9. Jerry Jones/Stephen Jones, Cowboys
The Cowboys have three straight 12-win seasons but only one playoff victory to show for it. They have superstar players on both sides of the ball, but depth issues that tend to rear their head at the most inopportune times. They have a war horse head coach who somehow crumbles at all the biggest moments. This is a good roster, one stocked with homegrown talent. It is just impossible to shake the feeling it should be something more. Jerry Jones and his gang of cronies never quite get the credit they deserve because the finishing touches are always missing. The once-vaunted offensive line and skill player depth have become just as top heavy as every other unit. The bottom could fall out at any given moment. Jones and company do at least provide a ceiling. That is more than half the battle, and a lot more than can be said for most front offices.