Chicago Bears
Boomer Esiason said that Chicago is where quarterbacks ‘go to die.’ This sums up the team’s lack of success over the past couple of decades. Lovie Smith was their most successful coach in this period as he guided them to a Super Bowl appearance. He also left the franchise with a winning percentage of .563.

Meanwhile, there are several candidates for the worst coach in modern Bears’ history. But we’ve chosen Marc Trestmann because the franchise went nowhere during his tenure. They endured terrible losses including a 55-14 humiliation against the Packers. The Grey Cup maestro failed to hack it in the NFL.