The Crazy Eights are expelled from Stoolbend High School when Principal Wally declares them the worst kids in school in "Our Gang". Cleveland takes them under his wing and tries to teach them responsibility by forming a cookie-making business (Similar to the organization Junior Achievement) but they misunderstand his intent and sell drugs.
Cleveland Jr. is also inducted into the gang by Cleveland as a 'legacy'. A ninth expelled student, 'Nazi Greg' missed the activities due to attending a funeral for his grandmother. Cleveland's nickname in the gang is C-Bro.