19. DeSean Jackson (2014)
Nobody quite knows what Chip Kelly was thinking. In fact, Kelly probably doesn’t know either. But he chased one of the Eagles’ best players out of the franchise in Jackson. He also got rid of LeSean McCoy and Jeremy Maclin. Jackson told the Philly Voice that they had the potential to be Super Bowl champions but Kelly ruined their chances.
After the Eagles released him, he joined Washington on a lucrative three-year deal. After he completed his contract, he went on a bit of a tour of the league before finally joining the Rams in 2021. A three-time Pro Bowler, Jackson showed Kelly what he was missing. Not only did he allow great players to leave, but he didn’t restock the roster.