Dean has been gone for five months now. Sam tried looking at first, but after a while all of his leads turned into dead ends, and then there was nothing. Dean was just gone. No goodbyes, nothing really left behind. Just the Impala, a duffle bag of dirty clothing and an arsenal in the trunk.
Sam knew he could try looking for Crowley, but what could he really do on his own? Not much. He thought about calling up Jodie Mills or Garth, but what was the point? Replacing Dean? Sticking to a life that left him with nothing but bad memories and a pile of dead friends? No thanks.
The worst part was not knowing if he could come back. It was not knowing if he'd ever get to see his big brother again, and worse than everything, it was not getting to say goodbye. It was the fact that he still wasn't sure if Dean forgave him for the demon blood, for the apocalypse, for being soulless, for any of it. Not knowing if things really had gone back to normal, or if he'd just forgotten what normal was.
When he met Amelia Richardson, he was conflicted. Here was this opportunity to give it all up, everything, and move on with his life. He could finally be normal. He could have a girlfriend, and a house, and a dog. Everything he had before Jess died, and more. But he wasn't going to do it. He wasn't going to give up on his brother. Dean didn't give up when he said yes to Lucifer, and he didn't give up when he was dying in a mental institute. Giving up wasn't an option, it wasn't in the cards. Not for him.
Then came the day that he finally went through Dean's duffle, and underneath the thread-bare, blood stained t-shirts, there was an envelope. It was a little creased, but otherwise looked brand new. The front of it simply said, "Goodbye".
This must be from the day he went to say yes to Michael, Sam thought. It had to be. Unable to hold back his curiosity, he ripped open the envelope. With shaking hands, he read:
Sam & Bobby,
Given what's about to happens, I'll be surprised if this package ever finds you. But if it does, I want you both to know that what I'm doing isn't about giving up. Dad taught us better than that. This is about time. We ran out of it.
Left the Impala in Cicero. Where I'm going, we don't need roads. I know you'll look after her for me, Bobby- you've taken more for the team than anyone could ever ask. That makes you an honorary Winchester in my book.
Sam, you told me once that you pray every day. Not sure if that's still true. Probably isn't. But if it is, give it one last try, for me. And Sammy- one Winchester lost to this fight is enough. When it's over, you gotta move on. I know you've said an apple pie life is out of the cards for us, and maybe you're right, but if you can, you gotta try. And Sam, I forgive you for everything. I hope you can forgive me for this, too. Look out for yourself, Sammy. It's gonna be okay.
-Dean.
Sam sucked in a deep breath. With the back of his hand, he rubbed at the tears that threatened to overflow. He ran his thumb over the motel stationary, reading the note a second time, then a third. After what felt like a lifetime staring at the page, he picked up the phone, and called Amelia. Sam Winchester was out of the life.