An important aspect of Kaplan's New York Observer and its self-conscious inside media baseball was that the paper became the prime school for a new generation of media reporters flooding every other publication in New York as journalism itself became ever more self-conscious and self-referential. To everyone working in media in New York, Donald Trump represented the ultimate shame of working in media in New York: you might have to write about Donald Trump. Not writing about him, or certainly not taking him at face value, became a moral stand.