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in season 1, this is when he's hanging out with the vees on the accelerated extermination day. he's with the two people he's known and worked with for years. so here, his jacket is off: he doesn't have to be in the PR-ready CEO shell !

contrast this with his past in season 2: we don't actually know when the bax + pen showcase was, but at that point (given the designs of the characters we can see in this specific frame, also that they're not freaking out over zestial's presence) he was probably already close to/was overlord status. not to speculate more, but: with the extra bit of him wearing a sweater that's primarily red (thanks, al) and his antenna still not being damaged (pre-valentino, or pre-fight era, whenever the damage happens) it points a lot closer to when he was still friends with alastor. edit: xtra spec debunked! the head he has here aligns with one after the valentino photo, which is after the head in The Flashback. this can be found in the lineup seen in the office in 2x01 (thank you, @itsallalldeadair!!) it can still be noted to be before the antenna damage, at the very least !!

note how that outfit is different from the one he wears in The Flashback. while both are sweater vest and dress shirt combos without bow ties (just based on the angle in the frame of the. fuck ykw it's wordy let's call it the flashbax—if he wore a bow tie it should show anyway) you have one that's business casual in a ready-for-business sense, with rolled up sleeves on a striped, typical dress shirt, and one that's business casual in a "i would have to change if i wanted to look a lot more menacing" way.

and like i'd done with the season 1 cap, let's note the circumstances, as well:

in the flashbax, he's in the presence of (what i'm 99% sure are) other overlords. by all means, he's there to be on top of the newest innovations, but also... given we know bax helped create shok.wav, it's a no-brainer that this was also a personally indulgent decision.

pair this with The Flashback; he was in the company of his best friend. yes, he's another overlord, but he was an overlord he could trust, and one he considered his best ally. if there was any danger, by all technical means, it didn't matter how sharp, or business-ready he appeared; he and al could take on whoever dared to step in their territory.

let's also remember what he was proposing in The Deal:

"with your incredible power and my massive influence, we would be unstoppable. radio and video!" (2x04)

he's putting forward a specific image of their dynamic: alastor handling more of the actual power/fighting aspects, whereas he would handle the influence of the people. aka: i'll handle the PR while you hold the fort. and what's the easiest way to influence people and gain their trust? why, by looking trustworthy, of course! it's in the word, y'know?

you're probably wondering "ah, but what did you bring up the very brief season 1 thing for?" and this is the point where i remember why. in my personal and honest opinion, my thought is that when he's without a jacket to hide behind, he's a lot closer to his more emotional, authentic self.

the season 1 cap? he's with his friends! and he's watching his found-divorce ex get the shit beaten out of him, of course he's riding the emotional waves here, he's invested! the flashbax? hey, an anglerfish bio-engineer that's making awesome sea animal-like creatures is right up his alley! and maybe he can get a few personal things if he gets this guy on contract before the other overlords snatch him up! The Flashback? so maybe he had a biiiiit of a crush on his best friend, no biggie. surely he wouldn't turn down this fully genuine offer! (top 10 statements made before disaster)