There were many things John Winchester never told his oldest son. He never told him he was proud of him, even though he was immensely proud of everything Dean did, of the man he became, of the sacrifices and pain that he endured for the good of the world. He never told his son he loved him, even though he tried to show it even with his last act on this earth: selling his soul to save Dean's life.
John Winchester told his son practical things, things he needed to know to survive in this world, things that would keep him and Sam safe from the monsters and things that lurked in the dark. He told his son how to fight and how to kill and how to save people. He told him how to scam credit card companies and how to con his way into any situation; he told him how to pick up girls at a bar and how to leave them easily in the morning. He told him things a hunter needed to know, but he never told him everything. There were things that John could never say, words and memories that were carved into his heart that he could never voice; decisions he had made that weighed heavily on his soul. Impossible choices with harsh consequences that he kept hidden from everyone, even his only friend: his oldest son Dean.
Some three years after the fire that changed John's life forever, a choice was given to him. He had been consumed with sorrow and rage and sought only vengeance for Mary's death and for the lives of his children that were now ripped to shreds. He traveled the country with his boys, working easy cases in the beginning, all the while honing his skills and making contacts and learning all he could about the Yellow-Eyed Demon that stole his love. One night after a particularly crap day, John left little Sam and Dean at a motel in the care of a babysitter and went out to drown his pain in cheap whiskey.
Had he been a more experienced hunter, or maybe just a little more sober, John might have realized he had spent the last two hours telling his life story to a demon. The demon in question wasn't anyone of note, just a mid-level dealmaker wearing a 50 something used car salesman with a kind and compassionate face.
John downed his umpteenth shot of whiskey, upending the glass on the bar. "I would give anything to go back to that night and stop that bastard. Anything."
The Salesman smiled, this is what he'd been waiting to hear. This was what he lived for, finding the downtrodden sorry sacks of shit in this world and making them deals for their souls. But how fortunate that he had stumbled upon this man tonight. John Winchester... who could be more sad and desperate and willing to do anything? What a special deal he had in store for the hunter.
"My friend, what if I told you that you could stop him? That you could change everything and get your wife back?"
The hunter looked at him sideways and laughed, motioning to the bartender for another shot. "I'd say you're crazy." John slurred, "Or a demon." he turned and looked at the man full on.
The demon blinked and showed his black eyes, smiling at John. "Well it's your lucky day."
John stood up quickly, knocking over the bar stool, his hand reaching into his jacket.
The demon laughed "Woa cowboy, relax. I'm not gonna hurt you. And what are you reaching for? You gonna shoot me? All that's gonna do is kill Cliff here." He said, gesturing down at his borrowed body. "And I like Cliff, he's comfy."
"You evil son of a bitch." John spat, keeping his voice low, not wanting to draw attention to himself or the demon and get anyone hurt.
"John... just relax. Why don't you sit back down and have another drink, my treat, and we can just... continue our chat. No need for all the drama." Cliff patted the bar and waited.
John kept his eyes on the demon while he righted the bar stool and sat back down cautiously. The bartender filled John's glass again. "Leave the bottle sweetheart" Cliff said with a wink. She shrugged and walked away.
"What do you want?" John spoke through his teeth, suspicious and filled with hate.
"Why do you people always assume we want something? Can't we just be interested in the human condition? Maybe want to lend an ear for your suffering?" Cliff smirked, "You're right. That's bullshit."
"So talk or I'm out." John drank his whiskey and waited. He was tired and scared and ready for it all to be over, his whole life, everything. Maybe it was just the drunken haze he was looking through, but part of him wanted to hear the demon's deal, and would even consider it, if it meant he could see Mary again.
"I can go back and change everything for you. A snap of my fingers and Mary would be alive again, like nothing happened. It would be my pleasure." said Cliff, baiting the drunken Winchester.
"And what's in it for you? I get my wife and my life back and in what, ten years you come and take my soul to hell?" John poured himself another drink. He couldn't believe he was actually considering this. He should attack the demon with the flask of holy water in his jacket, knock him out and start the exorcism ritual. But he couldn't. He wanted to hear the deal. He wanted the deal.
"Aren't you smart John." Cliff smiled, eyes flipping back to human gray. "Those are usually the terms, yes. But I had another idea for you. Something special." He laughed at his own plan, watching John's eyes fill with anticipation. "I will pop back to that night and make it so Mary never even gets out of bed. You'll wake up from your chair in the living room and crawl into bed with your beautiful wife like you were supposed too. She'll live, you'll live, and none of this…" he waved his hand around the bar, "none of this life will have even happened. You'll be free and back on track."
"And…"
"Oh John, I like you. I do. I think you got a raw deal and I'm sorry about that." John gave a bitter little laugh. "It's true. I have feelings you know, all demons do."
"So what's the catch?" John put his glass down and turned so he was facing Cliff.
"Your boys. I'll give you your wife back but one of your boys has to die. Since I'm nice I'll even let you choose which one." Cliff stopped talking and sat back, letting the terms sink into John's booze addled mind.
"You're insane." John shook his head, shocked by the offer.
"Insane? No, but very serious. You choice John, one son for your wife. She'll live, you'll all be happy, the other boy will live a normal life, growing up with his mother and a father who's not hell-bent on killing himself for the sake of revenge."
"You want me to kill one of my boys?"
Cliff leaned forward and rested his hands on the bar casually. "No John, you're not killing anyone, it's a trade. And I'll make it so you don't even remember the one that goes. It'll be like he was never born. You cant miss what you never had. You'll simply wake up back in your old life, everyone safe and sound. And who knows, you and Mary were young, you can have a dozen more kids. This is an easy choice."
John wasn't sure why he couldn't bring himself to answer right away. There was no way he could ever give up his boys. They were all he had. But somewhere deep down in him he was considering it. Thinking honestly that it might be for the best. Hadn't he spent all this time praying and wishing and begging to go back to that night and set things right? Didn't he wake up every morning from dreams of Mary, alive and well with golden hair and perfect smile only to have reality crash down on top of him and hurl him back into the pit of despair that his life had become?
And what kind of a life was this for Sam or Dean? Dragged around the country, living out of the car and filthy motels; not knowing the love of a mother or having a home or a bed that was their own. Didn't they deserve better? If he took the deal, one of his boys would vanish, wiped from this horrible existence, but the other- the other boy could live. Really live a happy normal life. Yes, he was considering this for his own selfish reason of being with his wife again, but also for the boy who'd grow up and go to college and have a family of his own some day. Does the sacrifice of one child for the sake of the other make it ok?
John picked up the bottle of whiskey and drank straight from it.
He closed his eyes and imagined that night again. He felt the flames burning down from the ceiling, he felt the horror and grief and panic; he saw the look on little Dean's face when he woke up, hearing the screams. That was a horror that no child should ever have to see, and yet he did, and he stayed strong and carried his brother to safety. How could he choose? It was an impossible decision.
"I wouldn't remember any of this?" He asked suddenly.
Cliff smiled, "Not a thing."
John took another deep drink. He felt broken, defeated every day and here was his chance to be whole again.
"I know this seems like a hard decision John, but it's really quite simple." The demon put his hand on John's shoulder and patted. "But the offer won't last forever. What's it gonna be?"
John looked over at Cliff, his black eyes flashed back for a moment and John's senses returned. This was a demon, and you don't make deals with demons. There's always a catch, some trick that you don't catch on to until it's too late.
John stood up, a little unsteady on his feet and clasped the man's shoulder tightly. "Thanks for the offer, but I'm gonna have to pass. But I hope I see you again soon." He leaned closer and whispered in Cliff's ear, "Because when I do, I'm gonna send your ass back to hell."
Cliff laughed uncomfortably and looked up. "You're making the wrong choice here Johnny."
"We'll see." John said and made his way out of the bar back to the motel, picking up each of his boys and hugging them tightly.
John Winchester was a hard man; some would call him a bad father. But he gave everything for his sons. Sure he made many mistakes with them, he wasn't there for them all the times they needed him, but he did his best. John never told Dean about that night or the choice he made. Some days he would forget all about it himself. But each time he saw Dean hurt or struggling or covered in blood from a battle with some unearthly creature, he wondered if he'd made the right choice...