With the Dallas Cowboys sitting at 3-5, it’s tough to envision them amounting to anything in the 2026 NFL season. Sure, the NFC East is still “winnable” due to a lack of a serious contender in the division.

But for a Cowboys team that’s unable to put together a win streak in the regular season, it seems wildly optimistic to be talking about playoff chances. That brings us to a discussion about the future. And that in turn, brings us to George Pickens.

The Cowboys made Pickens’ future ambigous

The Cowboys willingly made Pickens’ future ambigous when they decided to place the franchise tag on him ahead of the 2026 NFL season instead of negotiating a long-term deal. So now, what do the Cowboys do with the young, rising wide receiver?

Next offseason, the Cowboys will have to make decisions on the future of CB Joey Porter Jr., S Malik Hooker, CB Cobie Durant, S P.J. Locke, DT Otito Ogbonnia (one of the few standouts on this defense), OT Broderick Jones (who they gave up a third-rounder for), among others.

Does Pickens fit into the plans of a front office that’s admitted publicly it’s not easy to pay top money to two different wide receivers? As painful as it may be to read for Cowboys fans, the answer is probably not.

The Cowboys have to decide if they plan to extend Pickens in 2027. It’s not like the projected contract for Pickens is a top secret. He will ask for top of the market type of money. He will want, in all likelihood, a four-year deal. Does Dallas intend to pay? Or do they intend to franchise tag him once again and deal with the drama that will likely come from it?

Or do they plan to let him walk? If it’s the the latter, then it’s time to move on and get something in return. Something better than a compensatory pick in 2028, too.

Now, the Cowboys are standing their ground saying they do not intend to sell. But if they lose to the Indianapolis Colts (which is very realistic given what we know of the Cowboys defense), expect the phone calls to come their way at 3-6. And some of the offers might be too good to pass on given the above context.

4 George Pickens trade scenarios

The above is why I fired up our A to Z Sports trade simulator to find fair offers for Pickens by WR-needy teams around the NFL. The simulator assings values to every draft pick and player, and calculates if an offer leans one way or the other, or if it’s “fair.” Additionally, I reached out to my colleagues to see their takes on specific scenarios.

Let’s kick this off.

Kansas City Chiefs

• Cowboys get: 2027 first-round pick
• Chiefs get: WR George Pickens, 2027 fourth-round pick (via PIT)

Charles Goldman, A to Z Sports Kansas City: “This hypothetical trade would give the Kansas City Chiefs everything they need at the wide receiver position. Pickens is coming off a season where he had the third-highest yards per route run against man coverage. However, this would be a bit of a sore spot for Chiefs fans.

“That’s because back in the 2022 NFL Draft, Brett Veach traded down with the New England Patriots. The Pats selected Tyquan Thornton (50th). Two picks later, the Steelers selected George Pickens (52nd), and K.C. took Skyy Moore (54th). Had Kansas City stayed put, they could’ve had Pickens themselves. Pickens has over 300 receptions for over 4,800 yards and 23 touchdowns during his career. Moore doesn’t even have 13% of that production over his career.

“The criticism would be: Why did you give up a first round draft pick for a player that you could’ve rightfully drafted back in 2022. It’s valid criticism and would be an indictment of the general manager to turn around and trade for Pickens now.”

Los Angeles Rams

• Offer 1
  • Cowboys get: 2027 second-round pick, 2028 third-round pick
  • Rams get: WR George Pickens
• Offer 2
  • Cowboys get: 2028 first-round pick, 2027 fourth-round pick
  • Rams get: WR George Pickens, 2028 fifth-round pick

Rob Gregson, A to Z Sports NFL: “I know that Sean McVay recently said that wide receiver Davantae Adams is on the “earlier side” of his 6-10 week rehab after injuring his hamstring, but the truth is, the Rams and, more specifically, their offense, don’t have 6-10 weeks to wait. Sure, they just beat up on the winless Chargers, but for this team to get back in the Super Bowl hunt, they will need more than just Puka Nacua on the perimeter.

“Insert George Pickens. For whatever reason, despite being back in the same offense, Pickens simply hasn’t received the targets and opportunities that made him one of the best WRs in the league last season. He’s still in a prove-it year; he’s still one of the better vertical stretch players at his position (see the Tampa Bay game), and by all accounts, he hasn’t been nearly the headache in Dallas that he was in Pittsburgh. Giving up a 2027 second and a 2028 third for a WR in his prime and with sights set on a Super Bowl seems like a light lift to me.”

Las Vegas Raiders

• Cowboys get: 2027 second-round pick, 2028 sixth-round pick
• Raiders get: WR George Pickens

Justin Churchill, A to Z Sports Las Vegas: “The Las Vegas Raiders’ biggest hole on their roster currently seems to be at wide receiver. They’re making up for it with the amazing play from Brock Bowers and Michael Mayer. But they still need a wide receiver. While you can expect them to take one in the first round of the 2027 NFL Draft, George Pickens has the talent that’s tough to pass on. If I were John Spytek, the Raiders GM, I’d take a look into the trade. A 2nd- and 6th-round pick is very doable. But for a team in a rebuild, do they really want to give up that second-round pick to a guy who needs a new contract?

“I don’t think they do it. Should they? Absolutely. If they did, Vegas would almost certainly need to move some money around to feel a bit more comfortable. They’re currently projected to have the 10th most cap space in 2027, at around $65 million. But after a deal with Pickens that could make him $30- $40 million a year, they may want to make some moves. But it’s doable.

“Final verdict: I think this would be an amazing trade, but I don’t think they’ll do it. Spytek has said he wanted to build this thing through the draft. So, as the clock winds down on the trade deadline timer, only time will tell whether he switches it up.”