Disclaimer: I don't own SPN.

Welcome! So, I recently realised just how awesome and badass Henry Winchester was and I wanted to explore the ripple effect of what could happen if he fell into an earlier year than 2013. This first fic will just be 8x12 and a bit after and then a second fic will come, which will explore the canon timeline with this ripple effect. Also, I don't usually write such short chapters but hey, it's a prologue. They're meant to be short.

Anyway, enjoy!

"Goodnight, son."

Henry Winchester smiled one more time at little John Winchester before closing his son's bedroom door. Downstairs, he bade his wife farewell for the night and then set off to his initiation and the event that would change his life forever.

"Josie," Henry smiled at Josie Sands when he was inside the Men of Letters headquarters. His dear friend's vibrant red hair was pinned up in an elegant bun and she was wearing a beautiful grey evening gown. Henry suddenly felt underdressed in his blue suit and tan overcoat. "No one told me this initiation was a formal affair."

"Well, someone had to class up the joint, right, Henry?" Josie laughed, standing up and stepping forward to fix up Henry's tie and membership pin.

"Ain't that the truth?" Henry said.

"But the hard part's over, right?" Josie continued to fix his outfit up. "We made it."

The door beside them opened to reveal a man wearing a hooded cape with the Men of Letters symbol sewn into it.

"Ms Sands?" David Ackers said. Henry smiled at Josie, who went to enter the room but paused and looked back at him hesitantly. He gave her another reassuring smile and she smiled back softly and entered the room, closing the door behind her. Henry took his hat and coat off, hung them up and sat down on the bench, his stomach rolling with nerves. This was it. After this night, he'd finally be a Man of Letters! And then he would be able to pass the legacy on to John when his son was old enough! The Winchesters had been Men of Letters for as long as they could remember and Henry was eagerly anticipating his opportunity to continue the legacy.

Loud screaming and banging from the next room jolted Henry out of his thoughts and he jumped up and sprinted into the room to see what was wrong. The sight that he was met with made him sick to his stomach. Two of the caped figures were lying on the floor in pools of blood – one was David Ackers and Henry couldn't make out the second – while another man was standing in front of Josie and chanting loudly in Latin.

"Secura tibi facias libertate!" he said. Henry recognised the voice as belonging to Ted Bowen "Servire, te rogamus, audi nos!"

"Henry!" Henry's attention was drawn to the floor, where Larry Ganem was clutching feebly at Henry's legs. Henry blanched when he saw that Larry's eyes were bleeding and he knew that the poor man was now blind, a realisation that only made him feel even more nauseous.

"Do not let Abaddon get it!" Larry said desperately, pressing a small wooden box into Henry's hands. The box had their symbol carved on it and, before Henry could wonder what was inside, his attention was drawn to Josie, who had grabbed Ted by the throat. To his horror, he realised that Josie must be possessed!

"That's impossible!" Ted choked. "How?"

When Josie turned around and screamed and Henry caught sight of her pitch black eyes, he began to back away. She wasn't Josie anymore! And now he had to get out of there and keep the box safe from the demon inside of her, who must be Abaddon! But how? How and when had Abaddon gotten the chance to possess Josie?

Henry couldn't worry about that now, though. As Abaddon snapped Ted's neck and turned to him, Henry bolted out of the room and down the hall to their laboratory, locking the door behind him. He flitted from shelf to shelf, grabbing ingredient after ingredient in a mad attempt to try and escape from Abaddon before she could find him and kill him. He couldn't die! His family needed him!

'Family…'

Henry quickly began to mix the ingredients together in a bowl, very aware of Abaddon flinging door after door open in the hallway in an attempt to find him. This spell would take him to his family. It had to. It just had to! He couldn't leave John and Millie! But he couldn't let the box fall into Abaddon's hands! The elders were trusting him not to!

Finally, feeling as though he had been at his task for hours, Henry completed the mixture and snatched up a knife nearby to add the final component: his blood. Blood led to blood and he had to get this spell just right! He wouldn't be able to tap into his soul again for a while afterwards if he did mess it up!

The ringing of Abaddon's footsteps painstakingly loud in his ears, Henry slashed his palm to drip blood into the bowl before dipping his fingers into the mixture and drawing a symbol on a nearby door. Abaddon's footsteps drew closer and the next door crashing in on itself was too loud for comfort.

"Kah-nee-lah poo-goh," Henry started to chant as he kept tracing. The symbol started to glow gold and Henry felt a tug on his soul as he kept chanting. To his horror, the door to the room started to rattle and he attempted to speed up the spell before Abaddon could get him!

"Kah-nee-lah poo-goh…kah-nee-lah poo-goh…kah-nee-lah poo-goh…" he said desperately. Finally, finally, he had completed the symbol! As the door to the laboratory started to crack and cave inwards, Henry feverishly shoved the door with the symbol open and fell through. There was a moment of blackness and then disorientation and bright light before Henry fell into something hard and solid – another door, he knew. The door swung out and Henry leapt out, landing neatly in a crouch. He straightened up, observing the room.

The room wasn't much. It looked like a typical motel room: small with beds, a sofa, a television and a small kitchenette, with a door nearby that Henry presumed led to a bathroom. A man with short, dark hair and matching, scruffy stubble sat in a chair, frozen in the process of cleaning his gun, while two boys were looking around from watching the TV. If Henry got his spell right then –

"Are you John Winchester?" he said desperately to the man.

-ATGB-

John Winchester's Saturday was a typical one: preparing to go out on a salt and burn, he was making sure that all of his weapons were in pristine condition (well, as pristine as possible) and that Dean knew to look out for Sam and what to do in emergencies. John wasn't a man who liked surprises or unexpected events. He liked to have all the facts and know exactly what he was doing.

So when the closet door nearby started to shake and rattle, John paused and eyed it suspiciously. What the hell was going on? Was it a monster?

"Dean," he growled quietly. Dean immediately looked away from the TV.

"Yeah, Dad?" he said.

"Get ready," John said. "Get Sammy out of here when I say so."

Dean nodded and Sam chose that moment to turn away from the TV and catch sight of the closet door. His round green eyes widened and he pushed himself onto his knees so that he could get a better look at it. It wasn't too long ago that he'd found out that monsters and the supernatural existed (something that John had been furious at Dean at for letting happen) and John knew that if a monster burst out of there, his youngest son would not be prepared for it.

It was a surprise when the door flew open and a man with short, neat, dark hair and a blue suit burst out. He landed expertly and then straightened up, brushing off his suit while surveying the room. John froze and nearly dropped his gun, something that hadn't happened in years. He knew this man! How the hell was this possible? He had disappeared over thirty years ago! Why was he falling out of John's closet?

"Are you John Winchester?" Henry Winchester, John's father, said to John immediately.