Cutpurse
Skill Progression: Cutpurses naturally specialize in Pick Pockets. Beyond this, they typically favor Move Silently and Hide in Shadows, as these may increase their pick pocketing talents.
Cutpurses are not always uncooperative, however. Some do join guilds, which they serve primarily as informants and tipsters, ears on the streets, catching gossip and scoping out prospective targets that can then be assigned to other thieves.
Cutpurses who don't belong to a guild often form their own little mob. Such a small mob usually develops a standard modus operandi (way of operating), and they use the same scam on every target. They may also design special, elaborate plans for lifting a particularly heavy purse. Cutpurses also may enlist the assistance of thieves of other kits in their operations (see the Beggar kit, above, for an example).
Suppose, for instance, that one thief has the job of accosting an affluent-looking stranger, whom the Cutpurses have guessed to be an out-of-town merchant. This first thief presents himself as a street-vendor. While he tries to sell the merchant a hot pastry, a second thief comes by carrying a large load (perhaps a basket full of dirty sheets), which he "accidentally" drops on or around the merchant. In the chaos that ensues, the first two thieves appear to help the merchant, picking up the fallen items and apologizing profusely; while a third Cutpurse does the actual job of relieving the merchant of his cash.
Like Beggars, most Cutpurses are of lower-class background and are born into their station.
Another proficiency check can be made to determine the approximate level of the character. The DM should roll this check secretly. If the check fails, the difference between the number rolled and the number needed for success is how far off the character's estimate is.
Sometimes a Cutpurse will "check out" a character who is in disguise. When this happens, the Cutpurse suffers a penalty of -5 on his proficiency check.
Example: Gorgar the Cutpurse is eyeing an opulent-looking foreigner. Gorgar succeeds in his first observation check, and determines that the man is a wizard. This could be dangerous, he thinks, and he tries to guess how powerful the wizard is. Gorgar needs to roll a 13 or lower for a successful observation check. The DM rolls the dice secretly for him, and gets a 16. This means that Gorgar's estimate will be 3 levels off. The wizard is in fact 4th level. The DM decides that, because of the mage's rich dress, Gorgar overestimates the character's level. "You guess that the wizard is around 7th level," says the DM. (Note that characters don't speak in terms of character levels; the thief would have information in less precise terms; but speaking about levels is clearer for communication among players.) If the DM wished, he could have determined randomly if Gorgar over or underestimated (e.g., roll 1d6; 1-3: over, 4-6 under).
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