Jerry Jones reveals his biggest regret as Dallas Cowboys owner

Philadelphia Eagles v Dallas Cowboys

Over the past two seasons, the Dallas Cowboys have seen two of their biggest names in recent franchise history in Tony Romo and Jason Witten retire from the NFL and start another career in the broadcasting injury.

Both Romo and Witten joined the Cowboys back in 2003 and went on to have illustrious careers with the franchise for over a decade until the quarterback retired in 2017, and the tight end retiring just recently.

Both players were able to pick up many NFL and franchise records in their respective positions throughout their playing careers, but one achievement has eluded both of them, the Super Bowl.

Speaking to Pro Football Talk’s Charean Williams, Cowboys owner Jerry Jones recently spoke about Romo and Witten and their time in Dallas, where he said he regrets not being able to provide both players with enough support to secure win the Super Bowl during their playing careers.

Jones said: “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.

“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.”

The closest the Cowboys have ever got to winning a Super Bowl during the playing careers of Romo and Witten is when they reached the divisional round of the playoffs in the 2007, 2009, and 2014 seasons. In each one of those seasons, they finished with 10-plus wins. Witten also made the divisional round again with Dak Prescott as the starter in 2016 when Romo was injured.

New Orleans Saints v Dallas Cowboys

The Cowboys may never have won a Super Bowl with Romo and Witten but they were one of the most reliable offenses in the NFL with them both on the field, providing stability for the franchise in their respective positions for a decade.

They'll both be in the team's Ring of Honor one day, and possibly even the Pro Football Hall of Fame, but they'll never have a Super Bowl ring. Jones believes if he had done more to help them, he could have changed that.

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