Amari Cooper
Cooper enjoyed two successful seasons with the Raiders before things began to fall apart. Nobody expected him to leave the franchise after a pair of Pro Bowl seasons. But then Jon Gruden landed in Oakland and Cooper’s on-field relationship with Derek Carr fell apart. They were both good players but they didn’t sync with each other anymore.

That’s why the Raiders agreed to trade Cooper to Dallas in one of the biggest deals of the past decade. Jerry Jones handed the Raiders their first-round pick on a platter for the proven starter. Cooper enjoyed Pro Bowl form in his first two seasons but left for the Browns in 2022 (via the Guardian).