On one hand, I think the line "I'd rather have you, cursed or not" is very romantic and amazing, and I can totally understand why it's one of the biggest destiel quotes.
But on the other hand, that quote is prefaced by dean saying "you know what, bottom of the ninth, and you're the only guy left on the bench." Which makes it seem like Dean is basically saying "even though you're not very good, you're the only option we have left" which doesn't feel nice at all.
I really want to love that quote. And by itself it's lovely. But with the context, I'm not sure how it's supposed to be sweet? What am I missing?
Hi there! and honestly I appreciate this question, because you are looking at more of the context of this line and trying to understand it that way, and there's just so much bad faith interpretation happening out of context in the world these days that it's refreshing to see folks try to dig deeper! Really!
But if context is what you seek, then you're still only looking at a convenient snippet of the conversation and larger context of the scene. To understand the fullness of the significance of this line, you have to understand all of s7 really.
Dean spent the better part of the season coming to terms with the loss of Cas, only to finally get him back and then "lose" him again in one go just a few episodes ago. And then when he began to recover-- sort of, to the extent that Cas wakes up and is walking and talking for himself again by this point in the series, despite clearly being not-quite-right and burying his own responsibility for their current situation under this mountain of denial and avoidance that manifests as what the fandom commonly shorthands to "crazy!Cas" even if I personally don't see him as "crazy" here but deeply, deeply in denial and horror with himself-- when Dean thinks maybe he might have a chance of getting his friend back, what he's left with is so incredibly frustrating to him.
I mean, look at Dean's own life. He's never been able to truly lay down this burden of "fixing everything." And he's TRYING to be understanding with Cas, but he's honestly out in territory that he can't even wrap his head around. Think back to the whole "your PLAYING Sorry" scene two episodes before, where he's trying to shake Cas back into recognizing the reality of their situation and just being that person Dean had known before... between Dean feeling the urgency of their situation and Cas deliberately and repeatedly glossing over his own part in it, he sort of reached the end of his rope. He is trying so hard, though.
By this point in 7.23, he's come to an acceptance of Cas as he is now, though. Cas won't fight, Dean knows that. But he also knows how Cas CAN help, without fighting. Cas can bring him back to where his car has been hidden all season, and Dean WILLINGLY allows Cas to teleport him there. Which, in itself, is something of a miracle, you know? Dean HATES teleporting :'D
He's trying to meet Cas on his level, but again, Dean is also feeling the burden of now having to fix everything on his own. He's accepted that this will probably be his Last Stand against evil in the world, you know? He believes there's a very good chance that this is a suicide mission, and that this could be the last chance he has to even talk to Cas at all.
So bearing all that in mind, let's look at their whole conversation, not just the two lines you referred to, and I'm gonna break it down line by line:
CASTIEL: If we attack Dick and fail, then you and Sam die heroically, correct?
[oh my, a shred of hope for Dean-- is Cas including himself in this mission now, after insisting for days that he will not fight? But Dean won't push it, he's just gonna be honest and let Cas make his point in his own time]
DEAN: I don't know. I guess.
CASTIEL: And at best, I die trying to fix my own stupid mistake. Or... I don't die – I'm brought back again. I see now. It's a punishment resurrection. It's worse every time.
[yes, it looks like Cas is actually considering what his own role in this fight could be, but oh fuck, is this really how he views himself? his own ongoing role? this sounds borderline suicidal and awful, but do we really have time to unpack that massive suitcase right now? that's a rabbit hole dean can't afford to go down, no matter how much he might want to understand and help Cas come to terms with this, it's so far above his pay grade it hurts his head to wonder about, so he's gonna attempt a deflection]
DEAN: I'm sorry. Uh, we're talking about God crap, right?
[oh good, at least this got Cas to change the subject back to himself, back to territory Dean can understand, because Dean feels exactly this same way about himself... this is something Dean can address via the same coping mechanism he's used for himself his whole life, because this is does understand 100%]
CASTIEL: I'm not good luck, Dean.
DEAN: Yeah, but you know what? Bottom of the ninth, and you're the only guy left on the bench... Sorry, but I'd rather have you, cursed or not. And anyway, nut up, all right? We're all cursed. I seem like good luck to you? [CASTIEL stares at DEAN.] What?
[but lolololol of course Dean's own coping mechanisms for feeling insufficient to any task yet forced to pick up all those cosmic burdens his entire life involve baseball metaphor pep talks... tell me this isn't EXACTLY how Dean has felt about himself every single time he's had to confront the responsibility the cosmos has laid on him-- from having to raise Sam to being resurrected from Hell and forced into being Heaven's champion to "play his role" in the apocalypse... he has literally told Cas before that he wasn't the guy they needed, that it was all too big and he couldn't do it... and yet... he didn't really have a choice. He just had to nut up and do it. It's all he COULD do, you know? So this is what he has to offer Cas in this moment of mutual understanding-- his own sense of personal helplessness in the face of cosmic chaos, and the only coping strategy he has for himself, which sadly happens to be self-deprecation, acknowledgement of his own uselessness and powerlessness in this situation, and choosing to do the stupid thing anyway.
And after delivering that bit of The Worst Pep Talk to Cas, he acknowledges that he was also speaking about HIMSELF with the "i seem like good luck to you?" line, which is actually what finally makes Cas blink. Cas finally understands, Dean's NOT just prodding him to be useful, HE'S PRODDING HIMSELF to be useful, just as much. Dean ALSO feels terrified, guilty, and useless! THEY HAVE BONDED!]
CASTIEL: Well, I don't want to make you uncomfortable, but I detect a note of forgiveness.
[YES. Cas understands! This is Dean's attempt at forgiveness! Despite the terrible Dean-mangled words, Cas sees right through him and knows, and understands]
DEAN: Yeah, well, I'm probably gonna die tomorrow, so...
[and because this is still Dean, of course he deflects, but he's also sincere here... he really does finally forgive Cas for everything he'd been holding against him since the end of s6. They have reached an understanding, at least, and have chosen to give themselves a clean slate-- as Dean once promised Bobby and Sam they would always do for each other, again back in s6 at the funeral they held for Rufus... they would never carry a grudge to their death. All would be forgiven. And despite Cas not having been part of that conversation at the time, he understands anyway. These words sound dismissive, but there's deep Character Stuff about Dean backing them up as earnest, and Cas accepts them on that level]
CASTIEL: Well, I'll go with you. And I'll do my best.
DEAN smiles slightly and nods.
This is so few words to convey SO MUCH about their relationship, about what they will be willing to set aside for one another, just because they understand, forgive, and accept each other where they are, and continue to do their best just because the other one asks and needs them. Even when they're both convinced they're doomed to fail, that won't stop them from at least TRYING to do what's right, the only thing they really can do.
So with the full context of that scene, does that clear things up?
