The Thieves Guild
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D&D Pickpocket Loot Table
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Pickpocket Loot

a needle that never bends
Random Roll: d10 = 5

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d10 Loot
1 Loot:  Lint or a bit of thread
2 Loot:  A piece of paper or parchment with a mundane note, list of items, or list of tasks on it
3 Loot:  A key (roll d6)
Loot:  1: A broken key
Loot:  2: A small brass key
Loot:  3: A heavy iron key
Loot:  4: A rusted key
Loot:  5: A key made from an unusual material
Loot:  6: A key ring with 1d10 keys on it
4 Loot:  A handkerchief (roll d4)
Loot:  1: A fine silk handkerchief
Loot:  2: A simple cotton handkerchief
Loot:  3: A lacy handkerchief
Loot:  4: A threadbare handkerchief
5-6 Loot:  A random trinket (roll d20)
Loot:  1: 1d8 chess pieces
Loot:  2: A tiny silver bell without a clapper
Loot:  3: A small knife
Loot:  4: A badge designating a military rank
Loot:  5: A glass orb filled with water, in which swims a clockwork goldfish
Loot:  6: A gem that looks like a lump of coal when examined by anyone else but you
Loot:  7: A rabbit's foot
Loot:  8: A four-leaf clover in a small glass vial
Loot:  9: A vial of dragon's blood
Loot:  10: A needle that never bends
Loot:  11: A whistle made from wood, with gold inlays
Loot:  12: A petrified mouse
Loot:  13: A tiny mechanical spider that moved about when it's not being observed
Loot:  14: A deck of 52 joker playing cards
Loot:  15: A tiny gnome-crafted music box that plays a song you dimly remember from your childhood
Loot:  16: A tooth from an unknown beast
Loot:  17: A piece of crystal that faintly glows in the moonlight
Loot:  18: A shard of obsidian that always feels warm to the touch
Loot:  19: A pair of old socks
Loot:  20: A pair of rigged dice
7 Loot:  A ring (roll d6)
Loot:  1: A wooden ring
Loot:  2: A heavy, iron ring
Loot:  3: A silver wedding band
Loot:  4: A simple, gold ring (worth 1d4 gp)
Loot:  5: An ornate gold ring etched with silver (worth 1d8 gp + 1d4 sp)
Loot:  6: An expensive-looking, platinum ring (worth 10d10 gp)
8 Loot:  A small vial or flask (roll d6)
Loot:  1: An empty flask/vial
Loot:  2: A Potion of Healing
Loot:  3: A Potion of Climbing
Loot:  4: A Potion of Poison
Loot:  5: A Potion of Resistance
Loot:  6: A Potion of Greater Healing
9 Loot:  A score (roll d12)
Loot:  1: 2d4 cp
Loot:  2: 3d6 cp
Loot:  3: 1d6 sp
Loot:  4: 1d6 sp + 1d10 cp
Loot:  5: 2d6 sp
Loot:  6: 2d6 sp + 1d6 cp
Loot:  7: 1d4 gp
Loot:  8: 1d4 gp + 1d10 sp
Loot:  9: 2d4 gp + 1d10 sp
Loot:  10: A gem or small piece of jewelry worth 5d10 gp
Loot:  11: A gem or small piece of jewelry worth 10d10 gp
Loot:  12: 1d6 gp and roll again on this table
10 Loot:  A big score (roll on the d12 table above, and then roll again on that table with a d8)


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Pickpocketing

Optional Modifiers: Typically, a pickpocket involves a Dexterity (Sleight of Hand) Check against a target's Passive Perception. However, if the target is actively searching or on guard, the DM may choose to use the targets regular Perception.

Optional Modifiers

Below are several modifiers that may affect a pickpocket attempt. DM's discretion.

Situation Roll Mod
Target distracted (successful Deception Check by another player) Adv.
Creature is sleeping +5
Random pickpocket (grab whatever they can) --
Object is visible (i.e. sheathed dagger, belt pouch) --
Creature is wearing the item, loosely (i.e. necklace, sash, hat) -2
Creature is wearing the item, tightly (i.e. ring, bracer, belt) -5
A specific object, hidden or concealed on the creature (if the object is being carried) Disadv.

Value Modifiers

Optional Rule: If the pickpocket successfully manages to steal something of value, the value may increase depending on the target's standing and role in society. The DM may choose to roll a d100 to determine the targets rank in society, which can affect the value. Note: This is a general table, mainly used in crowded cities, so a DM may modified the percentages as needed. For example, Farming communities may not have any wealthy merchants, lords or nobility. In addition, a city's district may affect this roll (i.e. there may be more beggers in a poor district, and there may be more nobles in the king's castle).

% Target Value Modifier
5% Beggers
70% Commoners (peasants, serfs, slaves, servants, tradesman, shopkeepers) x1
11% Wealthy merchants, skilled artisans x2
3% Nobility x4
1% Royalty (often escorted by guards and servants) x10

Failure - Notice

Optional Rule: If a rogue fails their pickpocketing attempt, it does not automatically mean that the target notices the item was taken. The DM can optionally make a second perception roll for the target, with the following modifiers.

Modifier Situation
Disadv. Distracted
-5 Target is sleeping
-2 Target was distracted
+2 Target is wearing the item, loosely (i.e. necklace, sash, hat)
+5 Target is wearing the item, tightly (i.e. ring, bracer, belt)
+5 The item is fastened to the targets clothing (i.e. by a rope or chain)
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