AN: Hope everyone remembers that they boys are still back in s5 in these letters. This is Set after 5.15 Dead Men Don't Wear Plaid...

Mentions things from 1.11 Scarecrow


I was there...the first time...

I'm getting scared Dean...Bobby. I feel like he's breaking too. I feel like everything is breaking apart. Well I guess technically it is. It's the damn apocalypse after all. I'm such an idiot. I lay in bed at night and think. WHY? Why did I trust her. Why did I let this happen. Why didn't I listen to you. Sometimes I think it's to do with being the younger brother. I just wanted to be the right one. The one that could fix things. And no matter what it takes. I will fix it. I will.

I feel like all I do is screw things up.

Or run away. Or hurt you.

Why do I run... I was thinking back to that case we had in Burkitsville, Indiana years ago. You mentioned some of our old cases in your letters and it got me thinking. The one Dad had us go on, looking for the young couples who were disappearing. It turned out to be the Pagon God in the ugly ass Scarecrow costume.

Why did I storm off then...well I know why. You wouldn't do what I wanted. You were going to do what Dad said. Find out what was happening to those people. Help those people. And all I wanted was to find Dad. Find out what killed Jess. You called me a selfish bastard...even though I don't think you meant it, sometimes I think you were right. My mind can get so focussed on things. And I don't think straight. I wanted to kill whatever had taken Jess from me. Revenge. That's all I could see, until I realised that you were willing to let me go...even if it hurt you. And it meant you'd be alone, again. No one to watch your back. I couldn't live if something happened to you that I could have prevented. So I came back.

It's never been as easy as it seems to walk away from my family. As easy as you might think it is for me. Even going to Standford was hard, even when I wanted it so bad. You said I always know what I want and I go for it. That you admire that about me. I guess I do. But that doesn't mean it's not ripping my insides apart to leave you behind. Like I said back then I knew I wasn't going to stop trying to get revenge for Jess and mom. But Jess and mom were gone. It was just me and you. And now Dad's gone too. This whole damn world is falling apart, but I know I'll be okay. Because I still have you.

You know what I admire about you. How you manage to put the ones you love first nearly every time. I really wish I'd done that more often. Although at the same time you scare the hell out of me with the exact same quality, taking it too far. You have to put you first sometimes Dean. You matter too. You don't have to keep sacrificing yourself. Putting everyone elses pain and problems on your shoulders. YOU MATTER TOO. You're important too! I know you think that you're not. But you matter to me. You're important to me.

A lot of what drove me to do what I did, to be how I was. Why I went after Lilith like I did, was because you weren't there. My whole life you were there. (And don't you dare blame yourself. Understand). I just felt like I was missing a big gaping part of myself. And I was the reason you were gone. Like I said earlier I couldn't live if anything happened to you that I could have prevented. Honestly I don't think I'd be much better if something happened that had nothing to do with me. But I promised I'd get you out of the deal, that we'd find a way to save you and I didn't. That time without you, knowing where you were destroyed me. It changed me.

With all this now. Ruby. Freeing Lucifer... I was so focused on revenge. Again. Killing Lilith... stopping the end of the world. Wanting to make her pay for what you went through in Hell. That made me so damn angry. Angrier then I'd ever been. And you know how mad I can get about things. You were hurting. And she was going to pay.

I didn't think you were thinking straight, with all you'd been through. I thought Ruby would help us. I didn't to start with. It took a lot for me to trust her. But when you were gone Dean. I just felt so broken. All I wanted was to fix things this time. And...well she was a way to do that. I knew I was hurting you. But I thought in the long run it would be okay. Because once I defeated Lilith, you'd realise why I did it. That I was right. That I was doing it for you. For the world. Turned out great didn't it?

It's not that I trusted her more then was, I don't even know. She was a means to an end I guess. And nothing we had was going to take Lilith down.

I'm sorry it seemed as if I chose a demon over you. More sorry than you will ever know.

You're my brother Dean. My family. No matter what stupid thing I end up doing next. I choose you.

...I always choose you.

AN: I know Sam seems pretty down on himself in these letters. But after what happened I think he would be. Poor Sammy. He never meant for it all to happen. How was he to know Killing Lilith was a bad thing.