Turns out the whole thing with him leaving ROCKETBOOM and going job hunting in Chicago was a joke. Instead, he was in Chicago so he could buy the Sears (Willis) Tower and the AT&T Corporate Center with all the jewgold he got from stealing memes. Now you can buy ROCKETBOOM insurance over ROCKETBOOM phone lines while you try to access a blocked 4chan through ROCKETBOOM internet.
tl;dr, Greg was trying to conceal his corporate takeover of Chicago and the internet. &troll;