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Cowboys' biggest question has fans wondering what Jerry Jones is doing

Dallas Cowboys owner Jerry Jones
Dallas Cowboys owner Jerry Jones | Kevin Jairaj-Imagn Images

The Dallas Cowboys have largely decided to operate without their usual degree of bombast in the 2026 NFL offseason, making some wise moves in the NFL Draft without making a big short-term trade. The only problem that continues to linger is the situation surrounding wide receiver George Pickens.

Pickens put together the best season of his career last year in Dallas, but the Cowboys have not been able to come together on any sort of long-term contract. The team has placed the franchise tag on Pickens, but they have been unusually blunt in saying they are not looking to give him a long-term contract right now.

ESPN insider Dan Graziano is confused as to why Dallas is going down this route, citing it as one of the biggest remaining questions left unsettled after the bulk of the 2026 NFL offseason. Pickens is going to cost a ton of money, but the longer Jerry Jones waits, the higher the price is going to go, and fans are confused as to why a deal still isn't done.

Dan Graziano wonders why the Dallas Cowboys have not extended George Pickens

After years of struggling with below-average quarterback play in Pittsburgh, Pickens exploded next to Dak Prescott despite missing out on some targets that went CeeDee Lamb's way. Pickens had career-best marks across the board with 93 catches, 1,429 yards, and nine touchdowns.

Still just 25 years old, Pickens has his best football ahead of him. While it may seem like a hefty ordeal to commit upwards of $30 million per season to two receivers on the same team, both Pickens and Lamb warrant such a move after their breakout seasons.

Why else would Micah Parsons have been traded? Wasn't one of the justifications (perhaps even the main one) the idea that Dallas could keep three or four other players with the money that would have been allocated to Parsons over the next half-decade? Pickens seems like an ideal use of that money.

In an NFC that has very quickly become very deep, it would be foolish of a Cowboys team that spent all offseason getting much better on the defensive side of the ball to throw all of that progress out of the window by trading away Pickens for a package that is not makret value.

There is nothing Jerry Jones likes more than getting in unusually long and drawn-out contract negotiations with players who most teams would have signed before they even got to this point.

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