Now the four-time Pro Bowl selection is on his way out of town, according to reports. And coach Jason Garrett might not talk to him until the two offer their goodbyes.
Garrett, who has coached Romo since 2011, hasn't talked to his quarterback since the Cowboys' season ended. He admitted as much Tuesday while appearing on NFL Total Access on NFL Network.
"I don't talk to a lot of players this time of year," Garrett told Steve Mariucci.
Mariucci then tried to FaceTime Romo, who didn't pick up the phone.
"Personnel decisions are challenging," Garrett said. "All personnel decisions are challenging. It's hard to decide what you think is the best decision for your football team going forward."
The Cowboys have not yet made a decision on Romo, through reports suggested the team would release him after March 9, the start of the new league year. Romo's top two suitors are reportedly the Houston Texans and Denver Broncos.
"It's particularly challenging when you have a situation like Tony Romo," Garrett said. "He has been a great quarterback for us, a great player, a great person for our organization for the last 10 years. His situation this year was very challenging." He was ready to have a great year for us. He gets hurt and then Dak goes in there and plays and really plays at a high level and our team wins a lot of games."
Romo was injured in the preseason, handing off starting duties to Dak Prescott. Prescott went on to lead the Cowboys to a 13-3 record and earn offensive Rookie of the Year honors.
"He did an amazing job working to get back and then understanding what the situation was when he was healthy. He did a great job privately in our locker room, did a great job publicly with the press conference, and then helped himself get acclimated to a different role, being a backup quarterback."
Romo, 36, is due $14 million next season. The Jacksonville Jaguars are also now rumored to be in the mix for his services.
Garrett admitted that he did have "heart to heart" conversations during the season with Romo.
"It was not easy for him but he handled it very well," Garrett said of Romo losing his job.
NFL Network analyst Brian Baldinger speculated that the Cowboys could opt against dropping Romo and instead pull of a trade with the New York Jets. Baldinger's suggestion related to the Cowboys needing pass rushers, such as defensive end Muhammad Wilkerson.
ESPN's Todd Archer also named the Jets Monday as a possible landing spot for Romo.
The Cowboys are in no rush to solve the Romo dilemma, as he has no bonuses in his contract requiring a decision by a particular deadline.