A/N: The backstory to this is in the prequel story Finding Family however you don't need to read one to read the other.
(The five times that Sam almost met Max and the one time he did.)
The first time Sam almost met Max he didn't even realise it. He and Dean were passing through some town in the middle of nowhere near Seattle after a hunt. It had been a simple salt and burn that actually stayed simple for once. They had split up whilst Sam gathered supplies of one kind and Dean gathered supplies of a more supernatural kind, leaving them to meet up some diner for lunch.
Sam sat in a corner booth, ordering a drink as he waited and watched the other customers with mild disinterest. There was a gruff old man sat reading a newspaper in the corner, eating the eggs and bacon breakfast option despite the fact that Sam was pretty sure the menu said they didn't serve it after eleven. Trying to look casual in a corner in a way that said that 'Yes, we do have permission to be out of school' were two teenagers on an awkward date. Finally, sitting in the booth opposite him was a youngish mother and her son.
"Mom, mom, look! They have pie."
Sam's lips quirked slightly in amusement. It seemed like such a Dean thing to say. The mother seemed to find something amusing in it too. "Yes, I know. Indoor voice."
"Yes, mom." There was a pause. "Can we watch Superman later?"
"We can even watch it with your dad of you like."
The boy's face lit up. "Dad's home? Wahoo!"
The boy's face flushed. "When does he get here? Can we go to the park? Can we play soccer? And have ice-cream? And cake? And pie?"
"Well we could have pie now or," she said holding up her mobile so the kid could see the screen, "we could go see your father right now."
The kid was out of his chair in an instant and rushing for the door when his mother caught the back of his shirt. "Not so fast. I have to pay for your drink first." The kid practically danced on the spot with excitement as his mother had the bill rung up.
It was another hour after they left before Dean sent Sam a message telling him that he hooked up with someone and had taken the car back to her place, leaving Sam in some middle of nowhere suburb, with bags full of groceries and no transport.
"Damn it, Dean!"
The second time Sam almost met Max he didn't realise he was on the verge of what could have been one of the most important events of his life. He and Dean were in the middle of some case which seemed even weirder than most. Explanations came when they stumbled into the basement and found weird writing written from floor to ceiling in blood.
"Minoan Hoodoo. That's a new one," Dean commented. Sam only had the briefest of pauses when he realised that Dean recognised it with just a single glance. But then he had been out of hunting for years so it was likely it had come up in a case whilst he was at Stanford.
"Well we won't know what we're dealing with until we know exactly what this stuff says," Sam lamented. The writing looked pretty detailed and Minoan was one language that Sam knew that Bobby didn't know or at least didn't keep reference books and dictionarys for beyond the basics from the amount of time he'd spent in the past scouring the man's library. "It could take weeks, of not months."
There was silence.
"Or I could call Professor Sexy and have her translate it," Dean offered after a moment.
"Professor Sexy?" Sam's voice was incredulous.
"Newly instated. She has some sort of degree in Minoan. She works as a guest speaker at universities when she's not at the museum."
"And what will Professor Sexy say when she sees curses and hoodoo written in blood."
"Max knows what we do." There was a guilty tone to the murmur.
"You told her? Do you tell all your conquests or something?"
"No I didn't tell her. Kind of. Remember that time when I was nineteen and tried solo hunting for a while and didn't call you?"
"Kind of hard to forget you went missing for most the year. Dad said something about a hospital."
"Well I only gave dad half the story. Yes I had a hospital visit that fixed those seizures I used to have."
Sam cut him off. "Seizures?" His voice was panicky.
"Before I had surgery my body couldn't naturally make a certain amino acid. You used to get really worried and upset when I was ill. You probably just forgot. You were really young when we decided to try and hide them from you."
Sam swallowed, remembering all the times when Dean had been particually pale or shakey in his childhood. He had just presumed his brother was particualy succeptable to the flu. "But you're better now."
"Yeh, I am. Any way I only ended up going to the hospital because one of those solo hunts I was on went wrong and I had a completely different set of memories. I didn't even know my name. I met Max in the hospital. We were in for the same surgery. She helped me remember. That's why she knows."
For a second Sam thought about asking what happened on that hunt however the dark look on Dean's face told him he probably wouldn't open up anyway. So instead he asked, "So how close were you and Max?"
Dean paused and opened his mouth to say something. Whatever it was he chose not to and instead grinned lecherously. "Close enough that Professor Sexy is a proven title," he bragged, taking out his phone and snapping shots of the wall, before walking a small distance away from Sam and phoned who he assumed was Max and spoke in low tones, before hanging up. "Max says to give her four hours."
Four hours later and with the knowledge that it was one rather spurned lover causing the damage Sam and Dean ended the hunt. A clue about the yellow-eyed demon later and the thought of an ex-lover of his brother from years before slipped from Sam's mind.
It didn't stop him remembering to look up how to help a seizure victim on Google though.
The third time Sam almost met Max, Dean ditched him after reading about an accident in Seattle where a man fell on a chainsaw. He remarked about meeting up with an "old friend" before leaving Sam in some hotel just outside the city. He cursed his brother to the high heavens for that.
He'd only been there a few hours before Dean rang him. "I think we've got a case," his brother remarked. "There's been lots of strange accidents around here recently. See what you can find in dad's journal about kids behaving oddly." Sam couldn't be sure but he thought Dean sounded stressed.
When Sam rang back an hour later and explained how he was pretty certain that the kids were being replaced by changelings, the fathers killed, and the mothers fed on, Dean sounded a lot more than stressed.
"Is everything okay over there, Dean?"
"No. My friend's kid has been taken. I'll call you back later."
Dean didn't call him back. Instead he turned up the next morning looking more tense than he usually did. "How'd the hunt go?" Sam demanded after he had a good go at Dean for not calling to let him know he was alright.
"Killed the mother of the changelings, which in turn killed the changelings, saved the kids, oh and I learnt not to mess with mummy. Mothers are really scary when their kids are in danger. Or maybe that's just my friend."
Sam snorted. "You'll have to introduce me one time."
"Yeah," Dean said. "Maybe."
Sam wondered at the odd tone in his voice and how he looked like he always did after Sam had a closer than usual brush with death.
The fourth time Sam almost met Max he had no idea that the meeting almost occurred. It was a Friday. Just three days after the Tuesday that just wouldn't end, where Dean died repeatedly over and over again without it stopping and two days after Wednesday when Dean died and Sam didn't wake up.
It was a small funeral. Just him and Bobby. It wasn't like he had anyone to tell about Deans' death. And apart from Cassie, the girl Dean insisted he was just friends with but Sam was convinced there was more, Sam didn't think there was anybody out there who would actually care that his brother was dead.
Sam was numb to the world. Dean was dead. Really dead this time. He hadn't even had the full year he was promised. His mind was glued on the Trickster. Aside from Dean, dead and not him not waking up, the Trickster was all he could think about. Like somehow if he found it and killed it then it would all be okay again.
Sam left the cemetery as fast as he could after the service, glancing back only once, where Bobby was talking to a woman who had just arrived with a child. Bobby looked shocked, before staring at the child.
Sam turned away. He had a Trickster to find.
The fifth time Sam almost met Max he was walking back to the motel of the week that he and Dean were holed up in. They'd just managed to save the day by exercising the ghost possessed vase from some ancient time that the local museum was planning on selling to a bigger exhibit and Sam was currently trying to find the next case as he walked with his face in the newspaper he had bought.
"Hey Dean," he called as he entered the room, "I think I have something. There's been a string of … whoa," he exclaimed, as he turned around and walked right back out the room. He really didn't need to see his brother in a tangled mess of sweaty limbs with some faceless brunette. There are some things that one just doesn't need to know about their family.
Sam kept walking till he hit a dinner several blocks away. Feeling malicious, he ordered pie. Not just any pie, Dean's favourite flavour pie. The diner actually managed to get the perfect mix of fluffiness and crispiness for pastry. If Dean was going to throw Sam out of the room that he paid for then he was going to eat pie and enjoy it too. Dean was missing out.
Okay that was a lie. Dean had a very attractive woman in his bed and Sam didn't. But damn it he was going rub that pie Deans face anyway.
When Sam finally did meet Max it was at Dean's funeral. His real one. Not Trickster time loop one that could be fixed. This time he noticed the woman right away, recognising her from the last time Dean died for him and Dean couldn't help but wonder who it was that cared about Dean enough to make it to both of Dean's funerals without any notice from anyone.
The woman was dressed in a black dress and holding the blond child firmly by the shoulders as they proceeded through the ceremony. Tears trickled down her cheeks but her son didn't cry, he just watched as the coffin was lowered into the ground with a devastated look.
When it was over and the small gathering began to break up he walked over to the pair. "I'm Sam," he introduced. "Sam Winchester. Dean's brother. How did you know him?"
The woman smiled sadly. "My name's Max. Max Winchester. I am … was Dean's wife. This is our son Ben."
The boy looked up at him with wide brown eyes and all he could see were Dean's eyes. Sam suddenly recognised the pair from the diner years before and realised that there was no denying the connection. It struck him like a sledgehammer to the chest. Why hadn't Dean mentioned this to him. He had a wife and child and Sam was an uncle and Dean never told him?
Max seemed to realise what he meant and smiled softly. "There are some things about your brother's past and I guess in a way your mother's too that you don't know about. Dean didn't tell you because he wanted to keep you safe from it and me and Ben safe from your world. But mostly I think he didn't tell you because he didn't want you to think of him any differently. He left this for you."
She reached into her purse and pulled out a cream envelope with the generic mark of some hotel that they must have stayed in at one point. It was quite thick and must have contained several sheets of paper. The envelope had yellowed with age and still has some dust motes on it where it had obviously been waiting for this day and purpose. Scrawled across the front in blue ink was 'Bitch'.
At Sam's dry, humourless laugh, Max remarked. "He always was a smart Alec." She said it in a way that seemed to mean more to her than it did to anyone else, her own private joke, before she pulled another piece of paper out of her bag and handed it to him. This time it simply held a couple of numbers and an address based in Seattle. "Look, I know it probably doesn't mean much coming from a complete stranger, but after you read that letter and if you need to talk it, about anything really just give me a call."
Sam nodded, not really sure what to say. His world was already spinning from Dean's death and now he really wasn't sure what to do.
Max looked down at her son, some maternal instinct drawing her attention seconds before the eight-year-old gave out a muffled cry. Not thinking twice she lifted the boy up onto her hip with ease that defied her small stature like he was still a young baby and wrapped her arms around him, whispering soft sounds under her breath.
"I've got to go. But it was nice meeting you. You meant so much to Dean. Goodbye Sam"
"Goodbye Max, Ben."
The young boy sniffed, looked up at him with the painfully familiar eyes of his brother. "Bye uncle Sam."
With that Max walked away with the only piece of Dean left in the world on her hip. Sam decided that he was definitely going to see her again at the very least to get to know his nephew, no matter what was in that letter. He also knew that he was even more determined than before to find a way to bring Dean back.
A/N: I planned for this to be set in a world where Mary, through the hunter grapevine, hears about a government project that possibly involves the supernatural. She gets involved in Manticore and, learning her husband, as a marine, is one of those people in prime physical and genetic condition get her to steal his DNA, of which some is used X5-493 and X5-494 and any following X series clones. When one of the pregnancy hosts unexpectedly dies Mary volunteers to carry the baby, X5-494. She runs away during the early stages of pregnancy and Dean is raised like cannon and thanks to enhanced memory can remember enough of his mother explaining to keep it secret, along with a hoodoo bracelet that Mary procured forces the enhanced Manticore genes, like the barcode down.
Sometime when he's nineteen/twenty he's on a mission gone wrong and Manticore finally track him down. He goes into phyops where he believes that he's been with Manticore his whole life and went back into phyops after a mission gone wrong involving Rachel, which is actually a mission a X6-clone of his partook in, hence why he was recognised. Max breaks him and the other transgenics out of manticore where on the outside she helps him regain his true memories.
Update 04/07/11: Prequel is up in which the background is seen in more depth and without Dean's human-friendly editing for his brother.