Analyzing the pros and cons of George Pickens joining the Cowboys

New York Times

08-05-2025

The Dallas Cowboys made their most significant trade of the last 6 1/2 years Wednesday when they sent the Steelers a 2026 third-round pick and a 2027 fifth-round pick in exchange for wide receiver George Pickens and a 2027 sixth-round pick.
Pickens is the most notable acquisition Dallas has made since trading a first-round pick to the Raiders in exchange for wide receiver Amari Cooper in October 2018.
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Pickens, a second-round pick in 2022, is entering the final year of his rookie contract. The 6-foot-3, 200-pound wide receiver has averaged 58 receptions for 947 receiving yards and four touchdowns over his first three seasons.
To get a better understanding of what Dallas is getting, Jon Machota, The Athletic's Cowboys beat writer, had the following exchange with Mike DeFabo, The Athletic's Steelers beat writer.
Machota: This move makes a lot of sense for the Cowboys. Wide receiver No. 2 was their biggest need. Arizona wide receiver Tetairoa McMillan would have been Dallas' pick at No. 12 if he had not been drafted eighth by Carolina two weeks ago. While Jerry Jones said two days before the draft that the Cowboys were working on two 'substantive trades' that could happen before or after the draft, the expectation was for a move similar to their recent trades for wide receivers Brandin Cooks and Jonathan Mingo. Pickens' ability is on a different level.
He gives Dallas the type of big-play receiver who should help CeeDee Lamb see better matchups. Had this move not been made, Dallas' opponents would have just done everything to take Lamb away and make anyone else beat them. Is there the possibility that things don't work out? Of course. But things were getting too boring in Dallas. It was time to spice it up.
What are the Cowboys getting in Pickens?
DeFabo: When Pickens is engaged and playing his best football, he has the potential to be one of the most dynamic deep threats in the game. The question is: Will he ever reach that full potential? From the time Pickens entered the league, there have been rumblings about his character concerns. Last year alone, he sported eye black that read 'Open F— Always,' pulled down Dallas Cowboys defender Jourdan Lewis by his face mask after a loss and got in a postgame wrestling match with Browns DB Greg Newsome.
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Often, coach Mike Tomlin defended Pickens, claiming that he didn't see the eye black and wasn't aware of either postgame incident. However, it appeared last season that even the coach's patience was running thin. After Pickens was flagged multiple times during a game against the Bengals, Tomlin said it was time for Pickens to 'grow up.'
Pickens missed the next three games with injury. The next game in which he was active, he responded by showing up about 40 minutes late for a critical game against the Chiefs. That type of behavior was routine in Pittsburgh. You can expect a supremely talented player who will fully embrace the diva side of the position. Considering the Steelers were never going to sign Pickens to an extension, it made sense to punt now rather than risk a messy hold-in situation in camp.
Machota: All of that is certainly concerning. The Cowboys have to be banking on their current team structure to be in a good place to handle those types of issues. Since Brian Schottenheimer was hired as head coach in January, it has been common for him to sound a little like Jason Garrett in his talks about building a strong culture and getting the right type of guys.
As we saw under Garrett, that didn't mean they completely avoided players with character concerns. The belief is that a strong culture puts the team in position to handle adding some very talented players who might not completely fit in that group. With Pickens being moved in a contract year, it wouldn't surprise me if the Cowboys let this season play out without getting a contract extension done. They can wait until next offseason when they can either sign him before free agency, franchise tag him or get a decent compensation pick for him leaving in free agency.
No question there is risk involved here, it's just the type of risk they should be willing to take. They haven't exactly been getting closer to winning a Super Bowl during this 29-year drought. Taking a swing like this is something the Eagles would do. And that's the type of success the Cowboys are chasing.
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How do you think Pickens would fit as a No. 2 wide receiver? Or do you think he believes he's coming to Dallas as a 1-A, 1-B with Lamb?
DeFabo: Pickens is one of the most explosive receivers in the game, averaging 16.3 yards per reception. The ever-present threat of the deep ball will force opponents to game plan to take away Pickens, which should open things up for other receivers.
Whether Pickens is officially WR2 or WR1B, the Cowboys will need to make sure to funnel targets his way. Pickens repeatedly grew frustrated when the Steelers failed to get him the ball enough. There were even instances when the Steelers scored touchdowns and Pickens didn't celebrate with his teammates. Navigating this part of Pickens' personality will be just as important as finding ways to unlock his big-play potential.
Machota: That type of behavior would certainly bother Schottenheimer and, just as important, quarterback Dak Prescott and Lamb.
Part of the reason Prescott is the NFL's highest-paid player is because of his leadership. If Prescott can't get him on the same page, it might be a good thing to part ways after one season instead of giving Pickens a long-term deal. But he's in a good situation because of the matchups he should see playing with Lamb, and a healthy Prescott should be the best quarterback he's had throwing him the ball.
Let's end on this. The Cowboys are known for allowing their contract negotiations with top players to drag out. They're currently in that situation with Micah Parsons. He's represented by David Mulugheta, who also represents Pickens. Do you think there's a chance Pickens would sit out until he gets a new deal?
DeFabo: That's a great question. In Pittsburgh, many fans were arguing that the Steelers should have simply rode things out in Pickens' final year and hoped that he matured. The problem is, the Steelers don't hold the cards.
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Just a few years ago, former Steelers receiver Diontae Johnson held in ahead of the fourth and final year of his rookie deal to force the team to give him more guaranteed money early. Around the league, this kind of behavior is common. Brandon Aiyuk earned himself an early payday just last year with a similar tactic.
That's why I felt trading Pickens now made more sense, rather than wading into uncertain waters and potentially inviting a messy situation in training camp. Pickens hasn't acted in a rational way previously. He's repeatedly been fined for on- and off-field situations and it doesn't appear he cares if he loses money that way. It wouldn't surprise me if he's willing to be fined in camp or even into the season by holding out.