Tony Romo
Romo is emblematic of the Cowboys’ problems over the past couple of decades. It’s easy to cast him as a statistical success because he holds many Dallas records. But he also went 2-4 in playoff appearances across 14 seasons. That’s atrocious and it’s bizarre that the franchise never moved on from him.

The four-time Pro Bowler was also directly culpable in some of their defeats. No fans will forget that failed snap in the 2007 Wild Card Game against the Seahawks. Romo was a great quarterback but he shows the mental weaknesses of Dallas’s front office. They wanted the new Troy Aikman and it terrified them to try another option (via Whiskey Riff).