Troy Aikman is preparing to call ESPN's first Super Bowl in February, but the biggest NFL game on the network's calendar could also mark the end of his five-year stint with Monday Night Football.
The former Dallas Cowboys quarterback is approaching the expiration of his $90 million contract, with no new agreement announced despite longtime broadcasting partner Joe Buck reportedly securing a lucrative extension.
Joe Buck makes Eagles fans laugh hard with a story of a woman that flipped off Troy Aikman at Philadelphia
That uncertainty has opened the door to speculation about Aikman's successor, with respected NFL analyst Greg Olsen now emerging as a leading candidate should ESPN decide to make a change.
Sports media insider John Ourand has suggested that Olsen could move from Fox to ESPN in 2027, potentially ending a commentary partnership that has lasted nearly 25 years.
Olsen's availability could prove significant as ESPN considers its broadcasting plans beyond the current NFL season.
The former Carolina Panthers tight end previously served as Fox's leading analyst before Tom Brady took over the network's premier commentary position.
Olsen subsequently moved into a secondary role alongside Joe Davis, although his performances have continued to earn recognition throughout the industry.
"My best sources are predicting that Greg Olsen will wind up in ESPN's Monday Night Football booth next season," Ourand wrote in his The Varsity newsletter.
Olsen's existing Fox contract reportedly expires after this season, creating a potential opportunity to pursue another high-profile position.
However, Fox has also discussed retaining the former tight end, while ESPN has made no official announcement concerning Aikman's future.
Aikman could leave ESPN after season ends
Aikman has done little to dismiss speculation about his next move, recently acknowledging that he expects to become a broadcasting free agent.
Speaking on Dallas radio station 96.7 The Ticket, the three-time Super Bowl champion addressed questions surrounding his future.
"There's probably a time and a place for all that to be discussed. I don't know if now is the time," Aikman said.
"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."
His comments followed reports of an argument with Buck ahead of ESPN's October 12 broadcast between the Buffalo Bills and Los Angeles Rams.
Front Office Sports reported that the disagreement occurred against the backdrop of contract uncertainty, although neither broadcaster has publicly detailed what happened.
Buck partnership faces uncertain ending
Buck and Aikman first worked together at Fox in 2002 before moving to ESPN in 2022, establishing one of the NFL's most recognizable commentary teams.
Their familiarity has become a defining feature of major NFL broadcasts, with Buck previously explaining why their partnership works so effectively.
"He knows where I'm going to go before I go there. Vice versa," Buck said during an appearance on Front Office Sports Tonight. "He knows I'm his biggest fan."
Buck's reported six-year extension, potentially worth more than $100 million, contrasts with Aikman's unresolved contract situation.
Both remain expected to call Super Bowl LXI on February 14, 2027, when ESPN broadcasts the championship game for the first time.
Aikman's departure is far from confirmed, but the combination of his approaching free agency and Olsen's potential availability has created genuine uncertainty around the network's future commentary lineup.