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Jerry Jones says biggest regret is not getting Tony Romo and Jason Witten to a Super Bowl

Frank Schwab
NFL writer

For most of the past decade, Tony Romo, Jason Witten and Dez Bryant were synonymous with the Dallas Cowboys, along with owner Jerry Jones.

Witten is going to the Pro Football Hall of Fame, Romo might have a shot and Bryant’s story hasn’t been totally written yet. But none of them made a Super Bowl with the Cowboys, and Jones told Pro Football Talk’s Charean Williams that’s his biggest regret in his nearly three decades owning the team, at least when it comes to Romo and Witten.

“I really dropped the ball”

Jones, who has final say over the Cowboys’ roster, took some blame when he looked back.

“There’s no doubt that the personal feeling I have about what Tony Romo and Jason Witten brought to the Cowboys during their career, I don’t think I’ve had a moment in the day that at some time I don’t reflect back on those good years and what they contributed,” Jones told Williams. “And I’ve said this: From my standpoint, I can’t help but say, ‘Boy, I really dropped the ball not doing enough to get them in a Super Bowl. That will be and is my biggest regret about my time with the Cowboys.”

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The problem with being in a competitive league is that nobody is assured of getting to a Super Bowl over eight seasons, which is how many healthy years Romo and Witten had together. Sometimes you just get unlucky — like a catch ruling going against you in Lambeau Field in a divisional round playoff game. The Cowboys were very good for a lot of the Romo/Witten era, but never made a deep playoff run. Romo was a part of only two playoff wins. Not only did the Cowboys not make a Super Bowl with Witten and Romo, they didn’t even make an NFC championship game.

And yes, some of that is on Jones.

The roster never seemed to quite be strong enough when Romo and Witten (or Bryant, or DeMarco Murray, or DeMarcus Ware) were at their peaks. The defense was rarely great those years, certainly never at a championship level. It’s easy to wonder if Jones is repeating history, because Dak Prescott is on a cheap rookie deal and the Cowboys still aren’t able to put a decent set of pass catchers around him. But that’s a debate for another day.

A negative mark on a remarkable career

Jones probably doesn’t have too many regrets about his football journey. He made one of the greatest investments, from a business sense, of anyone in any sector the past half-century when he bought the Cowboys for $140 million in 1989. The team was valued at $4.2 billion by Forbes last year. And Jones has three Super Bowl rings and a gold jacket from the Pro Football Hall of Fame. Love him or hate him, Jones has had a remarkable career in the game.

But Jones still has some regrets, and watching Witten retire hammered home his biggest one.

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Jason Witten, left, listens to comments by Jerry Jones at Witten's retirement press conference. (AP)
Jason Witten, left, listens to comments by Jerry Jones at Witten’s retirement press conference. (AP)

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Frank Schwab is a writer for Yahoo Sports. Have a tip? Email him at shutdown.corner@yahoo.com or follow him on Twitter!