19. Mike Riley
There really isn’t anything good about Riley’s NFL head coach career. The kindest thing that you could say about his three years with the San Diego Chargers is that he was unlucky. Often they did, in fact, perform well, but one poor play would turn the tide against them, like in their 2001 loss to the Seahawks.
After an 8-8 record in his first season, there was hope for Riley. But he proceeded to stick a pin in that balloon of cautious optimism the next year. Then the Chargers went 1-15, the worst record in franchise history. Somehow he survived Black Monday, although we don’t know why. Things didn’t improve in his third year and the Chargers finally fired him after he outlasted his welcome.