Tony Romo is still hoping Dak Prescott will be able to take the Dallas Cowboys where he couldn’t, to a Super Bowl.
During their coverage of the Cowboys’ 44-22 loss to the Denver Broncos Sunday afternoon, CBS noted Romo and Prescott are in rare company as consecutive quarterbacks with tenures of 10 seasons or more. According to CBS, the last three instances are Brett Favre and Aaron Rodgers in Green Bay, Joe Montana and Steve Young in San Francisco, and Romo and Prescott in Dallas.
The big difference, however, is the fact that the other four were able to get Super Bowl rings, while Romo and Prescott haven’t been able to get the Cowboys past the Divisional Round of the NFL Playoffs.
“It’s the only thing I regret, is not bringing a championship and a Super Bowl to Dallas.” – Tony Romo pic.twitter.com/UcjCGyRmiR
— Awful Announcing (@awfulannouncing) October 27, 2025
“This is incredible, I mean, you got the best of the best,” Romo told broadcast partner Jim Nantz of Montana, Young, Favre, and Rodgers. “I think Dak has done an incredible job. Proud of what he has done. They just need to get over that hump in the playoffs. And that’s where the other guys have done that. And honestly, it’s the only thing I regret, is not bringing a championship and a Super Bowl to Dallas.”
Romo’s best chances at a Super Bowl were probably his first and last appearances in the playoffs. He was on the verge of beating the Seattle Seahawks in the Wild Card Round during his first season as the Cowboys’ starter, but fumbled the snap on what would have been a game-winning field goal. And the 2016 Cowboys were widely considered to be one of the most talented rosters in the franchise’s modern history. But after fracturing his vertebra and losing the starting job to Prescott, Romo never got a chance to quarterback that roster.
Romo’s career would look a lot different with a Super Bowl win. Maybe he doesn’t get Wally Pipp’d if he had a Super Bowl, perhaps he doesn’t jump to CBS in 2017, and maybe he’s already a Hall-of-Famer. Instead, he’s a former quarterback with one giant regret about not getting Dallas to a Super Bowl. And Prescott is currently on the same trajectory, with Stephen A. Smith possibly being the only person who believes a run to the Super Bowl could still be imminent for the Cowboys.
About Brandon Contes
Brandon Contes is a staff writer for Awful Announcing and The Comeback. He previously helped carve the sports vertical for Mediaite and spent more than three years with Barrett Sports Media. Send tips/comments/complaints to bcontes@thecomeback.com