To say that this season was complicated for Dean Winchester is quite an understatement.  Like he told Sam in “Sharp Teeth,” someone changed the rules.  In Dean's case, that rules change resulted in the worst case example of what happens when your life is devoted to others but not yourself.  Did the punishment fit the crime?  All depends.  Based on his one very questionable act in season nine, absolutely not.  But when looking at the history of the show and seeing how much Dean has messed with the natural order and the amount of personal guilt he takes on for all the misfortune of this world, suddenly the consequences of his actions were bound to catch up with him eventually.  But we know Dean’s acts weren’t malicious or cruel.  No, everything he’s ever done has been for love of his family, blood and otherwise (I know that word makes Dean squirm, but it’s true!).  

Dean did what he’s always done, find ways to survive, for both he and Sam.  It’s always been his job.  He gave up on his obsessive vendetta to close the gates of Hell because he wasn’t willing to see Sam die in the process.  But Sam was dying anyway.  He failed Sam before, and he wasn’t about to let it happen again, especially after promising in that church he would find a way.  But what happens that in the process of coming through for Sam, other lives are catastrophically affected?  Dean’s downfall happens, that’s what.  

Before digging in and going through Dean’s progression in each season nine episode, I have a disclaimer.  The purpose of these “Deeper Looks,” something I’ve been doing since season three, is to interpret how the writers have handled characterization for the season.  The effort of individual writers is put to a collective test so to speak.  I’ve heard plenty of complaints that in my “Deeper Look at Sam Winchester” series for this season that I didn’t paint Sam in a very favorable light.  Well, that’s not true.  The writers didn’t paint Sam in a very favorable light and I called them out on it.  This isn’t about how much we love or respect a character, it’s about taking a look at what we’ve been given and seeing if it fits.  In Sam’s case this season, it didn’t fit very well at all.  Luckily things worked out better for Dean, for the most part.  There were still some glaring issues, but overall his arc made more sense and followed a more logical path.  So lets take a look at that troubled path.

I Think I’m Gonna Like It Here

Dean is scared.  I know that’s a simplification of what’s happening, but it’s the basic truth.  Fear drove his decision to go to extremes to save Sam.  Fear of losing his brother, fear of being alone.  It’s the same decision he faced at the end of “Two Minutes ‘Til Midnight.”  As you all recall in the next episode, “Swan Song,” he followed Sam’s play even though it went against every fiber of his being.  He let Sam sacrifice himself for the greater good.  He lived for a year in misery, grieving over his brother and living with that feeling of extreme loss and regret.  No doubt that was all circling in his mind when he saw his comatose brother on that hospital bed. 

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“’Inevitable’ – that's a fightin' word where I come from. There's always a way.”

Dean did a desperate act for sure by tricking Sam into being possessed by an angel.  Were his motives selfish?  They could be perceived that way, but Dean didn’t believe that.  His reasoning goes all the way back to the pilot.  He didn’t want to fight the good fight alone.  He could, but he doesn’t want to.  That’s not a bad thing though and he has sound justification for it.  They are soldiers at war.  They save people.  They save the world.  They’re needed.  Someone has to have his back and Sam is the only guy he trusts.  As Dean has proven time and time again, even forgoing the chance to close the gates of Hell to save Sam, family comes above all.  “There ain’t no me if there ain’t no you.”  This statement has never rung more true in this entire series than season nine.  

Dean is an act first, deal with the consequences later kind of guy.  But no, he wouldn’t have guessed where this deception of not telling Sam he was possessed by an angel would lead.  Sure, he knew Sam would get mad and wouldn’t approve of this at all, but he was willing to do whatever it took, hoping that Sam would eventually come around.  If he knew ahead of time the chain of events his act set off and Sam’s reaction afterward would he have done it?  Would he have let Sam go?  No, he probably would have done the same thing.  This isn’t the first time he’s messed with the natural order and deep down what he did feels right. 

Devil May Care

“Yeah, it's just that, uh... this is on me. I was the one who talked Sam out of boarding up Hell. Okay? So every demon deal, every kill that they make... well, you're looking at the person who let it happen.”

Dean still isn’t very comfortable with this whole arrangement and deception, but Sam’s life depends on it so he must play along.  That doesn’t mean the guilt isn’t eating away at him.  Running into demons reminded him of the consequence of letting Sam live, Hell is still in business.  Zeke was right, he did do it out of love.  That’s been the underlying motive for everything he’s done.  He lost his parents tragically, he lost Bobby, who was like a father to him, he won’t lose his brother.  It’s his job no matter what to protect him.  It goes back to that scared 4 year old kid carrying his baby brother out of the burning house.  He now has to rely on Zeke though, an angel he barely knows, to keep Sam alive and that doesn’t make him feel easy at all.  Still, he knows keeping Sam alive is vital.  We see his justification in his closing conversation with Sam.  

Sam, listen to me. You have helped a hell of a lot more people than you have hurt.

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One other thing did happen in this episode that reminds us how important family is to Dean, using the family card to prevent Kevin from leaving.  He includes Kevin and Castiel in the family now.  This is kind of important for later, because one thing that tends to push Dean to his dark spot is the fear of his family leaving him.  

I’m No Angel

Not much to see here, except for a dumb continuity thing.  Meg has been calling Castiel Clarence since season five.  Dean didn’t know that or get the reference?  No, I don’t buy it.  Nitpick over.   

Dean is still fighting for family though, this time Castiel, which is why I have such a problem with Dean choosing to tell Castiel at the end to leave.  I know, it reinforces that Sam comes first in the pecking order, but what happened to his “We’ll find a way” attitude?  Suddenly that declaration that Cass is a part of the family in “Devil May Care” doesn’t sit true for me.  He’s putting Castiel in harm’s way by making him leave the safety of the bunker immediately after he begged Kevin to stay.  It’s inconsistent.  So I’m just calling this plot twist a very contrived foul. 

Slumber Party

Charlie joins the family tree now too!  Charlie is killed and just like with Castiel in “I’m No Angel,” Dean uses Ezekiel to bring her back from the great beyond.  This weakens Zeke, which means that he has to stay in Sam longer.  Dean is really pushing things here, but he finally has a way to save those close to him and he’s not squandering any opportunities.  Again, fear of losing “family” is driving him to these actions, and it’s beginning to spiral.  Sam is starting to suspect and each lie is really starting to eat away at Dean.  This can’t end well. 

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Dog Dean Afternoon

Aside from the fact that Dean was totally hilarious in this one, a couple things from  a character standpoint came from this.  First, he chose to take the potion, even though he doesn’t like dogs (or was that botched canon last season?) to spare Sam considering his state.  His lies are getting more blatant too, especially when Sam really should have figured this out by now.  What happened to him in this one was a big effing clue.  Dean is on borrowed time.  

Oh and yes, Dean let the dogs out.  


Heaven Can’t Wait 

Dean fascinates me in this one.  I find his behavior toward Castiel so endearing, and so part of the overprotective Dean Winchester we’ve grown to love.  He is a softie when it comes to his best bud.  There’s a very big angel threat looming, but Dean isn’t trying to drag Castiel into the fight.  He sees his pal adapting to human life, getting a job, going on a date (even if it turned out to be a date with a baby) and wants Castiel to remain safe and happy.  Sure, a lot of his actions could be guilt over having to toss Castiel out of the bunker on the insistence of Ezekiel.  Maybe by Castiel staying out of harms way like this, that will assure Castiel’s safety while he and Sam/Ezekiel figure out the angel problem.   Or maybe Dean wants to see Castiel genuinely happy after all he’s been through.  It’s very likely a combination of both.  

Whatever the motivation, Dean tried hard though to be a friend, and I loved it.  He gave Castiel advice on how to be human, and even gave him dating tips!  In the end when Castiel was feeling sad and wanting to be part of the angel fight Dean discouraged Castiel by encouraging him.  

Listen, Cas … Back at the bunker, I, uh... Sorry I told you to go. I know it's been hard on you, you know, on your own. Well, you're adapting. I'm proud of you.  

I believed those words to be sincere.   We see him using similar uplifting words with Sam in “I Think I’m Gonna Like it Here,” Kevin in “Devil May Care,” and later with Garth in “Sharp Teeth.”  He cares about these guys, and a little encouragement goes a long way.  You have to feel for Dean though, offering all this encouragement while he’s struggling with his own big secret and deception.  No wonder it beats him up later. 

Bad Boys

It’s hard for me to do a proper analysis on this one.  Honestly, I hated the episode.  We got to see Dean in a flashback, but I don’t feel like I learned anything new about him.  It carries on with the theme that I eluded to in the prior episodes, Dean is doing all for everyone else and sacrificing his own happiness in the process.  Maybe he’s happier doing things for others.  The role of protector is where he feels the most comfortable.  It’s sad to see he was this way at 14 (I refuse to believe it was 16), but we knew this already from “A Very Supernatural Christmas” and even “Something Wicked.”  

Rock and a Hard Place

I’m sorry, but any time Dean gets to cross a big item off his bucket list in a hilarious way,  everybody wins.  I loved Dean in this one, but it really was just him getting in one good fling before everything goes south.  He’d earned it. 


The big takeaway is the ending scene with Sam.  Everything is getting too complex.  Sam is starting to blame himself now for what’s been happening, and Dean desperately wants to tell him the truth.  Except Ezekiel won’t let him.  That right there is a major warning sign to Dean, and it has him rattled.  I wish at this point he chose to confide in someone like Castiel or Kevin, seek advice on what to do, but I guess the point his taking on this burden by himself led to a downfall.  So he does, and the ending is the smack you in the head foreshadowing that Dean is heading for serious trouble.  

Holy Terror

It’s Dean’s worst nightmare.  Not only does he have to see an adopted family member die in front of him again (I remember his line back in season four how he was tired of burying friends!), it came from the hands of Sam, who has lost control to Ezekiel.  His desperate plan to save Sam has backfired in the worst possible way, and this is the blow that starts his long slow descent into darkness.  

Perhaps Dean fooled himself to thinking he had control of the situation.  It still infuriates me though that the writers would give him the line “Would I lie?” in the beginning, deliberately using his brother’s trust of him to diffuse Sam’s suspicions because he’s flat out lying to Sam.  That’s not Dean’s style, and Sam could have easily answered “Hell, yes” (an issue I already raised in my deeper look at Sam).  Still, being caught in such a big lie I guess also adds to the harshness of Sam’s reaction, which is a catalyst to Dean’s downfall, yada yada.  That “Would I lie?” line doesn’t feel organic though and puts a kink in the progression of Dean’s character going from the beginning of this episode to the end of the season.  It’s a contrived twist for being the early traces of what happened to Dean.  

Despite that though, Dean’s attempt to get through to Sam without Ezekiel knowing is gripping and heartfelt, as is the ending scene when everything unravels.  Kevin is dead, Sam is in the wind under control of an angel Dean let in, and Dean is left completely devastated and facing hard choices.  Everything he did made things far worse; consequences for messing with the natural order (again).  Jensen does a perfect job of leaving us a potent visual going into the break - this is Dean’s breaking point.  


Road Trip

This episode is exposes Dean at his core vulnerability.  He’s emotionally wounded and very raw.  He’s ripe for manipulation, he’s ripe for taking deals that make no sense, despite having a friend around to help keep him sane.   

No doubt about it, Dean needed someone to reach out to.  Kevin’s death is killing him inside (thanks to that gorgeous opening montage) as well as the realization that the only option now is to kill Ezekiel (revealed to be Gadreel in this ep).  That means Sam will die as well.  Dean’s ready to right that wrong though.  It’s appropriate that Castiel is there to lend an ear, since Dean was there for Cass in “Heaven Can’t Wait.”  He tells Dean he did it for the right reasons, but as we know on this show, the road to Hell is paved with good intentions.  But, there is an option, and Crowley just happens to be the Devil they know.

You can’t blame Dean for going for the risky plan, trying to save Sam again while trying to kill Gadreel, even though the last time he tried to save Sam from death it ultimately got Kevin killed.  He’ll never be able to let go of Sam, no matter what.  Saving his brother is ingrained in his core.  It would be like cutting off an arm.  The scene that got me the most is when Crowley was pushing needles into Sam’s skull, causing great agony and torture for Gadreel.  Those cries were still coming from Sam’s mouth though, and that was enough to overwhelm Dean.  

Dean:  I can't watch that anymore. 
Castiel:   I understand. It's not Sam, but... It's still Sam. 
Dean [voice cracking with emotion]:  Pretty much, yeah. How are you doing? 
Castiel:  You want to talk about me now? 
Dean: I want to talk about anything that's not a demon sticking needles into my brother's brain. (Tears pooling in his eyes).  

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I love this scene, because it paints Dean as a very sympathetic character, something the writers have often failed to do recently (for both Sam and Dean).  All he wanted to do was save his brother, the one that matters to him more than anything.  Sure he created a real mess, but saving Sam will justify the means.  This is the real Dean Winchester and it’s rare anymore to see him open up this side of himself.  It’s poignant and so heartbreaking so see him this way, especially when we know what’s coming.  It’s also why Dean will deal with Crowley rather than let Sam go. 

This just plain hurts.  We know how much Dean has agonized over everything, but Sam was understandably angry.  Let’s go through the ending scene again.  Sam has been saved, but the brotherly bond didn’t make it out okay.  

Dean:  All right. Let me hear it. 
Sam:  What you do want me to say -- that I'm pissed? Okay. I am. I'm pissed. You lied to me. Again. 
Dean:   I didn't have a choice. 
Sam: I was ready to die, Dean! 
Dean:  I know. But I wouldn't let you, because that's not in me. 
Sam:  So, what? You decide to trick me into being possessed by some... psycho angel? 
Dean:  He saved your life. 
Sam:  So what? I was willing to die. And now... Kevin... (eyes fill with tears)
Dean:  No. That is not on you. Kevin's blood is on my hands, and that ain't ever getting clean. I'll burn for that. I will. But I'll find Gadreel. And I will end that son of a bitch. But I'll do it alone. 
Sam:  What's that supposed to mean? 
Dean:  Come on, man. Can't you see? I'm... I'm poison, Sam. People get close to me, they get killed...or worse.  You know, I tell myself that I-I -- I help more people than I hurt. And I tell myself that I'm -- I'm doing it all for the right reasons, and I -- I believe that. But I can't -- I won't... Drag anybody through the muck with me. Not anymore. 
Sam:  Go. I'm not gonna stop you. 
(Dean walks away)
Sam:  But don't go thinking that's the problem, 'cause it's not. 
Dean:  What's that supposed to mean? 
Sam:  Just go. 

Oh Dean, there’s your tragic error right there.  Thinking you have to do this alone.  You know that’s not a wise idea, especially when you did all this just so you and Sam could fight the good fight.  

I didn’t care for this twist at all.  I know Dean is in self loathing mode right now, but walking away from Sam like this doesn’t make a lot of sense.  What happened to the promise he made in “Sacrifice?”  Dean was sticking with that promise when he went to extremes to save Sam, why leave now?  Why not stay around, explain himself to Sam a bit better, see how his brother’s healing goes?  Yes, he was leaving Sam in Castiel’s angel healing hands, but he just got his brother back.  Dean’s act here pretty much wiped out the end of season eight.  I get it was a setup for the next episode, but I still think there were other ways to go.   

First Born

The pivotal episode.  The one that pretty much doomed Dean for eternity and it left us all pretty shocked.  All because he left Sam and went off with Crowley on an adventure.  You know Crowley was waiting for that perfect opportunity to get his hooks into Dean, but it must have been demon Christmas when emotionally raw Dean walked off on his own leaving a wounded moose behind in the bunker.  He had Dean hook, line, and sinker with the perfect premise, a way to kill Abaddon.  Given Dean’s mindset for revenge, Abaddon was the perfect bad person to take on.  

Before getting to the character study portion of the episode, a side note.  Who didn’t enjoy seeing Dean get to do a good ole fashioned ass kicking of three demons, at once!  It made me grin like a fool.  Dean was itching for a fight and he got one!  If there was ever a more worthy test.  

Now, the encounter with Cain.  

Your problem, mate, is that nobody hates you more than you do. Believe me, I've tried.

Oh Dean, Dean, Dean.  It’s interesting how eager he was to take on the Mark of Cain, not heeding the warning from Cain calling it “a great cost.”  It’s that problem Crowley said, that Dean hates himself more than anyone, that causes Dean to not even ask what that great cost is (now we know, it’s his life then his soul).  He takes the Mark of Cain willingly (and hastily) like he was receiving a gift.  Whatever burden it brings, the end justifies the means.  Plus he doesn’t think of himself to be like Cain, because he saved his brother instead of killing him.  Different circumstances, so he won’t make the same choices.  I always keep that in mind, because season 10 hasn’t happened yet, and I do wonder if that will come into play.  Would Dean kill his brother to save him?  

Why turn the obsession to kill Gadreel to Abaddon though?  Isn’t that Crowley’s fight?  Well, it goes back to “Devil May Care.”  Every demon roaming the earth is on him.  Top Hell bitch must go.  He’s already promised Crowley he’ll be next.  So Dean is already carrying an extraordinary burden, he probably figured what could the Mark of Cain do to him?  It’s giving him the power to kill all these demons and level that playing field.  That was exactly the mentality that Crowley counted on.  He knows how to play weaknesses, and no Sam around to keep him in check makes Dean an easy mark.


I often ask myself, if Sam was with him, would Dean have taken on the Mark of Cain?  I’m going to say yes, despite Sam’s protests.  It’s Kevin’s death that’s really burning him right now, not Sam.  The way he sees it (right now), Sam will get over what happened to him.   Of course he’s about to find out how wrong he is, and that’s where the MOC will take hold and never let go.  

Coming up in part two, Dean is overtaken by darkness and it’s as scary as crap.  Plus Sam’s choice to keep him at arms length emotionally really takes its toll.  It’s pretty sad.