The whole article is a ridiculous premise, but typical of the sensational, non-journalistic approach prevalent today in sports and the general news.
However, that said, if Tony Romo retires from the NFL without ever having at least a minimal amount of success in the playoffs, his supporters will have to give up any hope that he will ever be recognized as even a very good NFL QB. Stats won't mean a thing. The team surrounding him will mean nothing. He doesn't even need to win a Super Bowl, but if he retires without an NFC title game appearance or a solid string of playoff appearances with more first round wins than losses, history will not remember him fondly, if at all, despite his apologists and fans.
His time to build a legacy that will turn around the perception that he is a stats guy who can't win in the NFL or as a guy who makes the dumbest mistakes at the worst times is growing shorter. At some point Tony needs to find success that goes beyond stats.