Carson Wentz
The Eagles bet the house on Wentz as they traded multiple picks to secure his services in 2016. They saw him as their future franchise quarterback and believed that the sacrifice was worthwhile. It’s a tough one to gauge because they won the Super Bowl but he was on the injury list. But he did lead them towards the playoffs that season.

Wentz was on an MVP trajectory and made the Pro Bowl in 2017. But his downward spiral is one of the most notorious ever and finally, Philly dumped him. They opted to start Jalen Hurts instead of the former South Dakota star. Wentz went on a nomadic tour of the NFL as his career spiraled (via NY Post).