#thinking about it

Why is this relevant? Vox died in the 50's, and in the flashback he even admits himself that's he's still 'pretty new' in hell.

Valentino didn't die until the 70's, and presumably he didn't meet and get in with Vox immediately after death.

This means that for at least 20yrs Alastor and Vox probably kept up some kind of relationship.

I also just want to point out that this picture, must have come after the flashback

Judging by Vox's collection of heads from season 2, the photo is either his 2nd or 4th head? (I think it's 4th for reason I talk about later) It also looks like he's also got the pinstripe jacket, which we know he doesn't adopt until much later in the timeline.

Meaning that the photo was taken after Alastor rejected him in the flashback. (3rd head seems to be the one from the flashback of Baxter joining voxtex)

Alastor did say Vox threw a temper tantrum and he had to put him in his place. But that doesn't 100% say that this is when their relationship broke down, since Alastor is fully capable of being an ass, and then acting like nothing happened (which Husk is very familiar with)

Alastor says this in a mocking way to taunt Vox, but look at the difference between Alastor's mocking, and his reaction at the time.

Alastor is either loving the attention, or putting up with it because its Vox.

I think he doesn't like the thick compliments, because being at the top of the food chain at that point, he probably had a lot of people trying to suck up to him and act nice to get him on their good side.

Either that or there's a history of Vox playing nice when he wants something for someone, and Alastor is trying to give him the benefit of the doubt

This could just mean that people love the two of them separately. But to me it sounds like maybe they were actually known in Hell as a bit of a double act for awhile.

I mean, it doesn't seem as if Alastor really keeps people around him in general. He's not known for having friends. Mimzy is the only other person we've seen that people would know that he's associated with, because he's helped her multiple times. And even then Mimzy says Alastor wouldn't use the words friends, even though they knew each other even while they were still alive.

I think Alastor is already expecting the sales pitch from Vox here, but he's hearing him out just to be polite. He's been amused by Vox most of the conversation so far, so it seems he does enjoy spending time with him.

He's not impressed, but he doesn't have his big reaction until Vox asks him to outright partner with him, and Vox offers his hand to seal the deal.

Alastor is already locked into a deal he can't get out of, and he probably also assumed that Rosie would be a partner of sorts when he originally made the deal while alive. He's been burned by deals, and thinks that there is no way that Vox wouldn't screw him over.

Vox found Alastor inspiring. He looked up to Alastor, who presents himself as this ruthless loner, and somehow thought that Alastor might make an exception. Because it's Vox. The two of them are close right?

I also think that Alastor might be a bit tipsy here? It's clear they've been there a while, he's had at least 2 glasses of whiskey. And according to Mimzy Alastor is a lot softer when he's drinking.

Alastor barely swears in the show unless it's to make an impact. And here he does it just because he's so caught off guard and having strong feelings about the offer.

I know al lot of people point this out, but. He's also pulling his hair in this scene. He's only been shown to do that when he's distressed. In fact, the only times we've seen him do that, is in regards to him almost dying, and in relation to his soul contract that he desperately wants to break out of.

Alastor says you 'need' me to join your team, not want, need. He sees this as something that only benefits Vox, not himself. He feels he's being used.

And in present he admits that he had respected Vox when he was growing his power. He had thought they were similar.

This is one of two things:

Either Alastor is disappointed that Vox would stoop so low as to piggyback off Alastor's own power and reputation.

Or Alastor is disappointed because he believed that Vox could become as powerful as the radio demon (Approaching my level) by his own merit.

Vox is trying to take the easy way out, the same thing that Alastor regrets doing with his deal with Rosie.

Alastor projects onto others (THIS Post for my thoughts on that) So he might have been disappointed to see Vox needing help the same way Alastor did. He thought that Vox was better than that.

Jumping back to the present:

Vox clearly teamed up with Valentino at some point, and Alastor didn't like that.

Vox finally made the team he needs, but without Alastor who had already refused him. The fact the company is called Voxtex, and not anything with just the more modern 'Vee' motif, means Vox was probably already pretty big with his own company before Val joined.

Vox probably wouldn't have recruited Valentino until Val was an overlord himself. If Val died in the 70s, he probably didn't make overlord until the 80s? Which fits with Vox's outfit with the big lapels.

Its hard to tell because its cut off, but I'd say these photos are probably from around the same time. In both photo's Vox has either a fully black casing on his head, or a black outline around the front.

I think Alastor turning to Valentino when he says "And then you went and ruined it" was the thing that broke whatever relationship they had. Vox was proving he needed to share his power to become stronger (It's heavily implied in the show that all the Vee's souls are shared between the tree of them)

But also

I think Alastor and Vox got into a fight, which might not have been unheard of, since alastor apparently put Vox in his place after the flashback. But this time, Valentino joined the fight, making it uneven and unfair.

In modern day Alastor was mostly keeping up with all three Vee's at the same time, but he was struggling and wasn't at full power. In the finale he wanted to finally fight Vox one on one, with both of them at full power, but once again Vox needed to bring in reinforcements.

Val did say in stayed gone "You pissed he almost beat you that time?" Almost, and its a time that Val is very aware about, because he was probably there. Vox and Val also both have messed up antenna, which I think was from the same fight with Alastor.

I think the big fight they keep referencing ended with either Val and Vox running away, or Alastor leaving. Which might be why Vox says Alastor is a coward in stayed gone, because he refused to see the fight to the end.

Alastor is the strongest individual sinner, but teaming up he would have been outnumbered even if he wasn't overpowered. I think Alastor would have seen this as a betrayal from Vox, and that was the final straw for their relationship. Maybe one or both of them even hesitated because of their history?

I think we will eventually see the full picture in a later season, but for now, thanks for listening to my speculations