The Tale of Stingy Jack and the First Jack-o’-Lantern

Gather round my spooky friends, get comfortable as I share the tale of the first Jack-o’-Lantern.

So, once upon an eerie night (it’s a Halloween story, it can’t be a lovely summer’s eve now can it), there was a chappy called Jack (I bet you can see where this is going). Jack wasn’t just any chappy, oh no, he was a cheeky chappy.

Jack (also known as Stingy Jack… you’ll see why) was very well known for being, well, stingy, but also very, very cunning. Our story officially begins when Jack makes the bold move of inviting the Devil for a drink (not sure what they drank, but I imagine the Devil would quite enjoy a fireball whisky). As we’ve already established, our mate Jack here is stingy, so even though he invited the Devil for a drink (could even be a date, the lore isn’t specific), he didn’t actually want to pay.

This is when Jack gets the wonderful idea of asking the Devil to turn into a coin, so they could cheat their way into a free drink. I don’t see the real logic in the plan, they could’ve just done a runner, he was with the literal Devil after all, but no, they went for the old “turn the Devil into a coin so we can give the tavernkeeper fake money” trick.

For some reason, the Devil agrees to this completely one-sided deal where he gains absolutely nothing, and turns into a coin. Jack, realising that the plan was actually pretty dumb and he could just do a runner, did exactly that. He pocketed the now “coined term” Devil Coin (yes, I wanted to get the coined term pun in there), and placed it next to the silver cross in his pocket, trapping the Devil in coin mode. This works because… reasons.

It’s safe to say the Devil wasn’t best pleased, and asked to be released, which Jack eventually agreed to. Now, this is the part of the story I find hardest to believe. This man didn’t want to pay for his drinks, but he’s willing to give up his magical Devil Coin just because? Anyway, Jack agreed to release him, but added a condition (Jack seems to be a “go big or go home” type, giving the actual Devil a condition for freedom). He asked that the Devil not take his soul when he died. The Devil agreed, mainly because he obviously didn’t want to stay as a coin forever, and that was that. Jack faced zero, and I mean zero, repercussions from this, which is insane. The guy literally trapped the Devil, the angel/demon/monster/whatever who is famously petty and vengeful, but instead of a grudge, the Devil basically pats Jack on the back, says “well played,” and gets on with his infernal day.

Anyway, Jack eventually dies. Not right away, but later, because he clearly knew he’d peaked by tricking the Devil and wasn’t about to try conning Death next. When he finally did die, he went up to heaven as planned, but at the pearly gates, he was denied entry, for being stingy… or maybe it was because he invited the Devil round for drinks and the other angels felt jealous. So, Jack gets sent down to Hell, but he’s like, “Nah mate, I’m not staying here, we had a deal.” The Devil agrees, and instead gives Jack a glowing ember from the underworld. Jack pops it into a hollowed-out turnip, and from then on, he wandered the earth, living his not-so-living life.

And thus, the first Jack-o’-Lantern was born. People in Ireland and Scotland began carving their own turnips, beets, and potatoes (because you know… it was the olden days) with spooky faces to ward off wandering spirits like Jack. When the tradition hopped over to America, pumpkins became the veggie of choice (so pumpkin spice lattes could eventually become a thing), and the rest is spooky history.

So, there you have it, folks, the tale of the cheeky chappy that is Jack. The next time someone asks why they’re called Jack-o’-Lanterns, you can tell them this story of a stingy rogue and his devilish deal… or just make something up, like pumpkins used to be called “Jacko’s” back in the day because people were rubbish at naming things.