With every door closed in his face, it looked like Troy Aikman was finally coming home. The former QB had started the year with broadcasting duties for ESPN’s first Super Bowl and a job consulting with the Miami Dolphins. But just a few weeks into the season, neither role seems like it will continue beyond this season. That’s why when the opportunity for the Dallas Cowboys to bring Aikman back with a job offer, it added up.

However, former ESPN and Cowboys insider Ed Werder isn’t too hopeful about the idea.

“Well, Dan, you and I know that ESPN never lets valuable people leave the company,” he said on The Dan Patrick Show. “So it’s quite surprising to both of us, I think, that Troy Aikman’s not returning on an extension and going to be Joe Buck’s partner after these 25 years they’ve had together.

“… Jerry said again this morning, he’d be open to the idea of Troy joining the franchise. But I just don’t see it, Dan. … Troy thinks he had half a career because Jerry wasn’t a good general manager. And the thing he’s done poorest of all as a general manager is hire coaches. … We’ve seen Troy go, you know, be involved with, as a consultant, hiring coaches and the general manager of Miami.”

The ‘half a career’ reference goes back to 2000. The Cowboys finished 5-11 that season, and Aikman, who was embattled with back issues by this time, was released by the team before he announced his retirement. 

But since then, things have changed, right? Jones made his interest clear on 105.3 The Fan in Dallas, a day after the Cowboys beat the Eagles 38-21 on Monday Night Football, where Aikman was working the broadcast. Asked whether he would give Aikman a significant role, Jones answered, “Yes, I could and would.”

Jones also praised Aikman at last week’s owners meeting, calling him capable of just about anything in football except playing again. He also called a Cowboys role “very possible” and said Aikman is “certainly qualified” for an NFL front office.

However, the divide between Aikman and Jones is clear to everyone who has heard the former QB talk about the GM. He isn’t a fan of Jones’ hands on approach as the owner. 

In 2019, he told 1310 The Ticket in Dallas that being part of the Cowboys front office might not be for him.

“It’s unlikely Jerry will ever bring somebody in who can help this team in that regard because he’s been real stubborn and steadfast that he’s the one in charge,” he said.

“I think in a lot of ways, until that changes, this team is going to have some problems. But would he ever ask me to come be a part of it? That would be a real leap of faith. I don’t envision that happening and I don’t envision that happening at any point, quite honestly, no matter who’s in charge out there.” 

And in 2026, that stance hasn’t changed much. Just a few weeks ago, Aikman attributed the Cowboys’ lack of playoff success, asking Jones plainly to “make changes in how you’re doing it if for three decades.”

However, Aikman is now at a crossroads. Jones has expressed a solid interest in reuniting with his former quarterback, and his future behind the mic is up in the air. Aikman believes he will be a “free agent” after this season without a contract at hand. And returning to Dallas might be a good way of starting his next chapter. 

That’s why he told Cowboys Roundtable’s Mike Fisher that if an opportunity does come up with the franchise, he’d have a “hard time not taking a good look at that.” However, the former quarterback admitted that their relationship is “complicated.”

Perhaps Aikman can find some middle ground. While the former QB hasn’t gotten on well with Jerry, he sees his son Stephen in a different light. 

“From my interactions with him, Stephen doesn’t have the ego his father has. 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 just got this gift of making you feel like you’re the most important person he’s seen all day.” 

After all, he has known Stephen since the 1989 draft, when the 24-year-old flew with him to New York on Jerry’s Learjet 35. And even though Jerry Jones has made it clear that he doesn’t have any intentions of retiring, at 83, he could hand over control to his children in the next few years.

If Aikman signs up now, he could set up a solid system for the team when Jones steps away. It could be what the team needs to get over its lack of success. 

For now, Aikman will be focusing on finishing his contract at ESPN with the Super Bowl.