If the Cowboys don’t feel comfortable signing George Pickens to a massive extension, they could flip him for another first round draft pick

All things considered, the Dallas Cowboys have really set themselves up for a franchise-changing offseason in 2026. With two first round picks in upcoming draft, Dallas is abnormally positioned to be major players in the offseason’s most exciting event. Such are the benefits of trading a superstar player like Micah Parsons after all.

As if those two first round picks aren’t enough for the franchise, the Cowboys have a resource available to bump that two up to a three quite easily. That’s because they have control of wide receiver George Pickens, a player who’s sure to pique more than a few interests if dangled on the trade market this spring.

You see, Pickens is a free agent this March, and coming off a career season where he firmly established himself as one of the best in the game, he’s about to get paid. The Cowboys have first dibs. They could easily decide to turn their favorite mercenary into a cornerstone player and ink the 24-year-old WR to a multiyear deal. Or they could put off such a course-setting commitment and slap him with franchise tag instead. That second option could be used to keep Pickens in town for another year or it could be used to hold his rights while a trade was negotiated.

Looking around the league, half the NFL could use a player of Pickens’ talent. While he might have some baggage, he’s a ready-made playmaker with ball skills that are unmatched. A playmaker of Pickens’ level could prompt a return of a first-round pick, and possibly more.

The Cowboys can feasibly fit Pickens under the salary cap without massive long-term ramifications if they so desire. They can still build out a good defense and still strike while the iron is hot inside this three-year Dak Prescott window. But it does make things a little trickier from a financial perspective and it also means the Cowboys will be more reliant on their upcoming draft picks all working out. Basically, a re-signed Pickens shrinks their margin of error.

If the Cowboys decide that margin is undesirable and they’d rather save the money and add the pick, flipping Pickens in a trade would let them have their cake and eat it too. The money saved could be used on veteran defensive talent in free agency, while the draft pick could be used on a plug-and-play replacement in the draft.

As things stand today, there are at least four WR prospects who figure to go in the first round of the 2026 NFL draft. Jordyn Tyson, Carnell Tate, Makai Lemon and Denzel Boston are all WR1 prospects with plug-and-play polish. Three of the four project as true X receiver talents with the fourth, Lemon, being one of the most technically precise prospects seen in years.

Tagging and trading Pickens requires a trade partner and involves faith that one of the Day 1 starters listed above is there on the board when Dallas picks. It also hinges on scouting reports being correct and said prospect becoming the instant playmaker the Cowboys need him to be. It comes with some unknown.

This trade route also comes with freedom to move around more in the draft since it adds a third first-round pick to the mix. It prevents salary cap allocations from leaning too far into the offense’s direction and allows the front office to instantly invest in veteran talent on defense.

Sending a proven impact player like Pickens might not be a recommended course of action but it certainly has to be on the table. The Cowboys have already shown their willingness to trade stars for picks so it’s not like it’s out of character for this team either. Just one more thing to think about as the Cowboys approach the offseason. Three first round picks is a distinct possibility.

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