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Family Matters/All Dogs Go To Heaven/Clap Your Hands if You Believe
Once Dean got the bombshell from Castiel that Sam was soulless, his attitude changed. It was no longer a game of trying to guess what Sam was. His focus switched to doing whatever it took to get Sam's soul, thus the real Sam, back. In the meantime, he set the rule that he was calling the shots. He wasn't going to give Sam equal footing given his state. That worked out okay in "Family Matters" when Sam chose to stick with Dean, and also in "All Dogs Go To Heaven," but by "Clap Your Hands if You Believe" Sam started having doubts about getting his soul back. Dean suspected as much too when Sam said no to the leprechaun's offer (that still sounds pretty absurd, doesn't it?).
Still, in all those episodes, this is the Dean that stands out most in my mind:

Okay, maybe this too:

Caged Heat
Dean's issues fell with another family member, Samuel. Oh man, I definitely don't want to be on the wrong side of this:

He just doesn't take backstabbing well, does he? At least Sam was sticking by him, until the end. Castiel's warning to Dean is pretty clear about what could happen if he gets Sam's soul back. Surviving could be worse than dying. "Paralysis, insanity, psychic pain so profound that he's locked inside himself for the rest of his life." Dean decides the risk is worth it, they can deal with the complications when they get it back. Dean's able to make that choice, but an eavesdropping Sam doesn't appreciate that decision.
So why is Dean so easily able to make that choice? It's clear he's not seeing soulless Sam as an equal. He's seeing him as someone he has to make choices for. Even Crowley and Meg say that getting back his soul is a bad idea. At the end, when Sam raises the issue, Dean won't back down. Sam says he's telling Dean something he doesn't like. This actually parallel's Sam and Dean's struggle through the entire series. All Dean has ever wanted is Sam to be human. To act human, to stay human despite the demon blood inside of him. Here is no different. No soul is not human. He's willing to risk Sam suffering in very human ways in order to keep that humanity. The un-human Sam begs to differ, for his only purpose is survival.
Appointment in Samarra
It's the ultimate, mega huge, slap you in the face Dean Winchester character test. Dean is desperate now. He has himself killed (for a few minutes anyway) just so he can talk to Death and ask for Sam's soul back. He even wants Sam's soul returned undamaged so that he can convince Sam to go along with the plan. It's obvious he needs his brother back in the worst way when he gives his letter of final words to Dr. Robert. It's addressed to Ben, not Sam. He knows that whatever he says, Sam won't care. If there's one thing consistent with Dean's life though, these risky choices come with a high price.
Dean gets to be death for a day. Why? If you were Death and you had a chance to teach the one guy who wrecks the natural order on a regular basis a lesson, would you pass that up? This lesson has been a long time coming and as hard as it is to see Dean go through that, he had to see the consequences of his choices. His stubborn defiance kicked off a chain of random events that ended up getting innocents killed. Not to mention the person he chose to live, a 12 year old girl, would have chaos and sadness follow her the rest of her life now that she's alive. Wow, that sounds very familiar. Sam Winchester anyone? Or lets take it farther. Mary made the original deal and see what's happened to their family since then? That's another topic though.
Dean must see this first hand, for he's always been a "seeing is believing" kind of guy. He gets the message. Knowing what he knows now, he would have killed the girl first. He has new appreciation for the natural order, but that only puts him in more of a pickle with Sam.
Dean decides when he makes the deal with Death that a wall in Sam's mind is better than nothing. It's a compromise he's willing to live with. He knows why he must take this awful risk. Because as he's learned, anything not human is usually dangerous. RoboSam will stop at nothing, and his attempt on Bobby confirmed Dean's worse fears about Sam remaining soulless.
Ever since season two, Dean has done everything he possibly could to avoid making the most horrific choice he could, killing Sam if he became too much of a threat to humanity. It's been his unwavering commitment to save Sam from this awful fate. He's always known that if he couldn't save Sam, he'd have to kill him. After he stopped Sam just in time from killing Bobby and they had him restrained in the panic room, Dean sadly knew there was only one choice left. He couldn't leave Sam locked up and he couldn't let him go. He never said it, but his hopeless expression as he went upstairs for a breather said it all. He'd have to kill Sam. This is indeed Dean's worst nightmare come true. Lucky for him, Death was upstairs waiting.
Even at the end, when Sam was screaming, Dean knew this was his only option. It still hurt him to do it though. Sam's scream reminded him of the fact that no matter what, he was still putting his brother through a lot of pain and risk. He wasn't about to defy the natural order again though.

Like A Virgin
Dean at this point desperately needs some relief. It's been ten days since Sam's soul was put back in and he remains in a coma. Dean's now frantic with worry over if Sam will wake up. Summoning Castiel doesn't help. "If you wanted to kill your brother, you should have done it outright." Dean's look of guilt after Castiel left angry says it all. He had no choice, Sam couldn't walk free (I loved his T1000 opening fire line). Still, what was Sam up for when/if he wakes up?
When Sam awakes with no memories of Hell or being soulless, Dean is more than willing to accept that as good (plus a meaningful good old fashioned brotherly hug doesn't hurt). "As far as I'm concerned, it's a gift horse. And I'm not looking for teeth. I'm sending Death a damned fruit basket." However, he's got a new problem. Sam knows something isn't right. The wall is itchy and he wants to scratch.

Dean won't talk about what happened in his life in that year and a half either, especially with Lisa and Ben. Part of that is too much pain, but another is he doesn't want Sam remembering why they ultimately split up, because Sam returned. That would be kicking that wall. It's really sad for Dean, having his brother back, but not being able to talk to about that hole in his life. In the meantime though, Dean is looser and feeling better that "the real" Sam is back (that point I'll debate in A Deeper Look At S6 Sam Winchester). He's starting to have fun again. That is until Mother of All emerges. Now he's got a new problem.
Mannequin 3: The Reckoning
Dean gets to say "I told you so." Sam scratches the wall and the consequences are dire. Actually, it scares the crap out of Dean more than Sam. He decided to give Sam latitude and try it his way but when things got dicey, he pulls authority. No more digging into that missing year. Overprotective big brother is something too hard to shake.
Dean's forced though to deal with his "year." Ben sends an emergency call and Dean is practically shoved into the Impala by Sam to go check it out. It forces Dean to have an honest face to face with Lisa. He had to see that Lisa was getting on without him, but convincing Ben is harder. He has to leave, to say goodbye for their sakes, no matter how much it hurts. It's clear he still doesn't want to let go though. He also sees how hard it's been on them and knows he can't go back. This really depresses him and his only comfort is a pep talk and a thank you from Sam. At least he has his brother.

Comments
-AmyinSydney
I thought you brought up an interesting point with the whole Sam/Ruby and Castiel/Crowley parallel. You pointed out that Dean perhaps should have known better than to ask Castiel to choose between him and Crowley, especially since he asked Sam to choose between him and Ruby at the end of season 4 with disastrous results. I think that it was precisely because of those results that Dean refused to stand behind Cas - he had already seen what happened with Sam in a similar situation and was desperate to prevent it from happening again. Whether or not that was a smart thing for Dean to do, and however the ramifications of Castiel's choice play out, I think we will have to wait until at least the first few episodes of season 7 to judge both Dean's actions and Castiel's. Hindsight is, after all, 20/20.
What a wonderful examination of Dean in season 6! I agree that this was perhaps Dean's most difficult season yet, with Ben and Lisa, Sam, and finally Cas. Dean had so few wins this season, and so very many painful losses. I think that Dean is going to continue to be challenged mentally, physically, and emotionally in season 7, and I hope he can get a handle on his drinking (and drug use??) before he destroys himself from the inside. But honestly? If there is one character who can keep taking the punches and come back swinging, it's Dean Winchester. I have faith. Can't wait for S7!!
Though I'd love Dean to get his fighting spirit back, I wanna see some more of Dean dealing with his issues. sure he's not a caring & sharing kind of guy but seriously aside from his hell actual experience, he'd been in hell & back so many times & we never got the chance to see how he feels, properly. last time he had some talking about his feeling was in season 4 and still not much!
I agree that I hope he gets that fighting spirit back for this coming season. Despite the troubles Sam faces with his wall being collapsed and not being fixable, Dean might take that as a challenge to overcome. He hasn't given up on Sam yet, why start now?
I really hope we get to see Dean examine what has happened to him and Sam in the past few years and where they should go next. Obviously there is no "out" from the life, but he has to find a way to make the best of it, to pull as much good as possible from it. Dean's tenacity has gotten him into and out of a lot of trouble, and it's that he'll have to rely on again.
Again, great look at Dean here, Alice. He's had a rocky ride, yes, but I'm very hopeful for season 7 regardless.
You've captured beautifully the success of Dean's characterizatio n in season six. I especially love how you underlined the subtly at play with Dean's conflicting emotions and obligations. I liked season six, and one of the reasons I did was because of Dean's development and his isolation and confusion as well as his understanding of where he belongs, what he does, and how he tries to negotiate those issues.
Brilliant essay, Alice. Thank you for sharing.
-Linda
I'm finally back home to my computer (oh, the stories I could tell!) and this is one of the first SPN articles I've had time to read, since the beginning of July. It was great, and very thought-provoking.
What I particularly liked was the way you honed in on the fact that what Dean has always wanted was just to keep Sam human. And RoboSam is not human. Like you said, all the pain and suffering Sam will go through now because the wall is broken -- at least he's a person and can feel that.
It very much echoes what Dean said to Bobby in "When The Levee Breaks" and Sam is detoxing from the demon blood.
DEAN
No. I'm not giving him demon blood. I won't do it.
BOBBY
And if he dies?
DEAN
Then at least he dies human!
I think for Dean, keeping Sam safe and keeping him human are now all one in the same.
What I continue to struggle with is why everyone was so opposed to reuniting Sam and his soul? Surely that's what Real!Sam would have always wanted. He would have been and is now appalled at what he did while he was soul-free. So, again Dean was just acting in Sam's best interest. I think of it as Dean having Power of Attorney over Sam, and vice versa. They make decisions for each other, when the other is not in his right mind.
I also appreciated you highlighting the violent killer that is exists in both brothers. (Remember Sam killing Gordon with just his hands and a length of barbed wire?!) What I think is really sad for Dean is that he is choosing to define himself by that one character trait. Dean's low self-esteem means he's always looking for the worst in himself, and it's always there to find. (That's true for anybody. Does the phrase "I look fat in this dress" ring any bells for anyone?)
I'm also not sure that Dean refused to go along with Castiel's plan slowly because he felt betrayed. I didn't see it as a near-replica of Season 4 with Sam & Ruby.
I think Dean wouldn't go along with Castiels' plan because he had learned from Season 4's problems. He knew opening Purgatory was a bad idea, no matter what Castiel believed. Dean's mistake -- the one he keeps making in my opinion -- is that he never communicates why he believes something is wrong or a bad idea. He just says the equivalent of "No.. It's my way or the highway" and nothing will piss off people, and angels!, faster than someone who is unwillingly to at least listen to their side of the argument. (Perhaps you were saying the same thing)
The story of Sam's life seems to be misfortune piled onto curse piled onto pride piled onto body blow after body blow.
I think Dean's life story is a little simpler, but equally as tragic. It's love and loss piled onto heartbreak and grief.
I fear the writers might take him down the drug path. That's what would happen to a real person. It seems too banal for Dean, and too much against his "go down fighting attitude". There are suggestions that Season 7 will force Dean to do some soul searching about why he hunts and why he's good at it. Hopefully, he'll make peace with it and we'll see more of the BadAss Dean (and maybe a little more Sniper!Dean.. guh!!)
And I did just find a quote that intrigues me. Again from Season 4 and WTLB. Cue the ominous music:
DEAN
Fine, I'm in.
CASTIEL
You give yourself over wholly to the service of God and his angels?DEAN
Yeah, exactly.
CASTIEL
Say it.
DEAN
I give myself over wholly to serve God and you guys.
CASTIEL
You swear to follow his will and his word as swiftly and obediently as you did your own father's?
DEAN
Yes, I swear. Now what?
CASTIEL
Now you wait, and we call on you when it's time.
So now Cas is the new God. Do you think he'll remember making Dean promise to serve God, maybe even call him on it?
Sorry to be long-winded. It's what happens when I have two months of pent-up Supernatural thoughts!
Cheers all!
i completely missed the 'maybe drugs too' references in the episodes. maybe i was too busy angsting for dean and admiring jensen. i'd love to hear them though - can you share?
yeah, I haven't seen all of season 6, but the one reference to drug use I can remember is at the beginning of "Mannequin 3" when Sam is recovering from his brush with his hell memories and Dean offers him food and a bottle of pills. Sam asks what the pills are and Dean just replies, "Effective." This exchange has made some fans speculate that Dean has started taking drugs, possibly antidepressants or even something else, in order to cope with everything he has had to cope with. Hopefully we will not have to see Dean struggling with drug abuse as well as everything else this upcoming season, but I do think this issue must be addressed. Maybe someone who has seen the entire season can tell us if there were any other references?
Alice, that analysis was completely awesome and I couldn't disagree with a word of it! Completely enjoyed reading it over and nodding to myself in agreement. Dean is such a fascinating and complicated character, endearing and maddening at the same time, brave and fearful (of what goes on with his Sammy) and completely and sadly loaded down with low self-esteem. He never sees himself as worthy unless it is helping others, but never himself. He just has to be useful or he is so very depressed. I hope in season 7 he regains his badassery cockiness and wins a few more battles than he has losses. Hasn't he lost enough? Mercy! I would like to see him laugh and have a little fun again like he had in season 1.
In other words, I just love Dean Winchester and really want a little relief from suffering now and again.
Looking forward to the Sam essay. That poor boy his had all his fears come true and he needs some relief also. As long as he loves his brother and watches his back I can take a lot of their misery, but split them up and it is almost unbearable!
Great essay Alice! Thank you.
Dean also has a huge stubborn streak and a firm belief that he is right. I know when I watched Sam begging Dean to just this once "trust him", I was yelling at Dean to trust Sam. (Ruby had me totally fooled). But Dean was right, Ruby's road was the wrong way to go. I don't believe standing behind Cass and opening Purgatory would have been a good idea either. (Just a small quibble).
Your essay brought up so many excellent ideas and gave me lots to ponder on for the next 20some days. Being fairly new to the site, I haven't read your previous "Dean: season articles. Looking forward to reading those.
With all the terrific reviews, games, articles, etc, on this site, the hellatus has breezed by.
I think the most tragic thing about Dean's story is that most of the devastating events in his life were made by other people or beings and he was the direct sufferer of those actions.
With regards to Castiel and Deans relationship, I think "The man who would be King" is a showcase of how blind Castiel has become. God is in everything and every being. For the entire episode Castiel asks for directions from God, not realizing that maybe Dean's request to not open Purgatory and to trust him, is God answer.