Here's how he got there and what he's up to today in his profession. Tony Romo was one of the most divisive characters in sports during his time in the NFL. Tony Romo retired from the Cowboys without ever winning or even making it to the Super Bowl. He went on to have a successful career in broadcasting where he currently works for CBS. Romo entered the National Football League (NFL) as a first-round pick of the Dallas Cowboys in 2004. He played only two seasons with them, before being released by the team due to inconsistent play. He then signed with the Philadelphia Eagles, but was also let go after one season. He finished his NFL career with the Buffalo Bills, who selected him in the last round of the 2009 NFL draft. He started all 16 games that year for the Bills, but was eventually replaced by quarterback Tom Brady after a series of injuries occurred at the position. During his time with the Cowboys, Romo became known for his aggressive style of play. This often got him into trouble, as he was penalized 51 times over the course of his two years. In 2007, he suffered a broken collarbone during a game against the Washington Redskins and was later diagnosed with multiple stress fractures in his leg. The injury likely cost him the rest of the season and most of the next year too. In 2009, he broke another collarbone this time playing against the New York Giants.