Tony's biggest mistake is not establishing any order from the start lol. (And continuing not to as things evolved)
Punk shouldn't have to be the one to go tell Jungle Boy you're not doing a spot with real glass. Tony should've be the f***ing boss instead of his BFF and told him, "I'm paying you, you're not doing it." Similarly, Tony shouldn't have been cow-towing to Punk saying who was and wasn't allowed at Collision, to include his head of talent relations.
Firing him after Brawl Out was likely not an option. Legally, firing a guy because he got into a fight with 3 guys angrily busting into his locker-room isn't going to go well. They came to him. They outnumbered him. Even if he and Ace did more damage, those two factors are in their favor.
During AEW when he was sledgehammering his throne, or before AEW?
That matters considering the conversation is about AEW's hypothetical non-existence.