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.  

Family Matters/All Dogs Go To Heaven/Clap Your Hands if You Believe
Once Dean got the bombshell from Castiel that Sam was soulless, his attitude changed.  It was no longer a game of trying to guess what Sam was.  His focus switched to doing whatever it took to get Sam's soul, thus the real Sam, back.  In the meantime, he set the rule that he was calling the shots.  He wasn't going to give Sam equal footing given his state.  That worked out okay in "Family Matters" when Sam chose to stick with Dean, and also in "All Dogs Go To Heaven," but by "Clap Your Hands if You Believe" Sam started having doubts about getting his soul back.  Dean suspected as much too when Sam said no to the leprechaun's offer (that still sounds pretty absurd, doesn't it?).    

Still, in all those episodes, this is the Dean that stands out most in my mind:  

Okay, maybe this too:

Caged Heat
Dean's issues fell with another family member, Samuel.  Oh man, I definitely don't want to be on the wrong side of this:


He just doesn't take backstabbing well, does he?  At least Sam was sticking by him, until the end.  Castiel's warning to Dean is pretty clear about what could happen if he gets Sam's soul back.  Surviving could be worse than dying.  "Paralysis, insanity, psychic pain so profound that he's locked inside himself for the rest of his life."  Dean decides the risk is worth it, they can deal with the complications when they get it back.  Dean's able to make that choice, but an eavesdropping Sam doesn't appreciate that decision.  
So why is Dean so easily able to make that choice?  It's clear he's not seeing soulless Sam as an equal.  He's seeing him as someone he has to make choices for.  Even Crowley and Meg say that getting back his soul is a bad idea.  At the end, when Sam raises the issue, Dean won't back down.  Sam says he's telling Dean something he doesn't like.  This actually parallel's Sam and Dean's struggle through the entire series.  All Dean has ever wanted is Sam to be human.  To act human, to stay human despite the demon blood inside of him.  Here is no different.  No soul is not human.  He's willing to risk Sam suffering in very human ways in order to keep that humanity.  The un-human Sam begs to differ, for his only purpose is survival.  
Appointment in Samarra
It's the ultimate, mega huge, slap you in the face Dean Winchester character test.  Dean  is desperate now.  He has himself killed (for a few minutes anyway) just so he can talk to Death and ask for Sam's soul back.  He even wants Sam's soul returned undamaged so that he can convince Sam to go along with the plan.  It's obvious he needs his brother back in the worst way when he gives his letter of final words to Dr. Robert.  It's addressed to Ben, not Sam.  He knows that whatever he says, Sam won't care. If there's one thing consistent with Dean's life though, these risky choices come with a high price.  

Dean gets to be death for a day.  Why?  If you were Death and you had a chance to teach the one guy who wrecks the natural order on a regular basis a lesson, would you pass that up?  This lesson has been a long time coming and as hard as it is to see Dean go through that, he had to see the consequences of his choices.  His stubborn defiance kicked off a chain of random events that ended up getting innocents killed.  Not to mention the person he chose to live, a 12 year old girl, would have chaos and sadness follow her the rest of her life now that she's alive.  Wow, that sounds very familiar.  Sam Winchester anyone?   Or lets take it farther.  Mary made the original deal and see what's happened to their family since then?  That's another topic though.  
Dean must see this first hand, for he's always been a "seeing is believing" kind of guy.  He gets the message.  Knowing what he knows now, he would have killed the girl first.   He has new appreciation for the natural order, but that only puts him in more of a pickle with Sam.  
Dean decides when he makes the deal with Death that a wall in Sam's mind is better than nothing.  It's a compromise he's willing to live with.  He knows why he must take this awful risk.  Because as he's learned, anything not human is usually dangerous.  RoboSam will stop at nothing, and his attempt on Bobby confirmed Dean's worse fears about Sam remaining soulless. 
Ever since season two, Dean has done everything he possibly could to avoid making the most horrific choice he could, killing Sam if he became too much of a threat to humanity.  It's been his unwavering commitment to save Sam from this awful fate.  He's always known that if he couldn't save Sam, he'd have to kill him.  After he stopped Sam just in time from killing Bobby and they had him restrained in the panic room, Dean sadly knew there was only one choice left.  He couldn't leave Sam locked up and he couldn't let him go.  He never said it, but his hopeless expression as he went upstairs for a breather said it all.  He'd have to kill Sam.  This is indeed Dean's worst nightmare come true.  Lucky for him, Death was upstairs waiting.  
Even at the end, when Sam was screaming, Dean knew this was his only option.  It still hurt him to do it though.  Sam's scream reminded him of the fact that no matter what, he was still putting his brother through a lot of pain and risk.  He wasn't about to defy the natural order again though.   

Like A Virgin
Dean at this point desperately needs some relief.  It's been ten days since Sam's soul was put back in and he remains in a coma.  Dean's now frantic with worry over if Sam will wake up.  Summoning Castiel doesn't help.  "If you wanted to kill your brother, you should have done it outright."  Dean's look of guilt after Castiel left angry says it all.  He had no choice, Sam couldn't walk free (I loved his T1000 opening fire line).  Still, what was Sam up for when/if he wakes up?  
When Sam awakes with no memories of Hell or being soulless, Dean is more than willing to accept that as good (plus a meaningful good old fashioned brotherly hug doesn't hurt).   "As far as I'm concerned, it's a gift horse. And I'm not looking for teeth. I'm sending Death a damned fruit basket."  However, he's got a new problem.  Sam knows something isn't right.  The wall is itchy and he wants to scratch.  

Dean won't talk about what happened in his life in that year and a half either, especially with Lisa and Ben.  Part of that is too much pain, but another is he doesn't want Sam remembering why they ultimately split up, because Sam returned.  That would be kicking that wall.  It's really sad for Dean, having his brother back, but not being able to talk to about that hole in his life.  In the meantime though, Dean is looser and feeling better that "the real" Sam is back (that point I'll debate in A Deeper Look At S6 Sam Winchester).  He's starting to have fun again.  That is until Mother of All emerges.  Now he's got a new problem.  
Mannequin 3:  The Reckoning
Dean gets to say "I told you so."  Sam scratches the wall and the consequences are dire.  Actually, it scares the crap out of Dean more than Sam.  He decided to give Sam latitude and try it his way but when things got dicey, he pulls authority.  No more digging into that missing year.  Overprotective big brother is something too hard to shake.    
Dean's forced though to deal with his "year."  Ben sends an emergency call and Dean is practically shoved into the Impala by Sam to go check it out.  It forces Dean to have an honest face to face with Lisa.  He had to see that Lisa was getting on without him, but convincing Ben is harder.  He has to leave, to say goodbye for their sakes, no matter how much it hurts.  It's clear he still doesn't want to let go though.  He also sees how hard it's been on them and knows he can't go back.  This really depresses him and his only comfort is a pep talk and a thank you from Sam.  At least he has his brother.  

The French Mistake
Buried in all that screwball madness, there is a touching sentiment that comes from Dean.  He's willing to stay in the alternate reality if Sam could continue to have that good life.  A life that doesn't exist for them in their world.  Sam has wealth, a hot wife that loves him, no angels or demons to screw anything up, and all the bad in the world exists only in TV land.  Who wouldn't want that, let alone someone who has been cursed since the day he was born?  He gets though the answer he really needs to hear.  Sam doesn't want to live in a world where they're not brothers.  

My Heart Will Go On

This episode is another reminder of how important family is to Dean and his unwavering loyalty to them, even extended family.  It's all he has.  Sam, Bobby, and even  Ellen and Jo, that meant more to him than anything.  In the end it's all clear, they look out for one another.  Oh, and Celine Dion sucks (yeah, I had to get that in there).  

Dean Winchester in the old west is a dream come true!  Who doesn't want to watch the equivalent of a wide-eyed jovial kid loose in a candy store?  Best Dean Winchester episode ever.  We haven't seen this side of Dean in so long.  Loose, freewheeling, happy, he experiences the perks of the job for once.  He gets to be a cowboy!  Sure, the serape thing doesn't work out in old west Wyoming, but he adapts.  We knew he would.  He becomes the sheriff and looks oh so good doing it.  He's even telling raunchy jokes again!  Joy, joy, joy.  It's good to see him back into old form.  If anyone deserves this break, it's Dean.  
Mommy Dearest
Dean is back in his old form.  His focus is so clear, get the bad guys and protect the innocents.  He gets to be funny too, coming up with the best name ever for the new species of monster.  
He's still uncompromising though and draws the line when acts of humanity are required.  Take the case of the two boys they "rescued" after their parents were murdered.  It's something he and Sam could painfully relate to.  Castiel gets angry that they want to take the boys to their uncle because there's a bigger picture.  Dean refuses to stay.  These boys need their family and that matters most.  Sadly it's that human reaction that's used against them, but Dean wouldn't have done it any different.  
It's also cool to see Dean Winchester have his fighting spirit back.  They aren't going to take any more harm from Mother of All.  He will stop her once and for all, even going back to his reckless ways to do it.  He won't deal with her, for he doesn't make deals with monsters.  The memories of being forced to work with Crowley are too fresh.  The best part though is he defeats Mother of All doing what he used to do, take huge risks that border on reckless.  He's got guts, you've got to give him that.  Come on, you were all cheering wildly when he said "Bite me," weren't you?  Welcome back Dean Winchester. 

The Man Who Would Be King
Sigh.  It doesn't last.  

Poor Dean.  Between this and the next few episodes, an old theme is revisited.  Anyone that has ever cared for him has left him.  First there's his unlikely friendship with angel Cass, someone he regards as family just like Sam and Bobby.  Just like Sam a few years ago, Castiel has pulled the ultimate betrayal.  He's chosen a demon over him.  Dean takes this hard, very hard.  Dean learns of the plan, Castiel is going to open the door to Purgatory.  He can't allow that to happen.  
He and Bobby try to keep Castiel out, but it doesn't work.  Castiel wants him to back his plan, but Dean refuses.  He tries to appeal to Castiel and their deep bond, asking him to trust him.  They can find another way, they can fix this.  Castiel pushes the proverbial knife through his heart though, the plan doesn't need fixing.  Dean takes that as the ultimatum.  He's going to stop Castiel and his plan with Crowley.  Castiel challenges him to do just that and doesn't seem threatened.  After all, Dean's only a man.  Ouch.   
Let It Bleed
It's a forgone conclusion that Dean was going to become unhinged over Ben and Lisa being taken and threatened.  He went back to torturing, he single handedly took out a group of demons, and man did he let his violent side take front and center.  His behavior even got Sam drinking again!  All that's stereotypical Dean though and to expect anything else could be considered out of character.  But why he did that is something he's said before.  "Lisa and Ben, wherever they are, that's 100 percent on me."  He won't even accept Sam's help.  Oh yes, this man is drowning in guilt.  

Dean left his calm thinking behind and ruled with his heart.  All that emotional rage clouded his judgment.  I certainly understand that given the circumstances.  However, it left Dean vulnerable.  He's been struggling ever since "Mannequin 3" over his guilt of coming into Ben and Lisa's lives and breaking their hearts.  He knows despite his wants and needs, he should have never exposed them to his life.  He sees them suffer here again and can't take it anymore, especially when Lisa almost dies.  He can't take Ben being angry at him anymore.  In a moment of weakness, he has Castiel wipe their minds.  They won't remember he existed.  
This choice crushes Dean, and gets Sam angry (if anyone has a sore spot about having memories wiped...).  Poor Dean, he actually has to say goodbye to Ben and Lisa by telling them he was the guy that hit them in a car accident and he's sorry.  They were forgiving, not knowing the real truth.  No wonder Dean turned away and fell apart. He didn't want forgiveness.  He knows full well he's far from earned it.   This loss is as devastating as when he lost his Father.  The overwhelming guilt, the despair, the loss, this is going to haunt him for a very long time.  

On the other side is his strained relationship with Castiel and this is a headscratcher.  Remember "When The Levee Breaks?"  How Sam pleads with Dean to back him up, come with him to kill Lilith?  The deal breaker was Ruby.  Dean even calls Sam a monster and says he couldn't be trusted.  "Let It Bleed" plays out that scene all over again.  Castiel appeals to their friendship, to all he's done for Dean.  "Has anyone but your closest kin done more for you?"  Yet Dean refuses to stand down.  Why?  Crowley.  I do wonder, wouldn't Dean have learned?  Sure he was right with Sam, but that did so much damage to their relationship.  Wouldn't it have gone better if he had stood by Sam's side, no matter what?  That's exactly what Bobby tried to drill into his head in "Lucifer Rising" and it looked like he was getting through too. Now, he's going down that same road.  (Please note none of this is a criticism on the character, more a question of creative direction).  
Sure Dean is stubborn.  Sure he has a case of wounded pride.  He doesn't take betrayal well either.  But again, wouldn't the results have been different if he had stood by Castiel?  There's no way he could have guessed that Castiel would turn on Sam next, but it's interesting how he reverts back to this pattern.  Even after Castiel saves Lisa and Dean is grateful, all that happena is a "I wish this changed anything."  
The Man Who Knew Too Much
With his defiance of Castiel still firmly in place, everything continues to unravel for Dean.  Castiel, like everyone else, knows Dean's greatest weakness.  He takes down Sam's mind wall, putting Sam in a coma and kicking off the internal fight in his head.  Dean can't do a thing, which makes everything about a hundred times worse.  All he could do is go after Castiel and Crowley in hopes of stopping them from opening Purgatory.  He has to leave Sam alone to fight his own battles and hope that Sam will come around to help.  

He makes that choice to do what Sam would want, even if it wasn't the one he wanted to make.  He has that much faith now in Sam despite everything they've been through.  Yes, he spent a lot of season six worrying and trying to protect Sam and being there ended up make a huge difference, even if Dean didn't realize it.  The whiskey he drank left clues for Sam that he was at Bobby's.  He could smell it in his dream state.  The same went for shining the light in Sam's eyes, thus enlightening hi, to the presence of his stalking soulless counterpart.  
Dean's going into season seven with plenty of vulnerabilities.  His speech to Castiel at the end, even though it's placating, is truthful.  He has lost a lot.  Ben, Lisa, Castiel, and now possibly Sam too.  At least the Sam he knew.  Will he find his old fighting spirit, or will the burden's of Sam's issues and his own personal losses become too much?  We have another whole season (and likely more to find out).  I'm personally hoping that Dean gets his fighting spirit back, but he needs to address some of those lingering issues before that can happen.  Hopefully he and Sam can lean on each other for healing.  They both need each other more than ever.  

Coming up next, A Deeper Look at Season Six Sam Winchester.

Here's the links to the other previous looks:

A Deeper Look at Season Five Dean Winchester
A Deeper Look at Season Four Dean Winchester
A Deeper Look at Season Three Dean Winchester