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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.  


# Garrett 2011-09-01 00:06
this is awesome! i need to watch more of six before seven starts! i havent watched the whole season but i do know how he was depressed Sam was gone and how at first he didnt want his soul back. the vampire epi was sad but cool at the sametime. gosh! i need to watch more episodes. since you mentioned the hell part. i cried at the ending when he was calling for Sam and he looked so scared :-( still Dean is a fighter! ^_^ nice page! i like it :D
# Garrett 2011-09-01 00:19
i like the points you make i agree! he has had to go through so much! seeing him sad or hurt is heartbreaking and when sam lied to him eventhough he was souless was wrong! i just want to give Dean a hug. i admit there were times i wanted to slap Sam for what he did to Dean but it wasnt his fault.maybe. but the whole beating him up and going in the hole now that made me sad/mad. Dean is one of the best hunters/charact ers on the planet! still reading your page but sofar i agree with the points you made :)
# sweetondean 2011-09-01 01:59
Awwwwwwwwwwwwww wwww Alice! This is so ouchy, but so good! I always say, and I'm only ever half joking, that I know Dean Winchester better than the 'real' people in my life. He has lost so much, he has suffered so much, but he just keeps moving forward. I love that about him, that he can do that, just keep moving, just keep ploughing ahead. Most of us would have curled up into a rocking ball by now but not Dean. Yes some of that is because he masks it all but some of it is because he's that strong. He breaks my heart but he also floods my heart with love! I love this character with a (some would say unhealthy, but I know you wouldn't) passion. I believe in Dean. I believe he will always pick up his bootstraps. I believe that kick ass, give 'em hell attitude is alwasy just lurking under the surface and I really hope to see a lot more of it in season 7. I hope the brothers can lean on each other, that their relationship is so that they can help heal some of the rifts and tears in their heart from the past seasons. Dean is awesome. That is all. Thanks Alice! I'm going home to watch me some Dean!
# kmarie 2011-09-01 02:25
Wow, Dean sure did have it rough this last season, didn't he? *sniffle* Poor Dean!
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!!
# alysha 2011-09-01 02:45
I had so many issues with plot and conflict continuity in season six that I overlooked how great Dean's characterizatio n was. This man isn't the innocent devil may care guy we met in season one. I wouldn't expect him to be. This a complex show with characters who are multidimentiona l. This article highlights that, but i think more importantly helps me to appreciate the season more. Thanks!
# Haleh 2011-09-01 03:23
Loved the review!
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!
Far Away Eyes
# Far Away Eyes 2011-09-01 07:44
Excellent look at season 6 Dean. He's had a rough ride, hasn't he?

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.
# MariaVictoria 2011-09-01 10:02
Thanks so much for this insightful piece. Really gets me ready for the next season! So excited! Thanks Alice, always love to read your work!
# Sylvie 2011-09-01 11:30
Wow, Alice, that was one of the best essays I've read on this site so far. So much depth. I absolutely love Dean, and yes my friends and family always have to remind me he's fictional, but you know what? I don't care! He's the best fictional character there is. He's flawed, he's vulnerable, he can be funny, maybe not so much this past season, but he makes me laugh and he makes me cry. So many times I've watched this show and I can't help but think, "Oh, no, poor Dean". He's been tested so many times, lost so many people, it's actually quite sad when you think about it. This is why I watch a lighter episode after a heavy handed one. And what keeps all of us fans coming back for more is the beautiful relationship between Sam & Dean. I will be looking forward to your essay on Sam next. That poor boy has been put through the ringer so many times.
# Bookdal 2011-09-01 20:40

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.

Pragmatic Dreamer
# Pragmatic Dreamer 2011-09-01 23:21
Hi Alice,

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.

No. I'm not giving him demon blood. I won't do it.

And if he dies?

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:

Fine, I'm in.

You give yourself over wholly to the service of God and his angels?
Yeah, exactly.

Say it.

I give myself over wholly to serve God and you guys.

You swear to follow his will and his word as swiftly and obediently as you did your own father's?

Yes, I swear. Now what?

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!
Jayne Lamb
# Jayne Lamb 2011-09-02 01:29
I think Pragmatic Dreamer has touched on something that doesn't always get much face-time; Dean's lack of self-esteem. He was coded for the first three seasons as being a devil(!)-may-ca re, blue-collar tough guy, but after his resurrection it was made quite clear than Dean has suffered - and continues to suffer - a lot. I thought the Ep 'Sex & Violence' was a dead give-away; he doesn't indulge in anything because his 'desire','id' whichever is so beaten down as to be non-existent. I've always wondered whether the writers would touch on Dean's PTSD post-hell, and I think the very few mentions of him being alcoholic/drug- addicted (though not fully supported by the canon)reflect this. Can he really have dealt with those forty years just by confessing to Sam what happened? I'm not sure. But he's my favourite TV character by a long shot, and I just hope he gets some inner peace, eventually.
karen bg
# karen bg 2011-09-02 01:43
oh dean!! and can i just add what an amazing job jensen ackles did with dean this year. seriously blew me away many times.

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?
# kmarie 2011-09-02 21:29
Hi karen bg,
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 2011-09-04 17:38
The drug "implications" only came up twice. The first was Mannequin 3, just like kmarie said. The second was way more obvious actually. It's in "Let It Bleed" when Dean is interrogating the demons in Bobby's garage. Sam comes in and offers to help. He mentions Dean is running on coffee, whiskey and "whatever else he's taking." Chances are it's just amphetamines, but who knows?
# WeirdVision 2011-09-02 02:28
This was spot on! It's the main reason why season 6 was so painful to watch, beside the bad writing.
# Bevie 2011-09-02 16:22
Never noticed any "bad writing" myself this season. (or any other season for this show). Season 4 was the most painful for me to watch, as it split up the brothers and that is the worst thing to happen as far as my enjoyment of the series holds. Even so, I wouldn't trade season 4 for any other TV show ever!

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! :cry:

Great essay Alice! Thank you. :-)
# Marilyn 2011-09-03 11:45
Awesome essay, Alice. :lol: Season 6 just piled more and more angstiness on Dean. I kept asking myself how much more can the poor guy take without breaking?
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. :roll:
# trinaaron 2011-09-04 10:46
Regarding Dean's attitude about about Cas working with Crowley, I
# trinaaron 2011-09-04 11:04
Regarding Dean's attitude about Cas working with Crowley, I don't think it was Cas working with a demon that was the biggest issue (and I would have liked it if the writes were more clear about this). It was that Cas was actively working against the Winchesters while pretending to be on their side. Plus, they were talking about opening purgatory. If Dean thinks that is a BAD IDEA, why should he ignore his own instincts and opinions just because Cas says so?
# Cindy 2011-09-04 16:17
I was beginning to think that I was the only one who felt this way. I too thought it was more about Cas working with Crowley, while Dean and Sam were completely clueless pawns. It would be nice if this is clearly explained in this upcoming season.
# Liat 2011-09-08 11:49
I think there is one important history of Dean's that we seem to forget. Dean learned from Death that one shouldn't mess with the "Natural Order". What people forget is that it was Dean's un-death in "Faith" the first to screw up with the natural order. The Reverend said that god (or the Angels) told him to to that. And then John added to that by exchanging his life for Dean's when it was pretty obvious Dean was about to say yes to Tessa.
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.
# debhanley 2011-09-21 14:01
to be honest i was fed up this last season with sera gambles dean assanation to his character she makes out like he s a drunk and then the ref to the pills taking everything away from him it s about time dean was back on top and not unhappy all the time why should he have to take everything on his shoulders all the time he deserve a bit of happiness for once i would have been happier if he had nt wiped ben and lisa s memories he did nt have the right to do that which there again makes him look bad i hope the writers have a lot better season lined up for dean in season 7.z