FRISCO, Texas - Football season is getting closer and closer.
The Cowboys are set to depart for training camp in less a month. That's when we'll get an up-close look at Brian Schottenheimer's second season with this revised roster and coaching staff. When we get to Oxnard, that's when we'll start to get some real answers about this 2026 Cowboys team.
But what are the questions? We've compiled our annual list of pressing questions that need answers heading into the regular season. The staff writers, consisting of Patrik Walker, Tommy Yarrish, Nick Eatman, Mickey Spagnola and Kurt Daniels, weigh in on some of the pressing issues.
Today, we'll continue the series with a closer look at the contract-year scenario, asking who might be the next player to land a big contract with the Cowboys. Obviously, all eyes are on George Pickens, who is expected to play this season on the franchise tag. Maybe the easy answer is Pickens, but could someone else get a new deal before then?
No.14) Who's the next to land a big contract?
Tommy: I see why some would say George Pickens, but if that happens it likely won't be until next offseason. I could see a Quinnen Williams deal getting done before that, although the Cowboys do have the luxury of time and don't have extend him this offseason as he's still got two years left on his current deal.
It may be beneficial to get it done early, however, in order to get ahead of the defensive tackle market that'll be coming in the next 3-5 years. Tennessee's Jeffery Simmons became the highest-paid defensive tackle in NFL history earlier this offseason getting a 3-year, $105.8 million extension. That's just over $35 million per year, which is $11 million more than Williams is currently making.
Most years, we usually see some extensions get done at some point when the Cowboys go to training camp in Oxnard, California with Jake Ferguson and DaRon Bland being the 2025 examples. Could Williams be the one to earn a bigger payday this time around? I think it's possible.
Nick: Time is running out for the Cowboys to get a deal done with George Pickens before the season. The deadline is July 15 but it sounds as if they are holding firm to the stance they made back in April that no new contract will be given before the season. Sometimes that could be a strategy tactic and it wouldn't have shocked me if they were working on a deal all along but it doesn't seem as if that's the case. So if it's not Pickens, then who? And maybe Pickens is still the answer to this question, although it would have to be after the season.
I think it's possible Quinnen Williams gets a new deal before then. He's got two seasons (2026 & 2027) remaining on his deal that currently pays him $24 million annually. That has him right at the edge of the Top 10 in interior linemen. With Jeffrey Simmons getting a massive contract with the Titans that is paying him in the $35 million range per year, it's hard to think anyone will get close to that number but I could see Williams' deal getting around $30. There's a way to restructure the contract and add more years that would put Williams in the Top 5 without ballooning the contract to the point where it hurts the cap.
The big question to answer is if Williams, at age 29, still has 3-4 years at this level and I think the answer is yes. If the Cowboys also believe that then I'd be surprised if he's not the next one to get a deal.
Kurt: At first glance, it's easy – George Pickens. He enjoys another Pro Bowl effort in 2026, the Cowboys are on the doorstep, pay the man his money. But if Dallas isn't willing to spend mega-bucks on a second wide receiver, who gets the nod? After all, the core of the team is largely locked up. Will they splurge next year on, say, DeMarvion Overshown, despite his injury history? I have my doubts. Instead, I wouldn't be surprised if the Cowboys keep their powder dry until the 2028 offseason, when the likes of Quinnen Williams, Kenny Clark and Rashan Gary will be free agents. Cooper Beebe and Nate Thomas (if he locks down left tackle) will be coming off their rookie contracts and hitting the market as well. Among that group, even though he'll be 31 years old, you'd have to think Williams would still be at the top of the list. In fact, extending him in 2027 might be the best course of action.
