Decade-long Cowboys quarterback reveals his only real regret years after retirement

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Tony Romo spent over a decade as the face of the Dallas Cowboys, and the résumé backs up the hype. Over 156 career games, Romo threw for 34,183 yards and 248 touchdowns -- franchise records that still stand -- and earned four Pro Bowl nods between 2006 and 2014.

He led Dallas to the postseason four times. In three of those seasons, the Cowboys won 11-plus games and captured the NFC East title. What he never achieved was a Super Bowl ring. The Cowboys never advanced past the divisional round under his leadership, finishing with a 2-4 record in his six career playoff appearances.

That unfulfilled goal has followed him well into his broadcasting career, a point Romo made clear on Barstool Sports' Pardon My Take podcast. When asked what he would change about his playing days, the Wisconsin-raised quarterback didn't hesitate to share his biggest career regret.

"The only regret I would have is that my job was to bring a Super Bowl to Dallas, and I didn't do it," he said. "So, that always sticks with me a little bit. You give your whole body, heart, and soul, everything into it, and just wanted that for all the fans, Joneses, for everybody that you're around. That one always sticks with me a little bit, just because I had that opportunity and just wasn't able to do it."

“The only regret I guess I would have is that my job was to bring a Super Bowl to Dallas and I didn’t do it” -Tony Romo https://t.co/0eXjkMxOTE pic.twitter.com/7B23BVNLPR

— Barstool Sports (@barstoolsports) July 13, 2026

It is rare to see him open up like this, especially since he is usually so easygoing and fun on CBS broadcasts. Romo never seemed like a guy bitter about his past, but hearing this hits a bit differently. He threw at least 26 touchdowns every single year he stayed healthy, yet he still walked away without the one trophy that matters most to Cowboys fans.

Romo retired in 2017 after a back injury allowed Dak Prescott to take over. He quickly transitioned into broadcasting and became one of football's top analysts. For Cowboys fans who still remember the dropped snap in Seattle or the "Dez caught it" play, it's clear Romo is just as haunted by those moments as they are.