5. Randy Wittman
How did Wittman keep getting jobs in the NBA? For some reason, franchises kept hiring him despite his shambolic overall record. The Cavaliers and Timberwolves were decent when he took over. But then he ran them into the ground despite exciting young players and playoff form.

Somehow he got another job despite a then-overall record of 100-207. The Wizards hired him and he somehow managed to swing four years out of them. They made the playoffs twice but in his final season missed out. That was enough for the Wizards to cast him out on the street.