If I would have told you at the beginning of the offseason that a quarterback would get a six year, $108 million extensions with $55 million guaranteed, you probably wouldn't have guessed that the mystery quarterback was indeed Tony Romo.
In the grand scheme of things, the deal probably won't matter much. The Cowboys are in rough shape, and they're certainly not on the rise. Another poor contract won't exactly drive them into the ground. They're already there. The contract may, however, hold them near the bottom of the NFC East a little bit longer.
The problem isn't that the Cowboys paid a quarterback a huge salary. The problem is that they're paying Tony Romo, a quarterback that flops in big game situations, a salary that includes more guaranteed money than Joe Flacco. The difference, of course, is that Flacco wins big games. Romo chokes.
The deal to keep Tony Romo in Dallas only makes sense when you begin to consider the decision maker, Jerry Jones. Jones has become the most recent example of an involved owner that once built a great team and is now struggling to stay relevant in his own division.
There is no simple solution for Cowboys fans. Sometimes, a problem with a team isn't the coaches. In many cases, those coaches are given players that don't allow them to win football games. These are situations where the coaches can only do their best, and that isn't enough to win many games. The Cowboys are in that position now. The problem is that such a solution would normally result in a change of general manager. Since Jerry Jones won't give away his role as the Cowboys' GM, he'll eventually fire Jason Garrett, and Garrett will have become Jones' most recent scapegoat.
The Cowboys are on the brink of a full-scale rebuilding effort, and ironically, signing there franchise quarterback to a big deal only pushes them closer to that rebuilding state.