(Video) Jerry Jones Makes Brutally Honest Admission About Letting Cowboys Down in the Last 30 Years

Cowboys owner Jerry Jones is ready to splash go all in to build a roster that will challenge for the Super Bowl.

(Video) Jerry Jones Makes Brutally Honest Admission About Letting Cowboys Down in the Last 30 Years

Cowboys owner Jerry Jones and quarterback Dak Prescott (Image via IMAGO/X)

In Short
  • Jerry Jones admits he feels he has let Cowboys fans down due to the team's lack of success since the 1990s.
  • The Cowboys have won only four playoff games in the last 30 years and failed to advance past the NFC East for two consecutive seasons.
  • To improve the team, the Cowboys are restructuring contracts and targeting key players in the draft, including linebacker Sonny Styles.

Jerry Jones enjoyed massive success right after taking over as the new owner of the Dallas Cowboys in the early 1990s. The Cowboys won three Super Bowls, the last one coming in 1996. With such an illustrious history, it is easy to forget that Jerry’s Cowboys have not played another Super Bowl ever since.

The Cowboys have won just four playoff games in the following three decades. The horrible streak continued in 2025-26 season after failing to make it out of the NFC East for the second straight year.

With the new football calendar commencing in a few days, Jones reflected on the Cowboys’ failures and his desire to bring the Lombardi Trophy back to Dallas. Speaking with Jon Machota of The Athletic, Jones, 83, highlighted that he takes every input he gets, whether it’s from the fans, former coaches, or former players, to compile a roster capable of challenging for the Super Bowl.

Jones is so desperate that he is ready to “hitchhike back to Dallas to win a Super Bowl.”

It runs that way in my view. … Make no mistake about it now, if you told me I could, because I’ve done a lot of hitchhiking in my life. … I’d start here with you right now and hitchhike back to Dallas to win a Super Bowl.

Jerry Jones said on Friday night from the NFL scouting combine

Jerry Jones and the Cowboys restructure Dak Prescott’s contract

To win a Super Bowl, a club needs a solid base, and for that, they first require a significant amount of cap space. After the NFL announced this week that the 2026 salary cap will be set at $301.2 million, the Cowboys are reported to be $56.1 million over that ceiling, according to Over the Cap. This forced Jones to restructure quarterback Dak Prescott‘s contract.

(Video) Jerry Jones Makes Brutally Honest Admission About Letting Cowboys Down in the Last 30 Years
Jerry Jones (Image via IMAGO)

Todd Archer of ESPN reported that the Cowboys could also follow the same setup with WR CeeDee Lamb and guard Tyler Smith. By doing so, the Cowboys can save up to $66 million in cap room. However, that is still not enough to make a couple of big splashes. So, a few others also have to chip in.

Another significant move the Cowboys made was placing a non-exclusive franchise tag on WR George Pickens. Pickens will earn around $28.5 million for the 2026 season; that said, he can still negotiate a new deal with another team. Jones is willing to work with Pickens’ agent, David Mulgheta, to sort out a future deal.

The extra cap space will help Dallas bring in some quality players from free agency. Not only that, the 12th overall pick can be used to draft possibly the next Micah Parsons or Trevon Diggs. According to ESPN draft expert Mel Kiper Jr., the Cowboys are projected to take Ohio State linebacker Sonny Styles at 12.

Styles is a former safety, and it’s no surprise once you see his speed. He can close on ball carriers and pass catchers in a flash. With 174 tackles over the past two seasons, he’s a top-10 prospect for me.

However, Styles might be out of the Cowboys’ reach after the show he put on at the NFL Combine this week. Styles had a 43.5-inch vertical and a broad jump of 11 feet, 2 inches, and clocked 4.46 seconds in the 40-yard dash, increasing his draft stock.

The Cowboys are not the only ones who would love to have a player like Styles on their roster. So, Jones should have a backup plan ready for day one of the draft in Pittsburgh.

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