15. Steve Spurrier
Dan Snyder has pulled off some major gaffes during his tenure as owner of the Redskins. Giving Spurrier the head coach job was just one of these. His five-year, $25 million deal with the Redskins was the most lucrative coaching contract in the history of the NFL at the time. So naturally, he lasted just two seasons.
A tremendous college coach, Spurrier failed to translate to the NFL. Opposition teams were able to blitz and disrupt his preferred passing game. The Redskins finished 7-9 after his first season. But instead of dropping him that summer, they let him keep going. He’d resign at the end of his second season after going 5-11. A bleak time.