Cowboys’ Jerry Jones bets big on last hurrah at Super Bowl bid

This is it for Dallas Cowboys owner Jerry Jones, and he’s wheeling and dealing like it. The Cowboys either win the Super Bowl in 2026, or Jones may not see them win again under his watch. His aggressive trade moves and the pressure put on George Pickens are evidence that Jones has pushed his chips to the middle of the table.

It’s different from his gamble of the late 1980s. Jones was still in his 40s then. He had plenty of time to build an NFL empire to match his oilfield millions.

Fast forward some 40 years, and time is no longer on his side. The Cowboys have the pieces in place. Look for Jones to maintain fierce aggressiveness in an effort to get back to the Super Bowl.

Cowboys owner Jerry Jones won’t back off in 2026

Things started with last year’s trade for George Pickens. Few people, if anyone, saw it as a critical addition that would put the Cowboys on the Super Bowl map. But when Pickens shook off the Steelers’ blues and elevated himself to one of the best receivers in the NFL, the Cowboys found themselves with a nearly unstoppable offense.

So what does a man like Jones do when half of the puzzle is neatly in place? He gambles and maneuvers to make the other side fit.

First, Jones sent star edge rusher Micah Parsons to the Packers. Many NFL observers piled on, saying Jones made a bad trade. But the Cowboys got Kenny Clark. And then Jones acquired defensive tackle Quinnen Williams. That didn’t fix the defense, but it created avenues for fixes in the offseason. Included in the mix was another trade with the Packers for Rashan Gary.

And now the Cowboys enter 2026 with a lineup of Clark, Williams, and Otito Ogbonnia up front. They have Gary, DeMarvion Overshown, Dee Winters, and Donovan Ezeiruaku at the linebacker spots. Rookie Malachi Lawrence will likely work his way into a starting role before the season gets old.

In the secondary are Cobie Durant, DaRon Bland, Jalen Thompson, and Malik Hooker. Also, promising rookie Caleb Downs will have a starting role.

If you look up and down, this defense is ready to compete. And it doesn’t have to be great. Just good.

But that’s not the best part for Cowboys fans.

Jones won’t stop aggressively building the Cowboys

Barring a bad injury to quarterback Dak Prescott, Jones will mortgage the future to win this year — if that’s what it takes.

The Cowboys are reportedly in the mix for Dolphins linebacker Jordyn Brooks. If they pull off that trade, the defense moves up to an even higher level. And if the Cowboys need help at the trade deadline, Jones will pull out all stops.

Sure, there’s still the issue of keeping Pickens happy and interested. And key players, including Overshown, need to stay healthy.

But age matters. Jones will turn 84 years old in October. Jones may not give up the team until he’s dead. He may win a Super Bowl when he’s 95. Who knows?

But the NFL is a tough league. Jones hasn’t been able to figure out the formula since 1995. The Cowboys have won just five playoff games in those 30 years, and haven’t gotten back to the NFC Championship game.

To just highlight the drought, the Cowboys reached the NFC Championship game 14 times from 1970 to 1995.

The game is different these days. Teams can have everything fall into place over the course of a season. But if they don’t finish it off with a Super Bowl title, contracts and injuries and bad luck can turn things in the other direction quickly.

And as sharp as Jones still seems to be at age 83, it’s hard to imagine he will be able to solve an equation that has dogged him and his once-proud franchise for three decades.

The Cowboys are creeping up a list that no franchise wants to own. The 30-year Super Bowl drought ranks only behind the Chargers (31), Bills (32), Commanders (34), Dolphins (41), Vikings (49), and Jets (59) among the teams that have been there. The Browns, Lions, Texans, and Jaguars are seeking their first trip.

Jones acknowledged the pain, according to a post on X by Jon Machota.

“I really am better when I’m getting my ass kicked than I am when I’m having success,” Jones said. “I’ve seen some of the decisions I’ve made work.

“We get one team that gets to go to that Super Bowl every year. Two that get to go to those (conference championship) playoff games. I’m looking forward next year to getting back in that championship game and maybe beyond. And then I’ll be right at the top of the list of how long it’s been since you’ve been to one. And that’s how you do it. Right at the top. And this will all go away.”

To the point, the Cowboys have a Super Bowl contender in 2026. And Jones will throw everything at his disposal into winning this year. This could easily be his last hurrah.

The good news is the Cowboys’ players still think Jones has a little kick left. That includes Prescott, who said he still sees that fire, according to The Athletic.

“Maybe as much here recently as I’ve seen,” Prescott said. “And whether it’s him against the clock (in life) and him knowing, which he’ll tell you that, or the deals and the things that we’ve done have been invigorating. You can tell he’s excited to help this team to make moves and do whatever he can in his power.”

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