Troy Aikman Warns Cowboys’ Big Spending on Dak Prescott & Offense Will Leave ‘Holes’ on the Roster

The Dallas Cowboys have a recurring pattern of restructuring contracts each year to get under the cap. It worked each time, but the next year became harder to manage on the cap sheet. NFL legend and franchise star Troy Aikman has been watching this loop unfold in his old team long enough to notice when it will become a real problem.

Troy Aikman has backed Dallas quarterback Dak Prescott ever since the latter was drafted in 2016. But that didn’t stop him from pointing to Tom Brady and the New England Patriots as a blueprint during his recent Fox 4 interview. The reason? Brady was paying at a discounted rate to give the team space to build around him.

“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, you’re paying CeeDee [Lamb] near the top of the market and George Pickens with the franchise tag… directing all of your energy and resources on offense, there’s going to be some holes.”

Aikman doesn’t want Dak to follow in Brady’s footsteps. But Prescott is the highest-paid player at $60 million a year. Dallas restructured his contract alongside wide receiver CeeDee Lamb and guard Tyler Smith, pushing roughly $66 million in charges into future years to get cap compliant.

Dallas wasn’t the only team to play this card, though. Even the Kansas City Chiefs restructured quarterback Patrick Mahomes’ contract this offseason to create cap flexibility. The Baltimore Ravens did the same with Lamar Jackson’s deal. But money isn’t the only issue with Prescott and the Cowboys.

There’s also the age factor. Prescott turns 33 in July. Former Cowboys quarterback Tony Romo’s career was chipped apart throughout his mid-30s. What started as a vertebral disc injury at 33 snowballed into multiple back and shoulder injuries each year until 2016. The Prescott era began that year, and Romo hung up his cleats. Romo’s history is the institutional memory Aikman is pulling from.

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

Aikman also brought up Joe Burrow, the Cincinnati Bengals quarterback who has played at a high level while his team still fell short around him. Dallas lived that in 2025; Prescott held up his end, but the defense kept bleeding points and yards all season.

As for Aikman himself, he isn’t analyzing this from a broadcast desk anymore. He spent his offseason doing exactly the kind of front-office work the Cowboys never asked him to. And the gap between what he has done in Miami and what’s happening in Dallas is hard to miss.

Aikman is ready, but Jerry hasn’t called

After a 7-10 season, the Miami Dolphins knew something had to give. The hammer fell on former Dolphins head coach Mike McDaniel and general manager Chris Grier. Troy Aikman was named a special consultant for the Miami Dolphins, helping the franchise identify and hire a new GM and head coach. It was the front-office role that he said he always expected to take on someday. But he was also specific about his fit.

“I’ve thoroughly enjoyed it,” Aikman said of his consultant role. “I really felt that when my playing days were winding down, I thought that eventually I would go into the front office, even when I took on broadcasting. I’ve been asked a lot over the years if being a general manager was ever of interest to me. It has been, but I think my real strength was kinda in this sweet spot that I was in for the Dolphins in helping them identify the right people for those positions.”

Through Aikman’s efforts, John-Eric Sullivan became Miami’s GM, and Jeff Halfley became the new head coach in January. Miami has since started its rebuild, and has one of the best quarterbacks in the league rooting for them. But why not do the same thing for Dallas? When asked if Jerry Jones and the Cowboys had ever called him for advice, Aikman was very clear.

ESPN’s Troy Aikman explained to @clarencehilljr that the #Dolphins hired him this offseason “knowing that I have information they don’t have or can’t get,” leaning on his relationships from all the games he’s called and the people he interacts with.

It’s something the #Cowboys… pic.twitter.com/bqHBiXpCUj

— Ari Meirov (@MySportsUpdate) April 5, 2026

“The short answer is ‘no,’” Aikman said. “I’m not sure, really, that they’ve reached out to anyone for that matter. Maybe they have a few other people that might be able to assist them in some of their decision-making. But it’s just how they’ve operated.”

Aikman’s answer describes an organizational reflex that predates the cap problems, predates Prescott, predates all of it. Even Brian Schottenheimer was an internal promotion, rising from the offensive coordinator to the head coach. Dallas has always run its football op through Jerry Jones and kept outside voices out. But if a call did come through, Aikman plans to answer and see it through.

“I don’t anticipate a phone call,” Aikman admitted. “If I did get a phone, then that would mean that he was receptive to whatever it was he was seeking. And so, from that standpoint, then I would think that it wouldn’t be a problem working with him whatsoever.”

The Cowboys don’t need Troy Aikman to explain the numbers; anyone can read a cap sheet. What they don’t have is someone in the building asking whether the structure itself makes sense. But the man best positioned to ask that question says he doesn’t expect a call. And based on how Dallas operates, that call might never come.