Tony Romo Says Failing to Deliver a Super Bowl to Cowboys Is His Biggest Career Regret
Former Dallas Cowboys quarterback Tony Romo says the one achievement that continues to weigh on him years after retirement is his inability to bring a Super Bowl championship back to Dallas.
Speaking on a recent episode of the Pardon My Take podcast, the longtime Cowboys signal-caller reflected on his NFL career and admitted that falling short of a championship remains his biggest regret.
“I’m not a guy with big regrets,” Romo said. “The only regret I would have is that my job was to bring a Super Bowl to Dallas, and I didn’t do it.”
Romo explained that he poured everything he had into the organization throughout his career and wished he could have rewarded Cowboys fans, the Jones family, and everyone connected to the franchise with a championship.
The former quarterback entered the NFL as an undrafted free agent in 2003 before becoming Dallas’ starting quarterback in 2006. Over the next decade, he developed into one of the franchise’s most productive passers, throwing for more than 34,000 yards and a franchise-record 248 touchdown passes. Dak Prescott, currently close behind, is expected to surpass that touchdown mark during the 2026 season.
Despite his regular-season success, postseason victories proved difficult to achieve. Romo led the Cowboys to four playoff appearances but finished with a 2-4 postseason record, never advancing beyond the NFC Divisional Round.
Romo also revealed that before retiring in 2017, he considered continuing his career with another team in pursuit of a Super Bowl. Ultimately, he decided it wouldn’t have carried the same meaning as winning one with Dallas.
Although injuries limited the final years of his career and opened the door for Prescott to become the Cowboys’ starting quarterback, Romo said his connection to the organization made staying loyal the right choice.
Today, Romo remains one of the most accomplished quarterbacks in Cowboys history, but he admits that missing out on a Super Bowl title is the one goal that still lingers in his mind. As Prescott and the current Cowboys roster continue chasing that elusive championship, they hope to accomplish what Romo never could.
