Dallas Cowboys franchise quarterback Dak Prescott has been shut down mid-season twice in the last six seasons, with a compound ankle fracture in Week 5 of 2020 and a severe hamstring tear in Week 9 of 2024. Between those two injuries, he played a full 17-game schedule just twice. He turns 33 in July, and legendary quarterback Troy Aikman has seen enough to distinguish a pattern.

“As Dak continues to get older, one, it’s hard to stay healthy,” Aikman said in an interview on FOX 4. “So, will he make it through a full game season? Will he make it into the postseason healthy and able to play? And then on top of that, how long is he going to play at the level that he played at last year?”

Aikman also drew a parallel to Cincinnati Bengals quarterback Joe Burrow, who exploded in 2024 with 4,918 yards and 43 touchdowns against just nine picks. Burrow has played at an elite level even when the rest of his team collapsed around him. In 2025, that was Dak Prescott. He put together arguably one of his best seasons since his rookie year. Dallas still missed the postseason, and Aikman called it a wasted year.

Troy Aikman’s warning isn’t speculation about what might happen at 33. Prescott’s already had two surgeries significant enough to end his season before January.

So far, he has already missed more than 25 games from 2020 to 2024. Such history cannot be ignored, especially considering that it reflects that of Dak’s predecessor, Tony Romo, during his later days at the club. There is also the financial angle to the whole matter.

The city of Dallas has banked its financial future on him. During this off-season, the Cowboys renegotiated Prescott’s contract along with contracts for receivers CeeDee Lamb and guard Tyler Smith, deferring $66 million in cap hits into the future. This makes Dak’s 2027 cap hit a massive $76 million ($86 M in 2028). But Prescott’s injury history makes that a harder bet to take than the front office might want to admit. That is exactly where another observation from Troy Aikman comes in.

Did the Cowboys fail Dak Prescott?

Since 2021, the Dallas Cowboys have restructured franchise quarterback Dak Prescott’s contract five times, six, if you count the restructure they did in March 2024. So when Troy Aikman was asked whether Dallas had let Dak down, his answer got stuck on the numbers.

“It’d be hard for me from where I sit to say they’ve let him down when he’s the highest-paid player in the NFL at $60 million a year,” Aikman said. “I would argue that it’s hard to imagine that they’ve let him down in that regard.”

Aikman even brought up Tom Brady. When he was with the New England Patriots, Brady accepted less salary each year to give the management space to work. The team’s drafts have not been perfect at times, but Brady’s salary cap has filled in the gaps. It is something that Aikman does not want Prescott to do. He was showing what that arrangement allows that Dallas’ current setup doesn’t.

“I’m not suggesting that Dak should do that,” Aikman said. “I’m just saying that when you’re paying Dak at the top of the market, CeeDee [Lamb] near the top of the market, and George Pickens with the franchise tag – you’re directing all of your energy and resources on offense, there’s going to be some holes.”

Prescott’s restructure brings his cap hit down to $43.8 M this season, but Dallas has pushed his money all the way to 2030. Star wide receiver CeeDee Lamb is set to make $19.65 M this season, but his payday has been pushed to 2032. Both of them enter free agency in 2029. Meanwhile, Pickens’ $27.3 M worth of franchise tag is fully guaranteed, and talks are underway for a long-term deal with a July 15 deadline.

Aikman acknowledged that no team escapes this problem. The Kansas City Chiefs restructured Patrick Mahomes. The Baltimore Ravens restructured Lamar Jackson. But both of these teams are usually playoff visitors, while Dallas has missed the playoffs for two straight seasons now.

Prescott was paid like an elite quarterback. Nobody has any problem with that. But whether a 33-year-old who has been through two significant surgeries can lift an over-budget team into the playoffs is where the controversy lies. Troy Aikman stated the criteria required for Prescott to succeed at this task. They cannot do much about their salary cap issues, but it all depends on Prescott staying healthy and throwing dimes.