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Dean's pain broke my heart, and Castiel's last evidence of conscience and friendship in the midst of so much ruinous wrong did the same. In this discussion, I'm going to look at how Dean deals with pain, and examine what we learned about Castiel in this episode.
I'm The Guy Who Hit You
In this episode, Dean confronted his worst nightmare of guilt, seeing Lisa and Ben endangered precisely because of their relationship with him. If he hadn't gone to them after Sam died, they would never have been put in such jeopardy; that's a truth that couldn't be disputed. His reaction to the situation and the decision he made at the end were all in keeping with who he is and what we've seen from him before. He always takes more than his share of blame onto himself, insists on carrying the load alone, lashes out at anyone trying to help him in order to make them keep their distance, and refuses ever even to talk about the things that hurt him the most. And in punishing himself, he makes decisions for other people without regard for what they want, imposing his own belief of what's best, however misguided, on them. These things are all part of him, and all contribute to making him a tragically flawed hero.
We've seen this all before, right from the very beginning of the series. His insistence on accepting blame, concealing pain, and refusing to acknowledge it were some of the first real touchstones we learned about Dean throughout season one, as Sam slowly uncovered painful things from the past Dean had determinedly buried and never shared with him until then: discovering in Dead In The Water that child-Dean had been scared and gone silent after Mary's death;  hearing for the very first time in Home that little-boy Dean had carried Sam out of their burning house and had sworn to himself never to return to Lawrence; seeing Dean dealing in Something Wicked with his long-buried guilt and shame for having failed to protect Sam as a child. Remember Dean quickly figuring out what must have happened and blaming himself for John's death in season two, but angrily refusing to talk about John's death or his own feelings in Everybody Loves A Clown and keeping up that silence until Sam finally made him see, in Children Shouldn't Play With Dead Things, how badly he was scaring and hurting Sam by keeping it all to himself. Recall Dean doing it again in season three, resolutely hiding his growing fear of death and Hell behind silence and jokes until Sam made clear in Fresh Blood he already saw through the act. We saw it again in seasons four and five in Dean's extreme reluctance ever even to talk about Hell or how he felt about the things Sam had done that he saw as betrayals and rejection, things that hurt him badly. Listening here to Dean telling Sam flatly never to mention Lisa or Ben to him again, I heard the echo of young Dean angrily ordering little Sammy in A Very Supernatural Christmas to never, ever, talk about Mom, and similarly slamming Sam up against a bridge support in the pilot while telling him not to talk about Mom being dead and never coming back. Dean has always buried in silence the things that hurt him the most as if not speaking about them could lessen the pain, but we've seen all too well that by shoving them down and never letting them out, he's kept all those wounds open, never letting any of them heal. And now he’s doing it again – and Sam understands it, but can't stop it.
Dean claiming all the responsibility for himself and refusing to let Sam or anyone else help him carry the load is also characteristic, as is his tendency to make decisions for others by sacrificing himself. For example, he did both throughout the first half of season two when he hid John's last words about saving Sam or having to kill him. When he finally told Sam the truth in Hunted, he acknowledged that he deserved to have Sam pissed at him for not having told him earlier. He refused ever to apologize for having sold his soul to bring Sam back in All Hell Breaks Loose, Part 2, although he admitted from his own experience with what John had done that he understood the shame and guilt it would make Sam feel. He just admitted flatly in The Magnificent Seven that he hadn't been able to live without Sam. While he later admitted he understood that what both he and John had done had been wrong – witness his insistence from No Rest For The Wicked on that Sam not follow his example because the Winchester willingness to sell their souls for each other played into the bad guys' hands every time, and his concession to Death in Appointment In Samarra that he finally understood that disrupting the natural order had consequences he couldn't foresee or balance against each other – the simple fact was, he had made that choice and imposed the consequences on Sam. The biggest tragedy there was that Sam had died uncorrupted and free, and Dean's choice to bring him back was what opened the door to all the events leading to the apocalypse. Dean imposed his own similar decision on Bobby too, when he staked his own life on a game of cards in The Curious Case Of Dean Winchester to undo Bobby's own free if unwise choice and loss. Here, he refused to let Sam take over the interrogations because he vehemently denied that he deserved a break, since everything that happened to Lisa and Ben was due to him alone.

Given this long-standing pattern on Dean's part, I was saddened but not surprised when Dean chose to make Lisa's and Ben's decisions for them by having Castiel erase their memories of him. I emphatically agree with Sam that Dean was flat-out wrong in doing it, but I can understand why he did. He judged they would be better off without him and wanted them to be comfortable and happy in a normal life, free from fear of the supernatural and not feeling the mix of regret, confusion, love, anger, and loss they'd evidenced about their relationships with him in Mannequin 3: The Reckoning when he finally returned to face them. In his own mind and at the core of his heart, I think Dean truly was trying his best to protect them and leave them happy and content while he alone bore the pain of remembering how they'd been together and what they'd lost, but I also think he was unconsciously cheating and being selfish to spare himself knowing they might remember him with resentment as well as with love in the aftermath of what happened here.
I think there was no way for any of them to win after this, no matter what choices they made. Dean will always remember that Lisa nearly died because of him, saved only by Castiel's unasked intervention, and that under the pressure of the moment, he had treated Ben exactly the way John had treated him, dumping an adult's responsibility onto too-young shoulders simply because he perceived the brutal necessity for it. Dean will also always remember how Ben walked silently away from him in the hospital, seeing in Dean the whole reason his mother was dying, and knowing resentfully his mother was dying while Dean's own brother had returned to life. Had they been allowed to remember the events, Lisa would have remembered seeing her current boyfriend murdered and being helpless to prevent a demon from using her body to threaten her son and to stab herself, knowing it was all because she'd given succor to Dean. Ben would have recalled Dean slapping him and pressuring him into shooting possessed people, after having been adamant earlier about not letting him learn hunter skills, and would also remember being terrified and seeing his mother all but killed just because something just wanted to use them as leverage against Dean. I don't dispute the pain inherent in any of that, and I can appreciate Dean, loving them, wanting them not to share that pain.

But I submit Lisa and Ben would also have remembered all the good things about being with Dean, the things that led Lisa in Exile On Main Street to tell Dean the past year had been the best year of her life, and prompted her in Two And A Half Men to propose trying to beat the odds and find happiness in a continued episodic relationship despite normal hunter expectations. I would hold up her happiness at hearing from Dean early in Live Free Or Twi-Hard as proof their continued relationship had a tremendously powerful and decidedly positive influence even then, right up until Dean made the disastrous choice to visit them to say goodbye after having been turned into a vampire. Even after that, Ben's staunch support of him as a father-figure endured when Lisa began to date Matt, as evidenced by Ben's parent-trap call to him early in Mannequin 3: The Reckoning. Despite Dean's emotional trauma, his drinking, and his hunter paranoia, Lisa and Ben loved him – and I would submit they grew as people because of him and the love and support they gave him. I really resented seeing all of that negated because of Dean's desire to protect them from what they knew and felt. In taking away their memories and their choice, I can't help but think Dean diminished them, and that's entirely on him and on Castiel for granting it to him.
I also think it might yet bite him in the ass sometime in the future, because they aren't any safer for not remembering him; they may even be at more risk than they were. What puts them in danger isn't how they feel about him, but how he feels about them – and that hasn't changed simply because he knows they've forgotten him. They were snatched here to be emotional leverage against him. Understanding that, and knowing some small bit about the supernatural, they were at least a little prepared psychologically if not physically to deal with the situation. If they were snatched again later by something or someone who wanted either to hurt Dean or use him, Dean would still feel the pain and the obligation to respond even though they wouldn't understand what was going on and why. They are no safer for not remembering him, and may even be more at risk, because I'm sure they'll also keep no memories of the supernatural at all to give them any salt and iron edge if bad things happen again. Mind, I can understand Dean wanting them not to experience the pain he knows from their now-lost relationship, and to be able to return to a normal life without constant fear of unnatural things; what bothers me is the apparent concomitant assumption that now they're somehow safe from things like what happened here simply because they don't remember him. That's a false premise.
I'll confess that I loved the entire arc of Dean's relationship with Lisa and Ben, starting from his too late, sad, and surprising realization, prompted by his initial discovery of Ben's existence in The Kids Are Alright, that he would have liked to have had a family of his own despite having always disparaged such a normal existence; through viewing them as the impossible ideal that nonetheless stood for what inspired him to resolve to surrender himself to save the world in 99 Problems; to going back to them in Swan Song purely as the fulfillment of his final promise to Sam, only to learn he could actually live and sometimes even be happy with them relying on him and loving him. Dean losing them because of who and what he was in Live Free And Twi-Hard and You Can't Handle The Truth, and seeing how they'd moved on without him in Mannequin 3: The Reckoning, was heartbreaking, and his decision here to sever all ties and even deprive them of their memories while still knowing what he himself had lost just killed me. Family love has always been what defined Dean:  to have him here give up even any dream at all of a woman who could have been his wife and a boy who could have been his son was just too sad for words.
All Else Aside, I Just Wanted To Fix What I Could
Especially given where the season finale ended up, I think this was a vitally important story for us to see regarding Castiel because it established that the angel truly still did care, especially about Dean, and wanted to do what he could to make things right.
Castiel's relationship with Dean has always been complex. They were linked from the moment Castiel raised Dean from Hell, but neither could ever have guessed where that would lead them. Despite having observed humans through the entirety of the species' existence, close contact with Dean was a constant parade of revelations that gradually brought Castiel to see almost everything in a different light. Castiel rescued Dean and began to work with him because he was under orders from Heaven to do so, to secure the role Dean was expected to play in the apocalypse, but the human defied all preconceptions and expectations and quickly became much more to Castiel than just an assignment or a strategic piece on the board. I think that happened precisely because he was a puzzle. Castiel had been expecting the righteous man of prophecy: he was bemused to find instead a man who had no faith and didn't believe he was worthy of salvation, but who would sacrifice himself for others without a moment's thought or hesitation; a man who had no hope of winning but nonetheless refused to give up the fight. Dean could be crass, insolent, immature, and demanding, while at the same time being valiant, noble, astute, and generous. In trying to understand Dean, Castiel found himself having to question all of his own assumptions and beliefs.

I observed back in It's The Great Pumpkin, Sam Winchester that Castiel was in many ways a curiously apropos mirror for Dean – they were both loyal, unimaginative, and obedient soldier-sons still honoring absent fathers. But at the same time, Dean was more. He loved his father, but looking back, didn't hesitate to acknowledge where John had been wrong. And once he had grown into his own man, when what he believed to be right ran counter to the orders he was being given, he always went with his conscience and his gut in preference to blind obedience, even when that called for hard decisions and personal pain. Watching Dean, Castiel began to learn those same things for himself. That was what led him finally to rebel against Zachariah in Lucifer Rising and to labor as a rebel teamed with the Winchesters throughout season five.
I think Dean was the first human individual Castiel had ever personally known, and the angel found him fascinating and frustrating by turns. And I think in the end what surprised him the most was the way Dean came to accept and treat him as a friend, simply disregarding his wings most of the time. He found himself moved to friendship in his own turn, and almost despite himself. Sam and Bobby came to treat him much the same way, but never quite seemed to forget the differences between humans and angels as absolutely as Dean did. Their relationship has truly been unique.
In both this episode and in The Man Who Would Be King, Castiel demonstrated his genuine abiding care and affection for Dean. Facing off against Crowley last episode, Castiel flatly refused to kill the Winchesters or to let Crowley do it, either; when the demon threatened to do it anyway, Castiel said flatly that if he did, the angel would tear their whole agreement down – and I believe he meant it. In that moment, he put Dean's welfare ahead of everything else, even the war with Raphael and the prevention of a second apocalypse. Learning here that Crowley had opted for emotional pain since physical damage was off the table, Castiel once again acted to try to protect Dean, but this time, I think he'd gone so far down the heavenly war path that he couldn't contemplate not seeing it through to the end. In addition, this wasn't a question of Dean's survival, but only of his emotional security; heavy stakes, but not quite as dramatic. When Dean's life was directly threatened by the demon who broke free in the shed, however, Castiel was instantly there to save his life. He's invested in the friendship.
I think Castiel was genuinely torn between preserving his friendship with Dean and pursuing the single course of action he'd persuaded himself was his only hope of winning Heaven and thus saving Earth. He wanted Dean in his corner; he wanted Dean to support him and validate his choices because he couldn't see any other plan, especially after doing all the terrible things he'd already done. He couldn't afford to admit he'd been wrong; that would have meant admitting everything he'd done, and all the ways he'd compromised himself and violated his own integrity, had been for nothing, and even worse, were utterly unjustified.  
Throughout their conversation in the shed, while Castiel maintained he had no choice but to do what he was doing and asked if trust shouldn't go both ways, I desperately wanted Dean to say, Don't you see, you're doing the exact same thing Sam did, when he deliberately lied to us all, listened to and cooperated secretly with Ruby, and wound up opening the door to Lucifer's cage? That's why I can't trust you – you're making all the same mistakes for all the same reasons, and you can't even see it, any more than he could. You both believed you were doing the necessary thing, that you didn't have any other viable choice, that the stakes were too high to take a chance on failing – and you're both wrongBoth Castiel and Sam convinced themselves they were just doing what had to be done, but both hid what they were doing from others not just because they feared being misunderstood and opposed, but because they both knew, in their heart of hearts, what they couldn't afford to consciously admit to themselves: that what they were doing was shamefully wrong. Both truly still did care about Dean and wanted him to be all right, but neither was willing to listen to him, because they both thought the bigger picture mission stakes were simply too high; that everything would be lost if they failed, and therefore they had to put the good of the many ahead of the welfare of the one.
I'm guessing that even if Dean had laid it out that simply and openly, Castiel wouldn't have been willing to listen to him because that truth would have been just too bitter to accept after he'd done such things as deceived his followers and friends, killed his lieutenant Rachel, and been responsible for triggering Eve's violent assault, with all its collateral damage.
But what Castiel did in the end here still gives me some hope for the future. He hadn't been willing to jeopardize his plans to save Lisa and Ben, or – if he'd known about the angel-proofing on the foundry – to help the Winchesters do it as Balthazar did, but once Dean and Sam had accomplished the rescue on their own, Castiel cared enough to set right what he could that he healed Lisa, and when Dean asked, did him the further favor of erasing the memory of him from their lives. He didn't do it as a bribe or a lesson and it didn't change anything between them – but it said their friendship was still alive and still mattered to them both, and Castiel was still sensible of decency and honor.
Even after the finale – which I'll talk about separately – that gives me hope.


Far Away Eyes
# Far Away Eyes 2011-05-28 14:07
Wonderful, spot on review of Let It Bleed.

I am always struck by how willing Dean is to cut off his own arm. Here, I get the sense that he has cut his nose off to spite his face. I understand WHY he cut himself out of Lisa and Ben's lives, but I, too, think it wrong. He may think he's protecting them and keeping them from the horrors that is his life and the supernatural that stalks it, but he has ultimately put them in more danger.

If he had heeded Soulless Sam's warning that perhaps he couldn't have this Apple Pie life with them, he might have had them floating around out there for when he should or could truly retire for real. Instead, he held on tight and tried. It's hard to say if we will see them again, but it is a shame that Dean has chosen to carry this alone.

I am hopeful that in season 7 we will see Sam, and his stubbornness, despite Dean's threat to break his face, coax Dean into talking about this painful moment. Dean can only shove so much pain down and at a certain point it will kill him for good.

I agree with your wonderful assessment of Cas. He truly does care for Dean, despite the awful monster he becomes at the end of The Man Who Knew Too Much. I felt he was trying to apologize to Dean in Let It Bleed, and the question becomes what would have Cas done if Dean had given him the forgiveness he had given Sam and Bobby at Rufus's grave side? Had Cas witnessed that, too, invisible? Had he hoped that Dean would extend that wonderful heart of gold and embrace him with that forgiveness, despite the hurt? It's hard to say.

I am a fiction writer by trade, so I don't know as much about screenwriting or direction, but I found your analysis of the use of camera shots and angles to enhance my understanding of this episode. I will be looking out for these elements in this and other episode, and it gives my meta loving heart more fat to chew on, so I thank you for that.

All in all, I have enjoyed the Lisa and Ben storyline. We got to see a different side of Dean because of them, someone softer and more patient. In fact, I think it is because of them that Dean has the patience to endure Soulless Sam. I think a younger Dean would have possibly made more of an attempt to put Soulless Sam down, but here he has the patience to not only endure but to help Sam recapture his soul. If he hadn't had them in his life, I think it would have been different.

I will be curious to see if this storyline has been closed for good. I, too, think much like you that this is a part of a trilogy or four part arc of episodes. It's not much different than the way All Hell Breaks Loose 1 and 2 blend into The Magnificent Seven.

So, again, thank you.
# Bardicvoice 2011-05-28 15:43
Thank you! Glad you liked!

I'm with you in hoping that Sam may yet get Dean to talk about Lisa and Ben, both in terms of what he had and what he lost. Sam and Bobby are the only people we've seen able to pressure him into talking. Sam has done it time and again by making it about the effect Dean's pain has on him, manipulating Dean's "protect Sammy" wiring by showing Dean how upset it makes Sam to see Dean transparently trying to hide pain, shame, and fear. When the only way to alleviate Sam's worry is to talk about himself, Dean eventually caves in and 'fesses up. Bobby has done it by being accepting and holding out a father's unconditional love; Dean knows that when Bobby shakes his head and calls him an idjit, it's as much a term of love as the "bitch/jerk" mantra he and Sam share. I really do hope it will slowly come out, but I definitely won't expect it to come soon or all at once when it finally does happen.

You make a great point about Dean's time with Lisa and Ben likely having contributed a lot to his ability to deal with soulless Sam. I hadn't thought of it, but you're right; he had to learn a whole new balance and an unfamiliar patience that served him in good stead when Sam felt so very off. Thanks for that!

On Castiel: I think forgiveness and redemption are still possible, but not quite yet. I couldn't see Dean offering forgiveness in the middle of the argument, though; not when his whole point is how wrong Castiel is being in doing what he's doing. Dean's had time to process what went down with Sam earlier, and knowing how rapidly things can go south with no one meaning them to, wanted neither Sam nor Bobby to feel the kind of guilt Sam was carrying for his failings and Bobby was carrying for Rufus's death if his own death came on him before he could say the words. I think he'll get there with Castiel eventually, but Castiel admitting to having done wrong things and desiring forgiveness is an essential and currently missing part of that equation. Forgiveness means nothing if there's no awareness of guilt establishing the perceived need for it. Here, Castiel has stubbornly maintained he's done nothing wrong, but only what he had to do; he's maintained that Dean and the others were the ones in the wrong for not trusting him. Not feeling the need for forgiveness, I doubt he'd accept it even if it were offered.

When he does admit it and seeks to atone for it, forgiveness will be waiting; of that, I have no doubt. And I'm hoping that may be where season seven takes the story.

Again, thank you.
Far Away Eyes
# Far Away Eyes 2011-05-28 16:09
Sam has always had a manner of turning those puppy eyes on Dean and forcing him to admit things, yes. I expect, much the same way he had to drag it out of Dean about going to Hell in season 3 and then what had happened in Hell in season 4 we'll see Sam play another similar card to bring Dean out. Sam can take some of the blame for what happened with Lisa and Ben--as it was his idea to shove Dean at them. They must resolve this issue between them or face another fracture that could damage but not break their relationship.

It just occurred to me as I was thinking about your review and how Dean seemed to tolerate Soulless Sam as well as he had that it had something to do with his time with Lisa and Ben. The more I turn that thought over in my mind, the more I think it fits. It also pulls that thread and the thread concerning Sam and Dean together in a wonderful way. Each piece fits together well and would have been missed if omitted.

The only reason I say that Cas is trying to apologize through this episode is not because he feels he did wrong. I agree with you. He most certainly does NOT feel that he is in the wrong. His hubris is so entrenched at this stage for that. I think he's more apologizing for the fact that it somehow hurt Dean. He might not entirely grasp why it hurt Dean---and shame on him if he does---but I sensed that he was sorry that it hurt Dean in some way. If he had gotten Dean's approval, which is another thing he sought--along with some form of forgiveness, I don't think Cas would have taken either. He was so paranoid by the end of the season that anything anyone said to him was questioned and discarded as a lie by Cas. He might have sought it, but his paranoia would have forced him to reject it.

I do think, that if Cas is given the chance, to seek forgiveness and redemption it will be waiting for him. He has so much to atone for from breaking Sam's wall---which in a strange bizarre way may be a gift, to taking Heaven's throne by twisted force, to lying about resurrecting Sam from the Cage sans soul.

We know, as self sacrificing as Dean can be, that he is also forgiving. He has a large loving heart and I don't doubt that if he would open it to Cas again that they could find ways to heal this rift.

We shall see!

And you're welcome. I am just thrilled by this wonderful site and its brilliantly insightful writers such as yourself. I feel so privileged to sit amongst you.
# rmoats8621 2011-05-30 01:53
This was an amazing article as were the comments that followed. I have totally enjoyed this and look forward to the next one. Also, I am just as amazed of the insight that the writers and commentators of this site have into this wonderful show. :D
# Sylvie 2011-05-30 15:40
I desperately wanted Dean to say, Don't you see, you're doing the exact same thing Sam did, when he deliberately lied to us all, listened to and cooperated secretly with Ruby, and wound up opening the door to Lucifer's cage? That's why I can't trust you – you're making all the same mistakes for all the same reasons, and you can't even see it, any more than he could. You both believed you were doing the necessary thing, that you didn't have any other viable choice, that the stakes were too high to take a chance on failing – and you're both wrong.
That was amazing, I wish he'd said that exactly. You are truly an amazing writer (as is everyone on this site). I take off my hat to Jensen Ackles for the astounding acting all season, but most especially in this episode, you could feel Dean's vulnerability through the screen. These two guys are so great at what they do, I wish they would get acknowledged for it. But then again, maybe they are our well kept secret and I'm not much in to sharing anyway!

Keep up the good work on the writing, it's something I look forward to.
# BagginsDVM 2011-05-31 20:06
Similar to what Alice included in her review, I was quite depressed initially after this episode, wondering how much more sadness & loss Dean was going to have to endure. I just want some happiness for the man & his loved ones, & the eternal optimist in me is still expecting that by the time the series ends. In the meantime, I'll suffer along with the guys no matter what comes their way.
I'm in full agreement with your analysis of Dean & Cas & where their characters stood in relationship to each other in this episode, still respecting the other, trying to maintain that unique friendship. If only they would have tried to explain their viewpoints to each other! Then again, they were too entrenched in their situations to really listen to each other.
I certainly saw John in Dean during the Braeden rescue mission. Although I don't agree with Dean's decision regarding the memory wipe, it fits with where his head & heart were at. That's our Dean Winchester, flawed but definitely our hero.
I like the idea of viewing these last 2 episodes of season 6 as just the first part of an arc; cliffhanger absolutely!
I won't know how I feel about all that happened in these episodes until I see the resolution of these storylines in the beginning of season 7 (or maybe later!) I'm in it for the long haul!