What happened: Former Pittsburgh Steelers quarterback Kenny Pickett desperately wanted out of Philadelphia during the 2025 offseason. According to his former college coach, Pickett pleaded with the front office for a deal because he wanted to compete and knew he would not unseat Jalen Hurts.

Why it matters: The decision ultimately backfired and damaged his career stability. After failing to win the starting job for the Cleveland Browns over Joe Flacco, he was dealt to the Las Vegas Raiders and eventually landed with the Carolina Panthers in free agency.