d100 Pickpocket Finds

Let’s hear it for all thieves, rogues, bards, and other sticky-fingered types! 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 a little prep.

The next time you have a player attempt to snatch something from a pocket, pouch, or purse, consider these one hundred items to present your player. 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 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 magical or fantastical in some manner or another. Just roll a d20 and multiply by five to roll for only these items.

Have fun!


  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 dark secrets of the listener 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 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 whose possessor suffers 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, 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 a partial use.
  86. Genealogical notes that reveal that a seventh son of a seventh son resides nearby
  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 which 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 which converts 1 gold piece to its equivalent value in silver pieces, and vice versa. Only works for values equal to 1 gold piece.


What are some of your favorite pickpocket items or stories? Feel free to share in the comments.

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