Even an MVP-caliber season wasn’t enough to erase the doubts surrounding Dak Prescott in Dallas. While he delivered elite numbers and led one of the league’s most productive offenses, a Cowboys legend isn’t convinced it changes much. It’s not just about not having won a Super Bowl yet again, but also the bigger questions that now hang in the air, about how long he can keep playing like this while the team fails to bank on his caliber.

“When you have the type of season that Dak had and the offense had, and you failed to capitalize on it, I mean, that’s a big letdown,” said Troy Aikman. “Because one, you don’t know if Dak is going to stay healthy, which is not easy to do. And as you get older, it becomes even harder, so can he stay healthy again next year? And if he can, can the offense continue to play at the level they did?

“It’s not a given. Every year, it’s a little bit of an unknown. But they had opportunities, this year being one of them. Him being healthy as well as playing on the offensive side of the ball. So they got things that have to be addressed.”

Prescott wrapped up the season with 4,552 passing yards (third in the league) and 30 touchdowns (fourth), with a QBR of 70.2 that ranked among the NFL’s best. Even with one of the strongest statistical years of his career, Dallas Cowboys still missed the playoffs, another example of a prime season slipping away. And with Prescott now in his early 30s after multiple major injuries, Aikman’s hesitation isn’t just about this year’s failure, but about how many chances like this might still be left.

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While Prescott has been the Cowboys’ franchise quarterback since Tony Romo’s retirement, availability has quietly become part of his story. He has battled a compound ankle fracture in 2020, a broken thumb in 2022, and a hamstring avulsion in 2024 that required surgery, yet still managed to rebound with one of the best seasons of his career.

He also wasn’t doing it alone, though. With CeeDee Lamb on one side and George Pickens on the other, Dallas fielded one of the league’s most dangerous receiving duos. Together they piled up over 2,500 receiving yards and 12 touchdowns, the kind of production most playoff teams are built around. Despite the production, the Cowboys finished 7-9-1, watching the postseason from home after wasting one of Prescott’s prime seasons.

The fact that it still wasn’t enough only reinforced Aikman’s point about missed windows and wasted opportunities. But the legend’s perspective comes from experience.

His own career was shaped by repeated concussions and physical wear, issues that ultimately pushed him into retirement earlier than many expected. By the time he was Prescott’s age, Aikman had already won three Super Bowls. Prescott, despite elite stretches of play, is still chasing his first deep postseason run, and that contrast is at the heart of the legend’s concern. Moreover, looking ahead, the uncertainty grows.

Yet Prescott doesn’t see his career nearing an end. At 32, he recently said he hopes to keep playing into his 40s, pointing to modern training, recovery, and the joy he still feels being on the field. He’s signed through 2028, when he’ll be 35, and continues climbing the Cowboys’ all-time passing charts, already becoming the franchise leader in completions and passing yards.

Therefore, for the future, it’s uncertain whether Prescott will keep the momentum in 2026. He will be 33 years old when the new season starts, so age could be an issue for him. Staying healthy is where Aikman loses his confidence in Prescott.

Besides that, the three-time Super Bowl winner explored not just Prescott’s future, but also the possibility of the Cowboys’ offense failing. Aikman’s fear of the offense regressing could soon become a reality, as a major contract dispute with star receiver George Pickens looms, threatening to break up the Cowboys’ potent offensive duo.

George Pickens could leave Dak Prescott and the Dallas Cowboys

Wide receiver George Pickens came to Dallas from the Pittsburgh Steelers in exchange for a 2026 third-round pick and a 2027 fifth-round pick. Besides Pickens, the Cowboys also received a 2027 sixth-round pick. However, the wideout’s rookie contract will expire in mid-March 2026. With it, Pickens will enter free agency. So, what can the Cowboys do to retain him?

The easiest option is to give him a contract extension. But in his case, the easiest option is the hardest for the Cowboys owner, Jerry Jones. Based on recent reports, Pickens could demand a massive contract, ranging up to $140 million. That figure seems justifiable considering he finished the season with nearly 1,500 receiving yards and 9 touchdowns. Yet paying him that amount could cause problems for the franchise.

The Cowboys are almost $25 to $30 million over the cap. They need to deal with the extra amount to stay within the legal bounds. So, a $140 million figure is the last thing on their mind. Moreover, if he enters free agency, there are several franchises willing to give that amount to Pickens. Besides free agency, Jones could also trade him.

“If I’m the Raiders, why not go out and trade Maxx Crosby to the Dallas Cowboys?” said Jason McCourty on Get Up, ESPN via X. “You franchise tag George Pickens, you don’t work on a long-term deal. You trade him to the Raiders, get Crosby in exchange.”

The Cowboys are in need of good, defensive-minded players. Getting a superstar pass rusher like Maxx Crosby could be beneficial for their defense. But it will make Troy Aikman’s fear come true. The Tennessee Titans are also looking to make a huge splash for the wide receiver, with $77 million in cap space.

A lot is happening in Dallas. The former quarterback is doubtful of the present quarterback. The possibility of a major offensive and defensive overhaul is also on the table. Looks like Jerry Jones has a lot to deal with!