Tony Romo reveals his top career regret in 13 years with the Cowboys

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Tony Romo was supposed to be the next golden boy for the Dallas Cowboys. It was very clear that he had the makings of someone like Troy Aikman, and Jerry Jones was fully sold on his quarterback, too. Unfortunately, injuries had to cut his career short after just 13 years. Despite having a fair share of accolades during this time, he did have a large regret.

Romo reveals biggest career regret with Cowboys

Superstardom was the path in front of Tony Romo. He reached the Pro Bowl four times in his career and helped the Cowboys maintain a steady offense for 13 years. But the postseason success just was not there. The Cowboys only ever reached the divisional round when he was leading the charge.

This lack of playoff wins is precisely where Romo's regrets lie. He posits that there was an opportunity for the Cowboys to pull off a Super Bowl run, but they just could not. More than that, the ex-Cowboys superstar even publicly apologized to Jerry Jones, via Pardon My Take.

"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. So that always sticks with me a little bit. Because you give your whole body, heart, soul, everything into it. And you just wanted that for all the fans. The Joneses. For everybody that you're around. And so that one always sticks with me a little bit just because I had that opportunity and just wasn't able to do it. So that part of it kind of still sits there," Romo declared.

Immediately after Romo retired from football, Dak Prescott took over as the Cowboys' starting quarterback. Unfortunately, the Super Bowl ring still remains elusive for Jones and the franchise despite a new arm serving as their offensive cannon.

Entering the 2026 NFL season, the Cowboys seem like they are gearing up for a Super Bowl run. They have a revamped defense with Rashan Gary and defensive coordinator Christian Parker. George Pickens and CeeDee Lamb have also emerged as pass-catching stars. 30 years is a long time for Cowboys fans to wait. Will Romo's regret turn into elation once the franchise finally hoists the Vince Lombardi Trophy?