Any time a pickpocket check is made there is potential for a great deal of drama is introduced to the gaming session. Players, even of low level, should be able to create situations where odds are in their favor. The game master should feel new avenues of role playing are opened up to them. A ball or social evening could becomes a goldmine of thievery.
Many games have presented pickpocketing as a skill check that measures the ability of the rogue attempting the theft. There was the the assumption that failure would be bad, but little was concrete. I would advise before any roll is made four quests need to be answered.
1. What is being stolen?
2. What is the disposition of the target?
3. What are the environmental conditions?
4. Who else might see?
What is being stolen? Cutting a coin purse or lifting a wallet are easy tasks for professional thieves. Taking a watch or jewelry that is being worn if far more difficult. Removing a dagger from under a belt is going to be easier than removing it from a sheath at least without detection.
- Bag +2 +10%
- Rings,necklace -1 -5%
- Earrings -2 -10%
- Small weapon -3 -15%
- Large weapon -5 -25%
What is the disposition of the target? Stilling from someone in a drunk stupor is far easier than someone on the alert. I wear my wallet in my front pocket and will often check to assure it is in the correct location. Assume items in hand as not being able to be pick pocketed. Rogues or anyone whom professionally steals has and additional state that can be applied on top of their disposition.
- Drunk +10 +50%
- Distracted +3 +15%
- Apprehensive -2 -10%
- Alert -4 -20%
- Rogue -1 -5%
What are the environmental conditions? Darkness and crowds aid the rogue in their attempt. Also a particularly engrossing activity can help make the job easier. Apply all conditions that are present.
- Daylight -2 -10%
- Dusk +2 +10%
- Night +3 +15%
- Crowded street +6 +30%
- Alone -1 -5%
Who else might see? People generally will alert the target if they witness theft. The problem is most folks are not often looking. As we see above crowds actually make theft harder to detect. If the target is part of a host apply -1 or -5% to account for the added difficulty of being an outsider. If a bodyguard is present at the time of a theft; the rogue makes a single skill roll that is first used to determine success and then used as part of a contested skill roll against the guards alertness.
There are a few special situations I wanted to address. Pickpocketing can also be used to plant an item on a person. This is usually just popping an item into a pocket. You can apply penalties for larger items as you feel is best. Spells also can mimic the above effects. While others will not see some sort of alertness check should be allowed by the target to feel a shift of the weight on their person. You also have a few groups or individuals I call amenable observers. These can be anyone from a culture that does not have solid ownership of individual property like kinder, tricksters and other thieves. These observers often represent even more role playing opportunity. Thieves will not rat you out but may demand a cut. A guild may take even stronger steps to assure no one poaches from their patch. A spy network would perhaps coerce the players co operation .