I complain about Jerry a lot but it's mostly about the following
1. Pick a damn lane. Either you're a large market team or you're not. Structure the organization accordingly.
2. Being overly risk averse.
Jerry has had top 10 payrolls, but he's not willing to spend to put the team over the top. So he's not necessarily cheap, but rather overly risk averse.
3. Loyal to a fault.
Giving your FO a fair shot is one thing, but sometimes they've been given plenty of rope and hung themselves with it. It's ok to fire someone if they deserve it.