Trade Prediction Highlights George Pickens' Uncertain Future With Dallas Cowboys

One analyst predicts George Pickens will eventually request a trade from the Cowboys and it's certainly a possibility given his uncertain future.

Dallas Cowboys wide receiver George Pickens. | IMAGN IMAGES via Reuters Connect

When it comes to the biggest uncertainties surrounding the Dallas Cowboys' future, George Pickens is right at the top of the list.

After a career year in 2025, Pickens is playing out the 2026 season on the franchise tag after the Cowboys refused to consider a contract extension.

The reason for that decision is due to Pickens' unpredictable nature, something we saw plenty of during his days with the Pittsburgh Steelers.

Pickens was mostly on his best behavior in what was a career year for him, but that wasn't enough for the Cowboys to trust him with a long-term contract, nor should it have been. If Pickens wants the bag in 2027, he's got to both have another strong season and emerge from it without any issues.

So far, he's on the right track. Pickens didn't put up a fight about the Cowboys' decision to make him play on the tag and that has put any possibility of major offseason drama to bed.

But things could be very different down the road.

George Pickens predicted to request trade

Dallas Cowboys wide receiver George Pickens. | IMAGN IMAGES via Reuters Connect

Bleacher Report's Gary Davenport predicted six NFL stars who could request a trade at some point in the future and Pickens landed on the list.

Davenport thinks that Pickens could request one as early as this coming season if the Cowboys struggle out of the gate and/or if his target share goes down, which would hurt his production and chances of getting a big contract next offseason.

Even if that doesn't happen, Davenport believes the Cowboys slapping the tag on Pickens once again in 2027 could lead to a trade request, also.

"We've already seen Pickens' tenure with one team end unhappily," Davenport said. "What happens if the Cowboys are slow out of the gate in 2026, or if his target share doesn't translate into the kind of production that positions him for a massive payday in 2027?"

"And if Dallas elects to tag him again next year, that would mean another season in which his compensation lags behind other top wideouts. Under that kind of pressure, it's easy to imagine him reconsidering how long he wants to stay in Dallas," he added.

How realistic is a George Pickens trade request in 2026 or 2027?

Dallas Cowboys wide receiver George Pickens. | IMAGN IMAGES via Reuters Connect

The strategy for Pickens for this coming season is very simple: don't rock the boat, no matter what, and that's in terms of both behaving himself and not requesting a trade.

Doing one or both of those things will hurt his chances of getting a long-term deal in 2027, whether that's from the Cowboys or another team.

Everyone knows how talented Pickens is, but no team will trust him with a long-term deal if he doesn't further prove he isn't a threat to become a problem.

If Pickens goes on to have another big year and the Cowboys tag him once again, that's where things will get tricky.

Pickens isn't likely to be keen on playing another season on the tag in that scenario and we would expect him to request a trade, which the Cowboys should certainly oblige if it comes to that.

The last thing Dallas can afford is to have a disgruntled Pickens on the roster, and the Cowboys also shouldn't be spending a huge chunk of money on two wide receivers.