In my analysis of season six Dean Winchester, my heart was pretty broken for the guy come the end of it.  His struggles in that season were especially hard and no matter how much he tried, he couldn’t catch a break.  He fought on though and did the best he could, despite the fact that his drinking was at an all time high and he was reeling at the end over the betrayal of his best friend.  A betrayal that harmed the one person that Dean cherishes more than anyone, his brother.  That was crossing an unforgivable line.    

I so wish I could say that season seven continued in this same vein, with Dean finding enough of his fighting spirit and love for his brother to handle the numerous obstacles that came his way.  Sadly, Dean spent a majority of the season apathetic and depressed, going through the motions without any fire or desire to carry on the family business.  He certainly didn’t open up to his brother, which rendered the once tight brotherly bond stale.  We waited all season for him to finally get the kick in the pants he needed and slip out of his funk, but he never did.   

Season seven’s largest and most grossest failure is easily the characterization of both Sam and Dean individually and with their relationship.  In going through the “Deeper Look” segments this year, the tone at times will stray toward bitter and exasperated, for the lost potential and blatant stripping of these beloved characters into bland, emotionless machines just didn’t work for me.  While Sam’s story screams lost potential, Dean’s screams the inability of the writers to truly grasp his real spirit.  I don’t recognize this Dean Winchester, and quite frankly, I don’t want to. 

The purpose here is to explore Dean Winchester’s character progression from beginning of season seven to the end by going through each episode.  In past seasons, promising patterns and real character growth unfolded from this exercise.  With Dean this year, you will see no such progression.  In some cases, regression even happens.  It’s still an interesting study though, and if anything will serve as a good bottom line comparison for next season!  


Meet The New Boss

Poor Dean. I really feel for him in this one.  His spirit is broken, and for good reason.  He just lost Lisa and Ben in his life, Castiel is unstoppable in his sudden God complex, Sam collapses and falls into another coma, and even the Impala is damaged. She is about the only thing he can fix, so that’s where his attention lies. When Sam wakes up seemingly okay, Dean wants to pretend everything is good, but he knows better.   He’s been burned too bad by the past. Turns out he’s right. 

After a little prodding from Sam, it’s nice to see he still cares by coming up with the risky plan to trap Death so he can kill “God”, but that doesn’t work.  All that’s left is to reason with Cass, but he’s too hurt to contact Castiel directly and Sam ends up doing it. Of course he’s also hurt because Sam didn’t tell him about the hallucinations either and he had to find out from Death. He’s not taking any of this well. He’s even resorting to spending his time drinking and watching cartoon porn (an interesting if not disturbing new vice). By the end his reservations about their bad luck are valid. He helps Castiel send the monsters back to Purgatory, but not the deadliest of them all, the Leviathan.  While this is happening, Sam disappears. 

Yes, this is the defeated Dean Winchester.  It’s not fun to watch, but in this episode, it was appropriate.  He had every reason to feel this way given that all the events of season six led up to this.  The standout scene for his is in the garage with Bobby, talking about whether Sam is really okay.  He wants to believe it, he really really wants to believe it, but he knows better.  “But I’m not dumb.  I’m not getting my hopes up just to get kicked in the daddy pills again.” 

Hello Cruel World

THIS is Dean Winchester at his finest.  Oh why oh why didn’t it last?  Why didn’t he evolve from this?  It’s not flipping fair!  (Storms off in tantrum). 

Dean jumps into full fledged protective big brother mode because Sam has fallen into a series psychotic break. This is the Dean we know and love. When the chips are down, family comes first. After finding Sam caught in a meltdown at the lab, he wastes no time trying to get some answers about what’s happening (after letting Sam have a long sleep). Sam comes clean, he can’t tell what is real and is seeing Lucifer now. This disturbs Dean a lot, but he’s determined to get Sam through this, despite his reservations that this kind of crazy is something he can’t easily fix. He opts to keep a close eye on Sam, taking precautions like turning on the GPS on Sam’s cell. In the meantime Bobby tries to get Dean to open up but he won’t. He’s too focused on Sam right now. 

Oh, that gorgeous scene in the warehouse. Sam is caught in a psychotic episode and can’t pull himself out of it. Dean calmly talks him through it, giving Sam the trick that will get him through a good chunk of the season. Sam needs to use the pain from his cut up hand to tell what’s real. Most important, Dean is able to get through just by appealing to their brotherly bond. 

“Believe in that. Believe me.  You better make it stone number one and build on it, you understand?"

Oh Dean, I just fell in love with you all over again.

The Girl Next Door

Let my primal screaming begin.

How can things tonally shift so positive to so negative with a character so fast? What were they thinking? The last episode closed with Dean frantically worrying about Sam going into seizures as they are in the ambulance together, headed toward harm’s way. How did everything shift from Dean pulling himself out of his rut by being in protective big brother mode to this?

From here on out, it all becomes a polarizing character shift. For one, as soon as Bobby finds Dean in the hospital, Dean doesn’t seem to be concerned about Sam at all. Then Sam has a little “episode” in the cabin for a minute and Dean freaks out. What happened to stone number one? Oh, but none of that compares to the rest of this atrocity.  Sam takes off (a point I’ll argue as completely stupid at another time), Dean angrily hunts him down and then punches him in the very spot on the skull where Sam was recently wounded by Edgar? The one that rendered him unconscious and seizing in a hospital?  Not only does he trounce on Sam physically, he pretty much takes any trust Sam has ever earned with him and throws it out the window.  

So suddenly Dean has a black and white view of monsters again and Sam’s plea to let Amy go means nothing to him? They’ve let plenty of monsters go in the past. How about the end of season five when he worked with Crowley, a demon, to get what he needed, the ring off of Death. He knew it was playing with fire but those were desperate times.  Dean hasn’t been a black and white hunter for a long while. So, when a past acquaintance of Sam’s shows up that just happens to be a monster and he hunts her down and kills her, because she’s a “monster”, we’re supposed to accept that as character growth?  Especially when he lets her monster son go after he kills her in front of him?  He left a boy without his mother? Dean? The man who is still carrying deep scars over losing his own mother?

Oh, but that’s nothing compared to the fact that Dean did this behind Sam’s back, right after promising him he wouldn’t kill Amy. Have we not gotten past this lying to each other crap?  Again, going back to season five, the brothers put all that dishonesty behind them and came to a new understanding. I do accept that Dean’s faith recently may have been shaken by Sam’s psychotic break, but his actions still screamed out of character to me. This even affected Dean’s actions in the upcoming episodes, for this indescribable drama was dragged on senselessly for four more episodes before getting an quick and “swept under the rug” ending. 

Welcome THE major blunder of season seven. Two seasons of rich character growth wiped away by one crappy script. 

Defending Your Life

And the *headdesk* banging continues to incredulous new levels. Dean’s depressed, no he’s angry, no he’s hiding something, no he’s confronting his past, no he’s too flipping resigned to care. Ugh.  Do not give a characterization heavy episode to a writer who doesn’t get the characters (I’m pointing at you Adam Glass). Both Sam and Dean were off in this one but man was Dean’s character butchered. 

If anything, this was a concept of lost opportunity. Fans usually like anything that will bring up the volumes of Dean guilt out there, the stuff that bogs him down to where he sometimes can’t function right (like this ep). Bringing back Jo certainly looked good on paper, and the scenes between her and Dean were gorgeous from an emotional perspective, but they were pointless. Dean didn’t learn anything from this ordeal of being condemned to Death for his guilt (yes, by an Egyptian God. That goes in the “What were they thinking?” archives). It’s even worse with Sam. He kept lying to Sam, which was one of those guilt things thrown at us like a bowling ball to the head. We get it, he suffers a ton of guilt over what’s happened to Sam. Thanks for bringing up character point that’s only been around since the Pilot. Isn’t he supposed to take this knowledge and move on, be better for it when seen in this light? Nope, he carries on like nothing is wrong. 

Of course maybe he’s too blown away by the fact that Sam is declaring with a smile he’s good, and that he’s paid for all his guilt by going to Hell. Wait a second, I seem to recall another Winchester brother spending some valuable penance time in Hell as well. Hold on, it’s on the tip of my tongue…Yeah, you get it. It’s almost like Adam Glass never watched that crucial part of the series in which Dean was flung into Hell and then pulled out months (or 40 Hell years) later.  Absolutely none of this so called character trial of Dean amounted to anything other than frustrated fans primal screaming over what senselessness has attacked their beloved older Winchester.  

Shut Up Dr. Phil

The lies continue, the bile rising in my throat continues, and it’s especially heavy handed considering they’ve blatantly started with Dean the drunk having his morning cocktail while Sam the happy well adjusted health nut (yes, I’ll harp on that in the Sam Winchester article) is off for his morning jog. Oh, why don’t I use this to pull out an old metaphor form my high school days. “Gag me with a spoon.” 

All in all, the episode was fluff and did nothing for either character. In Dean’s case, it existed to just drag on this senseless rut he’s in - one that he just doesn’t seem to pull himself out of even when Sam finally begs for the truth at the end.  The primal screaming continues.


Slash Fiction

Dean gets some of that fighting spirit back, which is good, but seeing an evil version of himself didn’t hurt that’s for sure.  Actually, considering all the crap we’ve gotten the last three episodes, it’s a freaking breath of fresh air. However, instead of coming clean with Sam about Amy, his Leviathan doppelganger drops the bomb instead.  Sam gets hurt, then pissed, then doesn’t want to be with him right now (we’ll save that little critique for the Sam article). Dean doesn’t try to fight. He let’s Sam go away. 

I actually like this. Dean accepts he was wrong and trusts Sam to go off and have his cooling off period. It’s way more respect than he has given Sam all season, which is kind of why they’re in this mess in the first place. Perhaps he is learning. At least they didn’t show him going off to a bar to drown his sorrows. This Dean I understood.

The Mentalists

Dean is carrying on without Sam, continuing to work. It’s not really a coincidence to him that they end up in the same town chasing after the same case. He tries to keep it professional for Sam, but when they exchange words, he won’t apologize. He still thinks what he did was right. I’m still pounding my head on the desk wondering why they’re still talking about this. So Dean is shown to be a jerk by calling Sam a bitch. Ugh. Lucky for Dean, Ellen is out there in the great beyond to kick some sense in him. 

In the end it’s Sam that forgives, so after all that flipping drama, Dean FINALLY admits he’s having a hard time trusting people after Castiel and he’s sorry. Drama all done. Wow, that was so, logical and grown up. Why didn’t they lead with that in “Defending Your Life?” Is Dean finally back on the right track? He even bonded with the leading lady, which is something we haven’t seen in a good long while. It made us smile. This is how you treat your main character.


Season Seven: Time For A Wedding

Aside from the fact we got to see Dean exasperated the entire episode and in a sweater and jacket, this was a completely pointless hour of television for both guys. Although Dean trying to make bygones by giving Sam a waffle iron as a wedding gift was pretty funny. He does care. Too bad he wasn’t smart enough to see that Sam was being drugged. He should have suspected that right off the bat, or at least after he tried to rationalize with Sam and saw it wasn’t working. If anyone recognizes out of character behavior, it’s Dean. He figured it out in “Swap Meat.” I mean, marrying Becky alone should have involved a head thump and a forced trip to the institution for Sammy.  

How To Win Friends and Influence Monsters

Remember that recognizing the drugging thing? Sam and Bobby figured out what the turducken was doing to Dean halfway through the episode. At least they know out of character. To be honest, I really liked seeing Dean with a "who cares?" attitude.  For one, it was funny.  See what happens when such a character twist is put in the right care?  What was nice about his though is Dean was feeling quite defeated before he even tasted the sandwich, so that seemed to only exacerbate existing issues.  It was about time.  The only thing missing was Sam and Dean actually talking about it!  They talk to Bobby about their problems, but not each other?  I know that this likely suffered due to an issue in time, but considering they went the entire season without having that conversation, without checking in to see how the other was doing, it’s just another bit of  frustration to an already growing fire.



Death’s Door/Adventures In Babysitting

I’m putting these two together because they are related.  It’s Dean going through the very real grieving process.  Let’s face it, Dean was in a bad place before Bobby’s shooting.  This didn’t help, but his reaction was classic Dean.  At first it was angry outbursts and avoidance.  Sound familiar?  His grieving over Sam’s corpse in “All Hell Breaks Loose Part II” comes to mind.   

When Sam wanted to talk about the reality of the situation at the hospital, Dean couldn’t.  What’s sad is they never did have that talk.  When Sam tried bringing up calling Bobby’s contacts in “Adventures In Babysitting,” Dean shut him down there too.  It’s very fitting Dean would follow through with the numbers Bobby gave them before dying, focus on going after Dick Roman.  He needed that diversion. Otherwise he would have drunk himself into oblivion. 

New found mission or not, Dean is stuck. He’s hurting, he’s not feeling the good he’s doing in his life, but he continues to hunt because of Sam.  Frank tells him to quit, get up each day, do the job, and plaster on a fake smile while doing it.  Dean heartbreakingly tries in the end, but he isn’t fooling anyone.  Including himself.  

Dean doesn’t want to focus on the case, leaving it to Sam, but he’s reluctantly dragged into it because Sam goes missing.  He didn’t take well Chrissy’s talk that Sam could be dead.  The death of loved ones is still really raw with him.  Then he gets there and, cannot make the kill.  Sam actually has to work through his weak state and kill the monster.  Now we’re scratching our heads as to why Dean froze. Um, it’s because…no…he’s…well he’s been down a lot lately…perhaps he’s…nope, got nothing.  Ah well, at least he got to fist bump with a 14 year old girl. 

Time After Time

Dean is transported back in time where he gets to relieve another boyhood fantasy. He gets to hook up with someone in history who he deeply admires and worships, Eliot Ness.  He has a crap load of fun doing it, and we have a crap load of fun watching him. When they’re having a talk in the car, he confesses to Ness that he doesn’t know why he’s doing the job anymore. Ness responds by flat out telling him he’s being a crybaby. 

“Everybody loses everybody and then one day, boom, your number is up.  But at least you’re making a difference.  So enjoy it while it lasts kid, because hunting is the only clarity you’re going to find in this life.  That makes you luckier than most.”

This is exactly the kick in the ass Dean needed!  He can go on from this adventure with a new found love for hunting, right?  Perhaps the other writers forgot to watch this episode.

There’s one outcome that ends up carrying a theme from the previous week.  Sam is the jumping in for the kill after Dean returns.  Dean really doesn’t put up much of a fight.  He’s on the ground watching.  Sure, it could be he was stunned or hurt after being hurled through space, but he wasn’t there fighting by his brother’s side.  I didn’t think it meant anything at all until...

The Slice Girls

At first I took this episode to be a sign that Dean was getting healthier.  He still isn’t taking the job very seriously, at first anyway, but at least he wants to go out looking for chicks in bars.  Sophisticated singles bars, not the usual dives.  I guess that’s good, because he scored.  Of course he ended up banging a monster and essentially creating one, but hey, accidents happen, right?  

The fact is once Dean sniffed out a mystery he ran with it, and it was Sam throwing all the doubts and conjectures at him. Dean figured out the case and his one night stand were definitely related, and he was next on the victim food chain. He has to deal with the ultimate showdown, his own daughter now wants to kill him. I swear I read this fan fiction years ago. 

You’d think that Dean would be more emotionally invested in Emma’s plight, but perhaps he’s seen enough crap in his days where he just didn’t take the fact that his daughter wanted to kill him all that personally. The scenes between her and him were quite flat.  He did the right thing and gave her a chance to walk away. Wow, the same chance he didn’t give Amy. Ugh.  That issue again?

Yes, after Dean earned justification for what he did with Amy he can’t kill his own monster daughter in the same situation. No wonder Sam was pissed. But that finally brings to light why he’s been hesitating all this time. Sort of. No, actually we never quite figure out why Dean is so reluctant to pull the trigger recently. Sam tries to find out, but he gets nothing but a bitchy attitude about it. Of course Sam was in a bitchy mood himself but hey, he had a point. Instead, Sam just tells him, “Don’t get killed.” Dean angrily says he’ll try. After this, Dean goes on with his normal killing ways as if everything’s okay. Oh, then it all makes sense.  Um, no.  And the pendulum swings. 

Plucky Pennywhistle’s Magical Menagerie 

This episode really can just be counted for Dean as a weird standalone, not really at all consistent with his drama this season. It’s amusing to watch Dean like this. He’s happy to do his job. He saved Sam from a vicious clown beating, harassed his brother in the process for fearing a vicious clown beating, and there wasn’t much more than that. Except for the uptight and out of character “baby mama” rant at the beginning.   I do concede bringing that up is nitpicking though.  The final scene of those two laughing over a glitter covered Sam is too priceless for words.  Oh yes, this moment doesn’t last but it was fun to watch. 

Repo Man

Oh poor Dean. The guilt thing again. Ben Edlund does so get this boy, doesn’t he? I really love how Dean felt for Jeffrey and what they did to him four years ago. It was a truly terrifying glimpse and the messes they sometimes leave behind after these cases. Granted, Dean had to see the parallel. The drinking, the suicidal thoughts, pulling himself together for a cause. Dean has been going through that recently in his quest for revenge against Dick Roman. 

I don’t blame Dean for falling for Jeffrey’s act, but it was really sad to see him fall for Sam’s as well. After being so cautious about the signs earlier in the season, he really doesn’t know the private hell his brother is experiencing. I’m still chalking this up more to Sam’s ability to hide things than Dean’s inability to see them, but when did Dean forget about never catching that break?  

Out With The Old

Okay, massive frustration time again. Sam is finally coming clean with Dean about his hallucinations and how they’ve taken a serious turn. Dean is brushing all of that off, even getting impatient with Sam for losing focus on the case by being tired. WTF? He’s treating Sam’s sleeplessness like he’s having a bout of the common cold. Sure, I understand, Sam has had insomnia before. But why was Dean so overly cautious of the warning signs earlier and now refuses to acknowledge them?  Why is he now in uber hunter mode giving laser focus to the case? It’s kind of baffling. Or maybe not.  At this point, I’m not sure what Dean is going to show up every week.  

The Born Again Identity

No doubt, Dean was blindsided by Sam’s breakdown. He didn’t see it coming. He really had no idea how deep in Sam’s mind Lucifer’s torment went and that this latest bout of sleeplessness was killing his brother. His reaction is the only thing Dean could have done. He had to find Sam help.   That’s exactly how we’d expect Dean to react. 

Sure, there is no way that Dean could have expected to find Castiel, and we know easy forgiveness is not his thing. I didn’t expect him to actually forgive Castiel. I even expected him to put aside all that resentment for the sake of saving Sam. But Dean put the entire blame of Sam’s misfortune on Castiel. That’s obviously some of the hurt talking.  Sam was way more practical than that. Sure Castiel took down the wall in Sam’s head, but there was a lot of ugly crap behind that wall that couldn’t have been contained forever. Sam was right, that was what happens when spending a lot of time with Lucifer in the cage. If you happen to get out, your sanity isn’t spared. 

So, is Dean’s anger at Castiel misguided? Perhaps, but knowing Dean it’s consistent. I was just taken back by how Dean was often going through the motions here.  Save Sam was the mantra, but it lacked a lot of the feeling of past episodes, with “Hello, Cruel World” being the “save Sam” yardstick.  

This ends up being what’s bothered me about Dean all season long. He’s doing what he’s expected to, what he’s been trained to do, but he’s not doing it with any sense of urgency, passion, anger, distress, etc. Especially with Sam’s life on the line, there should have been more. But I get it, Dean’s burned out by this point. Still, it isn’t very fun or interesting to watch.  

Party On, Garth, Of Grave Importance, The Girl With The Dungeons and Dragons Tattoo

Oh man, time for another massive “WTF?” character shift.  These are killing me!  Ever since “The Slice Girls” Dean has been enthralled by the possibility Bobby’s ghost is hanging around and watching out for them.  Sam kept talking him out of it, but his heart knew better. Then they finally find out its true. Bobby gets through. So suddenly, Dean is hurt and hates the idea? He’s even angry and mean to Bobby because he ditched the reaper? Oh come on.  I seem to recall Dean being a ghost once himself in “In My Time of Dying.” He should at least understand why Bobby did it. Dean was trying to do the exact same thing. Fight it. His work wasn’t done. Why couldn’t he and Sam try to talk with Bobby instead? Why couldn’t they try to help their father figure through this? This is not the Dean Winchester we know. He helps those he loves, no matter what they’ve become.  Especially when Bobby hasn’t betrayed him.  

Reading is Fundamental

Here’s more chances to explore Dean’s issues with Castiel. No matter what Cass does, Dean won’t forgive him. Now Castiel is a little bonkers (okay, a lot) and Dean only wants to focus of the mystery of the stone, not on his strained relationship with his angel friend. That makes perfect sense, it’s how Dean has always dealt with hurt and betrayal. Look at how he was all business with Sam at the beginning of season five. Dean’s outburst during the game of Sorry shows how very much angry and hurt he still is. We didn’t need to see or hear more than that.  

There Will Be Blood/Survival of The Fittest

Oh wait, I see a few traces of the Dean Winchester we all know and love in these eps. They have their plan on getting Dick now and he’s rolling with it. He and Sam are in perfect sync regarding this. Yes, they’re still totally misguided with this issue of Ghost! Bobby hanging around and messing up their plans.  Instead of talking with Bobby and dealing with the issue, Dean locks the flask up. Oh, great going. That backfires since it only makes him mad.  

Both these episodes are a straight forward, “get the bad guy” type missions.  Dean thrives well with this kind of focus.  He was even finding his sense of humor again.  He’s amazingly patient with Castiel, and even shows a that hint of forgiveness that has us cracking a smile.  Even baby is back.  All this in time so he could kill Dick, yet get burned again by moving on to his next disturbing adventure.  

What Does It Mean?

So what did we learn from point A to point B? I’m going to call Dean’s plight in season seven “Frog in a blender.” It looked interesting at first, but the end result was an unrecognizable mess.  Okay, perhaps there were some small traces of old Dean in the very end, but the question is, will it last?  

Out of everything that happened in season seven, the most inexplicable thing to come from it is the two brothers somehow forgot how to talk to each other after the first two episodes. I love how Dean got upset with Sam in “Meet The New Boss” for not telling him about the hallucinations, and then Dean and Sam had that ground breaking brotherly moment in the warehouse during Sam’s psychotic break, but after that there wasn’t a lot of good honest, open or productive conversation between the two.  There was the whole Amy fiasco with secrets and lies that went nowhere. They couldn’t come eye to eye about Bobby’s ghostly existence until it was proven to be true.  Sam never shared with Dean the terror of his mental breakdown, although he did share it with Castiel. Dean never asked or tried to get to the bottom of what was going on with Sam outside of “Hello, Cruel World.”  Oh, and the very brief conversation at the beginning of “Party On, Garth.”  The one that should have been revisited at some point.  Again, that will be explored further when we look at Sam.   

The only time there wasn’t disconnect was when they were working a case. I’m sure all that was intentional in the writer’s minds, but what was the purpose? By shelving the brotherly dynamic, it shelved the heart of the show. The object was to strip them of everything so all they had was each other, right? Then why didn’t they rely on each other more? How did they grow more apart? Could one reason really have been that the car wasn’t there anymore?  We know how so many brotherly conflicts were hashed out in the Impala.  

Oh, don’t get me started about the car…

I hope that if any serious wrong is corrected in season eight, it’s that Dean emerges from this seemingly senseless ordeal with his fighting spirit in tact again.  Oh, and his spirit sticks around for the bulk of the season.  No more guessing from week to week which Dean Winchester will show up.  Is that too much to ask at this point?   

Coming up in the next part, A Deeper Look at Season Seven Sam Winchester.  Hint, it involves a lot more primal screaming.   

Here are the links for the previous "A Deeper Look at Dean Winchester" articles:

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