The Price of deals

This version of the Stingy Jack legend was published in a penny dreadful known as The Dublin Penny Journal on January 16th, 1936 — far from the shadowy glow of Halloween, but haunting all the same.

For those unfamiliar, penny dreadfuls were cheap, sensational booklets—thin little things, a dozen pages at most—that delved into the darkest corners of human curiosity: crime, mystery, the supernatural. They were the true crime podcasts and horror series of their day. The name came from their price—just a penny—but their impact was anything but small. Iconic characters like Sweeney Todd and Sexton Blake were born in their lurid pages.

This particular tale, titled Jack O’ the Lantern, was penned by an unknown writer who left behind only the initials E.W. It begins like many tales of Stingy Jack do—with a man you’d rather not meet in a dark alley. A scoundrel. A drunk. A fool.

One night, as he stumbles home from whatever pit of vice he’d been drowning in, reeking of bad decisions and ale, he comes upon a scene so unsettling, it cuts through his stupor like a cold knife through fog.

While crossing a fjord long whispered about in tales of murder, misfortune, and ghostly warnings, Jack suddenly heard a voice ring out through the misty night:

“For the love of heaven, take me to some human habitation; for I am no tortured spirit, but a poor, homeless wanderer who may have lost his way on the wild moor and lain down here to die. I dared not cross the rapid water. So may mercy be shown to you in your hour of need, and in the day of your distress.”

At first, Jack froze. Every instinct told him this was a trap—some trick of a demon, lurking in the darkness, trying to lure him to ruin. But something in the desperation of the voice... something real stirred in him. Against all his nature, he followed it.

There, half-submerged in the freezing water, was not a specter, but a battered, broken man—soaked, trembling, and barely clinging to life. And Jack—stingy, selfish Jack—felt something shift inside him. For perhaps the first time in his miserable, misbegotten life, he wanted to help someone.

Without hesitation, he hauled the stranger onto his horse and rode through the night. When he burst through the door of his home, his wife could hardly believe her eyes. Her husband—the one who’d never lifted a finger for anyone—was carrying in a wounded soul, begging for warmth and aid. And instead of turning him away, she welcomed the stranger with joy.

Together, they cleaned him up, wrapped him in dry clothes, fed him, and laid him in a warm bed. Then, exhausted, they went to sleep.

But when Jack woke the next morning, he was nearly blinded by an otherworldly light filling the room. The bed where the wanderer had rested was now empty—except for the glowing figure that stood in his place.

The poor man Jack had rescued… was an angel.

And so, in return for Jack's uncharacteristic act of kindness, the angel offered him a rare reward: a blessing upon his home, and any three wishes his heart desired.

Now, this is where the Jack we really know makes his grand return—the cunning, petty trickster with a grudge against the world. Not a moment of hesitation passed before he named his wishes.

First, he wished that anyone who so much as touched the sycamore tree in his front yard would be stuck to it—unable to move until he gave permission. Second, he asked for the same curse to fall upon his favorite chair. And finally, he asked that anyone who laid hands on his well-worn toolbox suffer the same fate.

The angel, startled by the sheer pettiness of the requests, let out a weary, audible sigh. It wasn’t malice that fueled Jack’s choices—it was vindictive annoyance, the kind that festers quietly over years of slights and trespasses. Still, the wishes were granted.

But the heavenly hosts had seen enough. That very moment, they made a quiet, eternal decision: Jack O’ the Lantern, no matter what good he had done that night, would never set foot in heaven. He had been given the chance to wish for joy, peace, healing—but chose instead to arm himself with tools of vengeance.

Even so, the angel’s blessing on his house remained. Jack lived on in earthly comfort: his home warm, his table always full, his fields golden with harvest. He fathered many children and grew old in abundance.

Twenty years passed.

And then, as promised long ago, a demon arrived—sent to collect Jack's soul as payment for a lifetime of deceit and sin. But Jack, as ever, was no easy mark. He greeted the creature with a smile and a calm suggestion.

“Why don’t you rest yourself in that chair while I go change into my Sunday best?”

The demon, perhaps amused or simply underestimating the old man, took a seat. the moment it did, it knew something was wrong. It tried to rise—and could not. Panic set in. That cursed chair held it fast.

Jack returned, not with fine clothes, but with a flail in hand—iron-studded, wicked, and well-used. And then he set upon the demon with the fury of every grudge he’d ever nursed. Blow after blow rained down, until the infernal creature was a heap of broken bones and bruised pride, writhing and pleading for mercy. breathless and blood-slick, Jack leaned in close and offered his terms.

“I’ll let you go,” he growled, “but only if you swear—you and all your kind—never to bother me again.”

The demon, shattered and desperate, had no choice but to agree. With a final, pained screech, it vanished back into the pit, defeated by a man too stubborn for hell itself.

When Satan learned that one of his finest messengers had returned from the mortal world battered, bloodied, and humiliated, his fury burned hotter than the flames of hell itself. He would not be mocked. He summoned a darker, more savage demon—one that knew only pain and how to inflict it—and sent it to finish what the first could not.

The next day, as the monstrous figure loomed at Jack’s doorstep, Jack didn't flinch.

"Alright," he said coolly. "I'll come with you. but if we're walking the road to hell, I need to fix my shoe first. pass me the mallet from my toolbox."

The demon, sensing no threat, reached out to oblige. But the moment its hand touched the mallet, it was trapped—stuck fast to the box, the box stuck fast to the wall. without hesitation, Jack reached for his flail. he brought it down with no mercy, each strike echoing through the room like thunder.

Bones cracked. Ligaments tore. With every blow, the demon shrieked—but Jack did not stop until his victim, shattered and defeated, vanished back to the abyss from which it came.

On the third day, Satan had had enough.

He would no longer waste his loyal servants on this mortal trickster. if Jack was to be taken to hell, then he would come himself to do it.

He appeared outside Jack’s door, towering and terrible.

"It’s time," he said, his voice like fire on stone.

But Jack, ever the schemer, met his gaze without fear. "I’m ready," he replied. "But I can’t walk to hell without my stick."

Satan narrowed his eyes. "You don’t need a stick."

Jack simply gave a weak cough and slouched pitifully, milking every ounce of false frailty. "Please... just something to lean on. I’m not what I used to be." with a scoff of irritation, Satan turned toward the sycamore tree nearby and reached to snap off a branch.

But the moment he touched it—he froze.

Bound. Stuck.

At this, Jack let out a triumphant yell—a wild, victorious sound that echoed into the trees. he’d done it. He’d outwitted the final boss. without wasting a second, he dashed back inside and grabbed his favorite flail—then two more for good measure. with all the flair of a man who knew he’d won, Jack returned and, one by one, shattered the weapons over Satan’s skull.

Even the Prince of Darkness wasn’t immune to pain. pleading, humiliated, and beaten, Satan begged for mercy.

Jack, standing over him with smoke curling from his flail's splintered handle, offered a deal:

"I’ll let you go. But you swear—you never come back for me. You don’t send anyone. You leave me alone. Forever."

And what choice did the devil have? He agreed. Bound by oath and bruises, he vanished back into the shadows, leaving Jack alone beneath the sycamore tree.

But no man, not even one as clever as Jack, can trick the natural order. death is older than hell, colder than the grave, and it does not negotiate so when it came for Jack, it came without messenger or warning.

And you already know how the rest goes.

His soul, unclaimed by hell, drifted downward, only to find the gates sealed shut.

In this version of the tale, Satan didn’t even bother facing him. He ran. Hid. Trembled like a cornered beast, fearing Jack might break out another flail and finish what he started.

Heaven, on the other hand, merely laughed. whatever Jack had done in life—his wit, his tricks, the deals and deceptions—it had left him unworthy of peace.

so he was cast out of both realms.

Neither damned nor saved, Jack was cursed to walk the earth in shadow, trapped between worlds.and so he roams, a flickering ember cradled inside a hollowed-out shell to light his way.