mark whatsoever. Approach unhurriedly and with your eye on somewhere else. When you are within reach and you are sure that your mark is not likely to notice, help yourself to any goods that he might have in plain view, or, if you are extremely skilled and dextrous, concealed within pockets. Once you have your quarry, make your way away from your mark as nonchalantly as possible.
As before, but fail miserably, get noticed, and then spend an exhausting few minutes with the Watch on your tail. Duck down an alley to get your breath back, only for the watchmen to follow you. Get the cud beaten out of you ("He was resisting arrest, your Honour!"), get found guilty by the judge, and spend the few remaining seconds of your short life dancing the Hemp Fandango.

Pickpockets traditionally work in urban settings rather than in dungeons or the wilderness. Cities are essential to the prosperity of a pickpocket. There are plenty of marks out there, so chances are you might never pick the same pocket twice. There are crowds in which you can lose yourself, and of course the more people there are and the more industry that goes on, the more money there is to be had. If you want to be the greatest cutpurse in the world, chances are you'll need an urban campaign before you'll really have a chance to shine. If the campaign shifts setting fairly frequently, taking characters all over the place, you won't have much to worry about.

If you want to be a pickpocket, you have a pretty difficult ethical decision to make. Taking stuff without the owner's consent is a pretty unpleasant thing to do, and when you factor in the idea of doing so without them noticing you'll probably end up being marked as a coward, whether you like it or not. If you're evil you probably won't care about that. After all, what's theirs is yours and what's yours is your own, right? Get it while you can.

If, on the other hand, you're of a more heroic disposition, you will have to be very, very careful, because the path of theft can often lead to evil. Pick your targets carefully -- make sure they can afford to have their purses lightened. Share the wealth too; pass some on to someone who needs it. If possible, pick specific targets and have objectives in mind rather than just indulging in random larceny. You'll need a Robin Hood ethic if you want to stay good.

In order to be a successful pickpocket, the most important ability score is Dexterity, with Charisma and Intelligence running a close second. If you're playing a rogue (as you should be!) then you should take the following skills:

Appraise is pretty useful to the pickpocket. You want to find out whether or not your pickings have been good, don't you? Well, take this and make sure the fences aren't ripping you off. Of course, chances are you'll have to take the price they give you anyway -- stolen goods depreciate in value very quickly!
Bluff is necessary for persuading guards of your innocence (it wasn't me what done it, your Honour!), making sure they don't believe you are a thief even if all the evidence is against you (what? How the Hell did that purse get in there? Some pickpocket planted that on me, they can do that, you know!) and also for passing secret messages on to your accomplices. Of course, 5 ranks in this skill gives you a +2 synergy bonus to Sleight of Hand checks. Even if you don't want to max this skill out, get the 5 ranks just for that!
Diplomacy is a pretty useful skill for plea-bargaining (oh, go on, yer Honour, go easy it was a first offence, and I can show the Watch all the tricks the pickpockets use!) and is also useful for fencing stolen goods too (tell you what -- how about you pay me fifteen gold for that jewel and I'll go for 10% off the next two I'll bring you? I only need the money to get Bob the Blackguard off my back. If he breaks my fingers that's your supply system knackered...)
Escape Artist. Now why on Earth would you need this skill? Let me explain. You try to pick someone's pocket. He notices. He tries to grab you, and you probably don't have a weapon handy. What if he grapples you? What do you do then? Slip out of his grasp like a greased pig and leg it, of course! Now, your Dexterity's going to be of some help, but you might as well learn how to do it properly....
Hide is one of the essential skills for those all-too-frequent occurrences when things go pear-shaped. Some form of escape route is always handy, although if you want to branch out a bit you might just want to focus on the stuff that makes you a good and undetectable thief rather than one who always gets away if things go horribly, horribly wrong.
Move Silently -- pretty much everyone in the thieving profession should be a half-decent footpad. If you're a pickpocket, you'll need this to sneak up on your mark and to sneak away again. The less he knows, the longer it takes for him to realise he's been robbed.
Sense Motive might seem like an odd choice, but it's almost as useful as Bluff. If you have accomplices working the street, then you want to be able to pick up any secret messages they might want to pass on to you. ("HEY! FRED! THERE'S A GUY HERE WITH A FAT PURSE! WHY DON'T YOU TRY FLEECING HIM?!?")
Sleight of Hand (no, really?) is the essential skill for a practicing pickpocket. Perfect this skill at all costs, and if you can spare the feat slots, take Skill Focus (Sleight of Hand) and Deft Hands -- those two feats give you a +5 bonus to your check. Not to be sniffed at!

The pickpocket in the adventuring party has a difficult to choice to make when plying his trade. Should he tell the PCs what he's doing or keep schtum? There are reasons for and against either course of action, and at the end of the day it all boils down to trust.

If you tell your mates that you're going out to cut purses, then chances are they know where to look if things go wrong (the jail, most likely), and you might even rustle up some semi-trustworthy accomplices too. If you can trust them not to hand you over to the Watch at the first opportunity, or even inadvertently let slip that you're in the business of redistributing other people's money, then tell them. You need all the friends you can get -- people to bail you out, spring you from jail, provide character witnesses in a trial -- friends are so useful to have these days.

There is a case to be made for not telling your friends too. If you've got a paladin in the party, it's almost certainly a good idea to keep your pie-hole shut. They'd probably cart you off to the cells themselves, while reciting from their Holy Book and tell you that it's for your own good! Additionally, if you really don't want to get your mates into the shit, it's best not to breathe a word about what you do. The less they know, the safer you'll be, and what they don't know won't hurt them.

With all this in mind, what sort of personality does a pickpocket have? Well, they can have almost any sort, really. There are a few traits that are worth bearing in mind. A complete lack of shame is essential. Plenty of nerve comes in handy, and if you're a naturally tactile person or can put that sort of image across, then you'll go far. If you find the idea of getting close to people repulsive, however, you ought to consider another line of work unless you can learn to manage that sort of impulse. You need to be patient and observant, and capable of realising when you've pushed your luck too far.

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