George Pickens’ Potential Extension Could Be Jerry Jones’ Biggest Test Yet
The Dallas Cowboys made one of the most talked-about moves of the 2025 NFL offseason by acquiring wide receiver George Pickens in a blockbuster trade. Now, with the regular season just weeks away, a new question looms over the franchise: Can Jerry Jones pull off a contract extension for Pickens — and should he?
This could be an all-time challenge for the Cowboys’ owner, especially as contract pressure already surrounds All-Pro defender Micah Parsons, who has yet to receive his own extension.
A Lethal WR Duo in Dallas
With Pickens now wearing the star on his helmet, Dallas may boast the most dangerous wide receiver duo in the NFL. Pairing him with CeeDee Lamb — already considered a top-three receiver in the league — gives quarterback Dak Prescott a dream scenario on offense.
In theory, this duo could define the Cowboys’ offensive identity for years to come. But in reality, the front office has to face the business side of football: contracts, cap space, and prioritization.
Pickens’ Value Is Rising
Pickens is heading into the final year of his rookie deal, and he’s not just a complementary piece — he’s a No. 1-caliber receiver. According to Spotrac.com, Pickens’ projected market value is a 4-year, $101 million deal, averaging $25 million per season.
That figure might sound steep, but it’s in line with what top-tier receivers are commanding in today’s market. Given Pickens’ production through three seasons with the Pittsburgh Steelers — averaging 62 receptions, 1,006 yards, and 4 touchdowns per year — the price is arguably justified.
Even more impressive: Pickens put up those numbers despite inconsistent quarterback play in Pittsburgh. Now paired with Prescott and opposite Lamb, his ceiling could rise even higher.
Can the Cowboys Afford Him?
Here’s the real issue: Dallas already has a growing list of financial commitments. CeeDee Lamb will command massive money. Micah Parsons is due for what could be a record-setting contract for a defensive player. Dak Prescott’s deal will soon need revisiting. And now, George Pickens?
If the Cowboys want to lock in one of the league’s most explosive offenses, they’ll need to make tough decisions — and soon.
The NFL has seen several teams successfully invest in two elite receivers. The Eagles (Brown & Smith), Bengals (Chase & Higgins), Dolphins (Hill & Waddle), and Buccaneers (Evans & Godwin) have all proven that devoting major cap space to wideouts can work — if the rest of the roster is built wisely.
It’s not out of the question for Dallas to do the same — especially with the salary cap set to rise in upcoming years.
Why It Makes Sense to Extend Now
The longer Dallas waits, the more expensive Pickens could become — especially if he has a breakout year in 2025 with a more stable offense. Signing him now could potentially save millions and secure continuity at one of the league’s most important positions.
It would also show a commitment to Dak Prescott and the offensive unit, sending a clear message that the team is all-in on building a championship-caliber passing attack.
Plus, with Pickens still young, a long-term deal would carry lower risk than locking up an older veteran.
Will Jerry Jones Make the Move?
Historically, Jerry Jones has shown the willingness — and boldness — to pull off high-stakes deals. But his timing is often unpredictable. With the Micah Parsons extension still hanging in the balance, adding another major contract negotiation to the list could be daunting.
That said, this may be a test Jerry needs to ace. Securing George Pickens could not only set the tone for the Cowboys’ future on offense but also define this era of Cowboys football — for better or worse.
Final Thoughts
The Cowboys are at a crossroads. On one hand, they have one of the most promising WR duos in football. On the other, they face complex cap decisions, with Micah Parsons, CeeDee Lamb, and George Pickens all deserving top-tier deals.
If Jerry Jones can find a way to extend George Pickens now, it won’t just be a win on paper — it’ll be a signal to the league that the Cowboys are finally ready to turn talent into titles.
And for a team long haunted by “what-ifs,” that could be the difference between another disappointing season — or a championship window that actually stays open.
