Greg had first seen you at Kendall's side a month or two after he'd started working at WayStar. You had always had such relaxed and open body language that he couldn't help but be comfortable around you.
From what he could tell, you were a friend of the family. A very good friend of the family that had known Kendall for years. Which was vaguely concerning in and of itself, someone who could deal with Roy family politics and come out the way you did.
Of course, it was there. The way your smile seemed too sharp, too aware, sometimes. You sort of reminded him of Shiv in that aspect, actually. The passing glint of vicious delight in your eyes that he caught sometimes. The mark of Roy adjacent survival.
Your confidence and friendliness oozed from your every pore, but in a way that was almost enough to set someone's hair standing. It was carefully curated. Even he could sense that much.
It was a few months later when he finally learned what kind of friend to the family you were. He'd waited outside a meeting room for you - you were speaking with an executive, and so he politely waited outside and out of earshot.
When you came out of the room, the side of your face was splattered with crimson, and a silver Desert Eagle was tucked into your belt - now visible due to your open jacket. Greg's mouth, which he'd opened to call out your name, stayed that way.
You were some sort of killer and he was going to die. Oh, God. He was too young to die. Yeah, he was pushing thirty, but - he was still a virgin! He had so much to live for!
When he opened his mouth, nothing came out but an "oh." He swallowed hard. "Holy shit." He whispered.