Drunk Jack

Jack was a drunk, that’s about the nicest thing you could say about him. At his best, he was merry and jovial, the sort of Falstaffian character we all love to be around in a pub. At his worst, he was deviant and destructive, the final destination all drunks inevitably make their way to. 

Yet, Jack’s reputation for drink extended into every surrounding shire. He was known, not just for his ability to put away pints, but for his craftiness. What he lacked in work ethic, he made up in craftiness. After all, all addicts will tell you, when it comes to scoring your next high, there is nothing you are not willing to do. 

Locals were warned. They knew that once Jack ran out of coin, he would turn to whoever was next to him for his next ale. His shiftiness was unmatched. In his youth, his charm and good looks were enough to lure people in. You would be having a good time with your new friend, and when it came time to settle up with the barkeep, you found an exorbitant tab and no Jack; however, once the drink took its effect on Jack’s body, his looks faded. Yet, that did not stop his mind from sharpening. He was quick. He was funny. He was manipulative. 

So, in his age, Jack turned to travelers and tourists, giving them a real taste of Ireland, and the story of the town drunkard traveled far and wide. Some people told the story warmly, the time they were conned by an old Irishman named Jack into paying his bill. Others, rightfully so, were more bitter at a barfly taking advantage of their goodwill. 

Needless to say, Jack’s reputation as a dreg of society spread far and wide. Names began to attach themselves to his surname: Stingy Jack, Drunk Jack, and Flaky Jack. 

Then, one fateful night, the story of Jack reached a particular bar patron. 

A handsome, well-dressed man stopped in to have a pint at a tavern where a few locals were swapping stories of the time Jack swindled them into picking up the check. Rather than being appalled, the traveler was impressed by the reputation this “Jack” had garnered. It appeared as though he was quite the silver-tongued devil, almost, some would say, enough to rival “the” silver-tongued devil. 

The man closed his tab, thanked the bartender, and then stepped outside into the sharp autumn air. The chill of winter was beginning to settle in, but the colors of fall littered the cobblestone pavement. 

There, just outside the tavern, the man lit his pipe and waited. 

Eventually, Jack came stumbling down the uneven path, in a familiar drunken stumble that is easy to recognize but hard to imitate. The well-dressed man grinned, emptied his pipe, and tucked it away into his coat. 

As Jack approached the entrance to the tavern, he noticed the man. At first, he saw a mark. The tailored clothes and top hat made the man look out of place in a town known for agriculture and community, just the sort of guy Jack could swindle into a drink or two. 

But before Jack could ask the man for a pint, the well-dressed met Jack’s gaze with an unmistakable grin. 

“Hello, Jack,” said the man in a raspy voice. 

Though he had never heard it before, it was the unmistakable voice of Lucifer. 

Fear shot through Jack. He always knew this day would come, but he never thought it would go so soon. Despite the fog of a night of drinking, Jack’s mind was as quick as ever. 

Before the devil could make Jack a bargain, the old lush thought up one of his own. 

“How ‘bout a pint, Satan? One for the road.”

It was true, thought the Great Deceiver, Jack was a charming soul. Just the kind of soul he’d love to own. 

“Sure. One for the road.” 

But as every drinker knows, one is never enough. Perhaps almost as famous as the story of Stingy Jack is the story of their night of drinking. 

As we all know, the Devil loves a challenge, and as the pint glasses mounted up, so to did their tab. Drink after drink, shot after shot, Jack and the Devil toasted the night away. 

Eventually, the night dissolved into the morning, and it was just the two men and the demon in the bar. It came time to close up. Naturally, Jack didn’t have a penny to his name and asked if Satan would pick up the tab. 

True to his name, thought the Devil, reaching into his purse to pay for the bill. 

“Now hang on a minute lad,” said Jack, “this here particular barkeep doesn’t believe you are who you say you are. He knows me, he’s seen me belly-up to the bar a many a night, and tell many a tall tale to a many a wayfarer, and I want him to account for everything that’s happened tonight. Is there anything you could do to prove your salt?” 

The Devil rapped his knuckles on the bar, weighing Jack’s request. Satan was impressed by the tactic. Jack was true to his reputation to the end. Even in the face of death and damnation, Jack did not falter. 

“Could you metamorphose yourself into something? Like, thirty pieces of silver?”

Again, the Devil weighed his options. He could just pay the tab and take Jack to Hades. But why pass up the chance to show off? It would, perhaps, push the poor bartender to make his peace with God, but it was just one soul.

So, the Devil acquiesced to Jack’s request and transformed himself into the thirty pieces of silver to pay the bartender. 

Jack seized the coins and placed them in his pocket, and there, surprisingly, in Jack’s pocket was the crucifix his mother had given him when he was a boy. The cross pinned the Devil to the wall, preventing him from morphing back into his human form.

If the Devil wished to escape, said Jack, then he would have to grant Jack ten more years on Earth. Then, Jack said he could collect his soul, and Jack’s debt would be paid.

Lucifer relented and granted Jack ten more years of nefarious living. After all, why do your work when you can have someone do it for you?

Ten years to the day, Jack bellied up to the bar, only to find the Devil himself waiting for him. This time he came in rags, dressed as an old sea dog. 

He was ragged and worn, but when Jack attempted to make his move on the sailor, he found the same Cheshire grin and evil eyes. Jack’s ten years were up.

“No more crosses, no more deception, Jack. It’s time to pay your tab.” 

But Jack was not done yet. He had at least one more trick in the bag. 

“Then how about a game? One...for the road.” 

The Devil was immediately intrigued. Games, after all, were his favorite past-time. Humans loved to risk their lives on winning. 

“Go on.”

“In the ten years since we last met, I’ve become the greatest drinker in the world. And I bet I can drink you under the table, this time.” 

The Devil grinned. No one could out drink him, and he agreed to Jack’s game. 

“You win, you get my soul for eternity, rapture, or not. I’m all yours. I win, you can never claim my soul. Deal?”

Jack asked for three pints and three shots of Irish whiskey, promising his seafaring friend would pay for the drinks. The barkeep relented and placed the spirits in front of the two men. 

“Now,” said Jack, “here’s the bargain. I bet you I can drink three pints before you take three shots. But, because I know how you operate, you can’t touch your glass until I’ve finished mine, and you can’t touch my glasses, and to make it fair and to show you there’s no chicanery, I can’t touch yours. Agreed?”

The Devil nodded. 

“Oh, and one more thing,” added Jack, “you got to give me a pint headstart? It’s only fair, right?”

The Devil thought for a moment and then nodded again. 

“Ready?”

Jack and the Devil took their positions, each poised to snatch the glass in front of them like sprinters at the starting line. 

In a slash, Jack snatched the first ale and chugged it in two huge gulps. The Devil was impressed. He really was the best drinker in the world, but no matter. As the thought slipped from Lucifer’s brain into the ethos, Jack slammed the empty pint glass on top of the shot glass. 

“See you around, pal!” exclaimed Jack picking up the other two pint glasses and heading to the other end of the bar. 

The Devil relented, laughing. The sound chilled Jack to his bones, after all, he had just won, right?

Jack looked back and the old sea dog was gone, never to be seen again. 

Yet, drink has a way of speeding the aging process. If it hadn’t been for the first bet, Jack would never have lasted ten years in the first place. This time around, Jack’s liver did not hold up, and Jack died as he lived, in drink. 

Yet, that is not where to story ends.

To his surprise, when Jack died, he found himself at the pearly gates, and not the gates of Hell; however, once he tried to enter the Kingdom of Heaven, St. Peter denied his entrance, rolling out a list of deceptions and malfeasances longer than even Jack had expected. He was drunk, after all, when he had committed the majority of those deeds.  

But bargaining is not part of the deal in Heaven. Just because you can craft a good defense in life, does not mean that you can wiggle your way through a loophole in death. And so, with no tricks left in his bag, Jack descended to Hell, where the Devil was waiting. 

But this time, the Prince of Hell was not welcoming. Satan reminded Jack of their agreement, he could never claim his soul. 

Laughing, Lucifer handed Jack a hollow turnip, and am ember from Hell. 

“Show them the path,” said the angel, “and enjoy the roads from Heaven to Hell.” 

And so, that’s where the old drunkard wanders, carrying the ember from Hell in the hollowed-out turnip, lighting the way to Heaven for souls, and the way to Hell. 

And some people say when the fog is dense, and the moon is dull, you can see Jack wandering from town to town carrying his demonic lantern. 

But maybe you’ve heard it a different way. Maybe Jack tricked the Devil into climbing up an apple tree. Maybe Jack was handed a radish instead of a turnip, or perhaps even a pumpkin, if pumpkins grow in your country. 

And perhaps, that’s why this story sounds so familiar to you, because this is the story of Jack of the Lantern, or, better known today as, “The Jack-o’-Lantern.”