Disclaimer: I don't own Supernatural or anything pertaining to it; only my writing. I also don't own OneRepublic's song 'I Lived.' All rights go to their respective owners.
A/N: Based in season 3. It's the letter Dean was going to leave Sam before he left that time…
Hey, Sammy. So I'm writing this at two in the morning; you're asleep, stayed up late researching God knows what and I'm exhausted but had to get this down before I didn't have the chance. I only have a few days left, Sam, and if you think of this as my last—what is it, Mr. Law School? Last Will and Testament? Well, then, that's fine by me. I don't have anything to give you but the Impala of course, and you can have my amulet. You gave it to me first after all, right? So other than naming things I don't have but would like to be able to give after I'm gone, I just want to tell you, Sammy, that I believe in you, okay? I know I don't say it enough, and I can be tough on you, but you know how it is. I was raised that way with Dad, we were raised that way, and all my life's been about protecting you first and myself second. And I'll be gone in a short while, Sammy, so you make sure to take care of yourself. (And my baby.)
And now, words of wisdom from your dying—or, rather, dead brother. Sammy, I think it sums it up to say that we've led a bat-shit crazy life together. It hasn't been easy, or anything close to normal, ever, but it's been better for me since you came back into my life. I know it cost you a lot, Sam, like sleeping on a cheap motel bed every night, and losing Jess, and I wish I could fix it for you. But all I can say is to make the most of what's left of your life. I hope that when your own moment comes you can say that you lived, killed every second. And that you fall in love with a nice girl, Sammy, and that when you do, it hurts like hell. That's how you'll know it's real. I wish I could be here to see all you accomplish, all your joy and all your pain, but since I won't be, I want you to know that even in Hell, you'll be the brother that I love more than anything. Don't waste your own time, Sammy. I know you want to save people. I get it, so do I. So did I… But, and I hate to sound morbid here, but this is the world. Normal people can't do what we do, they're all so completely ignorant, and I want you to know that if you choose to be one of them after I'm gone, I won't come back to haunt you, bro. It's your decision of course, but make the one you feel will make you happiest, alright?
There's a million things I wish I could say to you right now, Sam, and I know it isn't possible. For one, when you read this I'll be gone, and for another, you're passed out cold on the bed. So I'll settle for this. And I should probably go before you wake up and wonder what I'm doing. Alright then. Love you, Sammy. No matter what. Remember what I said, okay?
Your devastatingly handsome brother,
Dean
P.S.- Bitch.