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relation), who had started Spy magazine, a New York imitation of the British satirical publication Private Eye. Spy was part of a set of 1980s publications—Manhattan, Inc., a relaunched Vanity Fair, and New York— obsessed with the new rich and what seemed to be a transformational moment in New York. Trump was both symbol of and punch line for this new era of excess and celebrity and the media’s celebration of those things. Graydon Carter became the editor of the New York Observer in 1991 and not only refocused the weekly on big-money culture, but essentially made it a tip-sheet for the media writing about media culture, and for members of the big-money culture who wanted to be in the media. There may never have been such a self-conscious and self-referential publication as the New York Observer. As Donald Trump, along with many others of this new-rich ilk, sought to be covered by the media—Murdoch’s New York Post was the effective court recorder of this new publicity-hungry aristocracy—the New York Observer covered the process of him being covered. The story of Trump was the story of how he tried to make himself a story. He was shameless, campy, and instructive: if you were willing to risk humiliation, the world could be yours. Trump became the objective correlative for the rising appetite for fame and notoriety. Trump came to believe he understood everything about the media—who you need to know, what pretense you need to maintain, what information you could profitably trade, what lies you might tell, what lies the media expected you to tell. And the media came to believe it knew everything about Trump—his vanities, delusions, and lies, and the levels, uncharted, to which he would stoop for ever more media attention. Graydon Carter soon used the New York Observer as his stepping-stone to Vanity Fair —where, he believed, he might have access to a higher level of celebrity than Donald Trump. Carter was followed at the Observer in 1994 by Peter Kaplan, an editor with a heightened sense of postmodern irony and ennui. Trump, in Kaplan’s telling, suddenly took on a new persona. Whereas he had before been the symbol of success and mocked for it, now he became, in a shift of zeitgeist (and of having to refinance a great deal of debt), a symbol of failure and mocked for it. This was a complicated reversal, not just having to do with Trump, but of how the media was now seeing itself. Donald Trump became a symbol of the media’s own self-loathing: the interest in and promotion of Donald Trump was a morality tale about the media. Its ultimate end was Kaplan’s pronouncement that Trump should not be covered anymore because every story about Donald Trump had become a cliché. 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 HOUSE_OVERSIGHT_019940