4. jon gruden
The Raiders looked like they were probably going to get things turned around and have a legitimate shot at the playoffs that didn’t involved tiebreaker alchemy. They were 6-4 heading into Week 11, but took it on the chin 34-3 at the New York Jets and never recovered, finishing 7-9 on the year.
Fun fact: since Gruden won Super Bowl XXXVII with Tampa Bay, he’s not won a playoff game.