There are few images as instantly recognizable as the glowing grin of a jack-o’-lantern on Halloween night. Its crooked smile, its flickering eyes, the eerie glow spilling out into the darkness—it’s the very heart of the holiday’s atmosphere. But behind that simple carved pumpkin is a story, an old tale whispered across centuries, that begins not with candy, costumes, or pumpkins at all, but with a man from Ireland known as Stingy Jack. His legend is a story of trickery, darkness, and a strange bargain with the Devil himself, a story that somehow traveled through time and across oceans to inspire one of Halloween’s most enduring traditions. And tonight, on October 31st, it’s worth retelling in full, because the tale of Stingy Jack is more than just folklore—it is the spark that lights every jack-o’-lantern burning on porches around the world.
Jack was not the sort of man people admired. In fact, by all accounts, he was a selfish, miserly, and rather mean-spirited fellow, earning him the nickname Stingy Jack. He was known in his village for being clever but cruel, sharp-witted but dishonest. Jack liked to drink, and one fateful evening in a small Irish tavern, as the story goes, he met the Devil himself. Whether the Devil came for Jack’s soul that night, or whether Jack invited him for a pint out of sheer audacity, no one quite knows. What we do know is that Jack, even when faced with the Prince of Darkness, refused to give up his cunning. Instead, he hatched a plan.
After drinking together, Jack convinced the Devil to pay for the drinks. But of course, Jack being stingy, didn’t have the money himself. He suggested that the Devil transform into a silver coin to settle the bill. Amused or intrigued, the Devil agreed and changed shape. But Jack, instead of handing over the coin, slipped it into his pocket next to a small crucifix he carried. The holy symbol trapped the Devil in coin form, unable to escape. And just like that, Stingy Jack had outwitted Satan himself.
Jack kept the Devil imprisoned for some time, enjoying the power he held. Eventually, he struck a bargain. If Jack let him go, the Devil had to promise not to claim his soul for ten years. The Devil, caught and humiliated, had little choice but to agree. Jack released him, and for a decade he lived as he always had—selfishly, drunkenly, and without remorse—knowing that for once, death and damnation would not come knocking.
But time has a way of circling back. Ten years passed quickly, and the Devil returned, ready to finally collect what was owed. Jack, of course, wasn’t done scheming. As the Devil led him toward his fate, Jack asked for a last request—a simple apple from a nearby tree to quench his hunger before eternity in Hell. The Devil, perhaps still annoyed at being tricked before, climbed into the branches to fetch it. But once again, Jack pulled out his crucifix, carving crosses into the bark of the tree, trapping the Devil up among the branches.
This time, Jack drove a harder bargain. He demanded not just another ten years, but that the Devil promise never to take his soul to Hell at all. The Devil, cornered and angry, had no choice. He swore an oath never to claim Stingy Jack. Jack, smug and victorious, removed the crosses, and the Devil went free, his pride bruised and his patience for mortals running thin.
Years later, Stingy Jack finally died. His soul left his body, and he approached the gates of Heaven. But Jack’s life had been nothing but sin, greed, and cruelty, and Heaven wanted no part of him. He was turned away. With no place to go, Jack wandered to Hell. But true to his word, the Devil refused him entrance. Jack had trapped himself in the worst possible fate: rejected by both Heaven and Hell, doomed to wander the world as a restless spirit, caught forever in between.
The Devil, perhaps enjoying one last cruel jest, tossed Jack an ember from the fires of Hell to light his way as he roamed the dark earth. To keep it from burning out, Jack carved a hollow turnip and placed the ember inside, carrying it with him as he drifted endlessly through the night. From that moment on, he was known as Jack of the Lantern—or Jack-o’-Lantern.
This strange tale did not stay in Ireland. It became part of the folklore of Samhain, when the dead were thought to walk among the living, and villagers would carve grotesque faces into turnips and gourds, placing candles inside to frighten away Jack and other wandering spirits. The image of the glowing lantern, flickering against the night, became a symbol of protection as much as fear. Families lit them on doorsteps, warning away the supernatural while marking the night when the living and the dead brushed against each other.
Centuries later, when Irish immigrants carried their traditions to America, they found that turnips were not as abundant as the pumpkin, a native fruit that was larger, softer, and easier to carve. Soon, the pumpkin became the new vessel for Jack’s ember, and the jack-o’-lantern as we know it today was born. What had once been a story about a stingy man tricking the Devil evolved into a festive tradition of carving pumpkins, setting them alight, and celebrating Halloween with a mix of fear and joy.
Of course, Halloween itself grew and changed over the years. From its roots in Samhain, a solemn recognition of the turning of the year, it blended with Christian observances of All Hallows’ Eve, later morphing into the modern celebration of costumes, candy, and haunted houses. But through all these transformations, the jack-o’-lantern endured. Its glow remains a reminder of the line between life and death, between mischief and malice, between the safety of home and the mysteries of the night outside.
And what makes Stingy Jack’s tale endure isn’t just the supernatural bargain—it’s the humanity behind it. Jack wasn’t a hero. He wasn’t noble or virtuous. He was selfish, greedy, and manipulative. Yet, in his own flawed way, he managed to outwit the Devil, not once but twice. There’s a kind of rebellious charm in that, a sense that even the worst of us can, for a moment, outsmart the darkness that seems inevitable. And yet his story is also a warning: cunning and trickery may win battles, but they don’t always win wars. In the end, Jack condemned himself to a fate worse than Hell—eternal wandering, never finding rest.
When we light jack-o’-lanterns today, we may not think of Stingy Jack’s lonely walk through the night, but in a way, we are keeping his story alive. Each crooked grin and jagged eye carved into a pumpkin is a reminder of the trickster who made a deal with the Devil and lost in the strangest way imaginable. Halloween is a night of stories, after all, and every glowing lantern is a whisper of the old ones, telling us to laugh, to fear, to celebrate, and to remember.
And perhaps that is why the jack-o’-lantern became the perfect symbol of Halloween. It embodies the mischief, the fear, the mystery, and the fun. It connects us back to ancient bonfires and ghost stories, to the people who huddled against the cold and darkness of winter with only the warmth of firelight and folklore. It reminds us that even in the darkest night, there is a flicker of light—sometimes playful, sometimes frightening, but always alive.
So tonight, when you pass a row of pumpkins glowing in the dark, remember Stingy Jack. Remember the Devil’s coin, the apple tree, the ember in the turnip. Remember that behind every lantern’s grin is the story of a man who tried to outwit Hell itself and ended up lighting a holiday for centuries to come. That is the power of stories—they take root in us, twist through time, and carve themselves into tradition. Jack’s crooked smile lives on, flickering against the October night, daring us to laugh at fear, even as it chills us.