Some may think of Pickens' personality as a bit of a concern, especially after he was traded following three seasons with the Steelers. However, ESPN insider Peter Schrager is reporting that Pickens' personality is not an issue.

The Cowboys looked to replace Hall of Fame quarterback Troy Aikman’s top target after Michael Irvin sustained a career-ending spinal cord injury against Philadelphia in 1999. Dallas acquired Seattle Seahawks receiver Joey Galloway for two first-round picks and signed him to a seven-year, $42 million contract.

Before the 2025 NFL Draft, the czar of the Dallas Cowboys noted that he had a couple of irons in the fire with "two pretty substantive trades" in the works. One of those has since come to fruition with Dallas executing a deal to acquire wide receiver George Pickens from the Pittsburgh Steelers.