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The Story of Stingy Jack

Writer's picture: Paula WesselmannPaula Wesselmann

I love October and the wonderful stories that stimulate our imagination. One of my favorites comes from Ireland, Stingy Jack O’Lantern, also known as Jack the Smith, Drunk Jack, Flaky Jack or Jack-o’-lantern. As the story goes, during the 1800’s in Ireland, there lived a drunkard, despicable deceiver, and manipulator known as Stingy Jack. One night, Satan overheard of Jack’s evil deeds and persuasive talents. Not believing the rumors, the devil went to find Jack and check out his vile reputation.


Typical of Jack, he was drunk and wandering about in the night. While going home, he was surprised to see a body across his path. When Jack realized it was the devil himself, he made a last request before going to hell. Satan agreed to his request of one last drink at the local pub. Since Jack didn’t carry money, he asked Satan to pay the tab by turning himself into a silver coin. Intrigued Satan agreed, and Jack placed the coin in his pocket with his crucifix. Since Satan could not escape his form with the crucifix present, he had to agree to Jack’s demand. In exchange for his freedom, he had to spare Jack’s soul for ten years.  


As the story goes, ten years later, Jack tricked the devil again, and the devil promised never to take his soul to hell. Eventually Jack’s drinking took his life. Jack’s soul intended to enter heaven through the gates of St. Peter, but his sinful lifestyle, deceitfulness and drinking, sent him down to the gates of hell where he begged for admission into the underworld. Since Satan could not take his soul, poor Jack was doomed to roam the world between the planes of good and evil, with only an ember inside a hollowed turnip (a large rutabaga) to light his way. 


Years ago, when I was in Ireland during Halloween, many of the people there believed that the “Jack-o-lantern” was derived from Stingy Jack. In the past more than today, when children didn’t have all the technical devices to distract them, families told stories to teach their children life lessons and to keep them safe. I grew up with parents that were story tellers, and as we sat around the dinner table or before the fireplace, I would live my parent’s stories of danger, love, faith, and adventure. Their stories became mine and when I needed their wisdom when they weren’t present, I remembered their mistakes and how they survived them.


When I became a teacher and found myself deep in world history, my travels as a Pan Am stewardess brought to life warring countries, exotic places, and the lands of different cultures and beliefs. My stories opened the minds of my children and they lived the experiences and valuable lessons that I had learned. When I decided to write Pumpkins To The Rescue, and introduce my classes to three endearing pumpkins, Pete, Charlie, and Meredith, those beautiful orange characters became a hands on tool that brought adventure, comfort, and a best friend forever to those who chose to believe in their magic. I am hopeful that over the months ahead I will find the right publisher to help make Pete, Charlie, and Meredith a Halloween tradition that will encourage the kindness, courage, and curtesy they wish to share.


I wish you all a fun filled October with all the magic of past stories that trigger our imagination and keep us smiling, questioning, and sharing old traditions that delighted us as children. May we never be too old to not share in the freedom of a child’s imagination. 


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©2023 by Paula Wesselmann. Proudly created with Love by Liebe PR.

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