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The Song Remains The Same
Poor Dean. He still clung onto that hope that he could save his parents from their awful fate. He was even willing to not be born to make sure that happened. Sadly he was too late. Mary was already pregnant and Michael found his way to hit the reset button. His conversation with Michael especially led to more discouragement and contributed to his increasing hopelesslessness. Still, there was some fighting spirit left, aka Team Freewill. He wasn't not ready to back down yet. 

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Dead Men Don't Wear Plaid

Yes, I'm putting this before "My Bloody Valentine" because it was filmed first and always intended to be first. Dean's world order view had changed, likely because of "Abandon All Hope." He wasn't about to lose another person close to him and chose to protect Bobby over saving everyone else. He was perfectly willing to let Sam go save the town. So, did this mean he was losing hope? Was he losing the will to fight? Maybe. I know seeing Bobby crushed emotionally at the end didn't help his crumbling psyche. Especially when Death raised the dead in Sioux Falls to break Bobby so Sam and Dean would say yes. Guilt doesn't do Dean favors.


My Bloody Valentine
The one were Dean falls apart. It was about freaking time! He had good reason. His faith in Sam had slowly been getting stronger and he had been able to rely on him more recently. That all was shattered here. No, sucuumbing to Famine's spell wasn't Sam's fault but it was enough to shake Dean to the core. He was reminded under no uncertain terms how dangerous Sam was, how the demons knew how to manipulate him and exploit his weaknesses. He also figured out that without Sam by his side, he couldn't do this alone. He needed help. His breakdown at the end was his somber admission that he was human afterall.

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I know, what about Famine's chilling words that Dean was already dead inside? He had no deep hunger. In a way that was true. At this point, he was just going through the motions. His faith in everything he ever believed in was dwindling. He was tired, discouraged, and so hopelessly lost. He didn't know what else to do.   A weeping man though pleading to God for help is not someone who was completely dead inside. It was more like the act of a completely broken man. Sam couldn't help him and even Castiel was growing more vulnerable too. He really believed he couldn't save himself either. He may not have been dead inside, but he thought he was.

Dark Side of The Moon

Dean's hopelessness and disillusionment hit rock bottom. He had only had one hope left, finding God. Seeing Sam's happy memories being when he ran away from family, aka Sam's best being Dean's worst,   was the final straw with his brother. Sam could not be trusted and would eventually leave him. When he got the message from Joshua that God wouldn't intervene, that was all it took for Dean to lose all hope and faith in everything, especially Sam. The tossing of the amulet symbolized that everything he held dear didn't matter anymore, including family.

99 Problems
Sure he was killing so called demons, but this was all the backdrop to Dean comtemplating his next move. He was again going through the motions. Sam tried his plea to him, but Dean figured he had no choice left. He wanted all this to be over and saying yes to Michael was the only option left. His thinking was the last act of a beaten man.   He didn't consult Sam and Castiel on the plan though, probably because he knew they'd try to stop him. Which they did. 


Point of No Return

Sam and Castiel stopped Dean, but he reacted by going into defensive mode. He was rude to Bobby, he squabbled with Castiel, and the heart crushing things he said to Sam...oh it still breaks my heart. Sam didn't lose faith though and Dean finally saw the light in an extraordinary way. He couldn't find it within him to disappoint Sam after Sam put a huge amount of faith in him. Heck, Sam risked the welfare of humanity in the belief that Dean would do the right thing. How could he not go back on his "yes"? He wasn't dead inside after all. He finally made peace with Sam too, his decision being the ultimate act of forgiveness. 
Dean also had this angel/whore killing mojo going which may or may not have been related to him thinking about saying yes. It was perplexing, but I think it was meant to show that Dean was a true servant of God. So Sam wasn't the only one with the extraordinary faith in Dean. I'd call that a pretty big character leap. The guy is special. 

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Hammer of The Gods

A rejuvenated Dean tells Gabriel to go kill his brother. I don't get it either, especially after his big reconciliation with Sam. We cover our ears and pretend it didn't happen. Lalalalalala!!!! I can't hear you!

The Devil You Know
There's a big role reversal here. Dean in a desperate situation, just like Sam in season four, choses to trust Crowley, going against Sam's protests. He figures out that uncertain times call for the previously unthinkable, like trusting a demon. Just like with Ruby at the end of season three, the consequences of that choice remains to be seen. 

Dean was back to his subdued and somewhat depressed self (told you Hammer of The Gods was a fluke) but this time he had fight in him. He was still leary of their chances though. He had to have a cool head though to hold together an increasingly destabilizing Sam. He handled Sam perfectly. He didn't judge or chastise and even let Sam see Brady knowing what he would do. His attitude toward Sam had definitely changed. Sam's cold blooded calm when he killed Brady though unnerved Dean pretty good. He didn't hold that against Sam though. That was his way of seeing how much his little brother was changing.

Two Minutes to Midnight

Speaking of unnerving, this had to be the most intensely frightened Dean has ever been in his whole life. After all, not too many mere mortals get to have pizza with Death and live to tell about it. This visit with Death didn't do much for his already rattled state, but that was nothing compared to the deal he was forced to make. In exchange for the ring that they needed to trap Lucifer, he had to let Sam handle his own fate and not intervene. In other words, he had to go against everything he's ever done in his life, aka his identity. Such a thought was so heartbreaking for him that he actually considered going back on his word to the most powerful being in the universe. Luckily, Bobby saw the light and convinced him otherwise. So what was he afraid of, losing or losing his brother? Clearly the latter. Even the world ending wouldn't be worse to him than losing Sam.

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Swan Song
Oh Dean, what did this boy not go through? He had to let go. He had to let Sam take control of his own destiny.   All he could do was be there by Sam's side and watch while his brother took on the most horrifying burden imaginable. He wasn't happy at all about the plan but said nothing, brooding for the most part when it came together. When the plan failed at first, Dean was crushed but not broken. The end of days was here and all he could think about was Sam musn't die alone.
Dean managed to get through, or the car that he drove there did, but it was their brotherly love that saved the world. Still, it was an empty victory. All Dean could do was helplessly watch knowing either Lucifer/Sam would die or Sam would fall into the cage, thus spending an eternity in the worst possible Hell imaginable. When the latter did happen, Dean's fulfillment of his promise to have that apple pie life with Lisa was done with an empty heart. As Chuck said, all he wanted to do was die or bring Sam back but did neither only because he promised. His worst possible fear came true. He may have been with Lisa but had never felt more alone.
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So how does Dean go on in season six? He doesn't look comfortable in his life with Lisa but will he give it time out of obligation? Is it possible he won't have that luxury if duty calls, especially when Sam returns? How about his emotional state? Will he have anymore fight left in him? Does saving the world matter to him anymore? Will he end up like season one Sam and be a reluctant participant dragged into the life? I must admit, I'm far more intrigued about the season six possibilities for Dean than the beginning of season five. Adjusting to a normal life is the harshest test for any warrior returning from the battlefield. I can't wait to see how Dean fares.
So that's season five Dean Winchester in a nutshell. Coming up, season five Sam. Talk about having inner demons.


# elle2 2010-06-19 10:25

Once again you've done an excellent job. I must admit that you give me some things to chew on regarding Dean. I did not like the rollercoaster Dean in Fallen Idols thinking it was out of character but upon reflecting on what you wrote it does make sense, of course he's resentful but trying, couple that with distrust and being out of step with Sam it's no wonder Dean is all over the map in Fallen Idols. I reassess my initial opinion.

Dean's emotional journey this season was a difficult one, for Dean, but overall it showed the massive burdens from prior seasons as well as the self-imposed ones. I really like how you summed up that in the end he became what he feared, 'the last man standing'. Dean has always said that things (be it the world or this fight) will end bloody but that doesn't mean they shouldn't fight. Dean was resigned to die in this battle but he was going to go out swinging. Now the battle is done and he didn't die and has nothing to swing at; oh, the despair.

I am very intrigued at where this will go in Season 6 and with the big dramatic arc done and all of five years spent here with a new arc beginning, which may hold remnants of what has gone before, I think this is a time for showrunner Sera Gamble to do what she has done so well all along, focus on the intimate aspects of the heroes (and yes, I broaden that to include Bobby and Castiel). I'm very excited for what is to come in Season 6.

Looking forward to your thoughts on Sam.

Great job, Alice. I always look forward to these insights from you.
# Randal 2010-06-19 11:46
If anyone's suffering from PTSD, it's this poor guy, and in lieu of typing the same stuff using different words, I'll just say 'what elle2 said.'
# Bevie 2010-06-19 14:30
I agree with elle2 that this was an excellent job. I am so very sorry for poor Dean for what he went through in season 5.

Re Hammer of the Gods, when Dean advised Gabriel to kill his brother, I thought he was showing Gabe how impossible that was, and maybe letting Gabe understand why Dean could not be taking Gabe's advice to do the same. But then we can all interpret things a little differently. I just didn't take what he said as literally what he meant, as it did seem very harsh.

In season 6 I can hope that this terrible burden of guilt and hopelessness can be lifted from his shoulders and let him be a bit more like the season one Dean that I fell in love with. Let the PTSD gradually fall away with time and let him find his previous enthusiasm for his family's business. There's still lots of monsters running amuck out there that need to be done away with. Bring back the salting and burning!

And please please please don't have anything bad happen to Lisa and Ben for being good people and taking Dean in. Sera, I'm talking to YOU!
# Jasminka 2010-06-19 15:44
Those people that phrased that 'the promise of Dean's character direction at the end of season four went nowhere in season five' clearly have been watching a different show. On the contrary - he went a long way. Considering the trust issues to the immense loneliness he felt and the intended fate they were facing, Dean took some very brave turns to come to terms with what had to be done - even agreeing to Sam's saying Yes to Lucifer.

For a guy whose modus operandi has mostly been withdrawing into himself and playing it cool, being that open with his fears and issues was a step that required major courage.

I was afraid at first, in terms of psychological continuity (well, you know me), that they would just drop the PTSD thing and make Dean be as he was once which would have been illogical (and unnecessary - he will come out of this having grown more ,just as Sam).

Thank you for your insights. Coming from a person who does not deal in psych-stuff professionally, you again prove that a huge part of psychology is common sense and empathy. Thank you so much for this, Alice. Jas
Adi Darklighter
# Adi Darklighter 2010-06-19 23:41
I agree with you almost with everything! :geek: That was an excellent character analyzing for Dean! You took the words out of my mouth! I didn't think "Hammer of The Gods" was a fluke, I thought it was good that he was trying every possible solution. Too bad Gabriel had to die cause he's not as strong as his brothers Lucifer and Michael. I liked the guy. But at least he helped them by explaining them how to get to Lucifer's cage and everything.

I also hope Lisa and Ben wouldn't get hurt for taking Dean in. I don't care if he has to leave them to go back to hunting, but please keep them safe!

Anyway, excellent job! Looking forward to the season five Sam article!
# alysha 2010-06-20 08:19
Dean's character is always developing and growing. I loved your retrospective! It seemed a lot of people thought Dean was out of character in "Fallen Idols" so I was happy to see you had my take on it. Dean was not really comfortable being with Sam, but he knew it was the only way or the future he'd just seen would come true. So yeh, he was a bossy jerk, but he was still coming to terms with what Sam did in S4.

Last night my friend watched "Bloody Valentine" for the first time. she said at the end with famine: "Why doesn't Dean pick up the knife?" I said, look at his face. Look how shocked he is. Dean was very passive and shaken as he watched Sam go all powerful on Famine. Watching Sam be evil ALWAYS unnerves por Dean. And why wouldn't it?

I do also question "Hammer", was he encouraging Gabriel to kill Lucifer? Seems that's what Gabe got out of the conversation!
# Julie 2010-06-20 12:34
Thanks Alice for this wonderful analysis of Dean in Season Five, as you say `The guy is special`!
What a roller coaster of emotion we went on with him this year, how anyone can say that his characters direction went nowhere is totally beyond me, I think these are the same people who are still annoyed because he never did say `Yes` and they didn`t get `the big fight`, thank goodness. Like Jas I think some people watch a different show to the one we do at times. What on earth more did they want hin to through.
We saw him hurt and isolated with all trust gone, hit rock bottom to be saved by the faith Sam showed in him and then have to go against every familiar thought , feeling and instinct to witness Sam making his ultimate sacrifice.
I love your set up for Season 6 and I cannot wait to see where we go next, the prospect of Dean as a reluctant hunter is intriguing.
# Nathália 2010-06-21 16:54
I go to marry with dean !
because I love Jensen Ackles .. :lol:
# Sablegreen 2010-06-21 18:45
LOVE your first screencap, Alice! Great article too, but I'm going to be the 'odd man' out here, and say I do disagree with some things. First there were a number of times where both Sam and Dean were out-of-characte r and 'Fallen Idols' and 'Hammer of the Gods' were two of them. For some reason, many times the characters were written for the episodes, instead of the episodes for the characters, which is why they were off. That also lent itself to a lot of the 'patch work' feel to the season.

Also Dean's character didn't go where expected in s5. Did it develop, yes, and your analysis of that was great...but that's not what was expected. The real 'Dean' would never has lost faith in his brother to the extend they portrayed. And he would never have left his brother go in the pit alone. He would have saved him, or gone in with him.

Where he will go in s6 is unknown. I hope the powers-that-be take to heart the complaints about Dean's character. A lot of people would like to see the 'old' Dean back, myself included.
# Evelyn 2010-06-24 00:37
Thank you for this very introspective look into Dean's psyche, Alice. Watching Dean's spiral downward this past season has been heartbreaking and very difficult at times. Watching him lose faith and trust in those closest to him, including himself, hitting rock bottom and then trying to dig himself out of the hole called depression have all been very realistic and to me, very personal. I found this season introspective, cathartic, heartbreaking and I also enjoyed it immensely. Thanks for recapping the highlights of Dean's journey so poignantly. A lot of food for thought, especially as we go into unchartered and unknown territory with Season 6.

Additionally, I have to side with you when you responded to Sablegreen that you have to agree to disagree. I truly believe that the 'real' Dean can and did lose faith in his brother. He may not have lost it completely, there were still shreds of that faith and trust within him, or else how could he have turned around at the end of Point of No Return and killed Zachariah and regained a greater trust and belief in Sam. So, it was still there, just buried real deep within himself.

When family betrays you, it cuts deep. Deeper than any other kind of trust broken. And that is very, very hard to overcome and forgive and forget. Sam betrayed Dean in a big way and Dean did his best to let it go. But with that kind of betrayal and loss of faith and trust, even though you get to a place where you can start trusting again, there is always that underlying doubt and feeling within you. Snarky comments or actions come out when you least expect them to. You don't mean them and instantly want to take them back, but those comments and actions are all a product of the doubt that still exists deep within your soul. This deep-seated hurt takes a long time to heal, if it ever does. Especially if you experience additional instances of being let down by those people. It's a hard road to climb back from for the ones seeking redemption, because for the one that lost the trust (in this case Dean) your expectations are higher than normal and that is not an easy way to climb back into someone's good graces. So Sam really had his work cut out for him and I think he earned a lot of Dean's faith and trust back by the end of the season.

It will definitely be interesting in Season 6 to watch how Sam and Dean repair their relationship. Even though their halves will be made whole again by being together, there will still be a lot of reparations and mending fences to be done to get their relationship on the healthy side of the fence. And being that Sera, as you said, is known more for dealing with the more intimate issues of the brothers relationship, I look forward (and hope) that we will be able to see their relationship evolve stronger and better than ever.

And as for Dean going into the pit, I also agree that if his body were not as broken as it was, he would have jumped in the pit right after Sam and would willingly spend eternity in hell with his brother.

I can't wait to see what happens next. Is it September 10 yet?
# Sonya 2010-06-25 14:23
I agree with everything you said, most especially what you said in the "agree to disagree" reply. I certainly hope the PTB continue on with their vision. It's like writing a fanfic. I was once reading one where the person said the readers had taken over and was dictating what she should write. It's no longer your vision then. It's someone else's. The SPN vision has never let me down and as long as they stay on their course, it never will.
# BagginsDVM 2010-06-29 14:31
Thanks, Alice, this was a great article. I agree with your analysis, & ditto for Elle2's & Evelyn's comments too. I think Dean's sometimes rollercoaster actions & behavior made sense for the most part, considering what he's been through. He's human; he's going to have ups & downs in his attitude from day to day, even if he weren't dealing with the apocalypse! So even if his characterizatio n in a particular episode seems off to me on the 1st viewing, it usually does make sense on the 2nd or 3rd viewing, as I think about the character as a whole over the past 5 years.
I am very much looking forward to season 6!
# Karen 2010-07-01 10:03
Hi Alice
I loved your article on Dean and your take on the changes and struggles he went through.
What really stood out for me was the gruffness of Dean’s voice, so serious and angry most of the time. Even the delivery of his one-liners had become humourless and deadpan, no longer spoken with that Cheshire smile and wittiness. And I have to admit I really missed that in Dean, I truly missed the old Dean, but I also understood his decline in faith, trust and hope.
As if the experience in Hell wasn’t enough but to have the weight of the world now being put on your shoulders. To find out you’re a vessel for an Archangel and are expected to fight Lucifer in the vessel of your brother. To have your surrogate father become wheel chair bound because he was trying to save you. To have two of your closest friends die while trying to help and protect you. And on top of that to still be feeling the betrayal and mistrust of the one person that you spent your whole life protecting, defending and sacrificing yourself for.
Yeah I could see why Dean was a little depressed.
And who wouldn’t be, who wouldn’t be changed by all this? With our own experiences in life, are any of us the same person we were 5, 10, 20 …. years ago, I know I’m not.
Thanks again Alice.
# Ardeospina 2010-07-09 23:23
Hey, Alice. I'll just chime in here to say very well done, and I agree that Dean went through an incredible journey this season. I, for one, thought his progression did make sense for his character. It was heartbreaking to watch him lose faith in everything and to spiral so far downward. Can't blame him, really, because he certainly had enough happen to him to warrant that position.

As for wanting the "old" Dean back, I agree that it would be wonderful to see him so optimistic and hopeful, but think that Dean is long gone. After all that's happened to him, how can he possibly go back to that state? Maybe seeing the old Sam and Dean relationship is about all we can hope for at this point.

I, too, am really curious to see how Dean will fare at the beginning of season six. Adjusting to civilian life is going to be super difficult.

Thanks for this great look back at season 5 Dean! Now that I'm finally catching up on articles, I can't wait to read about season 5 Sam!
# zahra 2010-07-26 11:31
hey alice
this article was awesome.oh god,i always love dean and sam or more dean because i'm just like he always said'nothing is more than family'.
Syddie Baby
# Syddie Baby 2010-09-01 00:52
In "My Bloody Valentine" one of my theories is that dean may have hungered for something after all. to not feel anything anymore because all the loss and pain was killing him inside. famine saw this and told dean the reason was because he was dead inside. After all, demons lie right?