For 37 years, the Dallas Cowboys have operated like Jerry Jones’ personal empire. He owns the team, runs the front office, holds the general manager title, and rarely allows anyone else to become bigger than the man in charge. That formula helped turn Dallas into a financial powerhouse, but it has also come with three decades of Super Bowl frustration. Troy Aikman now believes the biggest change the Cowboys need may simply be life after Jerry.

Aikman has known Stephen since the 1989 NFL Draft, when the 24-year-old flew with him to New York on Jerry’s Learjet 35. Nearly four decades later, Aikman says Stephen’s quieter personality still separates him from his father.

“From my interactions with him, Stephen doesn’t have the ego his father has,” Aikman said, believing that difference could serve Stephen well once he takes over. “Stephen will be less inclined to want to get all the credit,” he says. “And I think he’ll create an environment conducive to winning.”

Stephen’s path to the Cowboys wasn’t originally supposed to involve football at all.

After playing at Arkansas, Stephen worked as a reservoir engineer for his father’s oil company, Arkoma. Football seemed behind him until Jerry called in 1988, saying he planned to buy the Cowboys and wanted Stephen beside him. Stephen immediately agreed.

He’s been by his father’s side ever since, working his way up from a low-level sales rep to Chief Operating Officer, executive vice president of player personnel, and president of AT&T Stadium, the title track that has him positioned as the clear successor once Jerry, now 83, eventually steps back.

And the transition is already underway. As Jerry has scaled back, Stephen has increasingly become the voice of the franchise and a leading presence in the draft room. He is not waiting for control as much as gradually absorbing it.

“Stephen’s just got this gift of making you feel like you’re the most important person he’s seen all day,” Aikman added.

Aikman isn’t alone.

The former Dallas Cowboys safety, Darren Woodson, who has a more blunt take on Stephen and Jerry, said, “Stephen’s going to chart a different path. He’s got a little bit more m*********** in him.”

Woodson believes the Cowboys have made too many emotional decisions because Jerry gets personally attached to players, a luxury he does not expect Stephen to allow.

Woodson pointed to the Micah Parsons saga, arguing Stephen would have resolved it much sooner instead of letting the drama drag on before Parsons was traded to Green Bay.

The Cowboys are now worth an estimated $15.5 billion, yet they have not reached a Super Bowl since January 1996. Stephen has admitted the 30-year drought weighs on him just as heavily as it does on Jerry.

That is the contradiction hanging over the Jones era. Jerry turned a $140 million purchase into the richest franchise in sports, but all that business dominance has not produced another Super Bowl appearance in three decades. Stephen will inherit the empire, but also the failure its fans care about most.

Their working dynamic hasn’t always been smooth either.

Stephen has challenged Jerry before. In 1995, he confronted his father over the Deion Sanders deal. In 2014, he helped steer Dallas away from Johnny Manziel and toward Zack Martin, who became a nine-time Pro Bowler while Manziel was out of the league within two years.

That willingness to push back on Jerry is exactly what Brian Schottenheimer sees today. The Cowboys coach says Stephen is willing to question decisions, dig into the reasoning behind them, and have conversations with Jerry that others might avoid. In a franchise long dominated by one voice, Stephen has never been afraid to challenge it.

Jerry has acknowledged that Stephen is one of the few people willing to push back on him, yet he still insists there is no formal succession plan. The structure, however, is hardly a mystery. Stephen, Charlotte Jones and Jerry Jones Jr. hold equal ownership stakes and are expected to run the franchise together after their father, with Stephen positioned as the strongest football voice.

Whether that shift happens in one year or ten, Aikman’s larger point is what follows.

He believes the Cowboys will begin to look more like a conventional NFL franchise once Stephen becomes its leading voice, with less emphasis on personality, publicity and one man’s presence. Jerry built the Cowboys into the richest franchise in sports.

Stephen’s challenge will be proving he can turn that empire back into a championship team.