With a young player under center, the Cowboys were a team to fear. In Romo's first three years as the full time starter, they had postseason berths in two of them. Their 2009 season got them a playoff win, something that wasn't seen since the 1996 season when they beat the Philadelphia Eagles. Despite the numbers he was putting up, there was Romo's infamous chokes. Long story short, there was the 2006 playoffs where he botched a field goal snap and tried to run for the endzone against the Seattle Seahawks. He threw the game ending interception against the eventual Super Bowl champion Giants a year later. The label has stuck ever since, even with a win against the Eagles in 09 and the Detroit Lions in 2014.
Heading into the 2010 season, the Cowboys saw a mediocre year where nothing worked early on and Romo getting injured on national television in mid-October with a broken clavicle. He would rebound and have very strong seasons statistically but saw major chokes in the last game of the season in 2011 and 2012. The team would rebound in 2014 and put themselves back in the playoff race and win another game. Though 2015 started off well, Romo would suffer injuries twice in the same body part like in 2010. Dallas faltered without him. With this past pre-season, he would injure his back and lose his starting job to Dak Prescott, who put up a good rookie season.
With the question that begs to be answered, where does Tony Romo go? The Houston Texans just traded Brock Osweiler away to the Cleveland Browns. He could fit in there with a decent ground game and some young talented receivers. There is questions on whether he goes to the Denver Broncos. As far as that team goes, they have some good receivers, but the ground game is a little concerning. That being said, Trevor Siemian didn't have that bad of a season. It was something that didn't become a huge problem.
If Romo were to go to one of those two teams, they are going to need to be sure there is a competent backup in place in order to avoid like what happened in 2015. Dallas caught a huge break with Prescott and running back Ezekiel Elliott propelling them to success. Whoever gets him has to know the injuries that have been there for the last two years. Romo may be turning 37 in April, but Denver and Houston may only have a few years with him if they want a championship immediately, especially Houston. They have that strong defense and decent ground game, but Tom Savage is not a proven strong backup. Siemian might help in a pinch in case of any injuries in Denver,
My personal thought is Romo stays in Texas and goes to the Texans. They have more than enough talent to have at least a 10 win season. Combined when you healthy players like JJ Watt in a strong defense, the opportunity and expectations to win a Super Bowl increases if the trade goes through. Other than the Houston Rockets in basketball, there hasn't been many championships in Houston sports, with the most recent being their soccer team in 2006 and 07. Whether it pans out in a conference where the biggest threat is Brady until he retires is up to how the Texans manage the next few seasons. The timetable is extremely tight and they better hope everything fits into place come September. Otherwise, it could be a potentially long year if injuries occur again if the trade goes through.