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It was 1984, barely a year after the fire that stole Mary and shattered everything John Winchester thought he knew about the world.
He'd been scraping by on odd jobs—mechanic gigs, bar brawls for cash—while diving headfirst into the hunter life.
Books on lore, salt rounds, and a growing arsenal funded by maxed-out credit cards. But the road was hungry, and vengeance didn't pay the bill on crappy motel rooms. Didn't pay for diapers. That's when he met Eddie Malone in a dingy Kansas City pool hall, a guy with mob ties who mistook John's haunted stare for the look of a man who'd kill for the right price. Well, maybe it wasn't so much of a mistake.
Eddie slid a manila envelope under and across the table, spilling cigarette ash onto the felt.
"Easy job, Winchester. Some lowlife sicko named Harlan Crowe owes my boss big. He's holed up in a cabin outside Topeka. Make him disappear, and there's five grand in it for you. Half now, half when it's done."
John eyed the photo inside: Crowe, mid-40s, gaunt face, beady eyes like black pits. The details screamed "normal" hit—gambling debt, skipped town. But something nagged at him.
Crowe's victims in the file weren't just dead; they were mutilated, hearts ripped out. John had read about that in one of Bobby Singer's dusty tomes.
Wendigo? Skinwalker? Even if he wasn't this creep was still a monster, if it was a monster, it was going down.
Might as well get paid.
He took the advance, bought a new shotgun and some silver knives with it—resources he couldn't afford otherwise.
The drive to Topeka was a blur of black coffee and radio noise, his mind replaying Mary's screams. Thinking about what he'd found out.
The cabin was a rotting shack in the woods, smoke curling from the chimney like a lure.
John approached at dusk, boots crunching on frost, the map in the envelope leading him right to the door.
Inside, it wasn't a man waiting.
Crowe—or what used to be him—lunged from the shadows, skin peeling back to reveal fur and fangs.
Werewolf, full moon rising.
John's first real werewolf hunt overlapping with his first paid gig. He dodged the claws, pumped silver into its chest, and watched it crumple, howling.
The heart was still beating when he carved it out, just to be sure.
No witnesses, no mess—Eddie's boss would think it was a clean hit, body dumped in the river.
Back in the city, John collected the rest of the cash, no questions asked.
Eddie even tossed in a bonus for "efficiency."
That night, staring at the wad of bills, John realized the potential: criminals dealt with monsters without knowing it, and hunters like him could benefit from that.
One job funded the next hunt, building contacts in the shadows. It wasn't clean, but neither was life.
Word spread quietly after that. John Winchester: the guy who handled "problems" that left no trace. His first taste of mercenary life hooked him—resources for the real war against the things in the dark.