The Dallas Cowboys enter the 2026 offseason standing at a familiar crossroads. The front office faces a series of pivotal contract decisions that will define the team’s identity for years to come. Roster
building is an exercise in ruthless prioritization. One bad deal or a premature departure can mess up the whole thing. As Jerry and Stephen Jones weigh the value of known commodities against the potential of younger replacements, the margin for error is thin. Making the right decisions this spring isn’t just about balancing the books. It’s about ensuring they still have a championship window to look through.
Several players will become unrestricted free agents this offseason, and a few others are under contract but may no longer be worth their weight in gold (or in this case, silver), making them potential cap casualties. Today, we’ll look at some of the most discussed roster dilemmas and decide what makes the most sense for each situation.
George Pickens, WR
Pickens was a revelation for the Cowboys in 2025, providing the vertical threat and contested-catch dominance the offense had lacked. Operating as the perfect complement to CeeDee Lamb, Pickens hauled in 1,429 yards and nine touchdowns, consistently bailing out the offense with highlight-reel grabs on third downs. His ability to draw double teams significantly lightened the load for the rest of the receiving corps, proving he is a true “X” receiver in every sense of the word. The Cowboys spent a third-round pick on him for a reason, and he’s lived up to that. What he and CeeDee Lamb can do on this offense together is too good to let go of.
VERDICT: Re-sign him. Pickens catches everything thrown his way, and let’s hope that includes a big bag of money this offseason.
Javonte Williams, RB
In a season where the ground game finally came to life, Javonte Williams was the engine that kept the chains moving. He churned out a career-best 1,201 yards and found the end zone 11 times. His “yards after contact” remained among the league’s elite, and he proved to be a reliable safety valve in the passing game. With rookie Jaydon Blue’s struggles last season, Williams’ value to the team has skyrocketed.
VERDICT: Re-sign him. Love to keep him if his price isn’t too high, and the team doesn’t have fallback options.
Donovan Wilson, Safety
Wilson has long been a fan favorite for his aggressive hitman persona, but last season exposed the limitations of his game in a modern secondary. Opposing offenses continue to prioritize speed and horizontal stretching, and Wilson’s struggles to change direction and his frequent lapses in deep coverage became glaring problems for the secondary. In a defensive scheme moving toward the philosophies of Christian Parker, the need for versatile, fluid safeties outweighs the need for an old-school thumper.
VERDICT: Let him walk in free agency. Wilson has been the king of pop for the Cowboys’ secondary, but unfortunately, it’s time for him to beat it.
Jadeveon Clowney, EDGE
Clowney proved that age is just a number when you possess elite functional strength and veteran savvy. He remained a nightmare for opposing offensive tackles, particularly in run support, where he consistently set the edge and forced plays back inside. Beyond the stat sheet, his presence in the locker room provided a stabilizing influence for the younger pass rushers. He still has plenty left in the tank, and the team needs a reliable veteran presence. He shouldn’t be that expensive, and the team can likely get him on a short-term deal.
VERDICT: Re-sign him. Clowney has been on so many teams, he’s practically an NFL tour guide, but we’re still interested in what type of local attractions he has to offer.
Kenny Clark, DT
Clark remains the unsung hero of the Cowboys’ defensive interior. Last year, his ability to chew up double teams was largely unrecognized, but he remained a top-tier run stuffer despite the heavy mileage on those tires. Many observers overlook his impact because it doesn’t always show up in the stat sheet, but the tape shows a different story, and that’s a player who still dictates the line of scrimmage. Many people don’t realize how good he still is and how helpful he is against the run. Restructure money if needed, but he shouldn’t be going anywhere.
VERDICT: Let him play under his current contract. $21.5 million isn’t cheap, but it’s still money well spent for what this guy clocks in and does on Sunday.
Malik Hooker, S
Hooker provided a necessary floor for the Cowboys’ secondary last year. While he doesn’t possess the elite range that made him a top college prospect, his diagnostic skills and positioning can help keep opposing offenses at bay at times. He remains the most disciplined deep-half defender on the roster, and the team has little to no options behind him. While there’s some cap savings to be had here, cutting Hooker is negligible, at least until the team can get reinforcements in the building.
VERDICT: Let him play out his current contract. Hooker is like a good Wi-Fi signal. You don’t really notice him until he’s gone, and then suddenly nothing works.
Terence Steele, RT
Last year was a decent season for Steele, who is always at the forefront of any discussion regarding roster cuts. He remains a powerful run blocker, but his consistency in pass protection has been shaky at times. With the development of young tackles like Nate Thomas and Ajani Cornelius, there is a range of outcomes that could see the Cowboys moving on from Steele. After all, there are savings to be had as they could get out of a $13 million base salary by releasing him. 2025 is the year the team could responsibly get out of his contract, and that time is finally here. But can the team function without him? Moving on from Steele prematurely could create a massive hole on the right side of the line.
VERDICT: Wait and see. Steele is often a lightning rod for fan frustration, but the grass isn’t always greener on the other side of the offensive line.
The Cowboys are dealing with a delicate roster puzzle this offseason, balancing the need for financial flexibility with roster needs. While the notion to strip it down and rely on the draft is always tempting, the front office has tried that before, and it’s never gone well. By forking out the dough to retain core playmakers, the Cowboys can use the draft to attack other areas on the roster where help is desperately needed. Success in 2026 will depend on whether the Jones family makes the correct investments, and those actions could have a lingering effect.
