I think it’s fair to say that Romo is a better quarterback and only in a few crowded circles in Chicago would anyone disagree. So let’s clear the air on that right now; never would I suggest that the Cowboys would be better off with Cutler.
The question is: would Cutler be better off with the Cowboys?
One area of familiarity that he could embrace immediately upon arriving in Dallas is running for his life. The Cowboys offensive line is as bad, if not worse, than anything he has had to endure since moving to Chicago.
One thing that Romo has excelled at—something required of any Cowboys quarterback—is making throws on the run and keeping plays alive with his feet. Cutler has made some fine plays under pressure, but he doesn’t have the same kind of awareness or scrambling ability.
Regardless, he would be well-served with the talent in Dallas.
DeMarco Murray is no Matt Forte, but he’s on his way to being one of the most respected running backs in the league. Dez Bryant and Miles Austin offer a much better wide receiver duo than Cutler has ever enjoyed, and Jason Witten is an elite tight end. Offensively, he should have no problem thriving.
Defensively, he would see a slight downgrade. Critics have often claimed that Chicago’s defense has carried them over the last decade.
The opposite has been true in Dallas. But that may be changing.
The 2012 season brings much higher expectations for the Cowboys, as they have completely revamped their secondary through free agency and the draft. Their front seven is, on paper, a top-10 unit and will provide plenty of short fields.
The biggest issue Cutler would face is the same one that’s followed him everywhere he’s gone: his attitude. He has a tendency to project his negativity on others, sulking on the sidelines and cussing at offensive linemen—behavior associated with weakness rather than leadership.
Romo handles things differently. He’s positive and encouraging, even after Dez Bryant loses focus and runs the wrong route. Romo doesn’t chew his head off on the sidelines; he grabs him by the shoulder pads and has a calm and honest conversation.
The word is maturity. It’s the only thing that could keep Cutler from having a more successful career in Dallas than he has had in Chicago. Imagine if he were to have the same offensive coordinator instead of going through three in a four-year stretch, which is what he's had to endure in his tenure with the Bears.
There’s no question Cutler would flourish with a star on his helmet.
And what about Romo? What if he would have been playing for the Chicago Bears for the last five years? What if I were to tell you that he would have more than one playoff win?
The thing we all know about Romo is that he is a terrific quarterback. And if we all agree that he is a better quarterback than Jay Cutler (which the facts support) and that the Bears have had a much better defense than the Cowboys over the years (also supported by facts), wouldn’t it ultimately mean that Romo would be more successful with the Bears?
Consider this: Romo has proven year in and year out that he can make good receivers great. Laurent Robinson and Miles Austin are prime examples. Without a top-10 quarterback, I’m not so sure that either of those guys lands their respective contracts.
When was the last time anyone said that about Cutler?
Instead, critics have credited the Bears defense for the team's success, which is fair. In Dallas, the defense has been the scapegoat for the Cowboys failures. Also fair. Give Romo Chicago’s defense, Chicago’s running game and a few good receivers, and I have no doubt in my mind that he would have more playoff appearances and wins than he does now.
It’s impossible to quantify these hypotheticals without considering every angle.
It might be unfair to call Tony Romo a warm weather quarterback but since he’s never played anywhere but Dallas (and has very few bad weather games on his resume), we can only assume that the climate and field conditions in Chicago don’t favor his style of play.
We also have to assume that Jay Cutler would benefit from having the same offensive coordinator for his entire career. These are factors that we can’t prove but are worth considering, as—were they to transpire—our perspectives could be dramatically altered.
It also seems as simple as saying “if Romo had a better defense, he would win more games.” That’s true of any competent quarterback. The difference between the Cowboys defense and that of the Bears isn’t so significant that it translates into several more wins. But the turnovers and short fields would certainly aid Romo in situations in which he has previously struggled.
In summation, a quarterback swap benefits Romo and the Bears more than it does Cutler and the Cowboys. It’s becoming cliché to call the NFL a passer’s league—just like it’s been cliché to say defense wins championships.
Imagine a team that features both plus an elite running back. And then add Brandon Marshall.