If Cowboys get George Pickens’ best, what would that mean for 2026 and beyond?

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For one moment, imagine that the George Pickens trade is a success for the Dallas Cowboys in 2025. Pickens fits seamlessly into the offense, produces on the field, raises the game of everybody around him and is a model teammate in the locker room.

Then what?

Pickens, who turned 24 in March, is entering the final year of his rookie deal and is set to be an unrestricted free agent in 2026. In his initial meeting with reporters on a conference call the day after the Cowboys acquired him (essentially in exchange for a 2026 third-round pick), Pickens felt at ease about the uncertainty of his future.

“I’m not really thinking about contract talks,” Pickens said. “I’m just glad to be with the Cowboys right now, trying to build a winning culture.”

All signs point to Pickens playing out the final year of his contract without an extension in hand. The risk of a one-year rental for a third-round pick may seem steep for the Cowboys, but it’s not as steep as parting ways with the third-round pick and tying up significant money for a player who may not blend in with the locker room culture long term.

The Cowboys are obviously hoping for the rewards side of the risk-reward equation. If that’s the way things go, they’ll be staring at a hefty price tag to keep the good times rolling.

The Cowboys have faced challenging offseasons on the business end recently. Last year was a messy situation with Dak Prescott and CeeDee Lamb, and this offseason has the potential to go down a similar path if Micah Parsons doesn’t get an extension soon. Although Prescott, Lamb and Parsons are the top players at the premium positions, there are a number of other quality players at important positions on deck in Dallas.

Assuming a Parsons extension gets done this summer, the Cowboys will have DaRon Bland and Brandon Aubrey as unrestricted free agents next year, along with Pickens. Then there are solid starter-level players at important positions, such as tight end Jake Ferguson and safety Donovan Wilson, who will also be UFAs. The team will also be on the clock to extend left guard Tyler Smith, who carries a fifth-year option for 2027 but is among the best at his position and is a long-term puzzle piece.

Most of those pieces of business will require the Cowboys to make some decisions. Smith would seem to be an inevitability, as would Aubrey. But the Cowboys will have to consider their cornerback situation when they think about Bland’s future. Dallas already paid one cornerback in Trevon Diggs, but that was before Diggs’ injury issues and before Bland broke out as a versatile starting cornerback. The Cowboys will have to weigh the price tag on Ferguson and think about whether they want to pay up or roll the dice on a cheaper in-house option, as they did a couple of years ago with Ferguson, when they let Dalton Schultz walk.

There will be things to consider before having a conversation with Pickens — again, even if everything goes right in 2025.

In Lamb, the Cowboys are already paying a wide receiver top dollar. They are also paying the quarterback the most money of any player in NFL history, as Cowboys owner Jerry Jones will often remind you. Without any restructures, that’s roughly 35 percent of the team’s salary cap tied to two players in the passing game.

Would the Cowboys add Pickens to that equation?

The messaging from the front office has been inconsistent. Jones has spoken often about funds allocation, in terms of the salary-cap “pie” and the limits for how much investment goes into certain positions. For a time, they pointed to the big contracts they gave out last year and stated that it was the responsibility of those players to raise the level of their games to elevate the passing game, and the offense in general. However, the tune has changed a bit over the past month. In drafting Tyler Booker at No. 12 and trading for Pickens, the Cowboys are investing in their investments.

As long as Prescott has glowing results in 2025, the Cowboys will likely continue to build around him. They understand that these next four years of Prescott’s contract are likely the final years of a contending window with Prescott in his prime. Prescott is one of the better quarterbacks in the NFL, but he’s not top-tier. He needs the right pieces around him. If the Lamb-Pickens duo proves to be the talent that elevates Prescott, it would serve the Cowboys well to keep the tandem together.

The Cincinnati Bengals are an example of a team that’s kept their high-priced starting quarterback and top-level receiver duo together, though they’re now at a crossroads with star pass rusher Trey Hendrickson. The Cowboys anticipate already having Parsons in the fold for the long haul by the time next offseason rolls around.

The first step toward a Pickens contract extension being a factor — assuming it doesn’t happen this summer — is a successful season on the field. If that happens, contract extension questions will again follow the Cowboys next offseason.

(Photo: Barry Reeger / Getty Images)

This news was originally published on this post .

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