This story came from a question. How did Agent Henricksen know so much about John Winchester and his kids, and why was he so set on catching them? I imagine the journey was a long one. He had been hunting John, at least, for many years before he ever caught up with Dean in season 2. This is not intended to be an AU, just a 'what if'. What if Henricksen had prior history with the Winchesters? What if he was hunting John back in the 90s, and found the boys instead...

Chapter 1: Dean's Bad Day

(August, 1995 Sam is 12, Dean is 16)

Everything about this day was going wrong.

First, Sam had spilled his spaghetti all over the back seat of the Impala. Dad had made Sam wipe it up, but Sam seemed to have forgotten about the many uses for soap and left a sticky, crusty mess that Dean had to go and re-clean. His little brother had been particularly whiny and clumsy lately. If he'd been a girl, Dean would have assumed PMS, but Sam had no such excuse. When asked why he was feeling crabby, all he did was glare and complain some more.

Then, the engine had started to overheat. Dad had insisted Dean help repair it.

Dean didn't mind. He loved learning how to take care of the Impala. There was something relaxing about caring for the aging engine. Every part had a purpose, and if they were maintained and kept in correct condition, they all worked together beautifully. Car problems were simple. Either something was broken, or it wasn't. Fix it, and it worked again. Dean liked the straightforward logic, and the warm, fuzzy feeling that accompanied the sense of accomplishment after a repair was completed. Baby was the one anchor Dean had in a world fast becoming complicated by puberty.

Today, though, Baby had betrayed him. Radiator fluid had escaped from under a broken cap, scalding Dean's hand. A helpful farmer's wife had seen them stopped for repairs and brought him a sticky green plant she called 'aloe' to put on the burn. It seemed to help, but Dean's hand still smarted.

Sick of the stinking leftover-spaghetti smell and hand throbbing, Dean had been almost asleep when Dad pulled into the motel, Countryside Inn. Situated across the road from the graveyard, it was a small, but cleaner than most places they had stayed with quilts on the beds. It was also tiny, with no phone in the room, and only one bed. Dean and Sam both whined that they were too old for the same bed, Sam was almost a teenager and Dean was old enough for a legal ID if he wanted one. Dad said there were no other options and he couldn't afford a second room. Dean begged for extra blankets and made a nest on the floor.

Then, there was the town itself. It was one of the smallest Dean had ever been in. A population sign next to the motel proudly declared "Roseville" to be the home of 1,150 residents. There was a Casey's, a bowling alley, an ice cream stand, and the motel. Nothing else. Dean even walked to the center of the town (it took ten minutes) and verified that he could indeed see a cornfield from every direction. They were, quite literally, in the middle of nowhere.

Dad had left with a few words about being back in time to enroll them in school somewhere else. It wasn't until after he left that Sam started to complain about the heat and Dean realized the air conditioner was broken. He called Dad, but there was no answer. He called the motel manager, and was told that the problem was with the whole building, not just their room, so moving wouldn't help.

Dean would have torn the A/C unit apart to fix it himself, but the tools were in the Impala with Dad. So the temperature climbed, and with it, so did both brother's tempers.

Dean paced the confines of the tiny kitchenette. He had dragged out the cooking of dinner and subsequent cleaning up as long as possible, but it barely put a dent in the evening. Sam, still grumpy, hadn't been much for conversation and had retreated to watch TV from his bed. Where in the World is Carmen Sandiego. It was a cheesy game show that tried to disguise geography and world culture lessons and make them fun.

Sam thought it was fascinating. Dean didn't normally mind, sometimes they would have a funny skit, or a hot chick. But Sam would always sit there, shouting out answers before Dean had finished processing the question. He was at it now, babbling at the TV screen, saying words like "Tippecanoe" and "Van Gogh."

Fixing Baby made him feel like he could do anything. Watching educational TV with his nerdy kid brother made him feel like a loser.

There was no place to go to escape, not even an arcade in the motel.

So Dean paced, wishing that something, anything interesting would happen.

Notes:

For you younger folk out there, Where in the World is Carmen Sandiego was actually a show that was on in the 90s. Also, Roseville, Illinois, is a real town, with one hotel, the Countryside Inn.

So, what do you think? Is anyone interested in reading more? Please review and let me know!