"Crowley's more careful than I took him for; this thing's probably big enough for two people." Guy said to Dean, taking a small, embroidered cloth out of his pocket and wiping at his forehead. It was long past dusk, but the heat of early July pulled through. Dean, in the much simpler attire of a dress shirt and slacks, was boiling. He didn't know how Guy managed to stick himself in high-end suits day after day, no matter how grungy the outfits got. The man usually laughed off complaints of the heat; he said it was in his black blood, the tolerance. "My great-great grand daddy was brought to Virginia over a century ago…" and that's how you got him started. Dean got it, though. Clothes made the man, and it didn't matter how 'forward' their generation was, a black man was still a black man, after all.

He had went to Crowley's a week after bidding Sam and Jess a very long good-bye. Most of the jobs took him straight to the black market. "Anything for anyone at any time," was the motto there. Sometimes Dean would be tasked for making personal deliveries, occasionally starting a fight to keep his end of the deal up. The strangest things had passed from his hands to others; paintings, whiskey, narcotics, estranged heirlooms, even iced body parts, once – Dean had never asked about that one.

On the other end of the spectrum, the admittedly much bloodier part, there was the debt collecting.

Crowley, like Alastair, had once been a high-end worker for Lucifer. Crowley still kept the relations between his former-boss lukewarm, while Alastair had more or less fled into the Northern part of the burrow to run his own legion of street thugs, not long after Dean had gone from his grasp.

Crowley's break off obviously had a great deal more class, and he now spent his time doing more off-color trades than all of the merchants on Wall Street. The difference between them was that he would make sure a debt was paid in full.

Breaking some bones, cutting a few extremities, Dean had done much worse for way less, and counted himself lucky. They were about halfway done now, him and Guy, making sure that the hole they were digging was deep enough for their assignment – Phillip Wong, a middle-aged second gen Orient that couldn't pay his dues on time.

"Pretty quiet tonight, Dean." Guy said, reaching down to give Dean a boost out of the pit they had dug. "What's a matter, cat got your tongue?"

"More'n that," Dean mumbled as he righted himself, wiping stray bits of grave dirt on his thighs. "Help me dig up some of that underbrush over there." They moved back towards the trees. Crowley and his company often lent out some cars for the men to use, if needed. They were in one of the most isolated parts of the entire city, in Queens, of course. There was still a lot of green, a lack of skyscrapers, and even a few plots of unclaimed land that sat on uneven ground, still covered with the typical lining of trees that differentiated it from a park, and made it a forest, good and proper. Given a few years, most of it would be plowed and leveled, but if they ever discovered Wong's body – and probably another thirty after that – the evidence would be long gone, and Dean just as scarce. "It's just the day, I think." Dean said, accidentally hitting his shovel against a pile of rocks. "The nineteenth gets to me."

"Anniversary?" Guy guessed.

"Yeah." Dean finished spreading around the dirt and lit up, leaning on the edge of his shovel. "Something like that."

"That's too bad." Guy began kicking some brambles and stray leaves about, confusing the already overgrown, organic path. Wong would've gone into the Jamaica Bay if there hadn't been rumors of some guardsmen lurking about. It put a damper on their plans, so instead of trying to get money to buy potential witnesses off, they had just borrowed a car and driven away. "When's Crowley's next party?"

"Why? So I can distract myself? No such luck; he had one last week."

"That one was fun."

"Didn't see you there."

"Well most of the people don't see much of anything except snuff powder after a few hours." Dean hummed in the affirmative, trying not to clench up his fists. He watched Guy spread out more rough top soil, before going back over to Wong's body, wrapped up in a staunch blanket they found in the man's bachelor apartment. "Might as well get him down there," he said, bending over, rolling the corpse towards the hole. Dropping the shovel, Dean shoved the body down, until it disappeared into the gaping mouth in the earth. It was too dark to see much of anything, and if it wasn't for the solid thump! that echoed out, he wouldn't have known what happened to the body after all. His accomplice let out a pleased noise that made Dean's stomach ache. Rising to his feet, Guy reached into his trousers to pluck out a white wrapped cigarette of his own. Dean finished his, threw it down into the hole and watched the small orange illumination flare in the ground for a scant moment. "Ever try it?"

"What?"

"That snuff stuff; not the tobacco, the other thing." Dean closed his eyes for a while, stuck a hand into his pocket. "Not as powder," he answered into the fissure. Guy seemed pleased at that, because he nodded his head and turned to face Dean with a flourish.

"Well, then, any last words?" Dean stared straight on at his temporary partner; the only parts he could pick out in the darkness were his smiling teeth, the whites of his eyes, and the stub of a still burning stick in his lips. He stretched his arm out from its resting place, letting it still at his hip.

"Yeah," there was a subtle click by Dean's side. "Crowley gives his regards; says, 'I'll see you in Hell,'"

"Wh-"

A quick bang from the gun; a flash of white hot light, and Guy was pushed back with not so much of a gasp; his body crumpling and falling down into the grave of Philip Wong – a grave probably big enough for two people - with only the flickering glow of his cigarette to light the way.

Dean stilled for a thoughtless moment, wondering if anyone was near enough to hear, but nothing and no one came by, and he gripped at his shovel and finished up, trying to will away anything but the sound of dirt being put back in the ground. Dean rarely took a partner on jobs, even with the array of foreign assignments he was given; this one counted as a double hitter: The first was for David, and the second was for a fellow employee that tended to get a little too trigger happy; Crowley said that Guy had screwed up 'negotiations' in the past, not intimidating the target of choice into spitting out information or a safe combination, but instead blowing their brains out. It was a crime against proper order, Crowley had argued, ruining his reputation and leaving holes in his balancing book. For all of Guy's irritating mannerisms, Dean thought to himself if the man would've had anyone watching over his grave, if he could have been allowed a proper funeral; if he had kids somewhere, left wondering where their Dad went. It could have been a twisted form of commiseration, or it could have been the date, Dean wasn't sure.

John Winchester had died on July 19th, 1924, somewhere on the north end of Jersey.

Dean had always said 'murdered', but not in a maliciously planned way. Probably. No one knew exactly where he died, because on Monday he had been getting a drink to celebrate a recent drug ring bust that went considerably nice, and that Wednesday his body was on the shore of the beach, seaweed all he had for clothes and gulls pecking about his ears. No gun-shot wounds or knife gashes, no traces of cyanide or an overdose of morphine, and no cement shoes. The bruises in the mid-section revealed a crushed ribcage. From what could be determined, John Winchester was killed by a drunken idiot who rammed into him at sixty miles an hour and dumped the evidence into the sea.

The police force John had temporarily wriggled into had paid for a cheap pine casket and a basket of lilies. Sam was seventeen; he picked out a plot of land. Dean, twenty-one, purchased the tombstone.

The service was unimportant. Sam and Dean dressed in their best black suits, their best black shoes, and long overcoats – it was hot, but they weighed themselves down with layers, just like John had always done – it was a mournful flare and an homage to their Father. Some of the attendees had whispered things like, John always wore an extra jacket; figures that his sons take after him. The two brothers carried the coffin with another quartet of police officers through muddy slush; remains from a storm that had probably brought John's body to shore in the first place. They adjusted their eyes by ticks as the coffin was lowered into the ground.

People shook their hands and wrote down their addresses and gave them a dollar or two to help with the cost. Everyone left the graveyard thinking what two young orphans would manage to do with themselves, miles from home and nowhere to go?

Sam and Dean pondered that, also. They stuck by the site, waiting for the grave diggers to come by. They both still half-expected John to show up – it was his own funeral, for Christ's sake.

"He could be funny like that, if he wanted to be," Dean had said on the subject, staring down at the pit.

"This isn't funny at all." Sam sniffed, his nose was red.

"It will be when he gets here." Dean insisted.

But John couldn't be bothered to show up, or even send them a postcard of where he'd gone off to. Dean figured Mexico, because all respectable villains went to Mexico and it was about time they left the country to chase them down. Sam thought that was ridiculous, that John wouldn't just up and leave without telling them, and there were plenty of demons and monsters and ghosts lurking around in the States still, anyway.

It never occurred to them that their Dad was just dead. Not for a long while. Even still, Dean woke some nights with the wispy vision of his Father, chasing down the cruelties of men in faraway lands. But it never really lasted. Of course John was dead, after the waves of stupid grief had passed and they could think right. They were left with more of a legacy than memories of their Father; John had spent the better part of twenty years going from town to city as a private detective, farmhand, hired muscle, police officer; an entity all his own, working below the law or in the shadows of it, ensnaring anyone from a pick pocket to a murderer. It was an indirect method of vengeance. To destroy the thing that killed his wife.

Dean remembered how they would trek through what felt like every square inch of land east of the Mississippi. Taking rides from strangers or hoping on storage cars and trains, even going on foot. Miles and miles crisscrossed all over, never once returning to Lawrence, never really returning anywhere they had been. At the time, there had appeared to be no reason. John was either trying to protect his children from his motives or thought them too simple to be of any use. He trained them at least, let them fight like boys and correct them till they went at it like men. He made sure their aim was exceptional, but he never once told him where he went after his work shifts had long ended. Nor why they often had to skip town in the middle of the night.

Eventually they figured it out themselves; that Mary's killers weren't faceless addicts like the saved newspaper clippings had alleged. John had names and plans that died with him, and he and Sam had been left ignorant, on a cold trail with nothing to go on. The moment after the funeral they were packing their bags – Sam already graduated from the twelfth grade – and they vanished, one of the few tricks their father had actually indulged to teach them.

They moved to a tenement in Brooklyn. It had rats and walls about as thick as rice paper, but they had spent weeks sleeping in sacks out in the sprawling forests of Virginia, they had spent half their lives being hungry, and Dean had already done plenty of unspeakable things for money when John had been too long between jobs and their savings were spent. The Winchesters were not strangers to hardship, though when an actual family relation – a teenage Adam Milligan – encountered them, it was a relief. Looking back Dean wasn't quite sure that the whole thing hadn't been a set up, but work was work.

Like most people being introduced to the mob, it wasn't ever said outright. Adam described his tasks as 'a little of this, a little of that,' and to most folks it would be odd, but acceptable. Sam and Dean already knew what this and that consisted of, though. They knew what they were getting into, possibly for the forseeable future, too. But their father was dead and gone, and Dean had no further instruction but the usual mantra of, 'Take care of Sam', and not starving seemed to be the easiest way to do that.

Adam was a lackey of Lucifer, and it was four months of working through the loosely tied boss Alastair – four months of hellish torture – before he and Sam got noticed by the Devil of Brooklyn himself. Everything seemed easier after that. And a few years later, Sam was married to a nice girl, living out in Venice, and soon enough Dean would be out there, too.

And that would be it.

Two, three more years. It was hardly a challenge, he persuaded himself.

Every day, he persuaded himself.

If that didn't work there was always something to grab. Cocaine had worked after John, and he kept vials around as a reminder after that, but it didn't feel good anymore. There was too much to feel, and no one to take him home and scream at him for being a stupid, selfish bastard; no one to make him promise not to do that again, so he stopped, for a brother that he only saw in bi-weekly letters.

The last of the dirt had been packed tight back into its original spot, and Dean grasped his and Guy's shovels, leaning his arm and body weight on them. He had taken to carrying a flask with him, nowadays, and he took it from a pocket, eyeballing the half of whatever was left.

"Wonder what you're up to now, Sammy." Dean said very quietly to himself, as if in the stagnant weeks he hadn't spent in a haze he had thought of anything else at all.

He wondered if the city was going to break him again, like back when he had first started. He felt exposed and fragile constantly; a blip of distress signals emanating from every pore, every word, every desperate reach for a distraction, a bottled emotion. He didn't think he was strong enough to survive this.

Or that there was anything left to him that was even worth ruining.

In one of the darkest and most isolated parts of the city, Dean Winchester said "Cheers," and emptied the flask down his throat.

xxxx

A/N: Now, Winchester Angst is the easiest thing in this fandom. So, a quick note on two things. Remember that this is a Historical fanfiction, and I try to keep things close to fact – this means referencing that African Americans and many other races were considered second class at the time. I'm certainly not advocating that was the right thing to do. Dean's own opinions on black people is indifferent; he's not racist, probably because he's been to the South and seen plenty of hate crimes, so most of his commentary is more of what the average Caucasian would think of Guy (Who is another reference to 'Season Seven, Time for a Wedding!') Moreover; the ethnic prejudice that holds dominance in this story is more centered on Russians and Italians not caring for one another. Secondly, Cocaine had been mentioned previously, and yes, Dean is a habitual user; it's not unlikely that he used drugs in the actual show, but due to network restrictions, the Supernatural writing team stuck to just borderline alcoholism. At this point, Dean mostly turns to the substance when he feels depressed, so the first time he tried it would likely have been after John's death. He stopped using it between chapters 8 and 9, for his brother. If you have any other comments about issues brought up in this chapter, feel free to leave it in a comment.