Neither Donald nor Jared, no matter their domineering fathers, went into the world with humility. Insecurity was soothed by entitlement. Both out-of-towners who were eager to prove themselves or lay rightful claim in Manhattan (Kushner from New Jersey, Trump from Queens), they were largely seen as overweening, smug, and arrogant. Each cultivated a smooth affect, which could appear more comical than graceful. Neither, by choice nor awareness, could seem to escape his privilege. “Some people who are very privileged are aware of it and put it away; Kushner not only seemed in every gesture and word to emphasize his privilege, but also not to be aware of it,” said one New York media executive who dealt with Kushner. Both men were never out of their circle of privilege. The main challenge they set for themselves was to enter further into the privileged circle. Social climbing was their work.
Jared’s focus was often on older men. Rupert Murdoch spent a surprising amount of time with Jared, who sought advice from the older media mogul about the media business—which the young man was determined to break into. Kushner paid long court to Ronald Perelman, the billionaire financier and takeover artist, who later would host Jared and Ivanka in his private shul on Jewish high holy days. And, of course, Kushner wooed Trump himself, who became a fan of the young man and was uncharacteristically tolerant about his daughter’s conversion to Orthodox Judaism when that became a necessary next step toward marriage. Likewise, Trump as a young man had carefully cultivated a set of older mentors, including Roy Cohn, the flamboyant lawyer and fixer who had served as right-hand man to the red-baiting Senator Joe McCarthy.
And then there was the harsh fact that the world of Manhattan and particular its living voice, the media, seemed to cruelly reject them. The media long ago turned on Donald Trump as a wannabe and lightweight, and wrote him off for that ultimate sin—anyway, the ultimate sin in media terms—of trying to curry favor with the media too much. His fame, such as it was, was actually reverse fame—he was famous for being infamous. It was joke fame.
To understand the media snub, and its many levels of irony, there is no better place to look than the New York Observer, the Manhattan media and society weekly that Kushner bought in 2006 for $10 million—by almost every estimate $10 million more than it was worth.
* * *
The New York Observer was, when it launched in 1987, a rich man’s fancy, as much failed media often is. It was a bland weekly chronicle of the Upper East Side, New York’s wealthiest neighborhood. Its conceit was to treat this neighborhood like a small town. But nobody took any notice. Its frustrated patron, Arthur Carter, who made his money in the first generation of Wall Street consolidations, was introduced to Graydon Carter (no 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 him at face value, became a moral stand.
In 2006, after Kaplan had edited the paper for fifteen years, Arthur Carter sold the Observer—which had never made a profit—to the then twenty-five-year-old Kushner, an unknown real estate heir interested in gaining stature and notoriety in the city. Kaplan was now working for someone twenty-five years his junior, a man who, ironically, was just the kind of arriviste he would otherwise have covered.
For Kushner, owning the paper soon paid off, because, with infinite ironies not necessarily apparent to him, it allowed him into the social circle where he met Donald Trump’s daughter, Ivanka, whom he married in 2009. But the paper did not, irksomely for Kushner, pay off financially, which put him into increasing tension with Kaplan. Kaplan, in turn, began telling witty and devastating tales about the pretensions and callowness of his new boss, which spread, in constant retelling, among his many media protégés and hence throughout the media itself.
In 2009, Kaplan left the paper, and Kushner—making a mistake that many rich men who have bought vanity media properties are prone to making—tried to find a profit by cutting costs. In short order, the media world came to regard Kushner as the man who not only took Peter Kaplan’s paper from him, but also ruined it, brutally and incompetently. And worse: in 2013, Kaplan, at fifty-nine, died of cancer. So, effectively, in the telling, Kushner had killed him, too.