Each year when I sit down and look at how the just finished season has treated the Winchesters, I'm constantly surprised over how rich the story lines continue to get. In Sam and Dean's case though, rich often means intense emotional angst and excrutiating physical and psychological torture. Just when you think that they can't go through anything worse, it gets topped.
In season six, that's especially true for Dean. He had it really rough. We all remember the end of last season when he was a broken wreck. The absolute most horrifying thing that could happen to him did, he lost his brother and helplessly watched him be condemned to an eternity of the worst possible Hell. One would think it's all up from there for him, right?
Nope. Season six has turned out to be his most heartbreaking yet. Yes, worse than season two when he lost John and had Sam die in his arms. Worse than season three when died and went to Hell. Worse than season four when he saw his brother betray him and then beat him to a pulp before starting the Apocalypse. And then of course, there was Lucifer's cage in season five.