There's the problem with the owner being the GM and having relationships with players instead of employer/employee like the 31 other teams.
Booger is too ego driven to learn form the best. The year he had Lawrence up, he acquiesced instead of learning from NE that didn't even franchise Trey Flowers, a player just as good as Lawrence because they knew the price was too steep even as a tag.
There is one character trait that Booger has that makes him a bad GM at contract time, his ego. He actually gets off on having players at the top in pay, goes with all that America's Team and stars BS. Think he didn't get all hot and bothered with the media coverage of his contract with Prescott after all the build up that he milked for as long as he could?
He wants to show off, that's in his DNA like knowing how much his toys cost and his franchise is the most profitable and valuable, championships take a far back seat because he has 3 and they were too easy to come by, he actually fools himself into believing he had more to do with that than he did.
I had this one client when I was in PA and he sold his company when it was at the zenith and when we were at a party I asked him if he sold it because he got such a great offer and I've never forgotten what he said because it hit home with me. He said "no, I put it up for sale and then the offer came (which was counter to the rumors we'd all heard) and I took it. I knew it was time to let it go, I had my ego intertwined with the business and that was affecting my business decisions". Wow, I had done the same thing without realizing it and almost every time I had done that, it was not the outcome I wanted.
Booger doesn't want his players to succeed because he loves them. He wants them to succeed because he loves himself and he picked them. Everything shines through his ego and he is overly impressed with himself. They are his; therefore, they will be better for him than anyone else. After all, he is the only NFL owner that is a star and gets asked for his autograph. His players like his autograph on their checks.