But, frankly, if my job was football manager, and I knew my chairman was SO INCOMPETENT that he wasn't brave enough to ever say no to me asking for more money, then I'd ask away.
I don't expect the manager to be an expert in economics. It's not their job.
"What's my budget? Great, I'll spend...
Don't get me wrong. I REALLY dislike the guy, but clubs going bust is NOT the fault of the manager.
Manager "Can I have this player"
Chairman "No, we can't afford it"
It's not difficult.