When the Steelers signed DK Metcalf, it seemed like HC Mike Tomlin would pair him with George Pickens. I mean, Pickens has been one of the best WRs lately and the 24-year-old is set to enter free agency after his rookie contract expires a year later. So, when Tomlin landed Metcalf, extending Pickens seemed like a no-brainer. However, just a week into the 2025 free agency circumstances have changed in this free agency and now, Pickens’ Steelers future is up in the air.

59 receptions, 900 yards, and three TDs over 14 games in the last season from a 24-year-old WR, Pickens would be an obvious choice for any NFL team. But still, there are some serious doubts about his extension. Why? We all know no matter how good Pickens is, the 24-year-old sometimes lands the Steelers in trouble because of his on-field antics.

The Steelers owner, Art Rooney II, is not very concerned about this; he said, “there’s definitely room for growth.” Veteran NFL analyst also warned the Steelers before offering him a big contract. “If you give him money, is he gonna change?” Pro Football Talk’s Mike Florio said. “And at what point do you come to the conclusion that this is just who he is?” And while we keep discussing Pickens’ Steelers future, the 24-year-old WR seems to have set his eyes 2,193 miles away.

From Herschel Walker’s trade bomb to Ochocinco’s Twitter antics. Now, Pickens’ latest Instagram post—a black-and-white snap with Tom Brady—has fans reading tea leaves like it’s the Zapruder film. On Tuesday, Pickens shared a photo standing side by side with Brady, the Raiders’ minority owner. The image, pulled from a 2024 game, lit social media ablaze. Why? Brady’s fingerprints are all over Vegas’ offseason moves. He pushed for Ben Johnson as coach and tried luring Matthew Stafford. Now, with Geno Smith onboard, the Raiders need a WR1…

And Pickens slides right into that conversation, whose $1.3M rookie deal expires in 2025. George is a talent, but Pittsburgh’s not building around him anymore. The Steelers just traded for DK Metcalf, signing him to a $150 million extension. Pairing two deep threats sounds fun. But.

But as Mark Kaboly of The Athletic bluntly put it: “You pay Metcalf $30 million. This is almost one and done [for Pickens.] I don’t see any way he would come back at all.” Hence, Steel City might be drafting a breakup letter. Besides, trading Pickens now nets draft capital.

And waiting risks losing him for nothing. Yet the Steelers, eyeing their first playoff win since 2016, might roll the dice. “They think they can win now,” Kaboly said. But paying two WRs top dollar? Ask Cincinnati how that goes. The Bengals just committed $70M/year to Ja’Marr Chase and Tee Higgins—a luxury Pittsburgh can’t afford.

Tomlin’s ultimatum for Pickens

Mike Tomlin doesn’t suffer divas lightly. Remember Antonio Brown’s helicopter exit in 2019? Pickens, fined twice for sideline tantrums in 2023, tested that patience. “He’s just got to grow up, man,” Tomlin said after a playoff loss. “This is an emotional game, man, these divisional games are big. He got a target on his back because he’s George.” With Metcalf now in town, Pickens’s margin for error vanished.

Pittsburgh’s QB carousel—Russell Wilson, Justin Fields, maybe Aaron Rodgers—hasn’t helped. Pickens’s stats (1,140 yards in 2023) sparkle, but his effort wavers. Meanwhile, Vegas offers a fresh slate. Tom Brady, ever the recruiter, could sell him on being the next Tim Brown in silver and black. Meanwhile…

Rodgers’s potential arrival complicates things. Pickens once called him a “dream teammate.” “My dream teammate would probably be Aaron Rodgers. Aaron Rodgers or Ed Reed, or someone like that,” Pickens had said. But at 41, Rodgers is a short-term fix. If he lands in Pittsburgh, it’s a quick fix, not a cure. Besides, George Pickens’s future hangs like a Hail Mary in the December wind.

Pittsburgh’s gritty identity clashes with his mercurial flair. Vegas offers glitz, Brady’s mentorship, and a blank canvas. But trading him now feels like surrendering a chess piece mid-game.

As the great Al Davis once said, “Just win, baby.” For Pickens, winning might mean choosing between the steel grind of Pittsburgh and the neon allure of Vegas. Either way, his next move will ripple through the AFC—and rewrite his legacy.