Jerry Jones doesn’t hit the trade button often, but when he does, there’s usually a wide receiver on the other end. Remember 2018? He gave up a first-rounder for Amari Cooper, and it worked. Dak got his guy, and the offense took off. In just nine games, Cooper had 53 receptions for 725 yards and 6 TDs. Then came 2023, when Brandin Cooks landed in Dallas for just a couple of late-round picks and voilà, 54 receptions for 657 yards and eight TDs.

It’s true that the Cowboys mostly stick to their draft-and-develop plan. But now and then, when a gap’s too obvious—especially if needing a solid WR2—Jerry gets itchy. Cooper once filled that void. Cooks did too. But fast forward to now, and the Cowboys were stuck in the same void. Again. They’ve got their WR1—CeeDee Lamb. Safe and sound.

But the Dallas team was lacking a true WR2. Sure, they’ve reportedly got 12 receivers on their roster, but let’s not sugarcoat this—most of ’em are of WR3 calibre. And the way things shaped up, it seemed like Jerry’s going to hit the trade button. Correction: he already did. If reports are accurate, the Cowboys have agreed to trade for none other than George Pickens with the Steelers.

Well, for the past few weeks, the rumor mill was buzzing that the Cowboys were going to trade for Pickens. And here we are, as Pickens will now join Lamb. Yeah, that Pickens who had a tremendous season a couple of years back. We’re talking about the wideout leading the Steelers in targets (106), receptions (63), and receiving yards (1,140) in 2023.

But his last season was marred by controversies, and Mike Tomlin literally remarked that Pickens “got to grow up.” And now? Yeah, his time is over in Pittsburgh. As per The Athletic’s Dianna Russini, the Steelers are finalizing the trade for the WR in exchange for future draft picks. Loud and clear. According to a team source, Russini reported that Pittsburgh will receive a 2026 third-round NFL Draft pick and a 2027 fifth-round pick.

As for the Cowboys, they’ll be getting Pickens, of course, who’s in the final year of his rookie deal. Plus, the Dallas team will also acquire a 2027 sixth-round pick. But let’s not forget the Pickens will play the final season of his rookie deal. So the big question: how will the Cowboys tackle his contract extension?

A long-term deal or franchise tag for George Pickens?

“It definitely was a big-time thought, but the train has not left the station if improvement is needed from what we’ve got on campus,” Jerry Jones said after the Cowboys failed to get a wide receiver via free agency and the 2025 NFL draft. And to address the need, the Cowboys called the Steelers for a potential trade of Pickens, and the Steelers answered.

Ever since the Steelers acquired DK Metcalf earlier this offseason, it seemed like a trade was at the table for Pickens. Why? Well, at first, the Steelers offered a $150 million deal to Metcalf. And the last time we checked, Pickens was also in his contract year. So the Steelers were unlikely to offer a contract extension to Pickens. The result? He’s traded to the Cowboys. But if you’re thinking that Pickens is going to get a contract extension in Dallas, think again.

As part of the trade, no new contract has been negotiated. That means the 24-year-old arrived in Dallas in his contract year. And that’s where things got pretty interesting. See, Jerry Jones and the Dallas team have a knack of stretching the extensions. We’ve seen ’em doing with Dak Prescott. And we’re seeing ’em doing the same thing with Micah Parsons as well. So an extension for Pickens? Yeah, it’s going to take some time.

To make it more obvious, Parsons is reportedly negotiating a $200 million deal that will make him the highest-paid non-QB in the league. In that sense, it’s more likely that Jerry Jones and Co. will franchise tag Pickens next year.