Thinking about Dex's moral wiring, and perhaps a lot of people struggle to understand him because they try to perceive Dex through a modern sense of morality, when actually, taking a homeric lense makes him much easier to understand.
Dex has about the same wiring as an ancient greek soldier following Homeric morals, which is different from later greek morality where big names like Socrates, Plato, and Aristotle come in. But while one is a product of culture & era, with Dex, it's of his own nature.
A virtue I see Dex caring about is metis, which is being cunning, intelligent, and adaptable. And as he grew, his influences (Mercer/military/FBI) taught him that he should also care about the people around him, as well as achieving kleos (lasting glory) and preserving timē (honor) for the community.
While Dex is selfish, having these parental/authority figures helped shape his idea of how metis should be practiced in life. And that's where Dex learns to care about being the "good guy" (hero). Fbi!dex wants to use metis for righteous purposes and see the community he fights for welcome him as the hero.
But the problem is that Dex, with his intrinsic sense of morality and personality disorder, struggles to force who he is into what modern society perceives as being an actual hero. Dex tries to act in accordance to these expectations, but it doesn't give him any real fulfillment; If we recall in S3 DD, one of the first frustrations he reveals is that, as an FBI agent, his actions are criticized by the public, while vigilantes "do the same" and get approval. Dex did exactly what the authority figures in his life said he should do, but he is still not accepted.
This definitely doesn't help Dex's issues with loneliness, alienation, piss poor social skills outside of work, etc. And the more alienated he feels from society, the more prone he is to seek acceptance from questionable figures (Wilson Fisk), or later on in DDBA, to lean into his own selfish nature. I think a huge part of why Dex is so changed in DDBA, is that he abandons (most) of what he was taught for the sake of being his authentic self. A self that is more selfish, and that does NOT bother anymore to force himself into these molds that he doesn't deem rational in the first place. He even stops pretending to care about the modern sense of guilt.
With Homeric morality, even concepts of shame and guilt are different because they're not internal, but rather what your actions bring to your group, because you need to fulfill your role/obligations to the community and the gods. Which is why I hate Nolan's Odysseus because that mofo did NOT feel bad about slaying Troy, he wanted to get home to bask in the glory. But that's a rant for another day.
While Dex's struggles with empathy are part of a personality disorder, putting it into a homeric lense helps you understand the train of thought. In homeric fashion, the hero doesn't feel bad about killing someone, because that was apart of the goal he set out to achieve. If the goal was achieved, that's what matters. The ends justify the means. What the fuck is catholic guilt?
Following the Odysseus example, the man isn't stone cold; he regretted the lives of his men, lost trying to return home, but STILL not what he did in Troy. Why would he? He achieved the goal and brought glory to Ithaca by displaying exceptional metis. The man is PROUD. Ok sorry I'm done talking about the Odyssey. Fuck Christopher Nolan.
Anyways, Dex had to deal with nature vs nurture, to fit his psychological wiring to the world around him. But after crashing and burning at the end of S3 DD, Dex stops caring about this. For example, while he didn't feel guilt about killing Foggy, he cared about the circumstances surrounding it all, about Vanessa taking advantages of Dex's situation.
Even "leveling the scales" is part a fixation on Matt, part needing revenge on the Fisk family, and part being lost as fuck because the life he worked so hard for is gone. DDBA!Dex is trying to be honest to himself, but being so lost makes him more prone to acting subconsciously, and unintentionally still trying to play a version of a "good guy", albeit a version that's more aligned to who he actually is.
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