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In the late half of Season 9, I decided to do something I'd never done: participate in a Supernatural Fan Fiction contest. I resolved not to do any slash but instead write up a big budget, movie style, possible "finale" to the show which tied up loose ends.  I chose it as my Auld Lang Syne feature article not only because it was a lot of fun to write (and had some great artwork by neigeausoleil) but also because it's somewhat humorous to look back two seasons later to see what I got wrong about the show's future plots... and what I ended up getting right.


Originally Published: July 22, 2014

Editor's Note: For the first time ever, The Winchester Family Business is very excited to present to you a complete work of fan fiction. Written by our very own Nate Winchester, this story follows Sam and Dean on one of the largest, riskiest adventures of their lives. Nate’s official story summary reads:

“Frustrated by too many losses, the brothers decide they need one decisive win, and take the fight straight to Hell.”

This story is classified as “General Fiction”, meaning there are no pairings or ships, and it strictly adheres to the canon presented on the Show. It is rated “R” for violence (no more than you would imagine from the Show) and graphic depictions of disturbing images (this is Supernatural and Hell after all, but again, nothing too far from Show standards). Nate wrote this mid-season 9, so consider that it takes place roughly where we are right now on the #WFBRewatch (i.e. sometime after "First Born"; maybe even after "Blade Runners", but before the season's finale episodes). There are no season 10 spoilers. We will be running installments of the story twice each week for the next four weeks (with the possible exception of next week because of breaking news from ComicCon). Most likely, you will find it on Tuesdays and Fridays.

I love this story. In my opinion, it just keeps getting better and better the deeper you get into it. I have read it many times, yet tears still stream down my face during one of the final scenes. The greatest reward fan fiction writers receive is feedback from their readers, so please let Nate know what you think of his story. I hope you like it as much as I do.

-          Nightsky

Author's Note: A bit of backstory first.  Those uninterested can skip down to the title card if they want to get right to the story.

Many months ago, fellow fan and writer here Bookdal alerted me to the J2 Big-Bang fan fic challenge.  Now normally I wouldn't pay much attention to it.  However...

As you might have noticed, I have not been a big fan of season 9, partly because of it's continued despoliation of canon.  Of course there's one reply that is ever waiting to be cried, always hovering in the back of your mind whenever you criticize something: "you think you can do better?"

Well that challenge can be fair enough, so given that I enjoy writing for fun, I decided to take up the Big Bang fanfic challenge.  I wanted to prove that canon should not only be respected, but can be used to tell a better story.  (I even jokingly posted the story's "ship" (relationship pairing) as "SPN/canon", though I don't know if anyone got the joke.)

Now because I'm a heartless monster who delights in the suffering of others, I recruited fellow writer Nightsky to be my beta reader & editor for this.  She accepted because ... well, actually I don't know why she agreed to do this. I think she might be a little crazy!  At any rate, she thought it was good and would fill a perfect niche for passing the long "Hellatus" with The Winchester Family Business.

We're breaking this up into a multi-part story that will be released over the next few weeks.  I hope you enjoy.

P.S. I like to think that if we were to ever get a big-budget movie for the show, this is what we would get.

 - Nate

The woods had a certain... majestic quality about them, helped no less by their infinite nature.  Sam and Dean Winchester crouched by a tall rock formation, each checking the contents of their army duffel bags.  Both had a metal, gasoline can holding a gallon of holy water and two of the “demon grenades” Kevin Tran had built for them so long ago.  Around their torsos they wore a bandoleer holding fifty shotgun shells sparkling white with the rock salt inside them.  Around their waists each wore a belt holding another twenty-five salt shells.

            Dean broke open his trusty, Baikal sawed-off shotgun and double-checked that it was loaded before he made sure the magazine on his forty-five Colt MK IV was similarly full.  “You still got the map and compass, Sammy?”

            Sam nodded as he pulled out four salt shells from his jacket pocket and loaded them into his twelve gauge Ithaca shotgun before stuffing it into his duffel bag.  “You got the First?”

            Dean reached behind and patted the First Blade strapped sideways on the back of his belt.  “You got the knife?”

            Sam patted the sheath that was strapped to his right thigh, Ruby’s knife resting within it.  He pulled out a bundle crudely wrapped in newspaper and said, “I got you a gift.”

            “Why?” Dean asked as he accepted it.

            “Days like this…”  Sam searched for what he was trying to say.  “A person better say everything he needs to.”

            Dean held up his hand and started to speak but Sam interrupted him.

            “Yeah I know.  Figured this gift would be less ‘chick-flick-ee’ than actually talking.”

            Dean tore open the wrapping.  Inside he found a golden, circular amulet with a Celtic knot design on the interior and the word ‘BROTHER’ inscribed on it.  He held it up with a questioning look.

            “It represents eternity and how we’ll always be brothers.  It’s good luck and…”  Sam stopped and shrugged his huge shoulders.

            Dean chuckled in an attempt to hide his deep appreciation for the amulet as he donned it.  “Hey Sammy, got a gift for you too.”  He held up a bottle of beer.

            Sam took it, cracked it open, and took a long drink while Dean took out a spray can, shook it a few times, then painted a bright, florescent-orange X on a tree.

            “Where’s yours?” Sam asked when his brother remained dry.

            “Had to give it away,” Dean said with that tone Sam knew meant a story he had to hear later.  Sam reached into the front mini pocket on his jeans and pulled out a shiny, mechanical pocket watch.  It had been made in the fifties, but was still nearly brand new having crossed the centuries in their grandfather’s hand.  He opened it up and checked the time.

            “Well?” asked Dean.

            “Time to go,” Sam said, closing the watch and stuffing it back into his pants.  “Hey, Dean?”


            “Good luck.”

            “You too, Sammy.”

            Sam finished his beer and tossed the bottle aside.  They zipped up their bags and shouldered them.  Dean stepped onto one of the smaller boulders at the bottom of the pile and, with Sam’s help, pushed aside a large rock, revealing the dark gap behind it.  From it spilled out a wind so foul it felt like their very souls recoiled.

            “Let’s go, bitch,” Dean said as he put on a pair of black, horn rimmed glasses that bore signs of having been scorched by fire.

            “After you, jerk,” Sam said as he donned his own pair of safety goggles that had been similarly toasted by holy fire.

            They entered the hole and though their feet never left the ground, both of their stomachs felt like they were tumbling end over end as they passed from Purgatory – into the shallows of Hell.

            They emerged from a forgotten cranny at the end of a hall.  Around them were walls and columns built of stone that looked older than the Earth itself.  A red light bathed everything in a fiery glow.  Beyond the hall, they could hear the indistinct screams and cries of hopeless souls.

            Dean glanced around to make sure the place was empty then nodded to Sam.

            The younger brother pulled a folded piece of parchment and a cheap directional compass out of his pocket.  Although the parchment was blank at first, lines quickly began appearing and spreading out over the square, until a diagram off the hall they were in was displayed, with attached rooms and branching paths.

            “Which way?” asked Dean.

            Sam looked at the compass.  The red end of the needle was pointing ahead, but slightly to their left.  “There.”

            Sam led the way down the indicated hall, a small flashlight in his hand so he could see the map and compass.  For a place of eternal flames, there were a lot of shadows and darkness around, which was helpful since occasionally he had to signal his brother to duck behind a crevice or to take cover to avoid being detected by demons and creatures of darkness.  The demons they passed were either in bodies or vaguely human forms of billowing black smoke, as if the strange gravity of Hell kept them from flying like clouds.

            “Shouldn’t there be... more?” asked Dean after only two demons and one hound had passed them.

            “Maybe we’re in the wrong zip code,” Sam replied as he pulled out the map and checked it again.  “They could all be wreaking havoc on earth.”

            “Maybe we’ve wiped out that many of the sons of bitches,” Dean said with a touch of prideful glee in his voice.

            Sam stopped.  The path curved to the left, but on their right, there was a huge gap in the wall.  They inched forward and looked out.  It took a moment for them to comprehend the vast gulf they were seeing.  It stretched for miles and plunged down beyond the sight of their eyes.  The cries and howls of tortured souls echoed up unceasingly from its black maw. 

            “Maybe not,” said Sam.

            “Think what we’re looking for is down there?”

            “You trust the express route?”

            Dean shook his head no.

            Sam looked at the compass.  Its red end pointed at the hole.  “Then we’ll have to keep looking for another way down.”

            They stepped back from the edge and resumed their walk.  After forty paces, Sam found a set of narrow stairs and led the way down.  The passage was so cramped they had to duck to avoid hitting their heads; causing both to grumble under their breaths as they went down one flight of stairs then another and another.  Sam reached a landing with a square doorframe that wasn’t as misshapen or foreboding as the previous ones they had passed.  Cries of torture and pleas for mercy drifted from it and he waivered a moment wondering whether they should help or not.  He checked the map and compass and neither pointed to it.  Trying to ignore his instinct to help, Sam turned away… and froze up.  Less than a yard from him was a daeva.

            With his holy glasses Sam could make out its form.  The creature was shaped like a human but smoke and black bugs were spilling off it as if it was perpetually melting.  Black claws glistened from the ends of scaly, bony hands – its only notable feature aside from the numerous teeth that gnashed together within a featureless head.

            The daeva lunged first, knocking Sam through the doorway behind him.  Sam felt his flashlight, the map and the compass go flying out of his hands as he struggled to keep the creature’s claws and teeth from tearing him apart.  He needed to grab Ruby’s knife but to let go of the daeva for even a second would be fatal.  Its putrid breath filled his nostrils as it leaned forward, trying to bite his face off.

            Suddenly the daeva stopped.  Its body arched forward as its head snapped with a blood curdling scream.  Flies, beetles, and other bugs made of smoke poured out onto Sam from a fresh, gaping wound that extended from its back through to its chest.

            Dean withdrew the First Blade from the creature and pushed it off his brother.  “That felt good,” he said with a creepy expression.

            “Now’s not the time,” Sam said as he furiously swatted the bugs off him.  He got to his feet and while it looked like all the insects had fallen or evaporated from him, Sam wasn’t sure his skin wouldn’t have that creeping sensation for the rest of his life.  “Where’s the map?”

            “Not the issue,” said Dean.

            Sam turned around to see where his brother was looking.  The daeva had knocked them through the doorway into a circular room.  The walls of the room were lined with jail cell after jail cell, each one a hand’s width apart from the next, all around the entire room.  Above the first row of cells was another ring of cells, then another and another, up to six total levels before ending at the ceiling.  Each cell was so small that its captive was forced to stand.  The ancient stone bars themselves were close enough that only those with the thinnest arms could even reach out past their wrists.  In the middle of the room was a large square table made of wood, with something writhing on it that they couldn’t quite see.  Beside it was a smaller table with numerous torture instruments of every era and make.  A tall, thin demon that looked like a man, and every bit the part of a classic mad scientist with his glasses and lab coat, stood beside it in a bloody apron and gloves.  Closer to the door they had just come through were two other demons with bodies of smoke, advancing on the Winchesters.

            “Come on, plenty more where that came from,” Dean said, brandishing the First Blade with glee.

            Sam faced the demon on their left, raising his fist in a brawling stance.  The large demonic guard charged and Sam stepped back, placing his hand on Ruby’s dagger.  He withdrew it at the last moment, driving its point into the bottom of the demon’s skull before it realized what had happened.  The demon’s body burned away, the consuming embers flowing out from the fatal wound Sam delivered.

            Looking over his shoulder, he saw Dean slicing the other demon apart a piece at a time, even as it tried to get away from him.  Sam was about to shout a warning but it was too late.  He watched helplessly as a small, shiny projectile flew through the air, heading straight for Dean’s head.  Luckily Dean raised his arm for another blow, causing the doctor’s scalpel to hit it instead, but not hard enough to pierce the leather jacket he always wore.  Sam dropped his duffel bag, pulled out his shotgun and fired on the doctor with a round of rocksalt, knocking the demon back.

            “Dean, finish it!” Sam shouted as he jumped over a waist high divider.

            Dean, sighing loud enough for Sam to still hear it over the ruckus, thrust the First Blade into the center of the fleeing guard’s mass.

            Meanwhile the doctor was trying to get to his feet but Sam’s long legs crossed the distance too quickly, and he slammed Ruby’s knife into its back.

            “Wonder why the guards didn’t get their own meatsuits?” Dean said as he sheathed his weapon.

            “Doesn’t matter,” Sam said, waiting for the lights of the dying demon to leave the doctor’s eyes.  “We don’t have time to answer every question today.”

            “Not even for an old friend?”

            Both Winchesters looked around, scanning the room for the source of the voice.  The first thing they saw was a waist high divider that turned out to be storage for many larger torture devices that wouldn’t fit on the smaller table.  Three such storage cabinets were spread equidistant around the room, dividing the torturing center from the cages in the walls.  The occupants of said cages had withdrawn from the doors and fallen silent, fearful of the invading brothers.  Finally they looked at the table in the center of the room and saw someone they hadn’t seen for many years.

            Sam couldn’t tell if his brother’s face was an expression of pity or smug delight at the person strapped to the table.  Dean’s tone of voice also seemed to reflect a mix of emotions as he said, “Hello, Bela.”

            “Hi, darling.  Doesn’t the nerd look just suit you.”  The thief was laying there naked, gaping wounds in her side and legs with a strange hybrid of smoke and blood pouring out of them.

            “Can’t say the demon look has done you any favors,” said Dean.

            “Being tortured for centuries will do that to a person.”

            Sam walked over and undid one of the straps on her ankle.

            “What are you doing?” asked his brother.

            “Dude, we can’t leave her here.”

            “Sure we can!”

            “Come now, honey,” said Bela.  “Do what you want with me before letting me go if you want.  We never did get that angry sex.”

            “Shut up,” said Dean.  “Sam, she’s practically one of them.”

            “But not yet.  What if someone had freed you while you were in here?”

            His brother wasn’t happy, but knew Sam was right, so they soon had Bela out of the restraints and on her feet.

            The Winchesters then went back to where they had fallen during the fight with the daeva and guards.  Sam put his gun back in his pack and re-shouldered his bag while Dean pulled his mini flashlight out of his jacket pocket. 

            “What are the two of you doing?” asked Bela as they searched the crevices of the room.

            “Not your concern,” said Dean.  “And put some clothes on.”

            With the light’s help, he and Sam located the flashlight, map, and compass Sam had lost.  Gathered up, they turned to see Bela standing there in a sleek black evening gown.

            “Sorry,” she said.  “Here the clothes are what we think of and for some reason I can’t help but think of this certain party...”

            “Lovely.  Now do your own thing.  We’re busy,” Dean snapped as Sam reoriented themselves to the map and led the way out of the room and back down the stairs.

            “What a fascinating map and compass,” Bela said, following them.  “Wherever did you get it?”


“Here you go, Moose,” said the sharply dressed man handing a folded piece of paper to Sam.  “And this,” he said, holding up an envelope, “will be properly filed in case anyone ever needs to try again.”

            “What the hell, Crowley?  This is blank.” said Sam.

            “Of course it’s blank.  Hell is not some simple, Euclidean place that obeys the laws of physics,” said Crowley.  “It is infinite.  Ever changing.  Obeying the laws of ‘metaphysics.’”

            “Long way to go to make a joke,” Dean said, glaring at the former king.

            “It’s not a joke.  You can’t make a simple map.  When the winds of Hell blow on that paper, the map will be visible and it will change as Hell does.  Make sure you leave it folded unless you need more.  Then unfold just what you need.  Oh.”  Crowley reached into the pocket of his fancy coat and brought out a small rectangle about the size of his palm.  “You’ll also need this.”

            Dean took the object.  In a circle on the rectangle, a thick needle with one end painted red slowly spun around without end.  “A boy scout compass?”

            “Enchanted.  The red end points towards the cage.  The white will point the way out.”

            “You sure you’re going to be alright?” asked Sam.

            Crowley shrugged.  “The Bunker will still be here if you two make it back.”

            “Mr. Crowley?”

            The three of them turned to face a young woman in glasses and business clothes.

            “What is it, kid?”

            “Charlie says that Dorothy isn’t getting in less danger the longer she has to wait.”

            “Finishing up, I’ll be there in a moment.”  Once she left, Crowley turned to the brothers and said, “Well, duty calls.  These new Men of Letters aren’t teaching themselves after all.”

            “Seems you caused a lot of trouble last time you were in a clerical position,” said Dean.

            “True, but it’s what I’m good at.”  Crowley stopped a moment and let the words sink in, like he did every time Dean reminded him.  “A lot of years, a lot of wrongs to right.  I only hope the time I’ve been given as a man – thanks to you, Sam – is enough to do so.  Good luck, boys.”

            They watched him walk away in the white suit he now always wore.

            “You sure we should have finished curing him?” asked Dean.

            “Like you said, we lost sight of the family business.  First step of saving people, is to make them people.”

            “Doesn’t mean he won’t betray us all.”

            “That’s why we told Krissy and her friends to act as Men of Letters recruits.  They’ll keep an eye on him.  We have to start letting go of the future, Dean.”

            “Yeah you’re right.  That Aiden always struck me as a bookworm anyway.”

            “Speaking of, you going to say anything to Charlie?” asked Sam.

            Dean shook his head.  “She’s got her own worries in Oz.  We can tell her all about it when we get back.”

            “And if we don’t get back?” asked Sam.

            “Then Crowley can tell her.”


# YellowEyedSam 2016-01-09 11:29
Hey, whilst the plot didn't keep me going I just wanted to say it was nicely written and I hope I see more of your fics :D