Ol' Jack loved his whiskey, but nothing else. He was the meanest, weaseliest, two-faced scoundrel you ever did meet. And sharp, mind you; why, he tricked Satan himself not once, but twice. Devil'd been hoverin' over him for years, waiting to stoke his fires with this rotten soul. One autumn night, much like this one, in a tinker's tavern, the tentflap flew open and those sober enough to feel the steely chill on the back of their necks never missed Mass again. Ol' Jack was cornered. The damned asking Satan to at least pay his final tab, the Devil obliged and manifest himself as a silver coin. Being a tricksy bastard, Jack snatched the pence and tossed it in his bag of gold - stolen, no doubt - knowing the crosses on the other coins would trap ol' Lucipher and alllow Jack to run wild once more.
Left without paying his tab, too.
Jack - feeling mighty - made a deal to let the Devil go. "Promise to leave me be for ten years and I'll spill these coin in the sand right here." With not much in the way of options, the Devil agreed, but made sure to get one good scratch on the face when he bounded up from the ground after Jack spillled his bag. Satan's nails are long, sharp, and hot. The scar stayed with Jack all those ten years.
After a decade Jack's hair was getting a little grey, his back was getting a little weak, and his blade was getting a little slow. He still loved his whiskey, but the stories he'd pour out of that bottle were filled less with women and laughter and more with spectres and fear. Jack didn't know the day, but knew the season and the year. Satan waited until the first bitter cold night to remind Jack of the expiration of his reprieve. Never having been matched at wits before, Satan's interest in Jack was intense. He foolishly obliged again when Jack asked him to gather an apple from a nearby tree before heading toward Hell. Jack once again trapped the Devil, using speed with his knife he hadn't brought forth in years to plant four twig crosses in the ground around that apple tree. Satan was furious.
Before letting the Devil go, Jack made him agree to never, ever bother him again and keep him clear of Hell for eternity. Satan laughed, killing the apple tree instantly and turning all the fruit it yielded to stone, and agreed.
Jack never mended his ways. One night years later he crawled inside a bottle and died. When he arrived at the pearly gates there was much whispering. He was politely escorted away for his years of drunkenness and crime. With nowhere to go he visited the gates of Hell to inquire where he should be. Satan, always a man of his word, shunned the drunkard and ridiculed him. "You now want my fires? Never! For I am a man of my word and I delight in your fear. Be gone!" Jack pleaded that the way was dark and he needed a light. Satan cast him a coal from Hell's furnace, and Jack placed it in a gourd.
Jack will always wander between Heaven and Hell. On Hallow's eve, that one night every year when the plane of this world intersects with the fogs of the other, Jack will come to our streets, reminded of his living days. Put a fire in a gourd tonight and carve it a face to look like one of Satan's minions. If you don't, Jack may not be turned away. His fire - you can't see it - may light the way to your home. He has so sorely missed his earthly delights of rape and murder. And if any unknown creatures come and visit tonight, who may or may not be looking like that Jack, I advise you to oblige... with a bottle of whiskey.
"Happy" Hallow's eve.
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