Romo signed that first $10,000 signing bonus with the Cowboys during that 2003 season .
He has made plenty of money during his 14 - year career , over $100 million to be exact .
Since Romo signed that first $10,000 signing bonus with the Cowboys during that 2003 season , he has made plenty of money during his 14 - year career , over $100 million to be exact .