I would imagine that Boss Man would've had a few week angle with Austin but wasn't going to get a world title reign or even probably a PPV match vs Austin. There's no way that he would've gotten a title reign with the stacked roster they had then. Back then there were a lot of two week angles where one week, a guy would do something to someone and then the week after would be their match and that was it. Given that Austin was feuding with the corporation, I would guess that would've been the case here.
Yay! More toys!
As if the MCMG aren’t worth signing.
You can't help but to dread stories like his because from what I understand he died broke, no family, no kids just dust in the wind. Poor guy was a victim of circumstances and realistically if he had hung around, he might've found his footing and carried his career a little further. The WCW Power Plant was one of the worst things to happen to wrestling in those days and The Renegade is another unfortunate example.
AKA, he's likely fed up with people who just go there waiting to go to or back to WWE. Probably why he has no interest in Kross - Tony knows what's up there.
Yeah, I think that might be a bit exaggerated to say that mistake cost Boss Man a big run against Austin or something. I can't think of a PPV between Survivor Series 98 and Wrestlemania XV where they would have fought. I'm sure they had a RAW match around that time too, but things moved so fast back then it's hard to remember. Austin was feuding with the whole Corporation anyway.
Its not the signing, it's bollox that comes after. Big fanfare, talk of creative freedom and being themselves finally only to be quickly jobbed out and forgotten about. It will be exactly what happened to them in WWE, but people that blindly defend AEW like it's their senile parent are incapable of admitting this. ROH and Evolve are on the same level. MCMG will be stuck with some jobber and competing for the trios titles. They could be fed to the Nu Dayz whenever those pricks show up.