This could possibly be a mulit-chapter but for right now, Sam needs some time for himself. Spoilers until about 14x01.
Disclaimer: I own nothing. Just borrowing.
The bunker was the most crowded it had ever been and Sam just couldn't take it anymore. That was an hour or so ago. Since he had snuck out of the library he'd been quietly listening to music in his room and looking through what Dean had called his Box of Treasures. Dean... that brought him back to his brother, like most things did.
Jack had been willing to sacrifice himself to save the family he'd found. Sam had jumped in to save Jack without even thinking but Dean? Dean had made the ultimate sacrifice.
Sam lifted the lid of the wooden box in his hands. It was about the size of a child sized shoebox and only about half full. He gently brushed aside Dean's amulet and a Moondor patch Charlie had given him at the last mid-year jubilee before she'd gone on the run (then died for a chance to save Dean).
Reverently, almost as if he was handling a priceless scroll of pre-biblical lore, Sam lifted a pamphlet from Oak Park Retirement Community and held it briefly afraid to open it. It was from the banshee case he and Dean had worked with Eileen a few years back. Inside, Sam knew, was the letter she'd written to him and Dean. The letter they'd only gotten after she'd already been killed.
Eileen. He'd failed her too. He'd failed her before he'd even gotten to spend any quality time with her. That hadn't stopped him from continuing to study ASL, even after Eileen was gone. It was his way of honoring the brave woman who not only refused to be defined by a disability she just happened to live with but had turn it into a strength.
Placing the pamphlet next to him on the bed along with Dean's amulet, the Moondor patch and a few odds and ends, Sam reached back into the box. Dean might make fun of him for it but these little odds and ends, reminded Sam of all the paths his life had taken and the people – and in some cases, creatures – that had come in and out of his life. In some cases, a few of them stuck around for a while or came back through every once in a while, just to remind him of his connection to this dark, bloody, world he loved so much.
The old polaroid that Sam pulled out of the box brought him back to a time before angels and demons. Back when this was the only world he had to worry about, and gods were more of an obscure piece of lore and THE God was the hope that there was something better after his work here was done. The polaroid was of the first people he and Dean had saved – from a wendigo back in '05 – after he'd gotten back into hunting … the first time.
It was of Hailey Collins and her brothers. Tommy and Ben hunted together now since Tommy'd survived Crowley's purge of the people the Winchester'd saved (with his brother's help, of course) and called about a case every now and then. Hailey, on the other hand, still hunted with her brothers once in a while but mostly, she stuck with her work a social worker out of Hibbing – yes, that Hibbing. She was the only social worker, as far as they knew who helped kids effected by the supernatural and she'd started a network that almost rivaled Bobby's network.
Next came a polished angel blade that could've belonged to either Anna or Balthazar. No it was definitely Balthazar's angel blade. Who else would've bothered to carve more eonian into the handle? He should ask Cas for a more accurate translation than 'don't touch' but he didn't want to cause his angel brother any more pain than confronting the weapon of a fallen angelic brother would cause him. Cas was a member of an endangered species now.
Come to think of it, Sam was sure that Anna's angel blade was one of the many in the bunker's armory… if other world Bobby hadn't melted it down yet to make angel killing bullets. He'd have to have a word with this new Bobby, and probably some of the other world hunters, about distinguishing the good angels from the bad ones. A lesson on sensitivity would probably be in order while he was at it.
Placing Balthazar's polished angel blade on the table beside his bed next to Ruby's demon knife and the angel blade from one of heaven's many foot soldiers that they'd defeated over the years, Sam thought back on the angels, and demons, and creatures who had gone against their very nature to stand with humanity; to stand with Team Free Will. Castiel, the angel of the lord who had literally pulled both brothers from hell and was now more than an ally. He was their brother.
Meg. She was the first demon they had ever met. She'd tried to kill Dad. He'd done a lot of evil but in the end she'd sacrificed to herself to Crowley in order help them rescue Cas and get away.
In the end, hadn't that been Crowley's end himself? He'd grown from the king of the crossroads demons to someone willing to give up his own life to save Dean and Sam Winchester.
Gabriel. The only archangel who really got the whole point of this humanity thing. The youngest of the archangels who'd died twice, and gone through years of torture in hell, all because he believed in humanity. The archangel who just wanted his brothers to stop fighting. He wanted heaven but Gabriel had died for humanity.
Then there was Balthazar. The serph who, though he'd never admit it, just wanted all the fighting to be over. He'd run away from the problems that faced him; taken some of daddy's toys from home and run away. And yet, when the odds were stacked against them, and the fight for humanity was kicking up, he hadn't turned and run. No, Balthazar had stayed and fought. He'd died fighting. He tried and in the end, wasn't that the whole point?
In the very bottom of the box were two beat up business cards that had definitely seen better days, one for Sheriff Jody Mills and one for Sheriff Donna Hannscum a tattered copy of The Hobbit. The bunker had 2 copies of this particular book... 3 if you counted the first edition in the library. Charlie's copy was one of the few non-lore related books on the bookshelf in Dean's room; but this one?
This was Kevin's. Mrs. Tran had given it to Cas to bring to them after Chuck had freed Kevin from the veil. Cas and Dean were the only ones - as far as he knew - who knew he still had it but neither of them had ever asked about it. Sam opened to the cover page to briefly reread Mrs Tran's neat handwriting. "Thank you for giving my boy the brothers he never had."
Sniffing back a stubborn tear, Sam flipped past several pictures and notes from Jody's girls tucked between the pages. About halfway through the book, the piece of paper he was looking for stuck out. Pulling it out, Sam reread Bobby's letter. As always, it was that last line that helped the most.
"Stay safe, keep fighting, and kick it in the ass. ~ Bobby"
