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If Season three was about the self-actualization of Dean Winchester, then what was Season four about? A self-actualized man must face his character tests. Dean's ultimate season four test ends up being the test of faith. Not faith in God or angels, but faith in everything he believes to be right and what matters to him the most, family. No matter what situation he faces, he has to keep honoring that humanity rulebook, not gray the line between right and wrong, and be willing to die over what he believes no matter what or who tells him otherwise, including the angels. Including Sam.
Test of faith are one of the most infamous trials faced by common man. What makes Dean's case so extraordinary is that he never had faith in God before. He only believed what he could see. So when he's pulled from Hell, resurrected by an angel, called for duty by Heaven to prevent the apocalypse, forced to deal with his PTSD from life in Hell, and watched his brother transform into a monster, it's incredible any faith at all grew from that. Somehow, it got stronger.
No one had a greater impact on Dean's character in season four than Castiel. What's even more fascinating is how Dean managed to have a huge impact on Castiel as well. From Castiel, Dean strengthened his resolve in the free will of man and exposed how flawed and immoral the other angels are. From Dean, Castiel learned that faith doesn't mean being blind and following orders.
Despite all his trauma, Dean held up extremely well to his tests of character except one. He kept his blinders on when it came to Sam and the results were disastrous. Dean dealt with Sam the way he always did and didn't see how bad Sam was drowning from his burdens and loss of control. Of course, Dean had a lot of crap to deal with from the get go himself so his issues with Sam were understandable and perfectly normal. Plus Sam shouldered equal blame. Often times duty got in the way of family, even if that wasn't the intention.
Going through the episodes gives a great sense of all the tests Dean had to endure.
Dean has a lot of crap to deal with in this one. I guess when you wake up six feet under in your own grave, that shakes you up a bit. After clawing his way out, Dean's left with the task to get answers for wtf happened. The answer he gets is even more jarring. Dean finally after a lifetime of denial has to face facts, God and angels are real. Enter Castiel, a force like none other he's ever had to deal with. They have work for him.
What's interesting is Dean's relationship with Sam resumes instantly with suspicion and mistrust. His very first thoughts are that Sam made a deal. Actually, that's his only theory, and his harsh accusations don't exactly keep their reunion heartwarming. While getting the story from Sam about what happened in Indiana and beyond, his mistrust still lingers when he asks Sam if he's using his powers. Not that Sam is right by lying, but he doesn't tell Dean the truth knowing that he would get mad at him and order him to stop (which is exactly what he did when he eventually found out). He'd rather let Dean go on thinking everything is still the same. Dean buys this for now, for he has other distractions.
Are You There God? It's Me Dean Winchester
Dean is forced to ask those philosophical questions that anyone pushed into a test of faith asks. Why did God pick me? If there is a God, why is there so much misery in the world? Naturally Dean doesn't get his answers, which frustrates him enough to lash out at Castiel and his vague "the Lord works in mysterious ways" answer. His new angel friend sets him straight though about the bigger picture. Seals are being broken one by one by Lilith and after 66, Lucifer walks free. So Dean not only has to accept God is real, but the Devil is as well. That's too much for a man to take on in a few days.
In The Beginning
Being sent back into the past is sure fire proof that this angel thing is real. Again, Dean is tested. It's much the same test he faced in "What Is And What Should Never Be." Does he put the welfare of his family over the welfare of humanity? In WIAWSNB, the answer was easier because it was his own welfare he was sacrificing. Here, it ends up being his parents, and he's going to stop what happened consequences be damned.
Castiel doesn't help Dean either by giving him false hope, thus suggesting this could be a test from higher up. He lets Dean believe he could save his parents by throwing him into the beginnings of the tragic Winchester family history. He sees how Mary and his grandparents were hunters. How Mary hoped for a better life. How Mary's deal for John's life doomed Sam. Castiel tells Dean he has to stop it, just about crushing Dean's heart when he finds out that wasn't about his parents. Of course once he finds out the real reason, that Sam is headed down a dangerous road since he's infected with demon blood and part of some endgame, Castiel literately puts the fear of God in Dean. "Stop him, or we will." You got to admit, it's a pretty powerful message for anyone, let alone someone who's had a very extraordinary few weeks. He rushes off to save Sam with some very big worry.
I'm not sure what Dean expected when he went to that warehouse, but one of his common reactions to fear is anger. Throw in a few feelings of betrayal and fists start flying. The two times Dean punches Sam and when he throws the lamp across the room is a pretty big clue to support that. Sam tearfully tries to explain, but Dean doesn't understand. "If I didn't know you, I would want to hunt you." Ouch! It's his turn to do the fear of God thing, telling Sam he was sent by angels and God to stop him. Sure, Dean is scared too and has every right to be, but that scolding doesn't help him with Sam. If anything, he ultimately ends up pushing Sam away.
In Dean's defense, Sam did deserve the brunt of the anger, especially when he lets it slip that he knew about being infected with demon blood as a baby for a year. Dean has a right to be offended, but his sardonic attitude instantly shuts Sam up rather than gets them discussing it. Dean eventually forces an outburst from Sam with his stinging comment, "Nice dude but he's got something evil inside of him, something in his blood. Maybe you can relate." Sam's outburst though is short lived. Based on Sam's refusal to talk about his issues in the end, Dean didn't set things right.