While Romo has already had a solid career for the Cowboys, the polarizing quarterback's legacy could be defined by his lack of playoff wins and his mistakes in the clutch.
Looking at Romo's career and his future with the Cowboys, we will see both the good and the bad portions of the quarterback's time in Dallas.
The pinnacle of Tony Romo's career was his lone playoff win in 2009 versus the Philadelphia Eagles, but the undrafted quarterback has posted some great regular season numbers.
Romo has a career 64.1 completion percentage and has averaged 8.07 yards per passing attempt. No one can say that Romo doesn't connect with his receivers or throw the ball deep enough.
So, many of Romo's statistics are on par with the best in the league, but will Romo be remembered for the good or the bad if he never gets the Cowboys over the hump?
For most fans who see anything less than a championship as a failure, Romo's legacy will be overwhelmingly negative.
While the pinnacle of Romo's career was his playoff win against the Philadelphia Eagles, the low points are probably his other three postseason games.
With a 1-3 playoff record, Romo hasn't played very well in the postseason.
In Romo's first playoff game in 2006, the Cowboys were in a position to beat the Seattle Seahawks with a field goal. There was 1:19 left on the clock, but instead of going ahead by one, Romo fumbled the snap and was tackled trying to run the ball into the end zone. The game ended with a 19-17 Cowboys' loss.
In 2007, after going 13-3 in the regular season and taking the NFC East, the Cowboys lost 21-17 in Dallas against the New York Giants. In the game, Romo threw one interception, one touchdown and completed just 50 percent of his passes. Although the loss didn't rest solely on Romo's shoulders, he took the blame for the failure.
In 2009, after Romo's first playoff victory, the Cowboys were stomped by the Minnesota Vikings and Brett Favre. Romo had three fumbles and an interception in the 31-3 loss, and the Cowboys didn't make the playoffs the following year (Romo broke his collarbone last season, but he was 1-4 in the games he played all of).
This season, Romo has gone back and forth between the labels of hero and choke artist.
Late game mistakes by the quarterback were the primary cause for losses against the New York Jets and the Detroit Lions, but his gutty performances against the San Francisco 49ers and the Washington Redskins after cracking his ribs made him the toast of the town.
Romo's legacy rests upon his ability to get better, but while he needs to improve in his late game decision-making, he shouldn't have to stop taking risks.
Romo is often compared to Brett Favre—a quarterback who can lose you a game as fast as he can win you one. Favre was criticized for his flaws and praised for his heroics, but the Green Bay Packers stuck with him long enough to get a Super Bowl win out of him.
For better or for worse, Romo is the guy who gives the Cowboys the best chance at postseason success. If he never gets Dallas to the Promised Land, he probably won't be remembered as fondly as Troy Aikman, but that doesn't mean he should be shunned or sent into exile.
Romo is a solid quarterback, and he deserves a couple of years with Dez Bryant, Miles Austin and Jason Witten on the field to see what he can accomplish (the team does need to grab another viable threat at wide receiver to add depth and help when guys are injured).
Will Romo ever win in all? No one can know, but if he doesn't he should be remembered as a guy who left it all on the field.