A quarterback can throw a perfect touchdown and still walk off the field feeling uneasy, and that’s been the story of Dak Prescott in recent years. Back in Week 5 of the 2020 season, Prescott was in rhythm before his season ended abruptly due to a compound fracture and a dislocated right ankle. History echoed again in 2024, when a hamstring issue against the Atlanta Falcons in Week 9 led to surgery and sidelined him for the rest of the year. Those setbacks linger, which is why Troy Aikman remains cautious, even after Prescott put up MVP-level numbers this time.

“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?”

He continued, “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 (3rd) and 30 touchdowns (4th). His QBR stood at 70.2 (5th). Even after such an amazing season, the team failed to make the playoffs. And that is where Aikman lost his confidence.

While Prescott has been the Dallas Cowboys’ star quarterback since Tony Romo’s retirement, injuries have plagued him. This season, Prescott regained his form, producing elite numbers and becoming the NFL Comeback of the Year finalist.

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In fact, he had a strong supporting cast in CeeDee Lamb and George Pickens. Together, they accounted for 12 touchdowns and 2,506 receiving yards. With that level of talent on the roster, it was a shame they didn’t make the playoffs. Opportunities like that don’t come around every year, and that’s what Aikman knows about.

After all, the legend himself dealt with ten concussions and other health concerns during his career, which eventually pushed him to choose retirement over football. That’s why he stresses the importance of staying healthy while playing the game. Prescott is now facing similar issues in his own career. The difference is that he hasn’t won a single Super Bowl, while Aikman had already won three by the age of 29.

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!