Jerry Jones
Jones is one of the few owners on this list who earns a couple of entries. One of the main problems with Jones is that he thinks that he knows better than everybody else. Dallas had a phenomenal opportunity to draft Randy Moss and it made sense. Even his scouts wanted to select the player because they recognized his high ceiling (via Bleacher Report).

But Jones sometimes takes a hands-on approach that damages his team’s prospects. In the end, they drafted Greg Ellis whose main crime was that he wasn’t Moss. Ellis was a defensive end who won the NFL Comeback Player of the Year award. The 12-year veteran also made the Pro Bowl but he wasn’t on the same level as the all-time great.