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The Dallas Cowboys need to make a difficult decision before the 2026 NFL trade deadline, and George Pickens should be at the center of the conversation. The Cowboys are sitting at 2-4; their season is already heading in the wrong direction, and the franchise has only a few weeks to decide whether it can convince its star wide receiver that his future belongs in Dallas.
Unless something changes quickly, the Cowboys should trade Pickens before the deadline rather than risk losing him for nothing next offseason.
The Cowboys have little time to change Pickens’ mind
There is no denying Pickens’ value to the Cowboys. After arriving from the Pittsburgh Steelers last offseason, he delivered the best season of his career in 2025, recording 93 receptions for 1,429 yards and nine touchdowns. He earned his first Pro Bowl selection and second-team All-Pro honors, establishing himself as one of the NFL’s most dangerous receivers.
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Dallas made an excellent move by acquiring him, but the situation has become more complicated.
Pickens is playing on the franchise tag in 2026, earning $27.3 million on a fully guaranteed one-year deal. The Cowboys opted not to pursue a long-term extension before the July deadline, meaning contract negotiations cannot resume until after the regular season.
Pickens wants the long-term security that comes with a major contract, and Dallas has not shown that it is ready to make that commitment. The Cowboys could still change course, but their disappointing start makes it harder to envision Pickens viewing Dallas as the ideal place to spend the prime years of his career.
Winning could change the conversation. At 2-4, however, the Cowboys have plenty of work to do before they can convince anyone that they are legitimate Super Bowl contenders.
Dallas could get a significant return for Pickens
The good news for Jerry Jones is that Pickens should generate interest if the Cowboys make him available. Teams looking for a difference-maker at wide receiver would have a chance to acquire a player coming off an All-Pro season, and his talent makes him an appealing addition for a contender trying to strengthen its offense.
Jones would be justified in demanding a substantial return. Pickens is not an ordinary rental receiver, and his ability to make explosive plays gives him serious value. However, the franchise-tag situation complicates any potential deal because an acquiring team would have to consider the possibility of negotiating a long-term contract after the season.
Some teams might be willing to surrender prime draft capital for the opportunity to extend Pickens. Others could hesitate to pay a significant price for a player they might only have for the remainder of 2026. That uncertainty would make negotiations challenging, but it should not stop Jones from exploring his options.
The Cowboys must weigh what Pickens can provide over the next several months against what they could receive in a trade. If the team believes a playoff push is realistic, keeping him makes sense. If Dallas continues to struggle, moving him becomes a much more logical decision.
Jerry Jones cannot afford to lose a superstar for nothing
The biggest concern is what happens if the Cowboys hold onto Pickens and fail to reach an agreement after the season. He could enter free agency in 2027, leaving Dallas without the receiver or the draft capital it could have acquired by trading him.
That would be a difficult outcome to accept after Jones made the decision to trade for Pickens in the first place. The move paid off immediately, with Pickens producing at an elite level and giving Dak Prescott another dangerous weapon alongside CeeDee Lamb. But acquiring a star is only part of the challenge. Dallas must also decide how to keep that player or maximize his value before the relationship reaches its end.
If the losses continue piling up, Jones should pick up the phone and listen to offers. Trading Pickens would not erase the success of last year’s deal. Instead, it could be the next step in making sure Dallas receives lasting value from an investment that has already paid dividends.
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