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Dean Winchester.  Let’s face it, his character is iconic.  The big brother, the protector of all bad, the macho hero in the leather jacket with the smart mouth… He’s that “no chick-flick” moments kind of guy that underneath it all has a soft and tender side who loves chick flicks and makes women (and some men too) swoon.  That tender side is most evident when his brother is involved and his quirky angel friend with some real self esteem issues.  Hell, he’s even the main voice of reason to the freaking King of Hell himself.  

I’ve traced Dean’s journey of growth and despair ever since season three, a season where he hit a point of “self actualization.”  Since then his journey has been captivating.  So what happened in season 11?  Oh man, what did happen? Instead of any kind of growth, we got a meandering Dean Winchester cliche who more found himself in situations based on happenstance than any sort of destiny.  He was walking the walk, talking the talk, and it all ended with Dean playing family counselor, providing off the cuff advice to save the world.  He didn’t get to play hero a lot of the time or be the bold and brash leader we have grown to love.  He was just…there.  You know that the writers clearly hit a wall in season 11 when they had no idea what to do with a character that helped define their series.  

As an illustration, let’s go through Dean’s journey through various episodes in season 11.  Perhaps you see a pattern, but except for a small attempt in the middle of the season, I see random events that in the end really didn’t add up.  As I mentioned in my “Deeper Look at Season 11 Sam Winchester,” at least Sam got 11 episodes of arc before they abandoned any kind of character development.  Dean wasn’t so lucky.  

Out of the Fire, Into the Darkness

As with Sam’s arc, Dean’s situation got off to a promising start in the opener.  Dean was back in hero mode, ready to save the damsel in distress and her baby at all costs.  This is the Dean we know and love, ready to make a wrong situation right again and he’s doing it his way.  He was saved by The Darkness based on their strange connection via the Mark of Cain.  They had a steamy talk.  Hmm, where could this be going? 


There was no character growth here whatsoever, just classic, iconic Dean.  We love you Robbie Thompson for reminding us of what Dean should be.  

Dean’s faith issues, something that has been happening all series long, are raised again when Sam brings up his visions.  He sticks with the same old “mantra,” God isn’t out there.  It’s just them.  

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Our Little World

It takes a few episodes, but Amara’s hold on Dean is as serious as we suspected.  He talks about killing her the second he gets the chance, but Dean suspects deep in his heart he can’t do it.  The connection is too strong.  Turns out he can’t.  Amara ends up saving Dean from Crowley, bargaining that Dean not be harmed and she’ll spare Crowley’s life.  Amara messes with Dean’s head and heart, acknowledging their attraction and how Dean won’t be able to hurt her.  To prove her point, she gives him back the knife and dares Dean to use it.  He doesn’t.  When talking with Sam and Castiel later, Dean sticks with the “overpowered by God’s sister” story, but at this point he clearly doesn’t understand what is happening.  Oh man, the sweet sounds of self denial.  So Dean Winchester. 


Dean berates Sam with the whole “God isn’t out there thing” and that his plan to visit Lucifer is whacked.  It’s nothing new, but Dean could never get out of big brother protective mode.  

Just My Imagination

It’s interesting that Dean is the one who talks the villain down, admitting the one thing he never did before, that Sam’s imaginary friend might have been a good thing after all.  Sully was there for Sam when he wasn’t.     

“Trust me. Revenge? Ain’t gonna make you feel better. Listen, I’ve seen more than my share of monsters. And I mean REAL monsters, bad. These guys? These are Sesame Street mother Teresas. But when I wasn’t there for my little brother, Sully was. Now, look, I’m not saying that he didn’t make a mistake, but you know that there is not a monstrous bone in his body.”

If Sully can listen to Sam, maybe it’s time Dean does too.  He still doesn’t want to let Sam go, but at least they’re talking about it.

O’Brother Where Art Thou?

Dean still hates the idea of Sam going to Lucifer, but he at least does the homework and visits Crowley with Sam, if anything in hopes that Crowley will tell him it’s an insane idea.  Dean gets distracted with Amara though.  Dean’s attraction to Amara though is so strong, he misses Sam’s phone call that it’s time to go to Hell, so SAM GOES WITH CROWLEY AND ROWENA BY HIMSELF!  (Sorry, I used the same shouty text about this in my Sam Winchester article.)  It still makes no freaking sense.  But I digress so we can move on. 

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Dean and Amara’s epic showdown is reduced to an exchange of awkward glances that don’t even resemble the lust and longing that should be happening by now. They looked like uncomfortable middle schoolers at the homecoming dance.  But hey, this was actually more watchable than Sam’s asinine conversation with the Prince of Darkness.  Was this meant to show Dean in a spiral?  How low could things go from here?  Dean tried to kill her finally, but it was half hearted and predictably failed when the knife shattered.  Amara saves Dean anyway, sending him away when the angels show up.  He is left confused.  He isn’t the only one.

The Devil in the Details

While Sam goes through “This is your Life” while trapped with Lucifer, Dean has smiting sickness.  Eventually he gets directions from Hell from Crowley.  Honestly, I’m trying like mad to figure out why Crowley would do that.  Just so Dean could humiliate Rowena?  It’s where the improbable, “Deus Ex Machina” plotting rears its ugly head again.  Didn’t Crowley want him dead a few episodes ago?   I’m very confident Dean would have found his way in eventually, but Crowley returning his phone call seemed so anti-climatic.  Poor use of a hero.  Dean does eventually arrive in time to help Sam, but ultimately it’s Castiel that saves them both.  Sort of.  He kind of backed into it by doing something idiotic.  But that’s a rant for another time.

Into The Mystic

The clever twist here is that screaming sound from the Banshees can only be heard by those that are the most vulnerable.  The beginning made it look like Sam, still raw after his ordeal with Lucifer, but it turned out that Dean was the one in danger.  Dean admits to “Castiel” that his connection with Amara scares him, but still can’t admit to Sam.  It’s pretty obvious though when the Banshee comes after Dean instead.  He’s in a spiral for sure!  He doesn’t tell Sam though, because Sam is too busy confessing his season eight mistake when he hit the f***ing dog, thus closing out his redemption arc.  So that means we can focus on Dean’s story now? Yeah, right. 

Don’t You Forget About Me

Dean gets to play counselor to a wayward 18 year old.  Oh yeah, good times.  It’s interesting how Dean spends some time this season solving other people’s problems instead of his own.  We aren’t seeing the “live and learn” from these encounters.

Love Hurts

Dean seems to be back to his sly dog ways, going out to pick up women on Valentine’s Day, no doubt to suppress his infatuation with Amara.  But as the events of this episode reveal, it ain’t working.  Dean even puts himself in harms way by taking on the curse to spare the victim of the week.  That means someone who Dean desires will come and get him. Is this Dean being reckless and doing things out of guilt for letting Amara get the best of him?  Probably.

Was anyone surprised that Amara showed up?  Sam and Melissa may have saved Dean from fake Amara, but it was enough for him to finally admit to Sam he couldn’t resist the real one.  He wouldn’t be able to kill her.  That will have to fall on Sam.  

The Vessel

This is a gorgeous Dean Winchester episode.  Dean volunteers for the mission to go back in time to the WWII submarine because he’s the “least valuable player.”  This mission no doubt had a profound effect on him though.  Seeing these doomed heroes in action while he helplessly watched is daunting to Dean.  It’s a nice parallel to how he feels about his situation with Amara and how ultimately he’ll have to be the bystander while others take on the fight.  It’s shakes him to the core.  

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Beyond The Mat

Dean gets to learn from the Victim of the Week, someone he idolized as a kid.  Bottom line, just keep grinding.  Okay.  Oh, he’s not going to give up on Castiel.  Great, glad to hear it.  At least he got in touch with his inner child for once.

Red Meat

This is episode from Dean’s POV felt too stereotypical, aka WWDD?  Everything that old Dean would of done he did.  He tried to save everyone at all costs.  I Sam had been shot and Dean needed to get his brother to a hospital no matter what, consequences be damned.  He just didn’t count on very jumpy Corbin “killing” Sam.  Dean had a very tough life or death decision there.  His core instinct was simple, stay behind with his dead brother and fight.  His reaction to Sam’s “death” was genuine and oh so heart crushing.  He was clearly filled with grief and despair.  But with two innocent civilians in his care, getting them to safety was more important.  Sam would have wanted it that way.

From there though, Dean went reckless and stupid again, killing himself so he could bargain with Billie the Reaper to spare Sam.  He’s done it before, why not again?  I liked seeing him do this because he finally got the message that there were no more deals, but at the same time, can Dean ever live with the grief of being alone?  Hasn’t he learned by now that deals are bad?  I was hoping that there would be some growth in this moment, this loss of his brother, but no, it was back to same old Dean.  

We even got stereotypical Dean at the very end when Sam asked him what he did when he thought he was dead?  Dean lied.  Oh boy, couldn’t he have been honest for once?  Was the lie necessary in this case?  No, it wasn’t damaging, but again, it’s a writer’s trap that’s too easy to fall into when it comes to Dean. 

After 11 seasons and all he’s been through, especially recent events seeing what happened when Sam went too far and let out the Darkness after he recklessly accepted the Mark of Cain, I just thought he would have learned something by now.   This would have been the perfect opportunity to show a better Dean.  Opportunity lost.  

Hell’s Angel

Did anything happen in this?  (Checks the transcripts).  Oh, Dean thinks he can get through to Castiel just by pleading with him to listen.  Doesn’t work.  But he still isn’t giving up!  Why does it feel like he’s going through the motions this time?  

It did kind of occur to me here, isn’t Dean supposed to have a big, undeniable, tearing him from the insides out attraction to Amara?   Yeah, looks like that plot line has been dropped, aka Dean’s purpose for the season.

Don’t Call Me Shurley

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This episode had a very crucial event for Dean, a ground breaking event that is series long coming.  When Sam was overcome by the fog and the end appeared near, Dean yelled out upward in desperation.  It could have been to God or Amara, but it was a big breakthrough for him, much like when Sam prayed back in episode 11.02.  He was putting the situation into someone else’s hands.  It was a very emotionally powerful moment.  And then the fog clears and Dean sees his once precious amulet glowing in his brother’s pocket.  He has no words.  He’s stunned but his expression shows that he’s touched that Sam had it this whole time (For those that dispute that interpretation, this was exactly what was in Robbie Thompson’s script.)  Then we get the ultimate payoff for both Dean and Sam, but especially Dean.  God did come to his rescue after all.  The God he constantly claimed wouldn’t do anything to save them.  It’s time to talk.     

All in the Family

I do appreciate that they cut to the chase and Dean, Sam and Chuck got to talk.  Well, Dean talked, and Chuck sort of answered (I already aired my gripes about Sam not getting his talk).  Still, for Dean, it was a moment that was a very long time coming for Dean. This is a very significant moment in his character in the entire series.

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Dean: Here's the thing, um...Chuck... And I mean no disrespect. Um... I'm guessing you came back to help with the Darkness, and that's great. That's, you know – It's fantastic. Um, but you've been gone a – a... long, long time. And there's so much crap that has gone down on the Earth for thousands of years. I mean, plagues and wars, slaughters. And you were, I don't know, writing books, going to fan conventions. Were you even aware, o-or did you just tune it out?

Chuck: I was aware, Dean.

Dean: But you did nothing. And, again, I-I'm not trying to piss you off. You know, I don't want to turn into a pillar of salt.

Chuck: I actually… didn't do that.

Dean: Okay. People – People pray to you. People build churches for you. They fight wars in your name, and you did nothing.

Chuck: You're frustrated. I get it. Believe me, I was hands-on – Real hands-on for, wow, ages. I was so sure if I kept stepping in, teaching, punishing, that these beautiful creatures that I created... would grow up. But it only stayed the same. And I saw that I needed to step away and let my baby find its way. Being overinvolved is no longer parenting. [Sighs] It's enabling.

Dean: But it didn't get better.

Chuck: Well, I've been mulling it over. And from where I sit, I think it has.

Dean: Well, from where I sit, it feels like you left us and you're trying to justify it.

Chuck: I know you had a complicated upbringing, Dean, but don't confuse me with your dad.

And…moment over.  What??  Was this talk satisfying for him?  It shouldn’t have been, not when his issues with faith have happened all series long.  Just one short talk and he’s good???   How could the conversation end there???  How could Chuck to even throw that last line at Dean without showing a proper response???  Dean is angry and he has a right to be.  He’s been mired in crap and heartache ever since he was four.  This shouldn’t make him square with things by any means.  Instead, they move on to the Chuck and Amara story like everything is hunky dory.  Did we miss more of the conversation off camera? Why is Dean good after this? 

Oh, and THERE’S NO MORE TALK ABOUT THE AMULET???  Where’s my brotherly moment of appreciation and pride?? Where’s the follow up conversation between Sam and Dean of these faith issues like they had in “Baby?”  They just move onto the generic wooden plot after this and choose not to explore character dynamics when the opportunity is exposed and ripe?  I give up.  

I accept that Dean will do whatever is best for the greater good, but the resentment should still be there.  The attitude should be there.  He should be treating Chuck like a deadbeat Dad.  Yet Dean gives Chuck a nice pep talk later, after finding out his plan from Metatron.  Dean does have the perspective of knowing Amara’s intent.  Chuck admits in this conversation that Dean and Sam are God’s chosen. After hearing that, wouldn’t that have solicited some sort of reaction from Dean other than “it’s all way above my pay grade?”  Has Dean always been aware that he’s one of God’s chosen?  I shouldn’t read too much into this, but again a big moment should have come from this.  It’s all so perplexing how this all could be mentioned and then glossed over.  

However, I’ll get to the biggest mess of all.  Dean visits with Amara so that Sam, Metatron, and Donatello can rescue Lucifer (yes, that still sounds utterly ridiculous to me).  Is this finally the big climactic showdown that’s been building all season long? A deepening of this season long “bond” and a slip into a more perilous situation for Dean?  Nope.  It plays out like a bad soap opera and goes nowhere.  All Dean acknowledges in the end is that Amara wants him to be a part of her.  I wish I was completely nervous about that, but I was just too underwhelmed with Dean’s emotional arc going nowhere.  The opportunities lost are astounding.  Forget astounding, criminal.  

We Happy Few

Dean: It’s like the worst episode of Full House ever. 

That’s all you really need to know.  Hijinks ensue, Dean and Sam try to get God and Lucifer to talk it out, and a hare brained scheme doesn’t go according to plan. This didn’t feel like “Supernatural.”  So, nothing to see here for Dean folks. 

Alpha and Omega

I don’t know why I keep thinking “accidental tourist” here, but Dean kind of clumsily backed into saving the world here, didn’t he?  It’s hardly the equivalent of Sam’s sacrifice in “Swan Song.”  

Still, I loved Dean’s reaction to Chuck being mortally wounded.  He went to the kitchen, pulled out a beer, and started chugging heavily.  This part isn’t out of character at all.  It’s pretty funny and classic Dean:

Dean: [taking another sip of beer]  That's right.  Look, man. If you've got something for me to punch, shoot, or kill, let me know and I'll do it.  I'll do it till I die. But how are we supposed to fix the friggin' sun?

Dean also takes some time to acknowledge Castiel as a brother, before giving his own brother a goodbye hug.  It’s time for the ultimate sacrifice.  Oh, but not before a revelation first to wrap up his season long arc.  Amara’s attraction to Dean is really just her wanting her brother.  Huh?  THAT’S IT??  Dean just has to tell Amara that Chuck loves her and he saves the world?  Gee, it looks like I’m not the only one giving up.  The writers have too.  

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Dean saves the world and gets his mother back.  A win?  I suppose, but all that longing for a whole season and this is the end result?  What a freaking waste.  

Bottom line, there was no real pattern to any type of growth or lessons learned.  Dean was just…there.  He reacted when stuff happened and in the end he was no better or worse character wise than when this all started.  Sure, the circumstances ended better, but the character growth was all but non-existent.  It reminds me of Forrest Gump.  Stuff happened around him and he went on as normal.  The difference was that the former made a great story and played all the emotional beats.  The latter, not so much.  Again, I shout to the rooftops that we have another season of opportunities lost.  Dean and Sam deserve better, as do all of us watching.  

So what do you think about Dean in season 11?  Is there a pattern that I'm missing?  Was his path better or worse that Sam's 11 episode character arc, or were they both equally as bad?  What are your hopes for season 12?  

Interested in my "Deeper Look at Dean Winchester" installments from previous seasons?  They can be found here: