As a hellhound's chew toy. The bitch made Sam watch it...
But before that, I failed to recognize that the damned broad I was seeing wasn't Ruby, it was Lilith. It would've helped if I'd seen Ruby like that before, but I hadn't. It would've helped if I'd realized it was her on time, since I'd seen her when she was in that little girl, but... I couldn't make the connection. I didn't. So we didn't get to kill her and she sicced her hellhound on me. And that's how I died.
But before that I wouldn't let Ruby tell Sam how to help out. I thought we'd be able to do it the human way. Our way. Why does she really want to help us anyway? She's a demon. Or does she want to help us, or just make Sam her tool? She has her own goals, her own agenda, that one. At least, at least I've never used my brother. Yeah, he's working towards the same goals as I am, and I've bossed him around a bit and we've gone my way instead of his now and again. But that's not the same. There are very few things I want for myself, and they're pretty easy to come by. The rest... he knows what I work for. Hell, he wants it too. Even past revenge. Some things just gotta be stopped.
But before that, I made a deal. With another demon, to bring my brother back to life. The demon I made the deal with, she wasn't easy on me. I should've realized she wanted me down South that soon for a reason. That maybe there was something more going on. But I wasn't thinking too clearly then, oh no. I made a deal and I was eager to make it, and I knew it'd get me killed in a year. And I didn't find a way out of it in the meanwhile, and that's how I died.
But before that, I'd been the one who got Sam killed. After Dad gave his life for me to be there to protect Sam and all. I failed, and not only that, I was the one who got him distracted for that knife to be put through his back and waste him. What did you do with your baby brother? Saw his blood stain the dirt on that road, saw the light leave his eyes. That's what I did, Dad. That's what I did, Mom... Good work, Dean.
And that's how I died. All my fault.