I've been doing a spot of musing lately on what sort of things could result when a PC thief attempts a bit of petty pocket picking on the side in between adventures. This comes up every so often, especially now we have three thieves in the party, and I'm never properly prepared for the event. Unprepared no longer!
I present my lovingly crafted pick pockets results charts! (Players in my campaign, please don't look at the charts, unless you love spoiling fun that is ;)
This is the second draft of these charts. The initial version I came up with included a lot more extreme results -- including being able to pilfer some pretty valuable items, and the accompanying possibility of severe punishment (incarceration or execution!). After some discussion with the players we decided that, while this was realistic, it wasn't much fun. So the final tables have been kind of smoothed out. Items of moderate wealth can be stolen, and moderately bad consequences of failure may occur, but nothing at either extreme.
I hope some other DM out there might also find these charts useful!