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.
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.
Found on common folk of most varieties, including tradesmen, craftsmen, merchants, travelers, adventurers and military personnel, brigands, and so on.
General Pocket Contents
Small wooden spool of bone white thread
Small ring-lock pocket knife, dull
1d4 wooden buttons
1d4 horn buttons
Small fabric pouch of tobacco
Three fishing hooks knotted together
1′ length of sinew cordage
1d4 simple bronze keys
3′ jute twine
Unaddressed love letter written in shaky handwriting
Pair of six-sided dice carved from horn
Wooden nit comb
Folding pot metal sundial
Scrawled food recipe on stained paper
Cork from an excellent vintage wine
Small rock shaped vaguely like a duck
Dingy iron shears with spots of rust
Piece of hard, dark chocolate wrapped in cheesecloth
1d6 small seashells
Curry comb with several russet horse hairs trapped in it
Poorly-drawn map showing the location of a nearby cottage
Short drinking horn with rudimentary etchings in geometric patterns
Lock of blonde hair tied with a tight bow
1d4 copper nails
1d4 discs of beeswax in a fabric pouch
Longstem clay pipe
Pair of knitting needles
Damaged iron bridle
1d8 glass beads with eyes painted on them
Lead plumb bob with 20’ of cord
Strange hook-shaped surgical knife
Lead pilgrim’s badge
Small earthenware pot of thick glue
Wooden box of salt
Small gourd filled with vinegar
1d8 sachets of strong-smelling tea
Small burlap sack of beans
Bundle of hot peppers tied together at the stems
Thin tin flute
Bulb of purple garlic
4’ long scroll of music and lyrics to a common song
Wooden weaving comb
Large knob of ginger root
Sour green apple
Small jar of honey
12’ of snare wire
Found on dwarves and those who are in constant contact with dwarves, as well as many miners and smiths.
Dwarven Pocket Contents
1d8 fine iron nails
Small tin funnel
Flint and steel
Jeweler’s steel stamp featuring a dwarven rune
Small tin flask
Recipe for homemade juniper spirits
Silver ring with an incomplete setting
Paper packet of dried cave moss for smoking
Leather band for tying beard
Found in the possession of elves, half-elves, and those who are in constant contact with elves.
Elven Pocket Contents
Sentimental bronzed leaf
Sparsely embroidered silk handkerchief
Green silk hair ribbon
Delicate sewing scissors in the shape of a crane
Folded paper with an expertly drawn erotic scene
Small card holding a dozen sewing needles
1d12 different teeth hanging on a length of cord
Small vial of perfume, which smells like rosewater and honey
Ornamental brooch of enameled ceramic in the shape of a brilliant red beetle
Leather sling tooled with a floral motif
Lump of fine soap
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.
Halfling Pocket Contents
Tin measuring spoon
Tiny vial of seasonings
1d8 delicious raspberries
Tin butter knife with smooth horn handle
Small earthenware flask filled with bacon grease
Ring of iron keys
4d12 tiny seeds in a paper packet marked CARROT
Pair of wool socks made for broad feet
Flat wooden tray containing small amounts of paint pigments in red, blue, and yellow.
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.
Monstrous Humanoid Pocket Contents
Crude iron shiv
Meat skewer, still dirty with baked-on lizard remains
1d6 small, round stones
Scrap of fur
Moldy domestic cat jerky
Damaged flint spearhead
1d12 human teeth wrapped up in a leaf
Long leather laces for wrapping makeshift sandals or boots
1d4 leeches in a small jar filled with water
Small gourd filled with vile liquor
Found on magicians of all types arcane; suitable for all mages, witches, warlocks, illusionists, etc.
Magic-User Pocket Contents
Large lizard hind leg
1d4 seeds of unknown origin
Tattered, absent-minded notes about carrier pigeons
Small linen pouch full of ersatz pixie dust
1d8 frog eyes
Half-finished scroll of an indecipherable spell
1d6 iron rings
Charred purple feather
Small glass jar with unknown organ floating in alcohol
Circular copper token marked with strange symbols and ADMIT ONE
1d4 mummified bird hatchlings
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.
Warrior Pocket Contents
1d4 lead sling bullets
Leather lace for securing armor
Stubby piece of chalk
Flint and steel
Rolled-up linen gauze bandage
Bronze challenge coin
Empty leather costrel
Serrated paring knife from an incomplete mess kit
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.
Holy Man Pocket Contents
1d4 cubes of incense
Wooden figurine of saint, spirit, or demigod
Empty alms pouch
Parchment square with seal of church/order/school stamped prominently
Bundle of small papers featuring handwritten prayers
Cheap wooden holy symbol
Wooden spoon inscribed with a truncated devotion of appreciation for food
Small ceramic flask of holy water
1d4 half-burned candles
Found on thieves, assassins, brigands, highwaymen, and assorted other criminals.
Thief Pocket Contents
Marked cards in leather sleeve
1d4 loaded dice
Wax mould of a key
Poorly-drawn map of the layout of the grounds of a nearby manor home
1d12 steel balls
Slim metal bottle filled with cheap booze
Small vial of oil
1d8 assorted keys
Broken stick of chalk
List of names on a rolled piece of vellum in fine penmanship
Small wedge-shaped prybar
Found on druids, primitive relicts, frontier humans where the old ways still reign, and feral tribes of elves or halflings.
Druid Pocket Contents
1d12 knuckle bones
Expertly-knapped flint knife
Crude wooden figurine of an elk
1d8 rat skulls
Rich, red soil wrapped up in broad leaves
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.
Most monstrous humanoids and rural or disenfranchised commoners, including paupers and those who have taken vows of poverty.
1d10 CP, explode the roll.
Many commoners and tradesmen, other adventurers, most clergy, some bandits.
1d10 SP, explode the roll.
Specialized tradesmen, landowners, successful merchants, ranking clergy members of organized religions, renowned adventurers, infamous bandits.
1d10 EP, explode the roll.
Lesser and intermediate levels of nobility, greedy or corrupt clergy, very successful merchants, bandit kings.
1d10 GP, explode the roll.
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!