For the Dallas Cowboys, the offseason contract headache is not new, as the franchise has spent the last few offseasons navigating major contract storylines, and George Pickens is now at the center of the current one. After a breakout 2025 campaign, Pickens has positioned himself for a massive payday, but Dallas may not be eager to rush into that conversation.
The problem is not simply whether Pickens deserves elite money: It is what that kind of deal could trigger elsewhere on the roster. With CeeDee Lamb already on a premium contract and the wide receiver market continuing to rise, the Cowboys are walking into a potentially messy balancing act. That is exactly why one former NFL executive believes this situation is far more complicated than it looks.
Why George Pickens’ Contract Extension with the Cowboys Is So Complicated
Former NFL general manager Mike Tannenbaum, during his latest appearance on ESPN’s “Get Up,” explained why he believes a long-term extension for Pickens could become one of the more difficult contract puzzles in the league.
His argument centered on how dramatically the receiver market has shifted and how Pickens’ camp is likely to view his leverage after last season.
“This is an impossibly difficult situation,” said Tannenbaum. “Last year with Micah Parsons was as easy as it could have been. Making the highest-paid pass rusher move on and we’re done. This year there’s a big nuance which is the highest paid receiver is now Jaxon Smith-Njigba at $42 million ($42.15 M) a year. Based on how George Pickens played last year, I’m hard pressed to think that he’ll take a dollar less than being the highest-paid receiver.”
That is indeed the heart of the issue, as Pickens is not likely to see himself as a secondary piece just because Lamb is already in Dallas. He just delivered one of the best seasons of his career and has every reason to push for top-of-market money. Tannenbaum then explained why Dallas’ likely counteroffer may not be enough to settle things quickly.
“With that said, I’m sure Dallas is gonna say, ‘no, we have CeeDee Lamb, we’re gonna make you the highest-paid number two receiver, approximately 28.7 million.’ That’s what Tee Higgins makes in Cincinnati. Because of that, I could see this going well past Labor Day in terms of when he signs his tender.
“And the other problem you have, and this is a tough part about being a front office, as soon as you sign George Pickens to any extension guys, above $36 million, CeeDee Lamb’s knocking on your door and say, ‘well, wait a second, I’m at $36 million a year. I need a raise.’ So you may solve one problem and create another,” Mike Tannenbaum added.
.@RealTannenbaum on the impact of a contract extension for George Pickens 👀
“As soon as you sign George Pickens to any extension, guys, above $36 million dollars, Ceedee Lamb’s knocking on your door.” pic.twitter.com/iERZlO1xu4— Get Up (@GetUpESPN) April 1, 2026
That creates a very real front-office dilemma: Reward Pickens now, and you may immediately reopen Lamb’s contract conversation.
Dallas Cowboys Appear Willing to Let George Pickens’ Timeline Play Out
For now, Dallas seems comfortable taking the slow route. Owner Jerry Jones recently suggested the team is in no rush and intends to let the franchise tag process unfold naturally.
“I don’t know. The franchise tag has an automatic timeframe on it, and all of us will, and it’s my plan and our thought that we’ll all be working within the timeframe of the conditions of the franchise tag,” Jones said, via Jon Machota of The Athletic.
He added, “It should play itself out is the best way for me to say it. Make no mistake about it, we have long-term plans in mind for Pickens.”
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That means all eyes now shift to the July 15 deadline, the final date for Dallas and Pickens to agree to a long-term extension. If no deal gets done by then, Pickens would play the 2026 season on the non-exclusive franchise tag, and the drama would simply carry into the fall.
The Cowboys clearly value Pickens, but valuing a player and pricing him correctly are two very different things. Over the next few months, Dallas will have to decide whether keeping one star happy is worth potentially creating a second, even bigger contract headache.
