Baltimore Ravens
The Ravens are in an interesting position because they’ve only had two coaches since 2000. Furthermore, both of these men won Super Bowl glory for Baltimore. However, John Harbaugh’s longevity earns him the top spot. In 2005, he masterminded a victory over his brother, Jim. Also, he has the most wins of any Ravens coach in franchise history.

Bizarrely, this means we’re calling Brian Billick their worst coach since 2000. The team had a phenomenal defense and held the Giants to 152 yards of offense in Super Bowl XXXV. Billick’s team also won the first Vince Lombardi Trophy of the new millennium. Baltimore fans adore him because he brought greatness to Maryland (via Baltimore Ravens). But a worst coach had to be named, so he was the only option left.