George Pickens demands long-term deal: Will the Cowboys repeat Dak Prescott's mistake?

Frisco, TX – June 7, 2025 – The Dallas Cowboys’ acquisition of wide receiver George Pickens from the Pittsburgh Steelers has electrified their offense, pairing the dynamic 24-year-old with All-Pro CeeDee Lamb to form one of the NFL’s most formidable receiver duos. But as Pickens settles into his new role, whispers of his long-term ambitions are growing louder. With the final year of his rookie contract looming in 2025, Pickens is reportedly aiming for a lucrative extension—a move that could test the Cowboys’ financial discipline and raise fears of repeating the costly missteps tied to Dak Prescott’s record-breaking deal.

Pickens, acquired for a 2026 third-round pick and a 2027 fifth-rounder, brings a tantalizing skill set to Dallas. His 2023 season with Pittsburgh—63 receptions for 1,140 yards and five touchdowns, averaging 18.1 yards per catch—showcased his deep-threat prowess. In 2024, he added 900 yards despite inconsistent quarterback play, per ESPN. Now catching passes from Prescott, the 2023 MVP runner-up with 4,516 yards and 36 touchdowns in his last fully healthy season, Pickens is poised for a career year. “I’m here to build a winning culture,” Pickens said in May, sidestepping contract talks but hinting at bigger goals. “I want to show I’m a top guy.”

That ambition could come with a hefty price tag. Spotrac projects Pickens could command a four-year, $101 million extension in 2026, averaging $25.3 million annually—making him the 12th-highest-paid receiver in the NFL. Such a deal would align him with elite No. 2 receivers like Tee Higgins ($28.7 million) and Jaylen Waddle ($28.2 million), but it poses a dilemma for a Cowboys team already strapped by massive contracts. Dallas currently has $10 million in projected 2026 cap space, per OverTheCap, with Prescott’s $89.9 million and Lamb’s $35.5 million cap hits consuming roughly 45% of the 2025 salary cap (estimated at $272.5 million).

The Cowboys’ decision to sign Prescott to a four-year, $240 million extension in September 2024, the richest in NFL history, has drawn sharp criticism. Radio host Dan Patrick called it a mistake, arguing Prescott, at 32, is “good but not consistently great” and injury-prone, citing his 2024 hamstring tear that sidelined him after Week 9. Former Cowboys coach Jimmy Johnson echoed this, suggesting Dallas should have let Prescott play out his contract to avoid cap constraints. With Prescott, Lamb, and a pending extension for Micah Parsons (also represented by Pickens’ agent, David Mulugheta), the Cowboys risk a financial crunch.

Pickens’ case is different but fraught with its own risks. His talent is undeniable—his 16.3 yards per catch career average and 515 deep-target yards in 2024 (second in the NFL, per NFL Pro) make him a perfect complement to Lamb’s slot dominance. Prescott has praised his new weapon, noting, “It’s hard to double-team two guys like that,” and expects Pickens to open up the offense alongside tight end Jake Ferguson and receivers Jalen Tolbert and Jonathan Mingo. Yet, Pickens’ history of tardiness and sideline outbursts in Pittsburgh raises red flags. Steelers coach Mike Tomlin urged him to “grow up” in 2024, and some Cowboys insiders worry about his fit in a locker room led by Prescott’s steady leadership.

The Cowboys are betting on their culture, shaped by new head coach Brian Schottenheimer, to harness Pickens’ potential. Early signs are promising: Pickens and Lamb, who have trained together in past offseasons, share a mutual respect, with Lamb praising Pickens’ ability to win 50/50 balls. During OTAs, Prescott was seen coaching Pickens after plays, a dynamic that could foster growth. But as former NFL receiver James Jones warned on The Facility, Pickens alone can’t elevate Prescott in playoff moments, where the quarterback has struggled (1-3 record, 91.6 passer rating).

Dallas’ strategy appears to be letting Pickens play out his 2025 contract, valued at $3.65 million, before committing long-term. This mirrors their cautious approach with Prescott and Lamb, whose delayed extensions sparked fan frustration. A breakout season could justify a $100 million deal, but a flop—or locker room discord—could make Pickens a one-year rental, costing Dallas a valuable draft pick. Posts on X reflect this tension, with one user noting, “Pickens could be a $240m headache for Dak if he doesn’t buy in.”

The Cowboys’ history with high-profile receivers offers cautionary tales. Dez Bryant thrived but required management, while Amari Cooper’s 2018 trade sparked a passing surge. Pickens, compared to Bryant for his deep-threat flair, could follow suit—or flame out if his maturity issues resurface. With Parsons, cornerback DaRon Bland, and guard Tyler Smith also due for extensions, Dallas faces a cap puzzle.

As the Cowboys prepare for their Week 1 clash against the Philadelphia Eagles on September 7, 2025, Pickens’ integration will be scrutinized. A successful season could lock him into Dallas’ core, but an overzealous extension risks echoing the Prescott deal’s cap woes. For now, Pickens’ focus on winning aligns with Schottenheimer’s vision, but the stakes are high. Will Dallas secure a star or stumble into another financial trap? Only time—and Pickens’ performance—will tell.