Tony Romo is one of the most productive Dallas Cowboys quarterbacks of all time. The former undrafted free agent rose to stardom with America's Team, setting franchise records and leading supercharged offenses throughout the 2000s and 2010s.
But he never overcame the postseason challenge that haunted him throughout his career. Romo finished his time with the Cowboys with a 2-4 record in the playoffs, failing to ever reach the NFC Championship Game.
Some of those offenses were talented enough to make a Super Bowl push, but they were never able to get over the hump. That shortcoming, understandably, still follows the former Cowboys QB, despite a successful post-playing career in broadcasting.
Tony Romo's playoff losses still haunt the Dallas Cowboys
Speaking on an episode of Pardon My Take, Romo named his failure to win a Super Bowl as his biggest regret, which comes as a shock to almost nobody.
"I'm not a guy with big regrets, I guess you could say," Romo said. "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, for the Joneses, for everybody that you're around.
"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."
Of course, Romo isn't the only Cowboys player to struggle in the playoffs this millennium. Dallas hasn't found its way to a conference championship in 30 years, a drought spanning the careers of multiple effective and successful quarterbacks.
Romo came as close as any, falling short in three separate Divisional Round games. One throw, one decision from the referees, one play call could have ended the unfortunate streak that still haunts the Cowboys.
As much as Romo tends to receive the blame for those playoff losses, he will be remembered as an incredibly productive passer. He was the Cowboys' all-time leading passer until Dak Prescott passed him by last season, and he's still holding onto the franchise passing touchdowns record (although Prescott will soon take that, too).
Unfortunately, NFL players are often labeled in ways they can't escape, and they are defined by their shortcomings. Romo earned All-Pro honors, was named to multiple Pro Bowls, and established himself as one of the greatest undrafted players in league history.
Still, when his name is mentioned, fans still think of those playoff losses. It sounds like Romo does, too.
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