Diddy Owes New York City $1 Million For Illegal Posters. Diddy loves New York City, but this time around New York City isn’t showing him the love back. The famed rapper and entrepreneur owes his hometown almost $1 million for illegally putting up promotional posters throughout Manhattan. Better known as Sean Combs, the hip hop star isn’t alone in his legal mess with the Big Apple. The New York Daily News reports that celebrities such as Doug E. Fresh, Mickey Rourke’s plastic surgeon and rapper Remy Ma’s defense lawyer are all in deep trouble as well for advertising their promotional work illegally in the city. According to Digital Spy, the city’s finance commissioner David Frankel says: “We are going to find these people. We’re going to turn them upside down by their ankles and we’re going to shake them until the money comes out of their pockets.” Combs has so far not commented over the fine.