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. 
 
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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



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.



 
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.





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. 

  
 
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. 




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.



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. 





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.


 
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.
 

 
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.

The dying of Dean began early in this show. When we look back, we detect signs of exhaustion and emotional wreckage, going beyond the disappointment of Sam leaving home, of dad doing his thing without really informing his eldest son (in the course of which just leaving while Dean was working a gig in New Orleans without letting him know why – John had a lead on YellowEyes – or when he planned on coming back, thereby sparking worry and fear in his loyal son).  

The moment Dean realized that his father had sold his soul for him to live we witnessed the knife sliding in and fate has been twisting it in his flesh ever since. He had been left with the impossible task of protecting Sam in more ways than one, not being there in the crucial second Jake’s blade cut through Sammy’s spinal cord, killing him. Dean had followed the Winchester tradition by trading his own soul for his brother’s life, but had not managed to keep Sam from going dark side (which he did for the same reason: save Dean or at least execute revenge).  

Dean then died countless times under torture in hell, returning from the pit a broken, scarred man only to learn what he did down there: break the first seal, setting train Apocalypse in motion.  Whatever he did he was confronted with the same truth others threw in his face: that the Winchester destiny was forged from indestructible material – and that Dean and Sam were going to be lethal enemies in the end, because it was written. Abel and Cain. Michael and Lucifer.   Or so the angels say.