By the time Monopoly stopped serving as his manager, West had racked up 10 Grammys and sold millions of records. Monopoly had his own impressive achievements- he ran G.O.O.D. Records, had his own nightclub in Chicago and could call many of the top rappers in the world his friends.
Now Monopoly is trying to break the next generation of Chicago hip-hop stars. His new label Lawless, Inc is pushing the career of rapper King Louie and his southern-influenced street rap. Louie and his contemporaries have a less enlightened take than the conscious lyrics of the previous generation of Chicago rappers. It's drawn some criticism from the older generation, including one of West's old collaborators, Rhymefest.
We ask John Monopoly about the changing of the guard in Chicago hip-hop on Wednesday's Afternoon Shift.