Its really just the fact that everything is personal to Tony.It is so weird, on one hand it looks like AEW buries people who they suspect aren't going to re-sign with them, and just not use them in the hope it hurts their brand before they go to WWE or whatever (Starks/Fenix/etc)....yet on the other hand they are fine working with some expired contracts like Dustin's, and just keep them on freelance week-to-week deals.
He's still just a fan with a checkbook. If someone wants to leave or takes the side of someone like Punk, he just gets butthurt and gets spiteful.
But on the other side he's an incredibly nice human... so you'll see him doing things like dropping $5k on every gofundme of a current or former wrestler.
It just really all comes back to the fact that he doesnt understand how to process feelings. He has the emotional intelligence of a teenager with aspergers.