The Legend of Stingy Jack

A creepy tale of a creepy dude for a creepy day

Can you picture the worst person you’ve ever known?

They were probably deceitful. Maybe prone to theft. Violent even. They probably snacked on turnips. Someone who the term “douchebag” wouldn’t quite fully encompass.

Stingy Jack was all of those things and more.

A few centuries ago in Ireland, Jack roamed the land stealing, drinking, and swearing at every person he came across. He became so infamous the Devil himself was struck with curiosity—and off he went for a little visit to see the mad man in person.

That fateful night led the devil in disguise to a local pub—where else in Ireland?—for the devil to observe Stingy Jack in all his glory. And sure enough, he completely lived up to the promise.

Happy to inform him of his newfound status, the Devil told Jack his clock was now ticked.

Frantic and thirsty, Jack begged the devil to pay for one last pint before buggering off. Happy to oblige, the Devil transformed into a silver coin to pay for the bevy.

But of course, Stingy Jack didn’t pay.

Rather, he plopped the coinish devil into his shirt pocket, nestled beside a lovely little ironic silver cross. Unable to transform back due to his religious upbringing, the Devil begged Jack to free him. And so he did—upon the condition Jack’s life and soul were spared for another 10 years.

Another decade of debauchery went by, and you can bet your pumpkin spiced butt the Devil came back to meet Jack again.

This time, Jack was met on a cobblestone road with nowhere to run. Once again panicked, he begged the Devil for one last tiny favor—to jump up a tree branch and pluck an apple for his hungry belly.

With a sigh and a leap, the Devil obliged, while Jack sketched a cross on the tree trunk below.

With angry mutterings of “fool me once, motherfu…”, the Devil once again asked for his freedom. This time, Stingy Jack was a bit more forward thinking. He declared the Devil would have his freedom for the price of never letting Jack into his hellish realm.

He agreed and left in anger.

A few years later, Stingy Jack’s poor lifestyle choices and lack of health insurance caught up to him. He croaked.

First, he ran up to the Pearly Gates, naively expecting entrance and of course being denied. He was swiftly cast down to the Gates of Hell, which some people call Cincinnati, where the Devil was only too happy to remind him of their deal.

“But where shall I go?” Stingy Jack pleaded.

“Back to whence you came!” said the Devil.

And back to Earth Stingy Jack was sent to roam the night, given a lump of coal from the fires of hell and a carved out turnip to carry it in.

It’s said if you look out your window every All Hallow’s Eve, you can still spot Stingy Jack of the Lantern roaming the streets in perpetual dark loneliness.

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Written by a Halloween loving J.J. Pryor.

Alternate last line: I am Jack’s lack of afterlife.

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