Jerry Jones built the Cowboys into a business juggernaut, but even he carries one regret: never working alongside his own father. So when he got the chance, he made sure his children were embedded in the family empire. The irony is that after decades of preparing them for the future, Jerry still insists there is no clear succession plan, even as Stephen Jones increasingly looks like the obvious heir.

“I don’t have a succession plan, I don’t,” said Jerry, per The Athletic’s Zak Keefer, admitting that he will soon be leaving his chair. “One day I just won’t be here to toss my two cents in.”

Jerry has held the Dallas Cowboys’ reins since February 1989 after purchasing it from H.R. “Bum” Bright for $140 million.

The Cowboys’ value has exploded under Jerry, while the team also won three Super Bowls early in his ownership. As the franchise grew into an empire, he brought all three children into the operation, giving Stephen, Jerry Jr. and Charlotte major roles in the business.

Of Jerry’s three children, Stephen is the one most clearly positioned to take control of the Cowboys. He joined the front office in 1989 and has spent 37 years at his father’s side, helping shape contracts, draft decisions and the stadium deal that turned Dallas into a commercial powerhouse. But the partnership has never been simple.

Stephen has built his case to succeed Jerry partly by doing what few inside the organization have been willing to do: tell him no.

Remember when Jerry had his sights set on Johnny Manziel in the first round of the 2014 draft?

But the father-son duo could not agree, as Stephen successfully led the push to select Zack Martin instead. Jerry, however, was skeptical of the move.

“I hope you’re happy,” Stephen recalled Jerry telling him. “You don’t do special things in life. I would have never bought the Dallas Cowboys making middle-of-the-road decisions. And what you just did is down the middle… You’ll never be great.”

But the move paid off well.

Martin proved to be one of the best players available in the 2014 draft, eventually becoming a nine-time Pro Bowler and likely Hall of Famer. Manziel went the other way, flaming out of the NFL after just two seasons.

Compared with Jerry’s other two children, Stephen has the most prominent football role and has spent decades beside his father across business and team operations. Jerry has called his eldest son his “devil’s advocate” and “barometer,” a telling sign of how much he trusts Stephen’s judgment.

By now, the Dallas camp too might be envisioning Stephen sitting on his father’s throne. 

“Publicly, he keeps sidestepping questions about the future, about how he’ll run the team when his father is gone,” wrote Keefer. “The mere thought can bring Stephen to tears. But Jerry is 83. He already beat back cancer once. More and more it’s Stephen speaking for the franchise, Stephen directing the draft room, Stephen inching into the camera’s view.”

With Stephen already carving out that space for himself, former Cowboys players believe the franchise could look very different under his leadership.

Cowboys Greats Predict a Different Future After Jerry Jones Era With Stephen

Stephen’s name has been trending among Dallas greats.

“Stephen’s going to chart a different path,” said former Cowboys safety Darren Woodson. “He’s got a little bit more m*********** in him.”

The Dallas alum believes that Stephen will be less forgiving when difficult choices have to be made. Having taken care of both the football and financial side of things, sentiment will not find a place when it comes to handing out contracts, roster turnover, and personnel decisions.

Woodson further established his case by taking the example of former Cowboys player Micah Parsons. He has been one of the most talented defensive players in Dallas but had to be traded because of a bitter contract dispute. According to Woodson, had it been Stephen, he would have shown Parsons the exit sooner. 

“I guarantee you Stephen wanted that to be a dead issue, and dad (Jerry) let it ride,” Woodson told The Athletic. “I think the off-the-field stuff the organization had to deal with: showing up late, not being a team guy, paying a guy that kind of money when he’s not really a leader? Yeah, that (expletive) ain’t flying. Jerry loves personalities, because Jerry is a personality. I don’t think that’s Stephen’s deal.”

Former Cowboys quarterback Troy Aikman thinks along the same lines as Woodson when it comes to Stephen stepping up in Jerry’s absence.

“I’m not pushing Jerry out by any means, but when that day comes, it’s going to feel a lot different,” said Aikman.

But not everyone sees Stephen as an automatic upgrade.

The Ringer has pointed to Dallas’ repeated low ranking in cash spending as evidence that Stephen’s growing influence has also made the Cowboys more conservative financially.

The team ranked 25th in cash spending from 2013 to 2016, last from 2016 to 2019, and 30th from 2021 to 2023. One source described Stephen as the person constantly trying to rein Jerry in financially, while a prominent NFL agent once told Yahoo Sports that Stephen had already taken control of major contract decisions and was far tougher than his father about handing out big deals.

The concern is that Dallas could replace Jerry’s impulsiveness with the opposite problem: too much caution.

Still, there are moments when Stephen’s willingness to go against Jerry has clearly worked in Dallas’ favor.