27. Jerry Jones - Cowboys
Jerry Jones is a clown. We’ve known this since he first bought the Cowboys in 1989. It becomes more apparent every time he opens his mouth. But there was a time when Jones was actually
underrated as a general manager. That ship has sailed. Increasingly aware of his
own mortality, Jones has become increasingly desperate to return the Cowboys to playoff glory. It’s resulted in the league’s most over-leveraged roster, not to mention its most nonsensical power structure.
“Jason Garrett has a very high tolerance for ambiguity.” ‘Ol Jer meant this as a compliment. In reality, it’s a more damning indictment of his managerial style than I could ever hope to write. No one wants to win more than
Jerry Jones. This, I actually believe. But no one has less of an idea of how to do so in the 21st Century. Jones is too meddlesome with his coaching staff, too loyal to his own players and just too damn ill-considered with everything. He’s patient when he should be rash (
Jason Garrett), and rash when he should be patient (his recent approach to Day 1 of the draft). No one in the history of the league has handed out more ludicrous in-house contract extensions. Jones is a giant of the game, but he’s gone from winner to laughingstock.
