Sometimes the best trades are the ones that never happen. When the San Francisco 49ers tried to land George Pickens from the Pittsburgh Steelers, they met with a strong rejection. Cut to 2025, and Pittsburgh shipped Pickens to the Dallas Cowboys, anyway. As speculation builds around Pickens potentially hitting free agency in 2026 with a $30 million price tag, the Niners might be back in the mix, along with a few other NFC counterparts.

San Francisco wasn’t window shopping. According to 49ers insider David Lombardi, they “wanted Pickens in return for Brandon Aiyuk during those 2024 trade discussions with Pittsburgh.” The Steelers wouldn’t bite. By the time they dealt Pickens to Dallas, “the ink on Aiyuk’s deal had already dried.”

That missed connection stings. Aiyuk tore his knee in Week 7 last season, and the Niners voided his 2026 guarantees amid recovery frustrations. Pittsburgh wanted second and third-round picks in the Aiyuk deal. The Niners passed. But with another year of Pickens’ off-field issues, the Steelers shipped him off for just a 2026 third-round and a 2027 fifth-round pick.

But now, Pickens is having a career year with Dallas. After Week 14, he’s already amassed 1,179 yards (second-best in the league) with 8 touchdowns. CBS now lists him as a must-sign if he reaches free agency, recognizing the damage Pickens can deal to NFL defenses. If Pickens hits the market commanding $30 million annually, San Francisco will need a lot more than draft capital to get their playmaker.

CBS’s Cody Benjamin calls Pickens the “hotter contested-catch playmaker at the moment.”

In a WR room that features CeeDee Lamb wearing the legendary No. 88, that’s a massive endorsement. While the Niner’s will certainly try to get Pickens given the chance, Benjamin also lists AFC destinations, including the Los Angeles Chargers, New York Jets, New England Patriots, and Las Vegas Raiders, as logical suitors.

The biggest question now is whether Cowboys owner and general manager Jerry Jones will hand Pickens a contract commensurate with his pedigree before the rumor mills get out of control. Dallas also has the option of placing the franchise tag, worth around $28 million, on Pickens while they work out the details of his contract.

But here’s the thing about Pickens. The talent was never in question. But Pittsburgh had grown tired of tardiness and on-field flare-ups to a point where they couldn’t keep him on the team anymore. Dallas doesn’t seem to mind, and so far, Pickens has played like a team player. But Week 14 against the Detroit Lions seems to have opened old wounds.

George Pickens’ off-field headlines return

After Dallas’ 44-30 loss to Detroit on Thursday Night Football, Hall of Fame cornerback Richard Sherman blasted Pickens. On Amazon Prime’s post-game coverage, Sherman called Pickens’ outing “Uninterested.” And that’s when everything went wrong.

“George Pickens, throughout the game, especially late in the game, looked uninterested,” Sherman said. “And that’s what you can’t have. If you’re going to be a superstar, if you want to be the best receiver in the National Football League, you can’t ever be disengaged.”

This didn’t go over well with Pickens when he saw it. The wideout took to social media and fired back at Sherman in a since-deleted story.

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“This is a team game,” Pickens wrote. “I’m not the only one on the team. Stop becoming [an] analyst and talking about one player when he playing a teams game.”

But before Pickens deleted it, people took notice, including Richard Sherman. While Sherman notably shrugged off Pickens’ comments, head coach Brian Schottenheimer addressed the situation Friday.

“I’m aware of what was supposedly put out there,” Schottenheimer admitted. “I’ve not talked to him yet. I understand it’s been taken down but I will be talking to him, just checking on him. Again, this is unfortunately things that we deal with in this profession… I have not spoken to him, but I will.”

To be fair, Schottenheimer also defended his receiver’s effort. He didn’t see the lack of engagement Sherman criticized. But this whole exchange captures everything about George Pickens: electric talent, combustible personality. Dallas has chosen to embrace both sides, betting his production outweighs the noise. Through 14 weeks, they’re right. But moments like Thursday reignite the questions Pittsburgh couldn’t answer.

Whether Schottenheimer’s upcoming conversation with Pickens changed anything is unclear. What’s certain? Pickens’ next contract will hinge on much more than just stats. Teams need to believe they can handle the volatility. If the Cowboys can’t, their Niners, or a squad from the AFC, will wait to give it a shot. For now, Dallas has no intention of parting with its new star.