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.  

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