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It's that time of year, another chance to go through the season gone by and examine closely how the beleaguered Winchester brothers fared in their fight against all odds. Needless to say, we're talking some major damage to their emotional and physical well being. Thanks apocalypse! Up first, the elder Winchester. 
Dean's character progression, much like the past two seasons, took a really intriguing turn in season five. Season three was Dean's season of self actualization. Season four was all about his character test. Season five too had plenty of tests, but for Dean it all ended up being about survival. Not just his though. So much more was at stake than his and Sam's safety. He had to step up and save the world. By the end he suceeded against impossible odds but it cost him everything. He became exactly what he didn't want to be, the last man standing. He reluctantly went into a new life mired with huge survivor's guilt, shattered faith, and a lost sense of purpose. Once again, Rufus Turner's "There ain't no happy ending" rings prophetic for poor Dean.
I've read a lot of complaints where the promise of Dean's character direction at the end of season four went nowhere is season five. I don't see that to be the case at all. Dean's character did go through some big shifts in season five, sometimes perplexing shifts. However, I think there was consistency with season four as well as the prior seasons in the direction he took. Sure he was more vulnerable this time, but considering how much has been thrown at him becoming worn down by it all was understandable. He came out of it all the tragic hero, which was a bit better than Sam's outcome, the martyred hero. Or, maybe not. Dean would have traded places in an instant.
As I left off in my season four analysis, Dean's major shortfall and biggest hanging issue was his relationship with Sam. He fought the good fight against Zachariah and convinced Castiel to fall from grace for doing the right thing, but his handling of the Sam situation led to disaster. Lucifer broke free. So that's how he started season five. He had to take on the Devil and try to rebuild his broken relationship with his brother.    Let's look at the key episodes and see how Dean progressed from that point. 

Sympathy For The Devil

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Dean tried, he oh so tried. Lucifer was free, Castiel was dead, he was wanted by angels, and he tried to derive a plan out of a hopeless situation while at the same time having lost complete faith in Sam. After all, despite his intentions, Sam did the unthinkable. He betrayed him for a demon. Dean tried to see past it and focus on task but the hurt was too deep and the betrayal too raw. He couldn't forgive. Despite all that emotional turmoil though, Dean drew the line in the sand that defined the battleground of the season. He wouldn't be a vessel. He'd fight his way. He just didn't believe that Sam had his back. This all kicked off his feelings of isolation that grew throughout the season.

Good God Y'all
Dean saw the hard reality, his life's mission had to change. Sam no longer could be his main priority. Despite all the mistrust and the hurt protecting Sam at this point was instinctive. It was what he wanted to do, but the world needed him more and this great burden from here until "Point of No Return" ate away at him slowly. When Sam suggested they part at the end Dean agreed without a fight. He made the decision with his head instead of his heart. Sam leaving meant one big burden off of him, freeing him to focus on the world alone. Yeah, reality caught up later in a hard way.

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Free To Be You and Me

Dean was still pretty delusional here. The burden of Sam may have been gone, but the emptiness of being alone became the issue. He tried to convince Castiel he didn't need Sam but who was that speech exactly for? I didn't buy it. I doubt Cas did either.

The End

Dean saw a lot of crap in this one. Was the future real or fabricated by Zachariah? I'm going for the "what if " reality. What if Dean and Sam stayed apart? Sam did eventually say yes to Lucifer for reasons we found out were purely strategic, so we could assume the same reason happened in this reality. So, what went different in this scenario? Easy, when Dean chose the world over his family he let the Impala rot and he let his morals slide. Without the Impala there to trigger the memories, without that strong brotherly bond, Sam failed in this reality in his plan to overtake Lucifer. In other words, neither could take on the world alone.

So, what made Dean see the light? What made him realize that he and Sam could only be stronger together?   I can only assume seeing Sam become Lucifer did the trick and I'm sure he didn't like his future self either. He had to go the other way. He didn't take Sam in with open arms though and an "all is forgiven" attitude. There was still some reluctance there but at least he followed his gut instinct. The pain over Sam's betrayal was still too raw though. So, enter the bittersweet reunion.

Fallen Idols
No, he didn't forgive Sam. He put his brother through the ringer instead. Many thought his actions were out of character but I thought they made perfect sense. He knew that he must stick with Sam but there was still that lingering resentment. In the end he got it out of his system and took Sam up on his request to meet him halfway. It was a good step forward that lasted about one episode.

The Curious Case of Dean Winchester
There was way more to Dean than meets the eye in this one. Dean essentially proved that older is not wiser. He and Bobby both had tremendous blinders on when it came to Sam and both were too caught up in their own sorry predicaments. Neither could fathom that Sam was a crafty poker player that could have gotten them out of this the honest way. Both instead stayed overprotective of the "snot nosed kid." In Dean's case though, his blinders extended beyond Sam. He took on the burden of Bobby's welfare too and tried to fix this mess by himself. This contributed to that long spiral downward. He had faith in no one but himself, even when given the limitations of being an eighty year old man. He may have convinced Bobby he wasn't useless, but he still didn't have much faith in Sam and only added to his growing internal pressure.

The Real Ghostbusters

This ended up being a refreshing perspective for Dean, his life isn't all that bad. Too bad that lesson that went nowhere. Still, it was nice for Dean to see the other side for once, wasn't it?


Abandon All Hope
If any episode drilled a nail deep into that Dean Winchester fractured psyche hard it was this one. The title was meant for no one but Dean. His self imposed burdens took their toll and the losses of Ellen and Jo were a major turning point for him. A turn downward. Losing people to Dean has always been hard but he couldn't take losing friends anymore. Especially people he always considered more than friends, more like family. His failure to kill Lucifer on top of Jo and Ellen's demise made it even worse because their deaths were for nothing. To Dean, there's nothing worse. This outcome will haunt him for a lifetime.

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Sam, Interrupted

The Dean Winchester mind bender. It was a very rare glimpse at what goes on inside that noggin and it was not pretty. We had to wonder how the boy could even function. He admitted to not sleeping much, that he drinks way too much and has never been involved in a long term relationship (except for the glaringly obvious choice, but I assume the question was about an intimate relationship). Sam insisted that they take the job because of Dean's depression over Ellen and Jo, showing us his already fragile state. So when the crazy spell started working, Dean's inner frailties surfaced in a stunning way. His single handed burden now involved saving all six billion people on the planet. That intense internal pressure surfaced, that inner fear that he can't save Sam, he can't save the world, he can't save himself. It all was going to burn and it was his fault. Once he got free of the spell, he took all that anxiety and did the worst possible thing. He buried it. Then he ordered Sam to do the same. Oh yeah, it came back to bite him.    


# 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?