Many candidates for president have made a virtue of being Washington outsiders; in practice, this strategy merely favors governors over senators. Every serious candidate, no matter how much he or she disses Washington, relies on Beltway insiders for counsel and support. But with Trump, hardly a person in his innermost circle had ever worked in politics at the national level—his closest advisers had not worked in politics at all. Throughout his life, Trump had few close friends of any kind, but when he began his campaign for president he had almost no friends in politics. The only two actual politicians with whom Trump was close were Rudy Giuliani and Chris Christie, and both men were in their own way peculiar and isolated. And to say that he knew nothing—nothing at all—about the basic intellectual foundations of the job was a comic understatement. Early in the campaign, in a Producers-worthy scene, Sam Nunberg was sent to explain the Constitution to the candidate: “I got as far as the Fourth Amendment before his finger is pulling down on his lip and his eyes are rolling back in his head.”
Almost everybody on the Trump team came with the kind of messy conflicts bound to bite a president or his staff. Mike Flynn, Trump’s future National Security Advisor, who became Trump’s opening act at campaign rallies and whom Trump loved to hear complain about the CIA and the haplessness of American spies, had been told by his friends that it had not been a good idea to take $45,000 from the Russians for a speech. “Well, it would only be a problem if we won,” he assured them, knowing that it would therefore not be a problem.
Paul Manafort, the international lobbyist and political operative who Trump retained to run his campaign after Lewandowski was fired—and who agreed not to take a fee, amping up questions of quid pro quo—had spent thirty years representing dictators and corrupt despots, amassing millions of dollars in a money trail that had long caught the eye of U.S. investigators. What’s more, when he joined the campaign, he was being pursued, his every financial step documented, by the billionaire Russian oligarch Oleg Deripaska, who claimed he stole $17 million from him in a crooked real estate scam.
For quite obvious reasons, no president before Trump and few politicians ever have come out of the real estate business: a lightly regulated market, based on substantial debt with exposure to frequent market fluctuations, it often depends on government favor, and is a preferred exchange currency for problem cash—money laundering. Trump’s son-in-law Jared Kushner, Jared’s father Charlie, Trump’s sons Don Jr. and Eric, and his daughter Ivanka, as well as Trump himself, all supported their business enterprises to a greater or lesser extent working in the dubious limbo of international free cash flow and gray money. Charlie Kushner, to whose real estate business interests Trump’s son-in-law and most important aide was wholly tied, had already spent time in a federal prison for tax evasion, witness tampering, and making illegal campaign donations.
Modern politicians and their staffs perform their most consequential piece of opposition research on themselves. If the Trump team had vetted their candidate, they would have reasonably concluded that heightened ethical scrutiny could easily put them in jeopardy. But Trump pointedly performed no such effort. Roger Stone, Trump’s longtime political adviser, explained to Steve Bannon that Trump’s psychic makeup made it impossible for him to take such a close look at himself. Nor could he tolerate knowing that somebody else would then know a lot about him—and therefore have something over him. And anyway, why take such a close and potentially threatening look, because what were the chances of winning?
Not only did Trump disregard the potential conflicts of his business deals and real estate holdings, he audaciously refused to release his tax returns. Why should he if he wasn’t going to win?
What’s more, Trump refused to spend any time considering, however hypothetically, transition matters, saying it was “bad luck”—but really meaning it was a waste of time. Nor would he even remotely contemplate the issue of his holdings and conflicts.
He wasn’t going to win! Or losing was winning.
Trump would be the most famous man in the world—a martyr to crooked Hillary Clinton.
His daughter Ivanka and son-in-law Jared would have transformed themselves from relatively obscure rich kids into international celebrities and brand ambassadors.
Steve Bannon would become the de facto head of the Tea Party movement.
Kellyanne Conway would be a cable news star.
Reince Priebus and Katie Walsh would get their Republican Party back.
Melania Trump could return to inconspicuously lunching.
That was the trouble-free outcome they awaited on November 8, 2016. Losing would work out for everybody.
Shortly after eight o’clock that evening, when the unexpected trend—Trump might actually win—seemed confirmed, Don Jr. told a friend that his father, or DJT, as he called him, looked as if he had seen a ghost. Melania, to whom Donald Trump had made his solemn guarantee, was in tears—and not of joy.
There was, in the space of little more than an hour, in Steve Bannon’s not unamused observation, a befuddled Trump morphing into a disbelieving Trump and then into a quite horrified Trump. But still to come was the final transformation: suddenly, Donald Trump became a man who believed that he deserved to be and was wholly capable of being the president of the United States.
2
TRUMP TOWER
On the Saturday after the election, Donald Trump received a small group of well-wishers in his triplex apartment in Trump Tower. Even his close friends were still shocked and bewildered, and there was a dazed quality to the gathering. But Trump himself was mostly looking at the clock.
Rupert Murdoch, heretofore doubtlessly certain Trump was a charlatan and a fool, said he and his new wife, Jerry Hall, would pay a call on the president-elect. But Murdoch was late—quite late. Trump kept assuring his guests that Rupert was on his way, coming soon. When some of the guests made a move to leave, Trump cajoled them to stay a little longer. You’ll want to stay to see Rupert. (Or, one of the guests interpreted, you’ll want to stay to see Trump with Rupert.)
Murdoch, who, with his then wife, Wendi, had often socialized with Jared and Ivanka, in the past made little effort to hide his lack of interest in Trump. Murdoch’s fondness for Kushner created a curious piece of the power dynamic between Trump and his son-in-law, one that Kushner, with reasonable subtly, played to his advantage, often dropping Murdoch’s name into conversations with his father-in-law. When, in 2015, Ivanka Trump told Murdoch that her father really, truly was going to run for president, Murdoch dismissed the possibility out of hand.
But now, the new president-elect—after the most astonishing upset in American history—was on tenterhooks waiting for Murdoch. “He’s one of the greats,” he told his guests, becoming more agitated as he waited. “Really, he’s one of the greats, the last of the greats. You have to stay to see him.”
It was a matched set of odd reversals—an ironic symmetry. Trump, perhaps not yet appreciating the difference between becoming president and elevating his social standing, was trying mightily to curry favor with the previously disdainful media mogul. And Murdoch, finally arriving at the party he was in more than one way sorely late to, was as subdued and thrown as everyone else, and struggling to adjust his view of a man who, for more than a generation, had been at best a clown prince among the rich and famous.
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Murdoch was hardly the only billionaire who had been dismissive of Trump. In the years before the election, Carl Icahn, whose friendship Trump often cited, and who Trump had suggested he’d appoint to high office, openly ridiculed his fellow billionaire (whom he said was not remotely a billionaire).