Dean couldn't help but laugh at that, seeing Jack stop himself and then back track like the hunter was some kind of polite company that the other man didn't want to offend. Then again maybe part of that was true. Harkness was on the prison council after all, though Dean still didn't quite know what they did around here, so maybe the man was looking for more votes come re-election. Jack didn't seem the type but he had one of those faces. The kind Dean could see blushing mothers thrusting their giggling babies at to kiss for some kind of publicity stunt. Now wasn't that a picture perfect image? Dean could already feel his lips stretch slow and wide at the thought.
"Whether you believe in god or not I can tell you without doubt that the devil exists and right now a part of him is stuck inside my friend's head. Cas says he's handling it, but the cold hard truth is that it's just going to get worse. I know because it nearly drove my brother crazy," the smile didn't last as Dean continued to explain, gratefully reaching for the cool, refilled glass and taking another slow, small sip, "You've told me a lot of crazy truths so I figure I owe you a few myself cause this, all of this that is happening right now that we're calling the 'apocalypse'? Well if we're getting technical its the second. The first apocalypse, the one prophesied by angels, God, whatever, was supposed to happen back in May, 2010. I know this because my brother and I were destined by our family bloodline to be the human vessels of the archangel Michael and Lucifer. I was pulled from death by Cas to be Michael's vessel and my brother Sam was meant to accept Lucifer into himself and bring about the end of humanity."
Dean knew it wouldn't take much more to get him under the influence, not with how long it had been since he'd had the good stuff, but even though the temptation was astounding the hunter resisted. He'd learned the hard way what giving into temptation could bring. "Needless to say it didn't happen. My family and Cas stopped it from happening, but at a cost to my brother. Cas brought him back, but he couldn't manage to pull Sam's soul from Lucifer's cage. Did you know a person can live without their soul? They look just like they should but they have no conscience, no human emotion. I couldn't see Sammy like that way so I made a deal with Death. And the horseman brought back his soul alright, but apparently a piece of the devil was clinging to it. To save Sam from going insane from his memories of hell Cas took all of that damage from my brother and put it in himself. If we leave it this way it will slowly drive him crazy too."
At this point Dean was looking at his glass, idly tilting it back and forth to watch the warm colored liquid move. He hadn't meant to say all of that but after the fact he kind of felt a bit relieved. Now at least someone else knew what was going on. Maybe Jack with all of his vast life's knowledge would be able to find another solution if he failed. "I think the sooner we can do this the better and pick whoever you want. I'll trust your judgment."