NFL contract negotiator predicts how George Pickens, Cowboys saga will end

A report from before the Easter holiday suggested that wide receiver George Pickens may stay away from the Dallas Cowboys throughout the offseason program after his rights were retained via the franchise tag worth around $27.3M for the 2026 season.

There's no indication the Cowboys are close to signing Pickens to the type of extension he wants. For a piece published on Thursday, insider Jason La Canfora of SportsBoom US spoke with an unnamed longtime NFL contract negotiator about how Cowboys owner and general manager Jerry Jones will likely handle Pickens' situation. 

Have Cowboys decided to not sign George Pickens to a multiyear deal?

"Jerry’s never shy about applying the tag," the negotiator said. "Even if Pickens keeps it together (in 2026), there would be some obvious concerns about how he would operate with the kind of guarantees that would come with a top-of-market deal…I don’t believe Jerry subscribes to the calculus of having two receivers on a mega deal and his quarterback at the top of the market."

In August 2024, the Cowboys and No. 1 receiver CeeDee Lamb agreed to a four-year, $136M deal. Pickens' stats from this past season -- 93 receptions for 1,429 yards and nine touchdowns over 17 games -- suggest the 25-year-old deserves to reset the market for players at the position. However, La Canfora noted that "Pickens brings considerable baggage with him from his time" with the Pittsburgh Steelers.

Specifically, Pickens was allegedly guilty of a "litany of violations" from 2022 up until the Steelers traded him to the Cowboys last spring. Multiple reports noted that some of those red flags seemed to follow Pickens to Dallas. 

Meanwhile, Cowboys quarterback Dak Prescott signed a four-year contract extension reportedly worth $240M with $231M guaranteed in September 2024. 

Cowboys can afford to make this George Pickens decision

"He can afford to carry a player like Pickens on a short-term deal, and hence a big salary-cap figure, this year and next year," La Canfora wrote about Jones. Meanwhile, the negotiator added that basically keeping Pickens in contract years for the next two seasons "is a smart strategy" for Dallas. 

Of course, Pickens could threaten that he's willing to forfeit money by not playing in regular-season games unless he receives a long-term contract. July 15 is the deadline for teams to sign tagged players to such deals.