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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.    
How can it be worse?  Because Dean had to face harsh truths about himself and his life.  He can't have that family life he's always dreamed of.  He can't leave the job and retire.  He's always going to be doomed to a life of brutal killer.  He once again got to feel the sting of deep betrayal from someone he considers family.  Worst off, no matter how hard he tries, he can't protect those that he loves.  He couldn't keep harm from Ben and Lisa, and he couldn't protect Sam from the horrors that constantly plague him.  He didn't have many "wins" this season.  
The biggest complaint I hear about Dean is that the sharp tongued, "give "˜em Hell" badass Dean Winchester has left the building.  Yes, that's true, but has his character been given a disservice?  I don't know.  He's grown quite a lot.  However, you do have to wonder how long Dean's unhappiness remains tied to Sam's every growing and never ending misfortune.  It just doesn't seem like it'll ever get any better for Sam.  Now he might be damaged beyond repair.  So how's that going to mess with Dean's psyche?  Plenty I say. 
However, that's season seven.  Season six raised some interesting dilemmas for Dean.  He's always wanted that family life so bad, but once he got it, he wasn't comfortable in his own skin.  He learned almost tragically he couldn't have both.  There's also the concern that Dean hasn't dealt with his prior issues, like his trauma from Hell.  His alcoholism has gotten worse, even during his time with Lisa.  Twice this season it was hinted that Dean is taking drugs now too.  I came out of season six with one burning (and troubling) question.
How much more can Dean Winchester take?  
Let's go through the episodes of the season six and follow Dean's troubling journey from  being from broken over his brother's death to getting him back, sort of, to experiencing even harsher losses than he did before.    
Exile on Main Street
Dean has spent a year in domestic life, but it's anything but bliss.  He's uneasy and going through the motions.  That shows in everything he does.  The troubled expression each morning as the alarm goes off (we know he's asking himself why is he there), the late evenings spent on patrol to assure that nothing is after him, Ben, or Lisa, the constant glass of whiskey that's in his hand, and just the blank overall feeling in his daily life.  The passion, the fire, good or bad, is gone.  This is more than just a man that lost the most important thing to him, his brother.  This is a man that is learning the phrase, "Be careful what you wish for."  

We expected Dean to be ecstatic when he found out his brother was alive.  We figured he'd be eager to get back out on the road with him, right?  No, Dean has new obligations and a new set of guilt to overcome.  By just being with Ben and Lisa, he's made them vulnerable.  Now that monsters have found him, he must keep them protected now more than ever.  Sam is doing fine on his own, especially since he's been hunting for the last year with the Campbells.  Dean has more important matters than being his brother's keeper.  
Two and a Half Men
Yeah, I know, it's obvious it wouldn't last.  Dean's doing domestic life out of obligation, not desire.  After the incident with the Djinn, Dean moves Ben and Lisa again.  They're miserable.  When Sam comes to Dean with his baby problem because he had no one else to go to (I think, I'm still shaky on the motive) it's Lisa that demands Dean go with Sam or she'll kill him herself.  She knows how much he's itching for a fight.  
Dean has his heart to heart with Lisa.  He doesn't know what to do.  He wants Ben and Lisa, but he can't ignore what's in his blood.  Lisa knows one thing for sure.  He's not a construction worker.  He's a hunter.  She's hoping he can hunt and remain with them.  She wants him to be happy.  
The uncovering of the Impala to "Smoke on the Water" is the single most satisfying Dean Winchester moment in the past several seasons, perhaps the series.  They're back!  Him, his baby, the open road.  They've both been out of commission way too long.  Cue the iconic Dean Winchester smirk.  There's the man we all know and love!  I've never been more thrilled.  He could finally go back to being who he was meant to be and you know it felt good.  

The Third Man
Yeah, Dean Winchester's luck has never been that good, has it?  Now he's got another big problem.  He doesn't have to spend much time with Sam to figure out he's not right.  He already had suspicions that Sam was using the baby as bait in "Two and a Half Men."  Then there's Sam not flinching as Castiel tortures the young boy.  He tries to talk with Sam in the end and gets the brush off.  He wants Sam to open up about going to Hell but Sam, aside from saying out in the open he thinks Hell is still torturing Dean, claims he's okay.  Let the unnerving begin.  Dean's troubled look at the end tells us the bumpy road is still many miles ahead.  

Live Free and Twihard
Oh my, my, my my.  Poor Dean.  Never have we seen Dean go through more intense ordeal that this.  I'm thinking Hell was a picnic!  Being turned into a vampire is bad enough.  But when it happens because his brother didn't have his back and willingly watched it happen?  
Dean loses it all in this episode.  He loses Ben and Lisa by scaring them in his vampire state and shoving Ben when he got too close.  He lost his faith in Sam.  He's practically violated from a mental and physical perspective and then he almost loses his life.  At the end he's shaken very badly by all this.  On top of that, we get a chilling display of how dangerous Dean can be when that monster inside of him is unleashed.  He takes out an entire vampire nest singlehandedly!  It's fascinating, but it's scary too.  No wonder he fears that hunting side of him (or as he tells Ben later in the season, what he doesn't want at his dinner table).  I'm sure that unleashing that killer instinct in full force was not unlike being a torturer in Hell.  It probably scared the crap out of him.  

Of all that worries him the most though, it's Sam.  All he's ever wanted, his words from "Exile on Main Street" was to have his brother back.  He knows now he still doesn't and faces the real possibility that whatever monster is in the form of Sam he might have to kill.    
You Can't Handle The Truth
The title is clever, and oh so painful.  It's all about Dean.  He gets plenty of truth in this episode and it pushes him over the edge.  
He's clearly bothered about Sam.  He doesn't want to be anywhere near him.  Heck, he's practically ready to kill him (his line about wanting to kill Sam in his sleep confirms that).  The idea of killing this monster is somewhat easy to him though.  He's convinced it's not Sam.  When Bobby tells him there could be a worst case scenario, that this may really be Sam, Dean can't accept that.    
Dean has another big problem though.  Thanks to triggering the spell of Veritas, Dean has to hear the brutal truth from Lisa.  They can't be a part of his life.  Sure he sensed that to be true but to hear it, especially so candidly, it really crushes him.  He's still reeling over what he'd become in the vampire's nest.  He tries to swallow Lisa's words, but we see how much it stings.  He doesn't want to lose them.  
Despite the hard truth from Lisa, Dean takes the fact that he's triggered the truth curse as a blessing.  He can finally get the truth from Sam and know it can't be a lie.  Sam confesses he froze (chilling how easily he can lie isn't it?)  Dean accepts that and it changes things.  He and Sam are able to work  the case in harmony.  It's what Dean desperately needs (and always has), his brother by his side.  

Sadly, Dean isn't done with ugly truths.  First he has to face the truth about himself when he and Sam are captured by Veritas.  To hear these words come out of Dean's mouth absolutely killed me:
Dean:  It's the gig.  Your covered in blood until your covered in your own blood.  Half the time you're about to die, like right now.  I told myself I wanted out, that I wanted a family.
Veritas:  But you were lying.
Dean:  No.  But what I'm good at is slicing throats.  I ain't a father.  I'm a killer.  And there's no changing that, I know that now.

Oh man, to hear that and the see that it gets worse.  Dean is at a real low when Veritas goes for the truth from Sam.  She's spooked to find he's lying.  She knows that's impossible and concludes he's not human.  She wants to know what he is.  This stuns Dean to the core.  Sam did let him turn into a vamp on purpose.  Even though Sam helps Dean break free by flinging him the knife and they kill Veritas together, Dean turns a knife on Sam next. 
All that anger, all that frustration, all that self loathing and hatred, it all manifested into one spectacular act of violence.  Dean historically suppresses his bad feelings and pain with drink, but he constantly releases through violence.  Only then does Sam come clean with Dean, when he's threatened.  He admits something's wrong.  Sam tries to act sincere, but Dean can see through it.  He can't take it anymore, all the lies.  He loses it and beats Sam unconscious.  Ferociously.  He has to stop himself from killing him.  I call this Dean's "powder keg" moment.  We never thought he would do this to Sam, ever, especially since his entire life's mission has been to protect him.  But then again, Dean didn't believe this was Sam.  


# 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