Jack And The Devil: Boo Who?

It’s been cold, wet and raining for days here in Pittsburgh, but perfect weather for Hallowe’en and soul-watching. So, for your amusement and edification here is a little story I wrote back 1993 that was published as part of my Visual Fiction™ series in The Pittsburgh Tribune-Review:

JACK AND THE DEVIL: Illuminating a Hallowe’en Legend

 Each year, as we search for the perfect pumpkin to adorn our windows and porches for the scariest night of the year, somewhere in ancient memory, the spirit of the original Jack O ‘Lantern is probably sporting the huge grin we’ve come to emulate in our annual feats of sculpture. Why? Because he’s probably remembering how it all began…

Long ago in Ireland, large rutabagas, turnips, and potatoes—instead of pumpkins (which were not available) were hollowed out carved into hideous faces and illuminated with candles to be used at Hallowe’en celebrations; all because of Jack.

 No one knows his last name, though as legend has it, Jack was well known to his village for his penny-pinching ways as well as for his drunkenness. One evening, at a local pub, the Devil appeared to claim his soul. Bolstered by a few spirits of his own, Jack cunningly persuaded the Devil to join him for just one more drink before their journey. In order to pay for his drink, the Devil turned himself into a silver sixpence, which Jack immediately snatched and put into his wallet. Now the wallet was held together by a clasp which was shaped like a cross, preventing the Devil from escaping. Triumphantly, Jack promised to free the Devil on the condition that the Evil One leave him in peace for yet another year. Reluctantly, the Devil agreed, thinking that a year in eternity was but a blink of his burning yellow eyes.

 Twelve months later, Jack was still reluctant to part with his soul, and invented yet another practical joke on the Devil. Unbeknownst to Jack, the Devil had been trailing him in the form of a huge black cat. On the night before the year’s end, Jack was heading home after an evening at the pub. Sensing someone or something behind him, he swiveled around to face the most hideous pair of cat’s eyes he’d ever seen. Under the unnerving gaze of those huge yellow orbs, Jack suddenly knew who the cat really was and contrived to chase it up a tree. This time, Jack made the Devil promise never to pursue him again, if he wished to be released from the tree.


And so the years passed, as Jack devised ever more clever ways to outwit the Devil.

Finally, Jack’s poor body wore out. But because of his ill-worn immortality, Jack could not die. He was barred from Heaven on account of his numerous transgressions, and he was banished from Hell for his devilish pranks. In desperation, Jack called on the Devil and begged him for a live coal to light his way out of that twilight place between Heaven and Hell.

 Feeling an uncharacteristic tweak of pity mixed with a grudging admiration for Jack’s fighting spirit, the Devil granted his wish. Jack put the glowing coal onto the turnip, which he had been chewing, and forever after is condemned to walk the Earth with his ‘lantern’ lighting the way to Judgement Day…

 Story & Illustration © 1993 Ilene Winn-Lederer

Originally published in October, 1993 as Visual Fiction, Focus Magazine, Pittsburgh Tribune-Review


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One Response to “Jack And The Devil: Boo Who?”

  1. Kiaran Obrien Says:

    Hi Ilene, Wonderful! Thanks, Kiaran


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