Cowboys-Chiefs Blockbuster Trade Prediction Only Makes Sense Under 1 Circumstance

An analyst sees the Cowboys and Chiefs pulling off a huge trade at the deadline, but this deal will only happen if Dallas falls flat on its face.

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

Trade speculation has swirled around wide receiver George Pickens all offseason long, but he finally put any doubt to bed after showing up for the Dallas Cowboys' mandatory minicamp and confirming he won't be holding out this offseason.

But that doesn't mean a 2026 Pickens trade is impossible, and Bleacher Report's Moe Moton agrees with that notion.

Moton predicts we will see one go down before the trade deadline, with the Kansas City Chiefs acquiring Dallas' star wideout in a blockbuster deal.

However, Moton sees a Pickens trade going down for the wrong reason. He believes the Cowboys will be willing to trade Pickens during the season if Flournoy takes the next step.

"If Flournoy blossoms in a complementary role, the Cowboys could trade Pickens to a receiver-needy contending team like the Kansas City Chiefs, who don't have a reliable lead perimeter playmaker," Sobleski wrote.

The Chiefs have a clear need at wide receiver with the uncertainty surrounding Rashee Rice and Xavier Worthy. Rice could get suspended again after getting in more legal hot water recently, and Worthy is coming off a very disappointing 2025 campaign.

While we agree with Moton that Pickens could be moved and that the Chiefs are a logical suitor, we do not agree with his reasoning why this deal could go down during the season.

Cowboys will only trade George Pickens in 2026 under one circumstance

Dallas Cowboys wide receiver George Pickens. | Chris Jones-Imagn Images

The only way we could see the Cowboys trading Pickens at the deadline is if their season is in a disastrous state by November.

What does a disastrous state look like? Dak Prescott succumbs to the even-numbered-year curse once again and the Cowboys are a one- or two-win team by early November.

In that scenario, it would make sense to unload Pickens before the Cowboys inevitably look to do so in 2027, when Pickens will likely get franchise-tagged once again.

But if the Cowboys are even remotely in the hunt, they are not going to pack it in by trading Pickens, who is a key piece in the Cowboys' elite offense. After all, we saw Dallas making trades despite having a 3-5-1 record in 2025.

George Pickens' 2027 outlook

Dallas Cowboys wide receiver George Pickens. | Chris Jones-Imagn Images

While we would never rule out Pickens getting traded at some point this coming season, we fully expect him to finish 2026 in Dallas.

From there, all bets are off.

The Cowboys will likely slap the tag on Pickens once again in 2027 and will then have to decide if they want to pay him or trade him.

Even if Pickens produces yet again and is on his best behavior, we still feel like the latter is far more likely. There's just no way Dallas can justify paying big money to two wide receivers and there is zero chance the Cowboys would commit to Pickens instead of CeeDee Lamb long term.