For those that missed part one, that can be found here:  

http://www.thewinchesterfamilybusiness.com/index.php/archive-articles/38-dean-winchester/17919-a-deeper-look-at-supernatural-season-eight-dean-winchester-part-one 

In the second half of season two, Dean became more focused as ever in his quest to close the gates of Hell.  He also became a bit of a serial hugger, but we didn't mind one bit!  

His role though ended up taking a direction he never anticipated but one he's grown quite familiar with - caretaker.  Destiny chose his little brother for this quest rather than him, and it became his job to keep Sam alive and somewhat well during the brutal trials.  Anyone who doesn't think that Dean didn't do much in the second half of the season might see otherwise after going through each episode.  He really was the glue that held everything together.  Dean was the one who had to decide, is their mission against Hell worth the ultimate sacrifice, his brother's life?  While the answer is not surprising, the path to getting there was worth every second to a viewer.    

As Time Goes By

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I hated Dean's characterization in this one.  I thought he was too bull headed with Henry Winchester and way too harsh on a guy that he really didn't know the whole story about.  He wouldn't even try to give him the benefit of the doubt, and I just think Dean is more open minded than that.  He was all over the map with double standards too.  He chastised Henry for not choosing family and then got on his case when Henry decided to go back and make things right?  A lot of his actions, or overreactions, regarding his attitude toward family were cliche, and that kind of pissed me off. 

Aside from my misgivings though, it's obvious Henry's presence triggered something that had been stewing inside Dean for a while.  He doesn't appreciate anyone that doesn't put family first.  He even defends John to Sam, after Sam rightfully points out that John was hardly father of the year.  "Look, Dad had his issues, okay, but he was always there for us."  So, even though what may have happened to Henry wasn't his fault, because John was angry at Henry his whole life, that meant that Dean got to carry on that resentment no questions asked.  Ugh.  

Anyway, Dean acted out, not really giving Henry a chance, until they had to work together to save Sam.  Because no matter what, Sam will always be his greatest priority.  "Henry, you need to understand something. When my dad died, I couldn't save him... no matter how bad I wanted to. I never want that to happen to Sam... ever. If there's a chance that I can save him, I'm gonna do it. He's my brother. He's the only family I got."  Henry understood, and suddenly they were all on the same page, just in time for Henry to die.  

The ending shot couldn't be more appropriate though, and that's where the characterization begins to shape up again.  Two brothers, side by side, sharing another family loss, recognizing that all they have is each other.  This time though, there's a family legacy involved, and they need to go check it out.  

Everybody Hates Hitler

"Sammy, I think we found the Bat Cave."  

Oh, this is much better, the real Dean Winchester.  I'm so glad he's back.  Unlike Sam, who's seeing this whole Men of Letters bunker to be a break that they've deserved for oh so long, a valuable resource to help them fight demons and other creatures, Dean isn't buying into the whole thing.  He's having more fun with the perks of the Men of Letter's bunker, like the fantastic water pressure, the robe, and the fun (yet very sharp) weapons.  

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Oh yes, there was some fun done at Dean's expense, the whole Aaron hitting on him at the bar to cover his tracks.  "I thought I was being followed earlier.  Turned out to be a gay thing."  Hee, sorry, but I thought the whole thing was hilarious myself.  It's a lighter side of Dean we sorely missed.  

It isn't until his encounter with Aaron and the Golem that Dean understands, they have legacies to uphold.  He sees that Sam has easily embraced the responsibility, and finds that to be a big step in the right direction.  The end of the episode is just pure joy for a fan.  

"So, uh, what? Aaron's a J.I., and you're a Man of Letters now? Is that it? (He pours scotch from a decanter on one of the bookshelves and sets a glass down in front of Sam).  Good."

Trial and Error

Things are looking up finally for Dean.  He has his own room!  He's decorated it with a few artifacts, and he even has a memory foam mattress now.  "It remembers me."  The most notable decoration in his room though is a picture of him and Mary on his desk that he's been carrying in his wallet.  Even Sam is really touched by the display.  

Despite his approval for Sam taking on this new family legacy, Dean isn't seeing himself following that path.  When Kevin tells them about the three trials, Dean decides he's the one doing them.  He doesn't tell this to Sam until later, but rationale is both perfect, yet very sad.  It's reminiscent of season two Dean, who just made a deal for his soul in order to get his brother back.  

And you told me yourself that you see a way out. You see a light at the end of this ugly-ass tunnel. I don't. But I tell you what I do know -- it's that I'm gonna die with a gun in my hand. 'Cause that's what I have waiting for me -- that's all I have waiting for me. I want you to get out. I want you to have a life -- become a man of Letters, whatever. You, with a wife and kids and -- and -- and grandkids, living till you're fat and bald and chugging Viagra -- that is my perfect ending, and it's the only one that I'm gonna get. So I'm gonna do these trials. I'm gonna do them alone -- end of story. You're staying here. I'm going out there. If landshark comes knocking, you call me. If you try to follow me, I'm gonna put a bullet in your damn leg.

Dean takes on the hellhound, ready to take his spot with destiny, but the hellhound bests him.  It's Sam that comes in and kills the beast in order to save Dean, and now Sam has to do to the trials.  Dean is so against this he's willing to kill another hellhound himself to that he can do the trials, but Sam won't hear of it.  Dean has plenty of reasons to live.  He just got his own room for one.  Mostly though, Sam thinks his brother is a genius, and the best hunter he's ever seen, even better than John.  Sam isn't going to die either, so together they will take on this trial and live.  Dean agrees, but he's not really confident about the whole thing after Sam doubles over in agony after completing the trial spell.  His worried face says it all, something is not right here.  

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Man's Best Friend With Benefits

Any Dean canon that was presented in this completely atrocious episode can be forgotten and dismissed.  That pretty much goes for Sam too, and just about anything that ever happened.  Let's put our fingers in our ears and say "LA, LA, LA, I can't hear you, this episode never happened, LA, LA, LA."  

Remember The Titans

Perhaps it was Sam's pep talk, but suddenly Dean is all into the Men of Letters thing.  It's really cool, and while in "Everybody Hates Hitler" I saw Sam easily carrying on the legacy, this was the first time I saw Dean taking on this role too.  It fits him well.  He was rather prideful with Prometheus and Hayley.  "It's a secret society.  This is actually their lair.  We are legacies.  No big deal."  

Dean knows something isn't right with Sam though, and he's worried.  So worried, he reaches out to the one being he knows can help.  Something might be up with Castiel right now and Dean is having trouble trusting, but Dean's willing to take that risk to save Sam.  He still thinks this should have been on him, and he's not going to let anything happen to Sam if he can't help it.  Aww Dean, you really know how to hit our soft spots.  

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Goodbye Stranger

Poor Dean.  He's never taken being lied to well, and when Castiel and Sam do it to him at the same time, it's a little more than he can take.  

Castiel is under control of Naomi, and trying to get over his strong feelings of friendship toward Dean is the primary goal.  The killing of hundreds of Deans is an effective method!  Upon coming across Sam and Dean, Castiel is forced to lie because Naomi says they can't be trusted.  Dean and Sam know he's off, but Sam reminds Dean, if he doesn't trust him, why is he praying to him?  Obviously Dean still believes in Castiel to do the right thing.  

It's also getting much harder for Sam to fool Dean these days.  Dean finds the bloody napkin, and knows Sam hasn't been quite himself.  He doesn't say anything though until a fit of frustration, and right in front of Castiel and Meg too.  When Castiel backs Dean on that one, Dean chooses to go with Castiel to find the crypt and leave Sam behind.  He does this partially out of anger but mostly out of concern.  Sam is safer staying behind, but it's hard for Sam to see that.  

Dean and Castiel find the tablet, but not before things go very, very wrong.  Castiel under the control of Naomi grabs the tablet from Dean and beats him to a pulp, but he can't kill him.  Dean, channeling his pleading techniques from "Swan Song," begs the real Castiel to come out.  "We're family.  We need you.  I need you."  Yep, that does it!  Once again, the angels underestimate the power of humanity.  Or in this case, Dean's amazing ability to get through by pleading.  There was no amount of preparation they could have done to have Castiel resist that.  The history is too deep.  

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Unfortunately, Castiel may have spared Dean's life, but he takes the angel tablet and runs.  He needs to keep the angel tablet away from everyone, including Dean.  By the final scene with Sam, Dean has had it.  He can't take the lies and deception anymore from those he cares about.  At least Sam isn't bailing on him.  Sam promises to be honest from now on.  That's enough for Dean to channel his inner Lord of The Rings geek.  "Listen, I may not be able to carry the burden that comes along with these trials... But I can carry you."  It may be a cheesy reference, but that ends up being exactly what Dean does.  In a spectacular way. 

Freaks and Geeks

Dean is good with kids, and he wants to close the gates of Hell.  Great, tell us something we don't know.  I looked high and wide for any new lessons in this one, and didn't get any. 

Taxi Driver

Oh Dean.  I really felt his desperation.  He was unable to go with Sam and have his back, and that alone drove him crazy.  He was worried sick.  He wasn't buying anything Naomi was telling him about Castiel either, even if she was very convincing.  She even told Dean that the way to Hell was through Purgatory.  It showed how much he still believed in Castiel despite everything.  When Ajay was found dead though and he wouldn't be able to retrieve Sam in Purgatory, poor Dean had to make one of the toughest decisions in his life. 

When it came to Benny, Dean's guilt was already tearing him apart.  This was Sam though, and he's willing to do anything for Sam, including asking Benny to go back to Purgatory and guide Sam and Bobby to the portal.  That meant that Benny would have to be beheaded, and Dean crushed us all over his heartache from the mere idea.  If the guilt was bad before, I'm sure it's really haunting him here, especially when Benny refused to come back with Sam.  

It was all worth it though, and Dean would do it again in a heartbeat.  His relieved hug when Sam came back from Purgatory told the entire story.  He would do anything, absolutely anything for his little brother.  

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Pac-Man Fever

This is Dean at his overprotective finest, and he really grows in this one.  He's not just protective of his brother, but his "sister" as well.  That's what Charlie has become, the little sister they never wanted, and she's earned the protection of an overprotective big bro.  Dean is even calling the Men of Letters bunker home now, and the idea of Dean finally having a home makes me grin from ear to ear.  

This episode has a very strong theme of family, but this time, it stretches into that whole "Family don't end with blood" territory that Sam and Dean are all too familiar with.   Sam is not good.  The second trial really hit him hard, and he's wobbly.  His firearm skills suck, and even Dean noticed the rather disturbing case of bed head.  He practically orders Sam to stay on the sidelines and get better, but Sam won't hear it.  This of course drives Dean nuts, especially when he and Charlie go out on a case only to find Sam working it from the other side.  

Charlie needs saving, and Dean doesn't even hesitate to put himself into harm's way, taking the African dream root to get to her.  He's already discovered Charlie's secret, her mother is in a coma, and Charlie has been secretly visiting her all these years and sending fake donations for her care.  One reason Dean connects so well with Charlie is he understands her on an emotional level.  He can relate, he too lost his mother at a young age.  He understands the pain and the inability to let go.  He helps her get through all that, and it ends up saving them both.  It's not unlike the time he got through to Bobby in "Dream A Little Dream of Me."  As I've said before, he knows how to get through to people he cares about.  

Of course, when it comes to letting go of Sam, not gonna happen.  After all, Sam was the patient that Dean imagined he had to save in the video game.  I love when Charlie asks him, "What about you, you're gonna let it go?"  Dean has the right answer.  "Never."  But in a way, he does.  After Charlie leaves, Sam is all apologetic, waiting for Dean to go off on him but Dean surprises Sam (and all of us) by just simply pulling Sam in for a hug.  Despite his worry, he's going to trust Sam and together they'll go find Kevin.  It's a big leap of faith for Dean.  He's trusting Sam, but he's keeping him close too.  It's something they have to do together, and only together.  

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The thing I loved the most about this episode was how much it showed Dean's maturity.  He really has grown from the earlier seasons and his wisdom with both Charlie and Sam really accented the years worth of growth we've seen him go through.  He's becoming a truly respected patriarch, and one everyone would be lost without.  

The Great Escapist

The brotherly goodness in this one still tickles me to this day!  Sam has easily taken a turn for the worst.  He's feverish now, not eating, and emotionally he's starting to fray.  Actually, he's just plain erratic.  Of course that's the fever talking, but that doesn't make it any less revealing.  Dean's role is more important than ever.  He not only has to take on the role of being physically strong one, but the emotional center as well. 

Since we're on the subject of fever, score one for Dean and his fast ice bath skills!  How did he manage to draw an ice bath and pull in such a large man into a claw foot tub so quickly?  Well done!  It made a difference, because Sam was just one degree in his fever from death.  Plus, we got a wet Sam scene and Dean there with a towel.  Ah, the simple pleasures.  

Dean actually got to see a side of Sam he's never seen before.  A side he probably never imagined was there.  The vulnerable child that somehow knew even at a very early age that he wasn't clean and pure.  Dean never saw Sam that way or even imagined Sam that way.  At that age it was all about protecting and taking care of Sam, keeping the truth away from him so he could life a normal life.  Even as adults, when Sam's abilities started to manifest and Dean found out the truth of the demon blood, he continued to protect and watch out for him, because he knew none of this was Sam's fault.  He even says that to Sam in this episode when Sam brings it up.  But still, coming to the realization that Sam always knew he wasn't right, that had to break Dean's heart.  I'm sure he wants to believe the trials are purifying Sam, but you have to wonder by his silence how much he thought that was the fever talking.  They've been burned before, and that is some pretty wishful thinking.  Still, I think he came out hopeful for Sammy.  

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It's Dean that ultimately though saves Kevin by appealing to Metatron.  He takes Metatron's warning to heart, what's coming is going to be brutal.  He's not wrong.  

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Sam is worn down, and Dean's big job right now is keeping things together.  He tries to nurse Sam back to health, but more importantly he's there to make sure Sam doesn't lose his focus.  That's a little hard since they're nursing Castiel back to health too, and Dean's not exactly impressed with Castiel.  His anger toward Castiel is understandable, but it's obvious he still cares otherwise Cas wouldn't be there at all.  He's not showing any support though.  

When Crowley though delivers the big blow and kills Sarah, while Sam and Dean helplessly are unable to find the hex bag, that crushes what little bit of spirit Sam has left.  Dean is the one that must keep the mission going.  "We'll figure this out. We will. Man, we'll get it done. We'll kick it in the ass like we always do.  Are you with me?"  That's the all important lead in to the third trial.  

Sacrifice

It's the final showdown, and Dean isn't backing down now.  They do come up with that plan, even if Sam's not exactly thrilled.  Dean is classic badass with Crowley in the Singer Salvage yard, exchanging punches with Crowley, and refusing to show any sign of weakness.  Crowley's ass is theirs, for he's the third trial.  Right on!  That scene felt so good.  

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Sam is clearly troubled about taking confession, so Dean offers his advice.  Start with Ruby.  Then he starts listing all the other sins Sam has done over the last few years, and now he's hitting that sore spot again.  Sure he's a little playful and joking, thinking he's not doing any harm and Sam just takes it, but this is hardly the first time Dean has brought this sort of thing up.  It still stings with him, and he really doesn't know how much such backhanded comments are sticking with Sam, and not in a good way.  

Castiel shows up and Dean has to decide, who needs his help more?  He refuses to leave Sam.  "Now, if anybody needs a chaperone while doing the heavy lifting, it's Sam."   Of course Sam is behind him the whole time listening to this, so Dean has to prove he trusts Sam by going with Castiel.  Good thing he does, because Cas is really in a mess.  

Dean takes some time to talk with Castiel in the bar as they're waiting for the cupid.  He's aware if the plan succeeds that means Castiel will be locked in Heaven forever, and will likely be killed by the other angels for his past misdeeds.  It's his chance to make peace with the angel, and give him his blessing for his sacrifice.  This is Dean letting things go, and I admire the gesture he makes here on behalf of his angel friend.  He's trusting Castiel to make his own decision and choose his own fate. 

Dean does force Castiel to let to Naomi speak though, because he believes she's not totally untrustworthy.  Her information is enough to send Dean into a panic.  As soon as Dean finds out the truth, that completing the trials will mean Sam will die, he begs Castiel to take him to Sam right away.  He doesn't need to take anytime to think through this one, Sam will not be the sacrifice as God intended.  

Sam by this time is so weary, so broken and raw he can barely function.  Dean has to talk Sam down from the ledge, and he's hanging off it pretty steep.  Sam wants to finish it, or other innocents will die.  Dean has another idea, take everything they've learned from the Men of Letters and use it to turn the tide.  "But I can't do it without you."  Sam doesn't believe that.  This is where all those hurtful words, those years of backhanded comments to Sam come back to haunt Dean.  Sam hasn't been ignoring all that.  He's been holding it in, letting himself feel inadequate and a constant disappointment.  In this twist of fate, it almost gets his brother killed.    

Dean has to prove that Sam has always and always will be his greatest priority.  He reminds Sam he killed Benny to save him, and he's willing to let the demons walk.  "Don't you dare think that there is anything, past or present, that I would put in front of you! It has never been like that, ever! I need you to see that. I'm begging you."  Dean tells Sam it's simple, let it go.  Let go of all those years of pain, of the quest for revenge against the beings that ruined their lives, its not more important than each other.  This is very reminiscent of "Devil's Trap."  All those years later, it still holds true.  Family is most important.  It's all sealed appropriately (given the last few episodes) with a healing hug.  He just doesn't hug Sam.  He is there to hold up a weary and exhausted Sam, who practically collaspes in his arms.  

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Just perfect. 

So season eight ends with a new, more mature, and more trusting Dean Winchester.  Considering how many issues this guy has had with trust, this is a big breakthrough for our hero.  He's found his purpose again and no matter where that purpose goes, his priorities are still in line.  Sam comes first.  It's the Dean that we remember from past seasons, with a new found sensibility thrown in just to show us how far he's come.  Considering the past two seasons, this is a major triumph for his character.  Now what is he going to do about this angel problem?  Something tells me he's going to be very busy next season. 

Coming up next, my deeper look at season eight Sam Winchester.