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For a number of reasons. The main reason is that because he was a part of this organization at such a young age, he might actually try to trick himself into thinking he knows something about football or how to run a successful organization.
We can't really separate him from Jerry, so I get that his reputation gets lumped in with Jerry's by default. I do think he's curbed the big FA spending tendencies we used to have. And I keep going back to how much respect Parcels had for Stephen when he was here. Parcels was a pretty good judge of coaches and management in my book.
Overall, though, I think people somehow underestimate the influence of Jerry Jones on the organization. It's Jerry's world, and everybody just lives in it. The problems we've had since Barry left (lol) are mostly related to Jerry, and nobody in the organization has the power to change it. He's built up a four billion-dollar empire doing things his way, and he's going to run it. He's not going to defer to his employees or his sons when it comes down to it. They can advise, and he probably does listen most of the time, but when it comes down to it, he's going to wildcat and nothing is going to change that.