Prescott has led the Cowboys to the postseason on five different occasions in his career, but they haven't come close to the game's biggest stage. Their last playoff berth was in 2023, when they were eliminated by the Green Bay Packers in round one.

When the Dallas Cowboys traded for George Pickens of the Pittsburgh Steelers, questions arose about what he’d look like on the field. Pickens is one of the top wide receivers in the NFL, but his issues, both on and off the field, are certainly concerning.