My guess is that Alastor made a deal not with Lilith (or even Eve, not directly at least). My theory is that he made a deal with something far more powerful, like the embodiment of Evil itself. (I don't have much details on Roo and we don't know if she's canon. Honestly I don't know much about her character so for now I'll just sticks with the things we can observe.)
While talking about the creation of Earth Charlie explains that Angels protected and shielded Heaven from Evil. That imply that Evil existed before Hell, before Lucifer, before Lilith, Eve and the Apple. And we see this ominous figure with red glowing eyes. Okay.
Then we see Lucifer and Lilith and the story explains like Lucifer was drawn by Lilith's independence and that they wished to share the Free will with Eve, by offering the fruit of knowledge. Red ominous apple. Okay.
"With that single act Evil finally find it's way into Earth." That's some weird wording for something that should be a concept and not a living and thinking being that was awaiting for something like this to happen. Okay
And we see all this red eyes glowing eyes, as Lucifer and Lilith get cast into Hell and after, as Hell start to grow. So, the red glowing eyes are not from Lucifer or Lilith. Okay.
And as we go around Hell we see those eyes everywhere, sprouting around like some kind of mushrooms or mold. Okay.
But can you guess where else they appear?
Alastor's shield. Same shape, same colors, black and red, unlike Alastor usual acid green, that seems to be the main color when using his powers.
So, my theory is that Alastor didn't made a deal with Lilith. I think that yes, their disappearance around the same time is correlated, but not because they made a deal between them.
I think Alastor made a deal with the embodiment of Evil, and now Evil is trying to find it's way into Heaven. And what best opportunity that having sinners (someone that had already in some way or another being tainted by Evil and sins) go into Heaven?
Just a theory. I don't know, but those eyes looks shady as fuck and it seems to be a little too repetitive as a details to be just a cool design.
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