Chicago Bulls
In the ’90s, this would be the most ridiculous inclusion ever. But the team went into meltdown in the 2000s after Jordan’s departure and the end of that era. They thought that they had the next big thing in basketball when they drafted Derrick Rose. However, that didn’t change their downward spiral.

Then they suffered because of their horrific front office situation. Jerry Krause broke up a winning team. Meanwhile, Jim Boylen went 39-84 as head coach. But they shouldn’t have allowed him to get that far. Finally, 2020 signaled a culture shift with the firing of GM Gar Forman (via The Ringer).