So, here’s my theory. Spoilers ahead for those of you who haven’t seen season two yet.
As we knew, Alastor had a deal with Rosie since the beginning.
Rosie knew that Alastor would become the most powerful demons in Hell. So the terms of their deal might be something like this: once Alastor is no longer the most powerful sinner, he gets to unclip his wings and breaks free from this deal.
Keeping this in mind, I think it’s highly possible that Alastor is searching for a sinner with the potential to become a powerful demon, but also someone he can easily manipulate.
That’s where Vincent comes in. When he arrived in Hell, Alastor recognized his chance: Vincent could become a powerful demon with the right guidance, so Alastor sought him out and soon established himself as a mentor.
But things didn’t go as Alastor had planned.
Vincent didn’t reach his full potential because he grew attached to Alastor. And Alastor himself found something like a friend in Vincent.
He reminded not only Vincent but also himself that there are, in fact, “no friends in Hell.”
Instead of becoming Vincent’s partner, he manipulated him into becoming a greater demon by destroying the last thing holding him back: his remorse about overthrowing Alastor as the media demon Vox.
On that day, Alastor laid the foundation for Vox becoming a brutal and remorseless demon by rejecting him and humiliating him to the core.
And in the end, Vox became the most powerful sinner. And Alastor was freed from his chains.
But at what cost?
Because Vincent was Alastor’s friend, but in order to empower him, Vincent had to die so Vox could live. And Alastor was the one who dealt the final blow.
So I truly think that they are, in their one way, bawlin’ about the past that could have been.
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