Back in his playing days, Tony Romo led some of the more explosive, exciting offenses in the NFL. However, the Dallas Cowboys could never find postseason success.
Romo's 248 touchdown passes currently rank as a franchise record – until Dak Prescott, with 243 TDs, passes him this year – and his 34,183 yards are the second most. Romo's 78 regular-season wins sit fourth in club history.
However, the QB could never get the Cowboys over the hump. Dallas went just 2-4 in four postseason appearances with Romo as the starter, and the Cowboys never made it past the divisional round.
The CBS analyst said on a recent episode of Pardon My Take that his biggest regret is not bringing a Super Bowl back to Dallas.
"I'm not a guy with big regrets, I guess you could say," Romo said via RJ Ochoa of Blogging The Boys. "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."
An undrafted free agent in 2003, Romo famously took over the starting gig in 2006 and was ultimately named to the Pro Bowl. He held the job for 10 seasons before his body began to give out. In 2015, he was relegated to just four starts due to multiple collarbone injuries. A 2016 back injury opened the door for Prescott to swipe the starting job.
Romo stayed on as a backup for a season, then retired in 2017, electing not to start over somewhere else at 37.
"But at the end it was like... I could go somewhere else and do it," he said. "Because I was like, I gotta win a Super Bowl. It's literally what you play the game for. Nothing else matters. And it just was like... but would that be the same? If I went somewhere else and did it? Because at that point I'd known the game at such a high level. My last 20, 25 games, we were pretty successful. When healthy. But I was getting injured more often. Body breaks down in some ways through the years. I think just it was as simple as it just wouldn't feel as important. It would be important to me, but it was for the people I was around. All the fans that we had."
Romo's inability to find postseason success will overshadow the memory of his on-field play, which at its peak was top-shelf. It's a fate that Prescott and the current Cowboys crew are trying to avoid repeating.