Tony Romo is one of those quarterbacks that is hard to put into a box. Romo had a solid NFL career and was viable starting quarterback, but he was never able to lead his team over the hump and into the promised land of securing some championship jewelry. From 2000-2002, Tony Romo attended Eastern Illinois University where he earned Ohio Valley Conference Player of the Year Award all three seasons he played football for the program. Romo also was the first and only player in the conference to ever win the Walter Payton Award as well.
Despite his award-winning showing in college, Romo went undrafted in the 2003 NFL Draft. Fortunately, Romo was signed as a rookie free agent by the Dallas Cowboys where he would play his entire fourteen-season career. Romo didn't earn starting quarterback honors until the 2006 season where he started ten out of the sixteen regular-season games. This is when the flood gates opened exposing Romo to some blockbuster contracts and endorsement deals. In 2007, Tony Romo signed a contract worth $67.5 million and in 2013, Romo signed a six-year extension worth $108 million. Unfortunately, that contract was terminated after Romo lost his starting QB job to Dak Prescott and retired the following year in 2016. However, he still left the game with $127.4 million big ones in his pocket.