On Saturday, February 25, 1989, Jerry Jones gambled $140 million to buy a struggling Dallas Cowboys franchise. With absolute control, his first order of business was firing legendary HC Tom Landry and GM Tex Schramm. The high-risk play yielded immediate rewards: three Super Bowls and a record-breaking franchise valuation. Yet, three decades later, that same dynasty has yielded an agonizing title drought. Now, franchise legend Troy Aikman didn’t hold back on what’s holding “America’s Team” back, identifying the root cause of the franchise’s decline while singling out the heir apparent who could finally break the curse.

“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.”

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

After playing at Arkansas, he 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.

His title track 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.

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 franchise’s biggest flaw is Jerry getting too attached to his players. That fierce loyalty earned him lifetime devotion from icons like Jason Witten, Dez Bryant, Sean Lee, and Jason Garrett. Jones stood by these players through personal tragedies, injuries, and off-field struggles. But sometimes, that loyalty went to shocking extremes. 

Take six-time Pro Bowl guard Nate Newton. In late 2001, Newton was arrested twice in six weeks after police seized around 388 pounds of marijuana from his vehicles. Yet when Newton returned to team facilities, Jones welcomed him with open arms. 

“Brother, by him letting me be around the Cowboys opened other doors for me, given me a chance to talk to people and be a part of other things,” Newton said. “He ain’t never turned his back on me. He’s always had a few kind words for me. There ain’t no doubt in my mind where I stand when it comes to Mr. Jones.”

That inability to separate personal affection from business has quietly crippled Jerry’s roster construction and contract negotiations for years. Remember the infamous Micah Parsons trade that happened last year on this exact date? Woodson argued that Stephen Jones would have resolved the Parsons saga much sooner instead of letting the drama drag on before Parsons was traded to Green Bay.

Much of the drama boiled down to Jerry’s habit of “hotboxing,” trying to negotiate nine-figure deals directly while completely bypassing Parsons’ agent David Mulugheta. Insiders and franchise legends agree that if Stephen held total control, he either would have extended Parsons months earlier or traded him as soon as off-field and leadership red flags emerged. 

That contradiction was on full display when Dallas locked down Quinnen Williams with a three-year, $105.9 million extension. Stephen seized the moment to heap praise on his new star tackle while taking a subtle, pointed jab at the drama Parsons left behind. 

“He’s [Williams] the best player on the field whenever he’s out there. The other thing is just what a man he is. He’s a leader. We didn’t have a lot of leadership on defense for the last couple of years,” Jones said. “To have him and Kenny Clark and Rashan Gary. I think they really picked it up over there in terms of the culture and the leadership.”

Sure, Jerry built an empire, turning the Cowboys into sports’ most valuable franchise at an eye-watering $15.5 billion. But that financial glory hides a painful truth: Dallas hasn’t reached a Super Bowl since January 1996. And Stephen admits the burden weighs on him just as heavily as it does on his father.

When Stephen inherits the empire, he would also inherit its failure. But he isn’t going to back down from what it takes to get this franchise back to its original glory. Plus, he isn’t even afraid to sometimes go against his father to make that happen.

How Stephen Jones challenges Jerry

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 head 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, Troy 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.