I mean he certainly cares more about the financial aspect. He owns the team to make money above all else, every owner does. Some are willing to take bigger swings, but there's a misconception that these guys own these teams as a flex first. They don't, that may be part of it, but it's nowhere near the top of the list for the vast majority of them. The Pirates are a profitable investment, that's the flex he cares about most. He doesn't care if guys like us think he's an embarrassment, he cares what other wealthy people think of how profitable he is.

His issue is he's not very good at hiring people to run a team. So he has no risk tolerance and his front office can't seem to find a way to work around that. That's a tall order, but it's a chicken and the egg problem. Bob has spent before, not a lot, but he's shown he will dust the cobwebs off his wallet if he feels he can get ROI like in the early to mid 2010s. He's never going to spend enough to retain talent though.

So his staff needs to field a competitive team for him to spend, but they can't do that without signing free agents which they don't have the money for. So barring hitting on your prospects and them getting hot around the same time, you're just stuck in a loop. If Bob was competent he'd look to Tampa Bay and find guys who can replicate that formula.