The Dallas Cowboys have made their priorities clear for the 2026 season. They need to fix their defense and worry about the quarterback later. But even though Dak Prescott remains the undeniable leader of the franchise, the front office has admitted that extending his contract is likely taking a back seat. 

“Dak wanted us to improve this defense and improve the guys on the defensive side of the ball,” Cowboys CEO Stephen Jones said during his appearance on the DLLS podcast. “Keep a guy like Quinnen Williams, guys like that. So, certainly hadn’t been on our radar right now, but we always keep things like that. Obviously, Dak’s the heart and soul of this team. He’s the Pied Piper. He’s the leader. He’s the ultimate leader on this team.

“The great thing he loves is the leadership that we’ve acquired on the defensive side of the ball, because you do need others to help lead. When you got 53 guys and a 17-man practice squad, it’s a lot of men, and you need more than one leader. And certainly he feels like we’ve made some huge jumps on the defensive side of the ball to not only have really good football players but to have leaders as well.”

Owner Jerry Jones aggressively answered Prescott’s request. He agreed to bring elite defensive tackle Quinnen Williams into the fold with a massive three-year, $105.9 million contract extension. But the move needed some changes around the roster’s finances. 

Back in 2024, Prescott made it clear that he wanted to stay with the Cowboys long-term. And the front office responded by handing him a four-year, $240 million contract extension. For now, Prescott will stay with the Cowboys till the 2028 season. But to make room in the salary cap for the restructure, the front office cleared about $30.5 million in cap space by converting $38.2 million of Prescott’s base salary into a signing bonus. Last year, the team similarly converted $45.75 million of his base salary. 

But despite the lack of extension talks, Cowboys insider Clarence Hill Jr. believes that the quarterback’s position is safe. Hill’s confidence reflects Prescott’s record over 10 years spent in Dallas. He has played 139 games, during which he completed 3,184 passes for 35,989 yards and scored 243 touchdowns. 

“Dak Prescott will be the Cowboys quarterback for years to come,” Hill wrote on X. “There is no succession plan, no developmental option in place.” 

It’s worth noting that Prescott is already 33 years old. By the time his current contract ends, he’d be 35. That’s a good age for many players to think of retirement. Nevertheless, securing the quarterback is only one piece of the puzzle. The Cowboys are also approaching a financial bottleneck. 

Keeping two highly paid WRs along with Dak Prescott is a problem for the Cowboys 

Navigating the salary cap hit with George Pickens, CeeDee Lamb, and Prescott all on the roster is a problem. As per Over The Cap, the Cowboys currently have a total cap liability of $325,013,779, and there’s a team cap space of $15,893,584. This is the reason why Prescott’s salary went down to $1.8 million. The Cowboys freed up another $18.6 million in cap space by converting $23.25 million of Lamb’s salary. But the team is still liable to pay $27 million to Pickens. And these high salaries are a problem for the front office. 

“You look at Dak, like anything, you don’t get to play this game forever,” Jones said. “You look at the situation we have with George Pickens going alongside CeeDee. I don’t know of any teams that really can pay two top receivers, top of the market. So that’s going to be a really difficult situation as we move forward. We’ve managed to figure out how we can do it for this year. 

“Certainly, if everything works out the way we think it is, which CeeDee and George both have huge years again, then it’ll be a bigger challenge next year,” Jones continued. “George is really wanting to put back-to-back years on top of one another so it’ll help his market. And certainly I know at some point, as does every player in this league, will want to be rewarded with a long-term contract. So that certainly puts pressure on us to have a unique situation there.” 

For now, the Cowboys are kicking the financial can down the road. After all, they’re hoping their investments will help end a 31-year Super Bowl drought that dates back to 1995. Who knows, a win might even guarantee a contract extension for Prescott.