Taking Stingy Jack from 5E D&D Warlock to Patron to Creature and Beyond

Over at Nerdarchy the YouTube channel Nerdarchists Dave and Ted take inspiration from an old Irish story for fifth edition Dungeons & Dragons. Stingy Jack — sometimes called Jack o’ the Lantern — is a mythical character associated with All Hallows Eve and in fact the Jack-o’-lantern may be derived from this story. In the video they discuss the legend and come up with several different ways to incorporate this figure of folklore into 5E D&D games. I came up with another one too. In this scenario Stingy Jack is neither a creature to fight nor an NPC to engage with. Not exactly anyway. So let’s get into it.

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Stingy Jack as a sentient magic item for 5E D&D

The tale of Stingy Jack is a compelling one full of the trappings of a great folklore story. There’s a lesson to be learned in there somewhere, a memorable central figure, supernatural elements and enough details to inspire superstition, myth and legend. Dave and Ted became captivated by the central figure Stingy Jack himself. The old reprehensible drunkard can make a fine NPC antagonist, quest giver or even a source of power for a character like a warlock in 5E D&D.

But what about the hollow turnip with the ember from Hell inside? When the devil turns Stingy Jack away at the gates of hell the ultimate evil entity feels some measure of pity for him and bestows a hellish ember for the wayward soul’s turnip lantern. Stingy Jack henceforth wanders between the worlds of the living and the dead for eternity.

“It was also used as a cautionary tale, a morality tale, that Jack was a soul trapped between two worlds, and if you behaved like he did you could end up like that, too.” — from National Geographic’s The Twisted Transatlantic Tale of American Jack-o’-lanterns

According to the 5E D&D Dungeon Master’s Guide “some magic items possess sentience and personality. Such an item might be possessed, haunted by the spirit of a previous owner, or self-aware thanks to the magic used to create it.” The book goes on to say sentient items are usually weapons (we’re throwing this right out the window) and they function as NPCs under the Dungeon Master’s control. A sentient magic item’s activated properties remain under the item’s control. They’re accessible to the one who possesses the item only while they maintain a good relationship with the item.

According to research there’s currently 12 sentient magic items in official 5E D&D material with eight weapons, four wondrous items and a ring. All the weapons are legendary rarity, the ring is an artifact and the other three are merely rare. There’s good baseline metrics to start from and the DMG goes on to describe creating a sentient magic item very similar to creating an NPC in terms of persona. There’s a whole other side to a sentient magic item though — special powers! I’m eager to see how things turn out when we take Stingy Jack the folklore character and translate him into Stingy Jack the sentient magic item for 5E D&D.

Stingy Jack

Wondrous item, legendary (requires attunement)

Stingy Jack is a carved turnip with eyes and a mouth and within the root vegetable lies a burning ember from the Nine Hells. While holding Stingy Jack as a bonus action you can cause the hellish ember to shed bright light in a 30 foot radius and dim light for an additional 30 feet.

While you are attuned to Stingy Jack whenever you make a death saving throw and roll 16 or higher, you regain 1 hit point. In addition whenever you make a Charisma (Deception, Intimidation or Persuasion) check you can roll a d4 and add the number rolled to the ability check.

When you hit a creature with an attack you can use your bonus action to instantly transport the target through the Nine Hells. The creature disappears and hurtles through a nightmare landscape. At the end of your next turn the target returns to the space it previously occupied, or the nearest unoccupied space. If the target is not a fiend it takes 10d10 psychic damage as it reels from its horrific experience. Once you use this feature, you can’t use it again until the following dusk.

Stingy Jack has 3 charges. While you are holding it you can expend one charge to cast scorching ray or 3 charges to cast antipathy/sympathy. Stingy Jack regains 1d3 charges daily at dusk.

Sentience. Stingy Jack is a sentient item of neutral evil alignment with an Intelligence of 12, a Wisdom of 8 and a Charisma of 16. Stingy Jack can speak, read and understand Common and it can communicate with you telepathically. Its voice is gruff and hoarse. It knows every language you know while you’re attuned to it. It has hearing and darkvision out to a range of 120 feet.

Personality. Stingy Jack is a miserable liar who enjoys playing tricks on others and manipulating them. Originally a turnip lantern carried by a selfish drunkard who deceived both celestials and fiends to spare his repugnant life the mortal was cursed to walk the world eternally. At some point the man’s soul became infused into his lantern. Stingy Jack is a scheming grifter who encourages the one who carries it to engage in the same sort of behavior.

*Featured image — An illustration of Stingy Jack, a man who is considered for the inventor of Halloween pumpkin carving [Art by Jovan Ukropina]