B/X Pickpocketing

In the glorious Basic/Expert rules of Moldvay and Cook, pickpocketing relies on rolling under a target score on percentile dice. Thieves begin with a 20% chance (meaning they must roll a 20 or less on percentile dice) and gain +5% chance each time they level. Some additional caveats apply as the character advances in level and attempts more complex maneuvers; I advise you to reference page B8 in the Basic book and page X6 in the Expert book for more detail. The important part here is that we all understand how a basic pick pocket attempt works, so I can introduce my subsystem to add randomized flavor items to pickpocket attempts.

New Pickpocketing Subsystem:

If the success is 0-5% better than the requisite score (e.g. a 16 rolled for a 20% requisite), roll once on the general contents table, and once on a single applicable subtable.
If the success is 6-10% better than the requisite score, roll twice on the general table and twice on a single applicable subtable if necessary.
If the success is 11+% better than the requisite score, roll three times on the general table and three times on any applicable subtables.


Example:
A 3rd level thief must score better than a 30% on percentile dice to pick the pockets of a 1st level neophyte elven archer guarding a tree house. The thief rolls a 15, which is more than 11 better than the required roll of 30. The thief therefore has earned three rolls on the general table and three rolls on any applicable subtables. The DM rolls on the general table three times, the elven table once, and the warrior table twice. The thief successfully steals a handful of goods containing some lint, a wooden spoon, jerky, a harp string, a whetstone, and a leather lace for armor fixtures.

Alternatively, if the dice slow you down and/or you hate fun and random chance, just eyeball it and pick the appropriate number of items from each list according to the results.

General Contents

Found on common folk of most varieties, including tradesmen, craftsmen, merchants, travelers, adventurers and military personnel, brigands, and so on. 

Dwarven Contents

Found on dwarves and those who are in constant contact with dwarves, as well as many miners and smiths.

Elven Contents

Found in the possession of elves, half-elves, and those who are in constant contact with elves.

Halfling Contents

Found on halflings and those who are in constant contact with halflings. Would also be found on gnomes or other small, homebody sorts of creatures.

Monster Contents

Found on mostly-humanoid monsters, such as goblins, orcs, hobgoblins, gnolls, and kobolds. Bipedal snakemen, lizardmen, or other weird hybrids of the animal kingdom might also have these items.

Magic-User Contents

Found on magicians of all types arcane; suitable for all mages, witches, warlocks, illusionists, etc.

Warrior Contents

Found on martial characters, such as fighters, rangers, guards, knights, cavaliers, most henchmen, archers, gladiators, and so on. Paladins can also be rolled on this table or the following table.

Holy Men Contents

Found on the persons of priests, clerics, paladins, mystics, and so on. Paladins may be rolled on this table or on the previous table.

Thief Contents

Found on thieves, assassins, brigands, highwaymen, and assorted other criminals.

Druid Contents

Found on druids, primitive relicts, frontier humans where the old ways still reign, and feral tribes of elves or halflings.

Determining Cash

In addition to flavor items, you probably were pickpocketing for a specific item – a key on a guard, maybe – or to inflate your own wealth. In the case of the former, if the attempt is successful, you automatically also steal the item in question. In the case of the latter, there’s a little more granularity.

First, the DM determines how wealthy the target is, and then a d10 is rolled. The result is the value of coins stolen – perhaps a pouch is lifted right off a belt, or a purse is cut and its contents are caught in the thief’s outstretched hand. These assume a gold-centric economy, as in TSR D&D; for in the case of silver standards like in LOTFP, please decrement all coin types by one (e.g. listed value of 5 gold coins becomes 5 silver coins, listed value of 4 silver coins becomes 4 copper coins). A roll of 10 naturally requires you to explode the roll, because that’s just fun.

These values are separate from treasure found on corpses, and should not count against treasure discovered on corpses. If a goblin in your system should have 10 silver pieces on its body when it dies, and it is pickpocketed earlier for 1 silver piece, it should still have 10 silver pieces on its body when it dies.

Impoverished
Most monstrous humanoids and rural or disenfranchised commoners, including paupers and those who have taken vows of poverty.
1d10 CP, explode the roll.

Getting By
Many commoners and tradesmen, other adventurers, most clergy, some bandits.
1d10 SP, explode the roll.

Comfortable
Specialized tradesmen, landowners, successful merchants, ranking clergy members of organized religions, renowned adventurers, infamous bandits.
1d10 EP, explode the roll.

Prosperous
Lesser and intermediate levels of nobility, greedy or corrupt clergy, very successful merchants, bandit kings.
1d10 GP, explode the roll.

Wealthy
Kings and queens, heads of state or religions, invincible overlords, and other tremendously powerful folk.
1d10 PP, explode the roll.

Hopefully this ruleset helps you make pickpocketing a little more interesting in your games when it comes up. Thieves need their chance to shine too! As an aside, these can also be used as “what is on the body” tables for littering corpses with trivial items. You should feel free to chop the tables up as you see fit. Replace items, expand them to larger dice, etc.

If you like this take on pickpocketing, or you hate it and it feels slow at your table, or you just want to take my lunch money like it’s middle school again, hit me up in the comments or over on Twitter @dungeonspossums!