Former NFL quarterback Troy Aikman has faced this question several times: Have the Dallas Cowboys ever reached out to him about a front-office role? Aikman has always been honest. Earlier this year, the ESPN broadcaster simply admitted, “I guess the short answer to that is no,” a reflection of how the Cowboys have operated. Jerry Jones has rarely looked outside his family when building his front office.

Aikman, however, has certainly entertained the idea of taking a front-office job. The Miami Dolphins brought him in as a special consultant to help hire a new general manager and head coach. But that raises an obvious question: Why hasn’t Jerry Jones considered bringing in the man who won three Super Bowls with the Cowboys for a front-office role?

With developments over the last few days, it appears the Cowboys’ owner and general manager could be warming to the idea of bringing Aikman into the front office, especially with the broadcaster’s future at ESPN beyond the 2026 season remaining uncertain.

“Well, that’s a loaded question,” said Jones on 105.3 The Fan, per The Athletic’s Jon Machota, when asked about Aikman being a part of Dallas’ front office. ” (There’s) nobody more qualified than Troy Aikman. … I’m a big Troy Aikman believer in terms of his ability to get the job done. I don’t know anybody who knows more (about) football.”

It’s the second instance this month that Jerry has addressed Aikman being a part of a team’s front office. Jerry addressed the same question at the owners’ meeting in New York. At that time as well, the owner/GM sounded confident about Aikman ever taking an NFL front office role.

“No, I think when I said no, Troy is very capable, and he’s so, really, relatively speaking, he’s in his youth as careers go,” said Jones. “And he’s very capable of doing any one of a number of things, certainly anything to do with football. I don’t know of any area, short of getting back out on the field. I don’t know of any area that Troy wouldn’t be qualified and competent to go into.”

Imagining Troy Aikman in an NFL front office role is intriguing, but picturing him in Dallas’ front office is a different story. Since buying the Cowboys, Jerry Jones has refused to give up his role as the team’s general manager.

Meanwhile, his son, Stephen Jones, serves as co-owner, chief operating officer, and director of player personnel, while Charlotte Jones oversees the team’s brand and Jerry Jones Jr. handles sales and marketing. All three also hold executive vice president roles, leaving the Jones family firmly in control of the franchise’s front office.

But that doesn’t mean Troy Aikman isn’t interested in joining his former team in a different role. He carries experience, considering his role in the Dolphins’ search for a general manager and head coach earlier this offseason. On top of that, Aikman has previously acknowledged that working with Jerry once again shouldn’t be a problem.

“Would it be difficult to work with Jerry? I don’t think so. I think. Well, let me first say, I don’t anticipate a phone call,” said Aikman earlier this year. “If I did get a phone, then that would mean that he was receptive to whatever it was he was seeking. And so, from that standpoint, then I would think that it wouldn’t be a problem working with him whatsoever.”

If Troy Aikman ever gets a front office role in Dallas, it won’t be the first time that a quarterback would be joining his former team in a new role. We’ve seen this script before. Two-time Super Bowl champion John Elway spent his entire career with the Denver Broncos and later became the team’s general manager for a decade and later President of football operations.

Former NFL MVP Matt Ryan left CBS and joined the Atlanta Falcons as the team’s president of football earlier this year. Certainly, there are chances that Aikman could join the list. When? That remains a big question. But the timing is worth noting.

Aikman is in the final year of his five-year deal with ESPN. While the network signed his booth partner Joe Buck on a reported six-year, $108 million deal, Aikman currently remains unsigned. That means while Buck will remain with the network till ESPN’s next Super Bowl in 2031, Aikman’s ESPN future beyond this season is uncertain.

Meanwhile, things also escalated when Aikman and Buck reportedly had an argument during the Buffalo Bills–Los Angeles Rams Monday Night Football. Subsequently, Aikman said that he will be a free agent after ESPN’s first Super Bowl in February 2027.

“I don’t know that it’s hard to figure out kind of what’s happened, but I’ll broadcast through this season, and I’ll be a free agent at the end of the year and kind of see what happens. But I’m looking forward to whatever the rest of this year does hold, and with the Super Bowl and all that, and where my next landing spot might be.”

That said, it seems like the 2027 offseason will open doors for Troy Aikman for multiple opportunities. If ESPN parts ways with him, he will certainly be one of the top candidates in broadcasting free agency. At the same time, there may be a possibility that Aikman joins his former team’s front office. For now, though, Aikman’s future remains speculative.