i love that steve yockey wrote michael's dialogue like that, "i'm gonna write the opposite of what dean thinks for every character in order to hurt them" which means you can reverse everything he says and learn his true feelings about each character. genius.

I think this is definitely a clever part of the writing. (Yay Yockey!)

Michael is good at twisting things to create a diversion/undermine his enemies. (Maybe even better at it than Lucifer, heh.)

I think another part is that AU Michael understands absolutes better than duality. He’s picks out and amplifies the negatives. I’m reminded of Cas’s line in season 9 about human emotion: 

AU Michael doesn’t grasp it. Not really.

He runs around asking everyone, “What do you want?” and if there’s any complexity at all to that answer, he brands that person/angel “lost,” “weak,” or “unreliable.” This is why he allies himself with vampires at the end of 14x01. Because he can’t comprehend shades of gray or nuance.

Humans feel a billion things every day. Moment to moment. But every fleeting discomfort, every microsecond of frustration, every scrap of resentment or bitterness? To Michael, these get magnified into absolutes. (This is often how demons present their truths: through the most uncharitable interpretations possible.)

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Loved ones are burdens

A more honest answer might be that our loved ones are, in fact, both beloved and burdensome. We trade strengths and share burdens, but that doesn’t mean they come without weight.

It’s only in relationships that are more figmentary, kept at arm’s length, or those that have ended and become idealized—like memories of people who never truly had a chance to be seen for who they really were—that we see relationships without real baggage.

This is especially true in a world like Supernatural.

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Dean wasn’t happier without Sam in his life

I think it’s probably true that Dean was occasionally relieved when it was just him and Dad, but mostly because it was a break from the turbulence and in-fighting.

At the same time, he felt abandoned by Sam, maybe jealous that Sam reaped all the rewards (education! freedom!) of Dean bearing the family burdens.

Yet, Dean also wanted what was best for Sam and was genuinely happy to see Jessica Moore in his djinn dream. More often than not in the series, Dean encourages Sam toward happiness, though not at the expense of what he perceives is a balanced work-life obligation the people in their lives that depend on them.

But it’s certainly not true that he was happier without Sam, nor that he wished it had been only him and John all the time.

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Dean’s not with Cas because he “owes” him but because he loves him

Michael mocks the line about being "gripped tight and pulled from perdition," showing us that this is a line Dean recalls often, perhaps replaying it in his mind over and over.

(AU Michael also coos: “Oh, Cas… I believe in you!” in an earlier scene, and it seems to me that he finds Dean’s emotions a bit… amusing.)

But to my point—maybe the bad parts are a little bit true. Feeling indebted to Cas might be intertwined with Dean’s gratitude, and it’s definitely true that Dean harbors real resentment over Cas’s mistakes. However, Michael can’t completely parse the complexities of Dean’s feelings for Cas. He can’t reconcile the bad with the good. It’s an alien’s perspective.

But Dean… The way Dean talks about love in Optimism shows us that he can handle all the complexities and put them into words. He feels a deep gratitude toward Cas for saving him, and he recognizes that Cas’s mistakes are part of the endurance of real love—not the idealized, immature kind.

Interestingly, while Sam and Jack are visibly shaken by AU Michael’s words, Cas doesn’t seem affected in the same way. Not only does he remain unruffled when he steps in to assure Jack that Michael is “loose with the truth,” but he also quickly picks up on Michael’s barbs as a deliberate strategy—he calls it out: “You’re stalling.”

By saying “Poughkeepsie,” Sam helped Dean break out of his loop of simplistic vampire hunts. But by mouthing off to Michael, it’s Cas who helps Dean rally his self-confidence. Cas's steadfast trust in Dean serves as a source of strength.

I personally think this implies that Cas and Dean have talked through their mistakes more in-depth than we think, even if they haven’t fully discussed their “feelings" per se.

They trust each other, even when they’re feeling completely downtrodden or vulnerable. Even when "their instincts might be screaming otherwise," you know?

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Finally: Of course Dean loves Jack

We have to remember that AU Michael’s attack is two-fold, here. Unlike with the others, Michael is absolutely seething about Jack turning him down on family bonding time in 14x09 The Spear.

What Michael probably really wants is to undo the murder of his brother, Lucifer. But Jack is unwilling to become Lucifer’s replacement. So Michael wants to cut Jack as deeply as possible. As punishment.

Ergo, following that mindset, maybe Michael’s a little bit right. Maybe part of Dean does see Jack as "another burden handed to him” and he might even he worried about Jack’s newfound weakness—but it’s also more complicated than that.

And it’s true: Jack isn’t like Sam or Cas, but it’s not because he’s not family. It’s because he’s a different kind of family. While Sam has grown into being a brother, an equal, Jack is and will forever remain wholly “son.” That’s a scarier bond. It doesn’t just come with love but with responsibility, hope, and an undeniable weight.

And as for Jack’s death—while Dean may have initially reacted with emotional numbing and shock, he was devastated. Time has shaped Dean's reaction to grief, and he is trying to do it right:

14x08 Byzantium via @spnscripthunt-inactive

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Appealing to the “you’re just a burden” is something Zachariah also made good use of in his nightmare-land from Dark Side of the Moon:

5x16 Dark Side of the Moon

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Oops, I rambled.

Anyhoo, that a wounded Dean echoes any of AU Michael’s words is, to me, a testament to how deep his psychological wounds are (late 14 through season 15).

The series told us over and over again about the psychological ruination that results from being the vessel for an archangel… with many humans implied catatonic afterwards. (The series also spent the majority of season 14 showing us how much being glued to Lucifer wounded Nick...)

But yes, I do love the double-speak in the writing and how it often implies the opposite of what’s being said. That’s so much for bringing this into my ask box!

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One more bit about indirect dialogue:

I also loved when Dean was hurling word-daggers in at Bobby, Cas, and Sam in 5x18. Dean was mocking his unique relationship with each of his loved ones:

Mocking his belief in Sam’s strength:

& Pretending he doesn’t see Bobby as a father:

& Making light of his deepening feelings with Cas:

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Finally, I can’t help that point out that fleeting moments of resentment and even longer moments of being angry/upset/disillusioned with our loved ones isn’t a big, abnormal thing. It’s just very human. And healthy.

(In SPN-world, it’s coded as more concerning when we see the opposite, when characters insist someone is perfect or never lets them down. This is a SPN “poughkeepsie” pattern that I mentally shuttle into the “pure” bucket. See: Harper, Amara, Chuck etc)

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But fleeting moments of negativity are real. Which is to me what makes Jack’s murder of Mary so very sad:

"Only for a second." :(

Where is that meta you have where Dean looks up towards Cas for emotional support? I think it's when they're talking to Ketch?

Ohhh. That's from The Spear! I was being very silly about it.

On a more serious note, that whole episode, Dean's leaning on Cas in these big, spousal-coded ways. (That's why I prefer the script on this aspect. Dean was letting Cas drive him to the case in the truck, relying on Cas visually and entrusting Baby with Sam and Jack.)

And honestly, I feel like the script is going out of its way to show us that Cas has been an emotional rock for Dean, both in this and in Peace of Mind, which is what makes The Empty Deal so insidious. It encourages Cas to pull away when his own emotions get overwhelming.

I think this is hinted at in Game Night with Dean's played-for-laughs stress/meltdown at the beginning of the episode. Dean is floundering because he can *feel* Cas's emotional distance. (He always does.) He just doesn't know why the emotional distance has become so inflamed.

EDIT: And on another note, when it comes to AU Michael, I think it's important to acknowledge how desperate Dean is to be safe from that intense violation. As @scoobydoodean pointed out, that desperation to be free from violation/voyeurism is also at play in season 15, giving more weight to Dean's deepening desperation to neutralize the threat of Chuck.