The Dallas Cowboys have earned a reputation for rolling the dice when it comes to their roster. There’s decades of evidence to back this up. They regularly go after controversial players and regularly seem to cost themselves tens of millions by not paying their biggest stars earlier than later.
While they’ve taken a lot of risks over the years, there haven’t really been a lot of rewards — most importantly the Cowboys haven’t even played in an NFC Championship Game since the 1995 season. The franchise has already shown they aren’t going to stop taking those kinds of chances in 2025.
Bleacher Report’s Kristopher Knox called out the Cowboys for making the NFL’s “Riskiest” offseason move by trading for mercurial Pittsburgh Steelers wide receiver George Pickens on May 7.
“Considering the Cowboys have long lacked a dependable second receiver opposite (CeeDee) Lamb and need to find a fast start under new head coach Brian Schottenheimer, this trade was a significant risk,” Knox wrote on June 15. “For one, Pickens’ on-field consistency was a major issue in Pittsburgh, which is why he was dealt in the first place. The 24-year-old has immense talent and, physically, could be an ideal match for Lamb. However, he’s struggled with focus and professionalism.”
“GEORGE PICKENS CLIMBS THE LADDER FOR THE TOUCHDOWN” – Ian Eagle
Cowboys Gave Up Minimal Assets for Pickens
While the biggest risk with obtaining Pickens might actually be in how he impacts team chemistry, is that really a concern for a team coming off a 7-10 season in 2024?
In black-and-white terms, the Cowboys haven’t risked much in going out to get Pickens, who could very well be a WR1 option for a lot of teams in 2026.
Pickens was a second round pick (No. 51 overall) by the Steelers out of Tennessee in the 2022 NFL draft and is in the final season of his 4-year, $6.75 million rookie contract and due just $3.656 million in 2025. While the Cowboys gave up a 2026 third round pick and 2027 fifth round pick for Pickens, they also got back a 2027 sixth round pick.
The best and most likely scenario for the Cowboys with Pickens is he plays out of his mind in 2025 and ends up as a free agent with another team on a massive deal — Spotrac projects Pickens’ market value at a 4-year, $101.54 million contract.
Pickens: Big Time Talent, Big Time Distractions
Pickens was essentially ushered out the door after the Steelers traded for Seattle Seahawks star wide receiver D.K. Metcalf on March 9 and signed him to a 4-year, $132 million contract extension the same day.
That was an understandable move. Pickens was a headache for the Steelers for almost the entire time he was with them.
In 3 seasons, Pickens has been fined a staggering 10 times by the NFL for a variety of offenses. That includes 3 times for taunting, once for making an obscene gesture and once when he wrote “OPEN (EXPLETIVE) ALWAYS” on his eye black tape against the Cowboys in 2024.
It’s behavior that has prompted Pittsburgh head coach Mike Tomlin to publicly tell Pickens he needed to “Grow Up” late in the 2024 season.
Somehow, Pickens made things worse after that when he showed up over 30 minutes late to the stadium before the Steelers’ Christmas Day game against the Kansas City Chiefs in 2024.
