Troy Aikman is entering the final stretch of his five-year, $90 million deal with ESPN. As that contract winds down, questions about what comes next for the 59-year-old are getting louder. One of those questions has followed him since the day he retired: Did the man who brought the last Lombardi to Dallas ever think about stepping into a head coaching role?

“No. Never,” Aikman said on the Rodeo Time podcast when asked if he ever considered coaching. “I have thought about being in the front office. In fact, I always thought that’s what I would do.”

That answer matters because of who Troy Aikman is. He was selected first overall in 1989 by the Cowboys. He first went 0-11 in his rookie year before rebuilding the franchise into a dynasty. He led Dallas to three Super Bowl victories in four years between the 1992 and 1995 seasons, a run of dominance that Big D has not tasted in 30 years. Despite all that, the Hall of Famer never once entertained the idea of coaching.

The reason for that was deeply personal for Aikman. When he retired after the 2000 season, he had recently married Rhonda Worthey, a former Cowboys publicist, and he was starting his family. He described the role as an “all-encompassing, consuming profession” during the football season.

“When I retired, I had just gotten married going into my last year, was just starting to have my daughters, and I just thought [taking a coaching job] would be really selfish on my part because I didn’t have to do it,” Aikman added on the podcast. “I didn’t have to go into coaching to make a living and to get pulled away from my family like that.”

But coaching and the front office are two very different conversations for Aikman. As early as 2019, he openly considered transitioning to a general manager role. He even consulted with Broncos GM John Elway and 49ers GM John Lynch about what that path looked like. His interest was genuine. But there was one team where that door would never open. 

With Cowboys owner and GM Jerry Jones firmly in charge of football operations in Dallas, Aikman was candid that Dallas was simply not an option. Years passed, and no GM offer ever materialized for Aikman. So by 2023, Aikman acknowledged that the window had likely closed.

“There’s still a part of me, I think, that down the road, the talk has always come up about whether or not I want to be a General Manager,” Aikman said back then. “And I think that has passed. But there may come a time that I’d be interested in just helping out with a club, with an organization, and not necessarily in an official capacity. I think that would be enjoyable.”

And interestingly, that casual prediction turned into reality. This year, Aikman stepped into exactly that kind of advisory role when the Miami Dolphins reached out and asked him to help with their general manager and head coaching search following the 2025 season. 

He served as an outside consultant while keeping his ESPN duties fully intact, which brings the story back to the broadcast booth, where Aikman has spent nearly three decades building a second career just as accomplished as his first.

But that long run is now approaching a crossroads.

Troy Aikman enters final year of historic $90M ESPN broadcasting deal

Troy Aikman’s run in the booth began in 2001, when he joined Fox Sports as a color commentator just one year after retiring. Over the next two decades, he became one of the most respected analysts in the business. But that ended with communication issues between the two parties. That’s when ESPN called, in 2022, with an offer for him to join Monday Night Football.

In 2022, the network signed Aikman to a five-year deal reportedly worth around $90 million, averaging $17 to $18 million per year. The contract was the largest broadcasting deal in sports casting history at the time. It surpassed longtime CBS analyst Tony Romo’s $17.5 million annual salary.

ESPN reunited Aikman with Joe Buck, a pairing that cost the network a combined $165 million between the two contracts. Now, as the ESPN season wrapped up, Aikman is set to enter the final year of that historic deal.

That creates genuine uncertainty about what comes next. At 59, Aikman has ruled out head coaching entirely. He has acknowledged that a full GM role has likely passed him by. But he remains open to an advisory or consultancy capacity, as his Dolphins role showed.