On the afternoon of November 8, 2016, Kellyanne Conway settled into her glass office at Trump Tower. Right up until the last weeks of the race, the campaign headquarters had remained a listless place. All that seemed to distinguish it from a corporate back office were a few posters with right-wing slogans.
Conway, the campaign’s manager, was in a remarkably buoyant mood, considering she was about to experience a resounding, if not cataclysmic, defeat. Donald Trump would lose the election — of this she was sure — but he would quite possibly hold the defeat to under six points. That was a substantial victory. As for the looming defeat itself, she shrugged it off: It was Reince Priebus’s fault, not hers.
She had spent a good part of the day calling friends and allies in the political world and blaming Priebus, the chairman of the Republican National Committee. Now she briefed some of the television producers and anchors whom she had been carefully courting since joining the Trump campaign — and with whom she had been actively interviewing in the last few weeks, hoping to land a permanent on-air job after the election.
Even though the numbers in a few key states had appeared to be changing to Trump’s advantage, neither Conway nor Trump himself nor his son-in-law, Jared Kushner — the effective head of the campaign — wavered in their certainty: Their unexpected adventure would soon be over. Not only would Trump not be president, almost everyone in the campaign agreed, he should probably not be. Conveniently, the former conviction meant nobody had to deal with the latter issue.
As the campaign came to an end, Trump himself was sanguine. His ultimate goal, after all, had never been to win. “I can be the most famous man in the world,” he had told his aide Sam Nunberg at the outset of the race. His longtime friend Roger Ailes, the former head of Fox News, liked to say that if you want a career in television, first run for president. Now Trump, encouraged by Ailes, was floating rumors about a Trump network. It was a great future. He would come out of this campaign, Trump assured Ailes, with a far more powerful brand and untold opportunities.
“This is bigger than I ever dreamed of,” he told Ailes a week before the election. “I don’t think about losing, because it isn’t losing. We’ve totally won.”
From the start, the leitmotif for Trump about his own campaign was how crappy it was, and how everybody involved in it was a loser. In August, when he was trailing Hillary Clinton by more than 12 points, he couldn’t conjure even a far-fetched scenario for achieving an electoral victory. He was baffled when the right-wing billionaire Robert Mercer, a Ted Cruz backer whom Trump barely knew, offered Trump’s campaign an infusion of $5 million. Trump didn’t turn down the help—he just expressed vast incomprehension about why anyone would want to do that. “This thing,” he told Mercer, “is so fucked up.”
Steve Bannon, who became chief executive of Trump’s team in mid-August, called it “the broke-dick campaign.” Almost immediately, he saw that it was hampered by an even deeper structural flaw: The candidate who billed himself as a billionaire — ten times over — refused to invest his own money in it. Bannon told Kushner that, after the first debate in September, they would need another $50 million to cover them until Election Day.
“No way we’ll get 50 million unless we can guarantee him victory,” said a clear-eyed Kushner.
“Twenty-five million?” prodded Bannon.
“If we can say victory is more than likely.”
In the end, the best Trump would do is to loan the campaign
$10 million, provided he got it back as soon as they could raise other money. Steve Mnuchin, the campaign’s finance chairman, came to collect the loan with the wire instructions ready to go so Trump couldn’t conveniently forget to send the money.
Most presidential candidates spend their entire careers, if not their lives from adolescence, preparing for the role. They rise up the ladder of elected offices, perfect a public face, and prepare themselves to win and to govern. The Trump calculation, quite a conscious one, was different. The candidate and his top lieutenants believed they could get all the benefits of almost becoming president without having to change their behavior or their worldview one whit. Almost everybody on the Trump team, in fact, came with the kind of messy conflicts bound to bite a president once he was in office. Michael Flynn, the retired general who served as Trump’s opening act at campaign rallies, 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,” Flynn assured them.
Not only did Trump disregard the potential conflicts of his own business deals and real-estate holdings, he audaciously refused to release his tax returns. Why should he? Once he lost, Trump would be both insanely famous and a martyr to Crooked Hillary. His daughter Ivanka and son-in-law Jared would be international celebrities. Steve Bannon would become the de facto head of the tea-party movement. Kellyanne Conway would be a cable-news star. Melania Trump, who had been assured by her husband that he wouldn’t become president, could return to inconspicuously lunching. Losing would work out for everybody. Losing was winning.
Shortly after 8 p.m. on Election Night, when the unexpected trend — Trump might actually win — seemed confirmed, Don Jr. told a friend that his father, or DJT, as he calls him, looked as if he had seen a ghost. Melania 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 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.