100 Pickpocket Finds for Your Fantasy RPG Game

For thieves, rogues, bards, and other sticky-fingered types!

Running a fantasy roleplaying game such as Dungeons & Dragons, Pathfinder, Fantasy AGE, or any other involves a lot of preparation. As talented a GM (gamemaster) you may be, it’s not a bad idea to have handy lists of possible outcomes for when player characters go down the road less traveled or, as in this case, go for the pocket less picked.

I have a personal fondness for thieves and rogues in roleplaying games. Wizards may have their fireballs and barbarians their axes, but there is nothing quite like a loveable rascal in the party to stir the pot. A well-timed pickpocket attempt can turn a boring encounter into one that might get just a bit too exciting.

The problem is coming up with an answer when the player tells you, “I reach into the sheriff’s pouch while he’s distracted by the bard.”

Sure, a successful attempt could net the player a few coins, but they could find something a lot more interesting… with some prep.

The next time you have a player attempt to snatch something from a pocket, pouch, or purse, consider one of these one hundred items for your player to find. Some are mundane. Some are mysterious. And some are even magical. Peruse the list and write down your favorites, or simply have the list handy for a quick d100 roll and some quick improv.

Should your pickpocket be attempting to steal from a special character, note that every fifth item in this list is somewhat more magical or fantastical than the rest in some manner or another. Simply roll a d20 and multiply by five to use these items.

Have fun!

100 Pickpocket Items

1. A note that says “Run!”
2. A set mousetrap
3. A broken locket with a picture of a beautiful elf boy inside
4. A piece of paper intricately folded into the shape of a wyvern
5. A magic ring that turns the wearer into a very combative giant frog. The wearer retains that form until killed or the ring is forcibly removed from one of its rear feet. Grappling rules apply if available. If killed, the wearer is restored — no harm done
6. A wooden coin of no particular value
7. A simple, but moving love letter
8. A single key to an unknown lock
9. A rabbit’s foot charm
10. A ten-foot pole. The pole is normal. The pocket it came from is not.
11. A small bottle of Samwell’s Miracle Hair Tonic
12. A preserved human ear
13. A small, featureless doll made of red fabric and crushed straw stuffing
14. A small pouch of crushed chalk
15. An enchanted sphere of marble, about 2 inches across, that, when touched, changes the toucher’s hair and skin to a random bright color (red, orange, magenta, blue, etc) for a full hour.
16. A live rat named Mr. Bitey. Yes, he bites.
17. A folding knife
18. A pouch of smoking tobacco and a small briar pipe
19. A bill of sale for a shallow-drafted cargo boat named The Tsarina
20. A gem that, when held up to the sun for a full minute, gives the holder an accurate impression of the weather for the next 24 hours.
21. An eight-ounce bottle of very strong dwarven liquor
22. A folded piece of paper with the pickpocket’s name written on it in a demonic script
23. A garrote
24. A single silver piece of which one side has been rubbed smooth by years of compulsive habit
25. A seashell which, when held up to the ear, reveals the listener’s darkest secrets in a hushed, diabolical voice
26. A hand-written receipt for 12 skulls and an obsidian dagger
27. A written message from the wife of a shopkeeper to a smith’s apprentice to come around during temple services… and to burn this note
28. A string of brightly colored beads
29. A string of brightly colored beads that conceals a message that, with a successful intelligence check to decode, says, “We strike at midnight.”
30. A magic coin that, when flipped, offers an advantage (heads) or disadvantage (tails) on their next roll. Works once per day.
31. A wooden collapsible cup
32. An elven arrowhead
33. A round piece of doily. Finely made, approximately 8 inches across
34. A blood-soaked rag
35. The fingerbone of a long-forgotten, but saintly cleric. Undead within five feet suffer a disadvantage.
36. A silver fork
37. A jade brooch
38. A small wooden comb
39. A powerful merchant’s calling card
40. An eight-ounce cup that can hold a gallon (liquids only)
41. A pewter egg cup
42. A small carefully painted lead figurine of a human warrior with sword and shield
43. A child’s toy top
44. A tiny pouch filled with toenail clippings
45. A note that says “You can do it!” Once read aloud, the words disappear and the speaker is granted an advantage (GM’s discretion, usable only once)
46. A small bottle of ink with a leaky stopper, guaranteed to stain one’s fingers
47. A blank piece of paper
48. A magnifying glass lens
49. A small envelope containing five sewing needles
50. A seed which, when planted and watered, sprouts and grows into a full-sized blueberry bush with edible berries with about three minutes
51. A vial of the pickpocket’s own blood
52. A detailed drawing of a member of the pickpocket’s party
53. A child’s toy horse
54. Three finger puppets of clerical characters
55. An explosive dart which deals 1d10 damage upon a successful hit
56. A written summons to appear before the magistrate by noon the next day
57. A folded paper fan
58. A one-inch thick candle about five inches long
59. A handful of dried beans
60. A reed straw which purifies unclean or poisoned water (fragile, will break after a few uses at GM’s discretion, works with water only)
61. A bloody, severed hand
62. A half bar of unused soap
63. A shaving brush
64. A biscuit shaped like a bone
65. An amulet featuring a fly trapped in amber that, when put around the neck of a medium-sized creature or smaller, removes all ability to fly — either physically or magically
66. A pair of brass knuckles with the words “Love, Mom” stamped into the side
67. A folded piece of paper with a black spot in the center
68. A handful of crushed rose petals
69. A human tooth, root and all
70. A dragon tooth that allows the possessor to suffer only half damage from any dragon bite (other forms of attack do not apply)
71. A potato that sort of looks like a goblin head
72. A complete and fully cleaned rat skeleton
73. A square of crushed velvet
74. A thorny rose. Beautiful, but ouch!
75. A whistle that can only be heard by those who are lawful good
76. A well-used skeleton key
77. A four-leafed clover encased in solid glass
78. A nicked plectrum
79. A license to kill one deer on royal property
80. A small crystal bell that when rung summons one minute of light rain. Outdoors only and only twice a day.
81. A token for one free ale at “Happy Hiccup’s House of Brew”
82. Three pieces of broken crockery
83. A fake gemstone
84. A small pouch of hard candy
85. A sparkling blue brooch that allows the wearer to survive comfortably without food or water for up to one week. Needs a full week to recharge even after partial use.
86. Genealogical notes that reveal that a seventh son of a seventh son and the seventh daughter of a seventh daughter reside nearby. They do not know each other
87. A metal fish hook
88. A wooden slat with the words “You may already be a winner!”
89. A lightly perfumed handkerchief
90. A silver coin upon which a continuous light spell has been cast
91. A live, angry beetle about two inches long
92. A pocket-sized sundial on a light chain
93. A small vial of poison
94. An uneaten apple
95. A cursed ring that removes any benefit from consuming food or liquid. User slowly suffers starvation and dehydration until the curse is lifted which allows ring to be removed
96. A small prayer book appropriate for a widely-worshipped good-aligned deity
97. A charm made of a dried frog and three iron nails tied together with red string
98. A handful of dried bees
99. A hand-drawn map of the local tavern suggesting a possible secret room behind the storeroom
100. A magical pouch that converts one gold piece to its equivalent value in silver pieces, and vice versa. Only works for values equal to one gold piece

I hope this list proves useful to you. Even if you don’t actively use it in a game, inspiration may strike from one or two of the above items and from there…who knows?

The nice thing about roleplaying games is that the possibilities are absolutely endless.

Cheers!