So the thing about s5 Sam & Lucifer, right.
The thing is that all along the way in the Kripke era, Sam is the one who overwhelmingly has sympathy for monsters. It's clear that, whatever he may say, Sam sees himself in them. Knows that he is monstrous, other, and destined for something that is completely at odds with hunting. He's instinctively much better than Dean at identifying which monsters are actually dangerous, and which monsters are victims. He encourages other monsters to avoid killing humans when he thinks they can.
He's not perfect, and he's still a hunter. But in comparison to other hunters or even other humans, Sam employs a bit more nuance and empathy. Because either consciously or unconsciously he sees himself as one of them, or at least someone with real potential to become one of them. Whether he wants to be or not.
So while I like the s5 ending & I think it works well thematically for the larger arc of s1-5? I do think it ignores that there could have potentially been a different, and a lot more archetypal, type of ending. Or alternate path.
Where, instead of just pathologically pretending he has nothing in common with Lucifer and couldn't begin to understand him (an outright lie on every level). Sam instead engages with Lucifer empathetically, trying to convince HIM to see things from Sam's perspective. (This of course is based a bit more on a s5 Lucifer interpretation without the retcon they do to his character later. Unsurprisingly as a result, there are like, a hundred different early-2010s fics where Sam does just this.)
But it's pretty canonical that Lucifer sees s5 Sam and himself as the same, as two people who can easily identify with each other. He expects himself and Sam to be able to come to a mutual understanding based on intimately shared commonalities. And, despite Lucifer's hatred of humanity generally, it just... never really translates fully into his relationship with Sam. Either in s5, where Lucifer genuinely goes out of his way to try to do what he sees as helping and protecting Sam. Trying to give him justice and peace. Or even later, when he is grating and mean and dismissive. Even then, Lucifer's resentful fixation with Sam just... doesn't fall easily into a category of "everything human = worthless and irrelevant." Where Lucifer sees all of them as just boring indistinguishable clones of one another.
He can't really see it that way or believe it. Because at the end of the day, that's not how he actually sees Sam. Based upon his actions.
When you look at him canonically, at his absolute worst, he needs Sam to play along, and not challenge him on his hatred and dismissal of humanity. He can't authentically maintain it singlehandedly, if even just on the inside. At his best, Lucifer barely seems to even care about actually hating humanity in practice. And mostly a lot more concerned about how he's been trapped into this role by God's unalterable forces of destiny.
There is definitely a world in which Sam could have at least tried to turn Lucifer to a different path. Especially considering Lucifer never really wanted to do the whole Michael apocalypse showdown anyway, and went out of his way to try to convince Michael maybe they should just not.
Even in s5, Lucifer is not always like, nice. He's not a peak example of emotional maturity. But he's also not committed to destruction for its own sake, and he's not above wanting to seek out peace with people he cares about. And that could have, and arguably did once, include Sam the human.
So yeah. In a world where Sam wasn't primed to reject every monstrous influence in his life, all because of what had just gone down with Ruby? In a world where Sam was able to see past his own defensive anger, his sudden rejection of anything Other (even when it was quite literally a reflection in the mirror)?
Sam might well have actually tried to connect with the Devil. Challenge him right back. And I'd argue there's a very good chance this could have worked
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