Tony Romo never won a Super Bowl during his time with the Dallas Cowboys. Heck, he never reached the NFC Championship game.
Not having postseason glory served as the biggest obstacle in Romo’s decision to walk away from the game last offseason. But, in the end, Romo decided he wasn’t going to chase a championship forever and landed as the top analyst for CBS Sports.
Romo’s buddy, Jason Witten, is facing a similar decision this offseason. Should he play a 16th season in hopes of finally reaching a Super Bowl, or should he become the lead analyst on ESPN’s “Monday Night Football"?