Monday, June 13, 2016

The art of picking a pocket

Of all the classic thief abilities, the one that seems to see use least frequently in my games is Pick Pockets. I blame the rather unimaginative name, as well as some misconceptions that I and my players have held about the ability.

As a young DM, I saw pocket picking as an act of stealth: You sneak up on someone, and if you manage to do so unnoticed, you carefully fish about in his pockets.  This, obviously, made it extremely difficult to pull off a pocket-picking, because it inevitably required a Move Silently roll to get close enough to the target.  Making one roll with a relatively low probability of success is bad enough; requiring two made it essentially pointless even to attempt.

But the classic pickpocket operates in a crowded marketplace, not a dark dungeon, and probably the most classic ploy is bumping into someone and surreptitiously relieving him of his valuables while pretending to apologize and dust him off.  That's much less about stealth and much more about manipulating the target's attention and perception.  Through a combination of words, gestures, eye contact, and other subtle techniques, the thief draws the mark's attention where he wants it, and away from what he's really doing.

What else might a thief do with such a talent for misdirection?  Planting an item on the mark is an obvious possibility -- the reverse of a traditional pocket-picking.  A sneak attack for double damage, a.k.a. "backstabbing" is another one.  A good line of patter keeps the target from noticing the dagger which the thief intends to stick between his ribs.  If the thief is good enough at it, he might even be able to pull it off in a crowded room without giving himself away.

Simple faux-magic tricks (i.e. prestidigitation) can be carried out with panache, as can all sorts of variants of the old shell game.  Switching a desired object for a worthless replacement right under the nose of the owner?  Absolutely.  Need a lock of someone's hair for some nefarious alchemical purpose?  Roll the dice.  Slipping poison or a sleeping draught into a goblet of wine?  Yep, that too.  Or maybe you'd rather save the king's life by switching his poisoned goblet for a safe one, without making a big scene.  Same principle applies. 

As DM, I'd ask the player for a general description of the character's "cover" -- what's his excuse for getting close to the mark and what's he saying or doing to divert attention and suspicion while he works?  Maybe he's flirting, or pretending to admire a piece of jewelry worn by the mark, or chatting with her about the artistic merits of a painting they're gazing upon.  If it seems decently plausible, roll the dice and see if he succeeds.

"Pick pockets" strongly implies that the ability is only good for picking pockets, but the same set of skills that allow a thief to lift items off an unsuspecting mark are useful for a multitude of other sneaky things as well. Terms like sleight-of-hand or (my new personal favorite) legerdemain are much less constraining, encouraging more imaginative use of the technique.  Pretty much anything a player can think to try that involves diverting a mark's attention away from some small manual task could be considered an application of this versatile skill.


  1. "climb walls" = parkour. (think assassin's creed)

  2. I think those are some very good suggestions. If anything, it requires a little forethought by DMs to help set up those situations so that the opportunity for a player to Pick Pockets exists. That helps me get out of the rut of how I build encounters.

    The only idea that didn’t seem to work was to Backstab. That seems to fall outside the intent of what the Pick Pockets ability is “meant” to do. Sure, I could see your point about how the Rogue might distract someone while talking, and it would be an extra step for him to set up the situation to allow a Backstab, but I’d want to be cautious as a DM in when it would work and when it wouldn’t. In a private meeting between the PC and the NPC, I don’t think I’d hesitate to allow it to set up a Backstab if they were talking face-to-face, and the Rogue decides to surprise them… but in a crowd? I’d probably allow someone to notice or (several someones and make the Perception roll at Advantage) for the possibility of alarming the NPC.

    I think what I just did there is reason myself into the possibility of having Sleight of Hand set up the Backstab! :D Anyway, great article.

    1. Actually I would have them role at disadvantage. Most people are VERY unobservent when it comes to what is going on around them. In a crowded market they are to busy tyring to get around through the crowd, get what they want, avoid the street urchines begging and stealing apples ect that they would not likely notice a dagger flipped up next to the sleeve, or even the act of pick pocketing someone. Unless you are trained, or clued in on the posibility of something happening the vast majority of people simply do not pay attention.

  3. Another excellent article
    In my own fantasy heart breaker, I also use

    SLEIGHT of HAND skill is used to either entertain or to deceive. This skill is applied when fetching items, picking pockets, concealing (< 2#) objects on one’s person or other feats of manual dexterity. Sleight of hand skill is applied when performing card tricks, the shell game or similar diversions. This skill does not allow you to cast true arcane or divine magic spells, but grants a +2 synergy bonus with RSW and adds +2 to spell DC (p.7) for spells that have an overt somatic component.

    When sleight of hand skill is directed towards a specific target, often this is an opposed roll; sleight of hand versus the targetz will save. Examples of usage of this skill are

    10 conceal dagger on one’s person
    12 make a coin ‘disappear’
    14 perform an amusing card trick
    16 conceal a scroll on one’s person
    18 make d10sp per day with the ‘shell game’

    On a natural ‘1’ the attempted crime has been observed by the local thief’s guild and the perpetrator will be target for retribution, ‘medieval style.’ It is not wise to attempt to sunder the fields of a local syndicate’s territory.

    On a natural ‘2’ the target and concerned guards or bystanders are aware of the attempt and will often respond in a hostile or violent manner. A fleeing criminal might have to contend with spell casting that can easily thwart any efforts to escape or evade such as magic missile, command, hold person, blindness, locate object, divination, etc..