10. Tom Thibodeau
After a nine-year run that saw the Bulls win six championships under Phil Jackson, the franchise decided it was time to make a change and move on. Chicago's brass knew there would be a bit of a regression, but they deemed it necessary to rebuild and start over, in hopes of getting back to the same dominance they had throughout the 90s.
However, they remained in this state for over a decade, as rebuilds aren't guaranteed to work in your favor. The Bulls won 60 games in three consecutive seasons under Jackson, only to go 12 seasons without even winning 50 games.
In came Tom Thibodeau, who guided Chicago to a 62-20 record in his first season at the helm. And it wasn't a fluke either, as Chicago won 50 games in two of the next four seasons.
Thibs nabbed Coach of the Year off the bat and guided the Bulls to the Conference Finals for the first time since 1997-98. However, he created dysfunction with the front office and made no secret for his disdain towards his bosses.
He also ran his players into the ground, which surely played a part in some of the Bulls' injury woes and postseason letdowns. To the point where he was unapologetic about his approach and too stubborn to change it, despite having glaring evidence of a need for change.