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.
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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 him an infusion of $5 million. When Mercer and his daughter Rebekah presented their plan to take over the campaign and install their lieutenants, Steve Bannon and Conway, Trump didn’t resist. He only expressed vast incomprehension about why anyone would want to do that. “This thing,” he told the Mercers, “is so fucked up.”
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.
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