The Dallas Cowboys spent the offseason searching for a true complement to CeeDee Lamb. Someone who could stretch the field and give Dak Prescott another reliable option. They found their answer in George Pickens.

It didn’t take much to get him, either. Dallas sent a third-round pick to Pittsburgh in a deal that also included a swap of late-round selections. For the Cowboys, it was a low-risk move with high-end upside. For Pickens, it’s been a chance to reset his image.

Pickens, a pending free agent this offseason, is not waiting on an extension.

But what exactly will his next deal look like? Will Jerry Jones retain him? While we don’t know what Jerry’s next move will be, we do know what Pickens had to say about his extension in his exclusive chat with EssentiallySports.

“That’s kinda up to what (team owner Jerry Jones) wants to do,” Pickens said during the EssentiallySports Exclusive Interview. “All I can do is perform at my best.”

And the 24-year-old is performing. Putting up numbers on the board. It’s a message wrapped in numbers, one that suggests Pickens is ready for a contract that reflects his contributions. And that Jerry will have to decide if and when to meet that challenge.

In just eight games with the Dallas Cowboys this season, he’s put up career-high numbers:

• 685 receiving yards,
• Six touchdowns,
• an NFL-leading 36 first downs,
• Zero fumbles,
• Currently ranked 39th overall, and
• 10th among wide receivers.

That’s where things get interesting. Pickens is playing on a rookie deal from his days with the Steelers, which pays him an average of about $1.68 million a year. The Steelers traded him after three seasons in which he notched 174 catches, 2,841 yards, and 12 touchdowns.

On May 7, 2025, the Cowboys traded Pickens from the Steelers. The deal saw Dallas give up a 2026 third-round pick and a 2027 fifth-rounder, while they received Pickens along with a 2027 sixth-round pick. Dallas was seeking a reliable No. 2 receiver to complement star wideout CeeDee Lamb. Number 3 fit the bill perfectly and jumped right in when 88 was sidelined.

Now, with Dallas, he will enter the 2026 offseason as a free agent. And this is what the wide receiver contract market looks like.

Names like DK Metcalf and Garrett Wilson are cashing in contracts north of $130 million. As per Spotrac, Pickens could command a deal over $150 million for five years if he keeps this rolling. So, the question remains: is Jerry Jones willing to pay that kind of money?

What’s Jerry Jones’ approach to George Pickens’ contract?

Jerry is no stranger to this kind of contract drama. Ask him about Pickens, and you get the typical showbiz act. On 105.3 The Fan, Jones said he’s “proud” of Pickens but made it clear: it’s about give and take. The Cowboys owner is a master at mixing praise with pressure because this dance is nothing new for Jones.

We have seen this in negotiations with Micah Parsons, CeeDee Lamb, Dak Prescott, and Ezekiel Elliott. And these are just a few names from the long list. Publicly, he showers players with compliments, but behind the scenes, the tension builds under the rug.

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Adding fuel to the fire is what Lamb said about Pickens. Lamb wants Pickens to make “most money in the NFL.” Pickens also shares a great relationship with Prescott and told us during the EssentiallySports Exclusive chat that “he’s got his back.”

But, history shows that players standing up for their teammates’ contracts has happened before in Dallas. Often, little change comes from it.

Pickens came to Dallas looking for stability. What he’s built instead is momentum and maybe, soon, a monster payday to match.