“I do not expect a long-term deal this year,” Rapoport said, via Bleacher Report. “If he plays well and does everything he did last year, I think next offseason he’ll be able to cash in and be one of the highest-paid receivers in the NFL. I don’t believe they’re gonna trade him. I think they just wanted to see more in one more year.”

Though there were no concrete rumors that the Cowboys wanted to trade Pickens, many analysts suggested they could explore deals before his contract expires at the conclusion of this year. Bleacher Report’s Moe Moton suggested that the Chiefs would be a good trade partner, making it part of his “bold” trade predictions for the upcoming season.

“Dallas’ hesitation to negotiate a long-term deal with Pickens opens up the possibility for a trade midway through the upcoming campaign,” Moton wrote. “If Ryan 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.”

The Cowboys will likely use Pickens as a building block as they look to get back into Super Bowl contention, while the Chiefs may need to find more help as they aim to return to the playoffs.

Chiefs May Need More Help at Wide Receiver

Even if landing Pickens is no longer a possibility, the Chiefs could still look elsewhere for help at wide receiver. The team’s receiving corps struggled at times throughout the 2025 season, and Rashee Rice faced a one-month setback after being sent to jail for violating his probation for his felony conviction from last year.

Some analysts have suggested the Chiefs could make a run at former All-Pro receiver Stefon Diggs, who is still a free agent after being cut loose by the New England Patriots just weeks after their Super Bowl loss.

Diggs had initially faced the uncertainty of felony charges after he was accused of assaulting a former personal chef, but the veteran wide receiver was acquitte in a May trial. ESPN’s Adam Schefter reported that the league investigated the incident and decided not to suspend.

“The NFL closed out its review of the matter involving Stefon Diggs and his former chef,” Schefter reported. “It said there was insufficient evidence to support a finding of a personal conduct policy violation.”

The league’s ruling lifts that cloud that had hung over Diggs, freeing a team like the Chiefs to make a run at him.