With a 44-24 loss to the Denver Broncos in Week 8, the 2025 season is getting away from the Dallas Cowboys. A season that may have begun with high expectations has been shaken with the trade that sent Micah Parsons to the Green Bay Packers and may now have the eyes of Cowboys fans pointed toward the future.

One of the biggest questions the Cowboys will have to address is whether to re-sign George Pickens to an extension. After acquiring him from the Pittsburgh Steelers last spring, Pickens has caught 43 passes for 685 yards and six touchdowns and has positioned himself to cash in as he enters free agency next spring.

While he’ll have to wait a while to get paid, it appears the Cowboys are already laying the groundwork toward their decision. Longtime Cowboys insider Ed Werder reports that the Cowboys “have not engaged in extension talks with Pickens or his representatives” with the Nov. 4 trade deadline approaching. Jerry Jones revealed the Cowboys may be playing the situation perfectly during an interview on 105.3 The Fan on Tuesday afternoon.

“Any and everything about George Pickens has crossed our minds,” Jones said via Jon Machota of The Athletic. “…Certainly he’s a topic of interest and discussions because of the success he’s having.”

Jerry Jones Keeps Door Open on George Pickens’ Future with Cowboys

Jones’s comments that he’s keeping all avenues open with Pickens’s future. While many believe that the Cowboys should trade Pickens by next week’s deadline if they don’t plan on keeping him, Jones’s comments give the impression that the team is more than willing to keep him if they don’t get what they’re asking for in a trade. It also keeps the door open for a potential franchise tag, which could be the best situation for everyone involved.

Spotrac currently projects Pickens to have a market value of $29 million annually if he hits free agency next spring. The contract is similar to the one that Tee Higgins (four-year, $115 million) signed with the Cincinnati Bengals last spring, and could have the Cowboys seriously considering their roster construction if they were to make that deal.

Of course, the franchise tag presents a different option. Over The Cap projects next year’s franchise tag to check in at $28.046 million, and it gives the Cowboys time to have Pickens prove that this year isn’t a fluke. While Pickens has put up the stats of a top target, his past, which included several incidents in Pittsburgh, should give any team pause before making a long-term commitment.

Assuming Pickens signs his tender, it gives the Cowboys flexibility moving forward. Pickens can play through another season, and if he plays at the same level, he could receive an even bigger contract after the 2026 season. If the Cowboys balk at that price, they can trade Pickens at the end of the season, getting an even bigger haul than they would if they traded him next week.

Higgins’s case provides an extra layer of thinking. Higgins proved himself by catching 73 passes for 911 yards and 10 touchdowns on the franchise tag last season, but his numbers have dropped to 25 catches for 360 yards and four touchdowns over the first eight games. Joe Burrow’s turf toe injury has contributed to the drop in production, but Higgins is making $28.75 million annually while producing a value of $12 million according to Over The Cap’s valuation.

Getting a chance to “date” Pickens for another year before making a long-term commitment could be appealing to the Cowboys, who also have to rebuild a defense that is among the worst in the league. The Cowboys are making the right moves with the deadline approaching, and should figure out their approach when Pickens hits free agency next spring.