A/N: So I was looking up stuff and found Dean's goodbye letter in 5.18 Point of No Return and that, along with procrastination for studying for finals, sparked this...
" Sam and Bobby—
Given what's about to happen, 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. John taught us better than that. This is about time. We've run 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 [...]"
He sighs, tossing down the pen, fingers trickling through his hair.
It's useless.
No matter what he says, Bobby will still curse him out, maybe throw something against the wall... And Sam will...
Will stand and stare because big brother screwed up in those hazel eyes. He smirks because even now, faced with the goddamn Apocalypse, his chest twinges as he pictures Sam staring, chest trapped between breath and exhale, brain whirring as he tries to figure out the ruse, the plan.
And okay, maybe his knuckles pale when Sam's Sasquatch brain catches up and realizes the truth...
It's not giving up, he promises himself. Not giving up.
So, he picks up the pen, ignoring the tremble in his fingers, and forces himself to keep going.
When it's over, don't be scared. I'll be in Heaven and as screwed up as that is, it'll be over, right? That's all that matters. Don't give up, Sammy... just don't give up.
Like me... He adds with his signature.