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Authors: Michael Wolff

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* * *

As much as it might have surprised him—for many years, he had humored Trump more than embraced him—Kushner was in fact rather like his father-in-law. Jared’s father, Charlie, bore an eerie resemblance to Donald’s father, Fred. Both men dominated their children, and they did this so completely that their children, despite their demands, became devoted to them. In both instances, this was extreme stuff: belligerent, uncompromising, ruthless men creating long-suffering offspring who were driven to achieve their father’s approval. (Trump’s older brother, Freddy, failing in this effort, and, by many reports, gay, drank himself to death; he died in 1981 at age forty-three.) In business meetings, observers would be nonplussed that Charlie and Jared Kushner invariably greeted each other with a kiss and that the adult Jared called his father Daddy.

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.

Media is personal. It is a series of blood scores. The media in its often collective mind decides who is going to rise and who is going to fall, who lives and who dies. If you stay around long enough in the media eye, your fate, like that of a banana republic despot, is often an unkind one—a law Hillary Clinton was not able to circumvent. The media has the last word.

Long before he ran for president, Trump and his sidekick son-in-law Kushner had been marked not just for ignominy, but for slow torture by ridicule, contempt, and ever-more amusing persiflage. These people are nothing. They are media debris. For goodness’ sake!

Trump, in a smart move, picked up his media reputation and relocated it from a hypercritical New York to a more value-free Hollywood, becoming the star of his own reality show,
The Apprentice
, and embracing a theory that would serve him well during his presidential campaign: in flyover country, there is no greater asset than celebrity. To be famous is to be loved—or at least fawned over.

The fabulous, incomprehensible irony that the Trump family had, despite the media’s distaste, despite everything the media knows and understands and has said about them, risen to a level not only of ultimate consequence but even of immortality is beyond worst-case nightmare and into cosmic-joke territory. In this infuriating circumstance, Trump and his son-in-law were united, always aware and yet never quite understanding why they should be the butt of a media joke, and now the target of its stunned outrage.

* * *

The fact that Trump and his son-in-law had many things in common did not mean they operated on a common playing field. Kushner, no matter how close to Trump, was yet a member of the Trump entourage, with no more ultimate control of his father-in-law than anybody else now in the business of trying to control Trump.

Still, the difficulty of controlling him had been part of Kushner’s self-justification or rationalization for stepping beyond his family role and taking a senior White House job: to exercise restraint on his father-in-law and even—a considerable stretch for the inexperienced young man—to help lend him some gravitas.

If Bannon was going to pursue as his first signature White House statement the travel ban, then Kushner was going to pursue as his first leadership mark a meeting with the Mexican president, whom his father-in-law had threatened and insulted throughout the campaign.

Kushner called up the ninety-three-year-old Kissinger for advice. This was both to flatter the old man and to be able to drop his name, but it was also actually for real advice. Trump had done nothing but cause problems for the Mexican president. To bring the Mexican president to the White House would be, despite Bannon’s no-pivot policy from the campaign’s harshness, a truly meaningful pivot for which Kushner would be able to claim credit (although don’t call it a pivot). It was what Kushner believed he should be doing: quietly following behind the president and with added nuance and subtlety clarifying the president’s real intentions, if not recasting them entirely.

The negotiation to bring Mexican president Enrique Peña Nieto to the White House had begun during the transition period. Kushner saw the chance to convert the issue of the wall into a bilateral agreement addressing immigration—hence a tour de force of Trumpian politics. The negotiations surrounding the visit reached their apogee on the Wednesday after the inaugural, with a high-level Mexican delegation—the first visit by any foreign leader to the Trump White House—meeting with Kushner and Reince Priebus. Kushner’s message to his father-in-law that afternoon was that Peña Nieto had signed on to a White House meeting and planning for the visit could go forward.

The next day Trump tweeted: “The U.S. has a 60 billion dollar trade deficit with Mexico. It has been a one-sided deal from the beginning of NAFTA with massive numbers . . .” And he continued in the next tweet . . . “of jobs and companies lost. If Mexico is unwilling to pay for the badly needed wall, then it would be better to cancel the upcoming meeting . . .”

At which point Peña Nieto did just that, leaving Kushner’s negotiation and statecraft as so much scrap on the floor.

* * *

On Friday, February 3, at breakfast at the Four Seasons hotel in Georgetown, an epicenter of the swamp, Ivanka Trump, flustered, came down the stairs and entered the dining room, talking loudly on her cell phone: “Things are so messed up and I don’t know how to fix it. . . .”

The week had been overwhelmed by continuing fallout from the immigration order—the administration was in court and headed to a brutal ruling against it—and more embarrassing leaks of two theoretically make-nice phone calls, one with the Mexican president (“bad hombres”) and the other with the Australian prime minister (“my worst call by far”). What’s more, the day before, Nordstrom had announced that it was dropping Ivanka Trump’s clothing line.

The thirty-five-year-old was a harried figure, a businesswoman who had had to abruptly shift control of her business. She was also quite overwhelmed by the effort of having just moved her three children into a new house in a new city—and having to do this largely on her own. Asked how his children were adjusting to their new school several weeks after the move, Jared said that yes, they were indeed in school—but he could not immediately identify where.

Still, in another sense, Ivanka was landing on her feet. Breakfast at the Four Seasons was a natural place for her. She was among everyone who was anyone. In the restaurant that morning: House Minority Leader Nancy Pelosi; Blackstone CEO Stephen Schwarzman; Washington fixture, lobbyist, and Clinton confidant Vernon Jordan; labor secretary nominee Wilbur Ross; Bloomberg Media CEO Justin Smith;
Washington Post
national reporter Mark Berman; and a table full of women lobbyists and fixers, including the music industry’s longtime representative in Washington, Hillary Rosen; Elon Musk’s D.C. adviser, Juleanna Glover; Uber’s political and policy executive, Niki Christoff; and Time Warner’s political affairs executive, Carol Melton.

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