Dean was feeling left out so he's getting a chapter. Of course, once I started writing Dean was being difficult because… ya know, feeling aren't something he can shoot. Yes Dean, we know you'd try.
Spoiler: through 14x02. Season 14 doesn't give us fic writers much space to fill in so I'm working with what I've got.
Disclaimer: I own nothing. Just borrowing because my imagination wouldn't let it go.
He was clean and back in his own clothes. He was never one to be overly concerned about fashion, but the jeans, black t-shirt, and dark flannel had never felt so good after the suits. Yeah sure, he'd told Sammy that he didn't remember and mostly he didn't. There were a few flashes and that was enough.
He probably should get Cas to dig through what was left of Michael's memories to see if they could figure out what the hell that scar was on his arm but right now all Dean wanted was his family. That and some time with his own memories. Mom was still in Deluth with AU Bobby but at least his brothers and kid were here.
Reaching into the bottom drawer of the desk in his room, he pulled out an old cigar box. It was held together with duct tape and hope but it was what he needed to bring up the specific memories he wanted rather than getting bogged down in the nightmarish ones.
Closing his eyes trying to think of a prayer to call out to Cas but nothing came up. He opened his eyes and pulled Charlie's copy of The Hobbit from the bookshelf before taking the few steps required for his long gait to reach the door to his room. It was time Jack get to know this story anyways.
He supposed that he should be surprised especially at how soundlessly a giant like his brother could move when he wanted to but years of experience had taught him that Sammy knew him, better than anyone else. Of course, Sammy would know that Dean needed family time. What did shock him however was to find Cas and Jack waiting in the middle of the hallway just outside his room as well.
Sam held up a bottle of whiskey in one hand and a six pack of beer in the other. "Which one?"
"Probably just the beer." Dean said not missing the look of concern that flashed across his family's faces before they moved out of the way to let Dean step out into the hallway and Sam put the whiskey bottle against the wall in Dean's room. They all knew it wasn't a healthy habit, but they also knew it wasn't one that was likely to change anytime soon.
Sam straightened up and closed the door behind them before falling into the tight little knot in the middle of the hallway. They hesitated there for a while before Dean handed Jack the book, he'd tucked under his arm only to replace it with the kid himself. He needed Jack to know that what happened to him – whatever Michael had done while wearing him – wasn't his fault. Dean would've said yes to Michael to save any one of his family.
Before he knew it, they were at Baby and Sam was handing him the keys. Even though he was reluctant to let go of Jack he took the keys and let the boy slide into his usual spot in the back seat. Cas had slid in behind Jack before Sam even made it around to the other side of the car and said, "The other world hunters will leave us alone if you don't feel up to a drive."
When they were all settled in their customary spots, Dean tucked the keys in his pocket and spoke to the steering wheel feeling the eyes of his family on him. "I know it's kinda weird but I'd rather stay right here."
"Of course, Dean." Sam said at the same time that Cas said, "Do you want us to go?"
The panic in his voice was not as well hidden as he looked up and caught two pair of blue eyes in the rear-view mirror. "Please don't. … I … I need you here."
Sam's big hand landed on his shoulder and Dean didn't break eye contact with the angels in the back seat. There weren't any words needed. Well, not immediately as Jack curled his legs under him and Sam withdrew his hand to accept the book of lore Cas handed him. Cas for his part took a worn, leather bound book from one of the inside pockets of his trench coat. They all settled in for as long as they were needed.
Dean smiled his first real smile in a while. His family wasn't going anywhere, and he just sat there staring at the box in his hands for a few minutes.
It wasn't exceptionally full, at least not of physical things. Charlie's copy of The Hobbit was the biggest memento that he kept, and he was seriously considering passing that on to Jack. Charlie would've loved Jack. He always had a Moondoor patch in the top of this box as a physical reminder of the girl who'd become a little sister.
Opening the box and pulling out the patch itself he thought back to the amazingly brave woman. Their Charlie's story had started much in the same way that AU Charlie's story had but their Charlie had so much more love and joy in her life and she'd radiated that joy and courage with every breath she took. Then she'd gone and sacrificed herself … and for him none the less. He didn't deserve that kind of love.
He knew exactly what Sam would say to that so before he could get himself caught up in anymore thoughts that might bring him to tears, he moved the patch aside and looked up briefly to see Sam watching him. They exchanged a sad smile, both knowing that Sam had seen and understood the importance of every item in the box at a glance. They weren't all items that would stand out as important to just anyone but, the Winchesters weren't just anyone.
As Sam turned back to his book, Dean turned in his seat to partially face the back. "Hey, kid?"
Jack looked up and tucked a finger between the pages to mark his spot and gave his dad his full attention. Dean was momentarily struck by the similarities that look held to one of Sam's. "Remind me to tell you about our Charlie someday. That was her book and I think you autta know about her. Actually, if you want, Cas could share some of his memories of her. It might be faster than doing it the human way."
"Dean." Cas said, in the tone that both humans in the car privately called his exasperated nanny tone. "You know I don't like implanting memories other than in life or death scenarios."
It was about to turn into one of their comfortable arguments until Jack said, "I'd rather hear it from you, Dean. Whenever you're ready to talk."
"Thanks kid." Jack's smile healed him more than he would've been able to put into words. "Maybe tonight once everyone's settled down."
Jack just nodded and everyone silently turned back to their respective books as Dean pulled himself back around to face front as he pulled out the small voodoo doll that Rowena had given him to play with back when she and Sam had saved him from that memory spell.
Rowena McLeod and her son Crowley – or Fergus McLeod to use his given name – had been constants in their lives almost more so than some of their allies. He didn't really know how to feel about either of them a lot of the time. Crowley had sacrificed himself to get him, Cas, and Sam back to their own world on the night Jack was born and Rowena?
Well, Rowena liked to joke about being Auntie Rowena stepping in to fix their problems. Dean wasn't entirely sure that it was completely a joke. He wasn't sure if he could call it the love he'd have for an aunt since he could barely remember a family outside of Sam … and Dad for a little while. Either way Rowena was one of the few people left outside of his immediate family that he could now say that he truly trusted 100%. Yes, even after that whole 'kill the reapers' kick she'd gone on.
Other than one of Dad's old cell phones, a pair of some of his and Sammy's first fake badges, and Pastor Jim's clerical collar, there were some charms Bobby had given him and Sam before they'd gotten their anti-possession tattoos. Bobby. Out of all the deaths that had happened in the Winchester's career as hunters. That one had hit him hard.
They'd grown up calling him Uncle Bobby and he'd been the closest thing he and Sammy had to a traditional father figure. And he'd told him as such. The man had been a gruff drunk, but he'd been dedicated to his chosen family and he was a good man. One of the best Dean Winchester had ever known. Hell, the man had even gone so far as to doge his reaper and allow himself to become a ghost just to protect his boys.
Right next to the charms was what looked, at first glance, like a small pile of small pieces of paper neatly held together with a paperclip. This little stack of papers held symbolized two families the Winchesters had made for themselves, one they'd lost years ago, and one they were trying very hard not to lose. Loss. It was a common theme in a Winchester's life – and apparently a Campbell's life. Loss like those, well… they left scars. Not the physical kind. Those he could deal with.
Pulling the paperclip off, Dean ran a thumb first over Jody's business card then Donna's. Who'd ever thought that Dean Winchester would count not one but two sheriffs as members of his family. These two women, who couldn't be more different, exuded love in all aspects of their life. Donna was definitely an aunt figure not just to him and Sam but to the girls that Jody had taken him in.
That thought brought him to the two pictures that were next in the stack. The first one was of one Donna had given him of her and Jody with Claire, Alex, and Patience after they'd rescued him and Sam from The Bad Place. His only regret about this picture was that it hadn't been taken earlier when Kia was alive so that she could be in it, but the picture made him smile none the less. These girls, they were the hunters this world needed now, and the monsters better watch out.
The next picture had both Sam and Cas breath catching in their throat. It was the original Team Free Will back when Bobby was still in the wheelchair. It was taken the night before Jo and Ellen had died. Another sacrifice to be put against him. The Roadhouse had been – outside of Baby and Bobby's – had been the first real home the Winchesters had really known and the family they'd made there had, for better or worse, made him who he was today. Their deaths still hurt.
Without looking he passed the picture over to Sam and he tried not to listen as Cas explained the story to Jack. Who these people were and what they had meant to Team Free Will. As if the loss of three, four counting Bobby, could be described in a brief conversation over a crumpled picture. Still Castiel, the Angel of the Lord who raised him from Hell, tried and he loved him for that.
That thought brought him to a stained and yellowing cardboard coaster. Flipping it over he smiled at the address in Ash's characteristically messy scrawl for some random case Dean didn't even remember. The address itself didn't even really matter anymore. It was more about the fact that it was in Ash's handwriting. That and the note written in the same messy scrawl just below the address. "Kick it in the ass, boys! – Dr Bad Ass"
Finding Ash's body in the rubble of the still smoking roadhouse after Azazel had taken Sammy had almost killed him. The only thing he could compare that feeling to was watching Gadreel use Sammy's body to kill Kevin and those two events had been about a decade apart if not more. That brought him to the last item in the box.
To anyone else, it just looked like a small block of amber but not to him. It was a piece of resin that Dean had picked up at a music shop two years ago when out on that banshee case with Eileen simply because it'd reminded him of Kevin. Eileen had been with him at the time while Sam had been picking up some more lore books and hadn't pushed him for an explanation.
They'd lost so many good people along the way. There was a lot of pain and darkness on their path; both behind them and definitely ahead of them before they were done. Still, there were people like the ones represented by these little mementoes and the ones they saved that made all the pain worth it.
And in the end, that was enough; to know that they had made a difference. That they were loved. Wasn't it?
Jack placed a hand gently on Dean's shoulder to hand him back the picture of the original Team Free Will and it hit Dean. It hit him as he collected everything neatly back into the box. This whole Family Business; the saving people, hunting things. This was why they did it.