Cowboys owner Jerry Jones claims he’ll be ‘disappointed’ if Dak Prescott fails to win Super Bowl this season as he recalls biggest Tony Romo regret

After a 13-year career in the NFL, Cowboys’ Tony Romo had to retire without a Super Bowl trophy.

As the 2023 season approaches its final few weeks, the post-season race is becoming more vivid. And Dallas Cowboys owner Jerry Jones isn’t going to take it easy if his quarterback doesn’t win the award that he deserves.

Over the years, Jones has seen several eras of the Cowboys, from all ups and downs, better and worse. There sure have been a lot of coaches as well as promising quarterbacks. Recalling back one amazing quarterback from franchise history, Tony Romo, who had to retire without any Super Bowl trophy after a 13-year career in the NFL.

Looking at how Dak Prescott has emerged as one of the top quarterbacks in the league but still hasn’t been able to win a title, Jones doesn’t want history to repeat itself.

This season, Dallas has hope as they lead the NFC East with a standing of 10-3. Especially after their week 14 victory against the strong contender Philadelphia Eagles, which heightened their chances of making it to the playoffs.

When Dallas’ owner, Jones, was asked about his Super Bowl aspirations, he called the failure of the team led by Romo, who achieved Pro Bowl status four times but never succeeded in the postseason. Jones still considers it to be his biggest regret and disappointment. And now, with Prescott, he doesn’t want it to happen.


Dak is a player who is qualified in every way to have a Super Bowl in his career.

He said via Jon Machota of The Athletic.

Furthermore, he claims that he would be equally disappointed if the star quarterback, Prescott, didn’t win the Super Bowl as he hoped.

What are the chances of the Dallas Cowboys winning the Super Bowl this season?

Coming off a nearly three-decade drought of Super Bowl appearances sure isn’t going to be easy for the Cowboys. The team hasn’t made it to that level since 1995, despite giving big-time performances numerous times but failing at the last moment.

Cowboys offense

Cowboys offense (Via Dallas Morning News)
The last Super Bowl win by the Cowboys was in 1995 when they won the Super Bowl XXIX title. However, since then, the team hasn’t been able to get past the divisional round.

As recalled last time, when the team made it through the Wild Card after defeating the Tampa Bay Buccaneers, they had to accept defeat in the Divisional Round against the San Francisco 49ers.

However, this season, there seemed hope as the team had emerged as the leading playoff contenders with 10-3 divisional standings. After the big win in Week 14, their chances for the playoffs became more evident. It can’t be denied that the Cowboys have good chances of making it to the Super Bowl if they keep on going with this pace and a solid offense led by star quarterback Prescott.

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