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.