It's kind of funny thinking about the Bruins as a Delaware North subsidiary that exists just to keep Charlie Jacobs busy.
He's the youngest son, so maybe you don't trust him to be involved in the business you actually value, but it's important that he does something relatively prestigious so he doesn't embarrass the family. You don't really care how the business does as long as it doesn't lose money, so you let the kid run it however he wants. He's not a serious person so he only hires sycophants whose main priority is shifting blame to others so they can keep their cushy, overpaid, semi-no-show jobs.
Wait, is this just Succession?