Cowboys executive vice president Steph Jones underscored the challenge of paying two receivers at the top of the market, noting that a high-priced quarterback on the roster complicates such a decision and that other star players must be considered in the equation.
One potential path for Pickens, if he chooses it, could be to sit out until Week 10 to accrue a credited season toward free agency in 2027. The move would be risky, risking a dip in trade value and raising questions about his team-first mindset while forgoing a large portion of the 2026 franchise-tag salary, estimated at about 65 percent of $27.29 million.
Separately, there is a belief within the Cowboys’ orbit that they never planned for Pickens to be a long-term piece. That view includes talk of a compensatory pick coming in 2028 if Pickens departs, and it aligns with ongoing interest in alternative receivers, including Jordyn Tyson, who could be on Dallas’ radar if Pickens exits after the 2026 season.
ESPN has noted that Dallas’ interest in Jordyn Tyson remains, with Tyson potentially adding depth if Pickens moves on. If Pickens is not retained, Tyson could be a logical add in the draft if he remains available in Round 1.
On the trade front, Pickens’ value could fetch a second-round pick in a market that often values established receivers. Analysts have suggested the Cowboys could flip a second-round pick for Pickens, then pivot to drafting a receiver in the same draft, given the depth at the position. Potential suitors for Pickens if he hits the market have been named as teams like the Raiders, Chiefs, Ravens, and Patriots.
In summary, Dallas faces a delicate balance between cap considerations, roster construction, and draft leverage. Pickens’ contract situation could influence the team’s 2026 strategy, including whether to add a receiver in the first round or pivot to defense with its early picks. The coming days will clarify whether the Cowboys pursue a long-term plan with Pickens or pivot to alternatives at receiver.
