Jack, The Hellspawn of All Hallows’ Eve

Medium Undead, Chaotic Evil
Armor Class: 15 (Natural Armor)

Hit Points: 144 (17d8+68)

Speed: 30 ft.

STR 16/+3

DEX 17/+3

CON 18/+4

INT 16/+3

WIS 10/+0

CHA 18/+4

Saving Throws: Wisdom +3, Charisma +7

Senses: Blindsight 60 ft., Passive Perception 13

Languages: Common, Thieves’ Cant 

Challenge: 7

Proficiency Bonus: +3

Fool’s Lanterns. As a bonus action, Jack can throw two pumpkin lanterns, each at an unoccupied space within 30 feet of him. These lanterns give off dim light in a 20-foot radius. They have 10 Hit Points, AC 12, and are immune to all conditions. There are two types of these pumpkin lanterns

  • Scoundrel’s Lantern. If a creature other than Jack spends their movement or enters the area within 10 feet of this lantern, it explodes and each creature within 10 feet of the Lantern must make a DC 15 Dexterity saving throw, taking 4d6 fire damage on a failure, or half as much on a success. Jack automatically succeeds on the saving throw if affected by the explosion. 
  • Hallowed Lantern. If within 5 feet of this lantern, Jack can use his bonus action to replace his own head with it, making him regain 2d12 Hit Points.

These two types of lanterns are very hard to distinguish between each other, if a creature uses the Search action, they can make a DC 15 Intelligence (Investigation) skill check, allowing them to recognize the type of all Fool’s Lanterns that they can see. 

Foolish Fire. If Jack takes at least 12 cold damage from a single effect or attack. He loses his blindsight until he replaces his head with a Hallowed Lantern 

Trick or Treat. When Jack ends his turn, each creature within his reach must make a DC 15 Charisma saving throw; on a failure, they can choose to gain a -2 penalty to all attack rolls, damage rolls and saving throws made until the end of their next turn. For each creature that chooses this penalty, Jack gains a +2 bonus to all the corresponding rolls until the end of his next turn.
If a creature chooses not to take the penalty, Jack can immediately make one attack against them. 


  • Multiattack. Jack makes two attacks with his Pumpkin Flail
  • Pumpkin Flail. Melee Weapon Attack: +6 to hit, reach 10 ft., one target. Hit: 12 (2d8+3) Bludgeoning Damage
  • Gourd Rain. If Jack Uses Fool’s Lanterns this turn, he can throw four pumpkins instead of two. 

Squash Escape. Jack burrows into the ground, leaving behind only his head, which turns into a Scoundrel’s Lantern. He can teleport to a Fool’s Lantern within 90 feet of him, destroying it in the process.

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