Trump won because he intuited that his celebrity would protect him from the far stricter standards to which politicians are normally held—one bad gaffe and you’re finished. He won because he understood that his outrageous behavior and intemperate comments only cemented his reputation as a decisive truth-teller who gets things done. And he won because he had spent almost forty years cultivating an image as a guy who was so rich, so audacious, and so unpredictable that he would be beholden to no one. People in much of the country believed that he really had the personal authority to make America great again, that he could actually “lock her up,” and that he would, as his campaign’s TV ad put it, “turn Washington upside down: day one.”
Trump ran against a barrage of accusations that he’d groped women, a near-daily drumbeat of stories about his boorish behavior and nasty insults, and he won there, too. In October 2016, on the day after the Washington Post revealed a video in which Trump explained to TV host Billy Bush how he would grab women by the crotch, a Trump supporter in Syracuse, New York, Shannon Barns, said that the video had only deepened her belief that he should be president. “This just put a human face on the guy for me,” she said. “I was worried that he was a billionaire and didn’t know about the lives of people like me. This showed me that he’s a man. You know in your heart every man talks like that.” Trump called himself a “blue-collar billionaire,” and he believed that he had so completely won the hearts of many Americans that, as he said, “I could stand in the middle of Fifth Avenue and shoot somebody, and I wouldn’t lose voters.”
Trump had spent his entire adult life pushing back against those who considered him an ostentatious boor or a bombastic show horse. The big real estate developer families in New York had long sneered at Trump as a brash, nasty, nouveau riche intruder on a business that cherished quiet diplomacy. The banks had treated him like an out-of-control adolescent who needed to be reined in and taught a lesson. When he announced his candidacy for president, other politicians humored him, then grew frightened; some renounced him, but many scrambled to be by his side to catch some of his reflected fame. Trump beat them all back, again and again, by appealing to the people, his customers, his admirers. Whether he was succeeding at building skyscrapers and casinos, or failing by going through six corporate bankruptcies, he turned again and again to show business and the media he had often condemned to make his case to regular Americans. In the campaign, Trump capitalized on his years of appearances on network sitcoms and WrestleMania and his fourteen-season run on The Apprentice. Newspapers and websites reported every day on his wayward behavior with women, his business troubles, his wild hyperbole, his insulting remarks. Still, many middle- and working-class Americans saw him as the straight-shooting billionaire who had the bucks and the brass to stand up to anyone.
From the moment he rode down the escalator of Trump Tower to his beloved pink marble lobby in the summer of 2015, Trump claimed that his path to victory was elementary. He would simply connect directly to the pains, fears, and frustrations of a nation that had been smacked around by globalization, terrorism, rapid demographic change, and a technological revolution that enriched and enraptured the kids with the stratospheric SAT scores, but left millions of Americans behind, their jobs lost to the latest apps, overseas outsourcing, robots, and a wholesale shift in the nature of commerce and community. He had blown through the primaries, swept aside the stars of the Republican Party’s next generation, and triumphed at the convention. To get past the debates, the metastasizing news coverage, and a voting public that was paying attention as perhaps never before, Trump needed to cement that connection with people far beyond those who came to his rallies. To get to the finish line and shock the elites, he needed to find the right balance between self-control and unpredictability. He needed to make Clinton’s deficits a bigger story than his own flaws. And he needed a little bit of luck. He got it all.
• • •
ON JULY 5, TRUMP and press secretary Hope Hicks were meeting at Trump Tower with Steven Ginsberg, the senior politics editor at the Washington Post, when FBI director James Comey came on TV to announce news about his investigation into Clinton’s use of a private email server rather than the legally mandated government technology. Trump, Hicks, and Ginsberg, joined by Ivanka and her husband, Jared Kushner, tucked into a nook outside Trump’s office to watch the news conference. Although Comey said Clinton didn’t violate laws governing the handling of classified information, he added that she had been “extremely careless” in handling “very sensitive, highly classified information.”
“This is big,” Trump said to the group in the nook. “Don’t you think this is big?” Even without an indictment, Trump recognized, this was a welcome serving of raw meat. He conjured his sound bite on the spot: if Clinton couldn’t keep her emails safe, she can’t keep the country safe. He would repeat the slogan at every rally, nearly every day, and the response from the crowds would grow louder and lustier as the fall campaign built: “Lock her up! Lock her up!”
Trump had relished the idea of running against Clinton, whom he saw as feisty and strong, but incapable of connecting with middle-class voters and beholden to exactly the power bases he planned to run against. He successfully took Clinton’s decades-long reputation as a shape-shifting politician who used excessively legalistic language and a deeply guarded public persona, and he twisted it into a searing, angry portrait of an outright criminal—“Crooked Hillary.”
• • •
IN MID-AUGUST, KELLYANNE CONWAY was on her treadmill at her New Jersey home, watching CNBC’s Squawk Box, when Trump called into the show. Conway, a pollster known for her sharp, biting bouts on cable news political panels, was about to start work as Trump’s third and final campaign manager, and she couldn’t believe what she was hearing. Trump was mired in yet another controversy, trying to explain why he had attacked the parents of Humayun Khan, a U.S. soldier killed in 2004 in the Iraq War. The soldier’s father, Khizr Khan, had stirred the Democratic National Convention with an emotional speech, waving his pocket copy of the Constitution at Trump and reminding the prime-time TV audience that soldiers of “all faiths, genders, and ethnicities” had given their lives for the United States, while Trump had “sacrificed nothing and no one.” Trump’s response to Khan’s address instantly became the stuff of Clinton attack ads: “I’ve made a lot of sacrifices,” he said, and he questioned the Khan family’s motives. Now, on CNBC, Trump refused to ease off his attack on the Gold Star family. Had he made a mistake? Trump pushed back: “You’ll have to define what a mistake means.” But Trump recognized the damage he’d done. If he lost the election, he said, “It’s okay. I go back to a very good way of life. It’s not what I’m looking to do. I think we’re going to have a victory, but we’ll see.”
When Conway saw Trump, she lit into him. “You can’t say what you just said on CNBC,” she told her new boss. “You know, ‘If I lose, it’s okay.’ It’s not okay. And it’s not okay because a lot of people out there feel like if you don’t win, they don’t win. . . . What life are they going back to? What skyscrapers are they building? What fancy vacation are they taking?”
• • •
DAVID FAHRENTHOLD HAD BEEN curious about Trump’s charitable foundation ever since the beginning of the year, when the Washington Post reporter discovered that the candidate hadn’t delivered on his promise to give away $1 million of his own money to veterans’ causes. Fahrenthold’s reporting led Trump to donate the money, but the reporter kept digging into Trump’s small charity. He uncovered a series of apparent violations of the law by the Donald J. Trump Foundation. In September, Fahrenthold found that Trump had paid the IRS a $2,500 penalty for an illegal gift the foundation had made in 2013.
Week after week, Fahrenthold uncovered other Trump Foundation actions that seemed to be improper. Trump spent $20,000 of foundation money to buy a six-foot-tall portrait of himself in 2007, and $10,000 to buy a four-foot portrait of himself in 2014. Federal law prohibits charity lea
ders like Trump, the foundation’s president, from using the charity’s money to buy things for themselves or their businesses. Fahrenthold didn’t find the six-foot painting, but he found the four-foot portrait hanging on the wall of a sports bar at Trump’s Doral golf course, outside Miami. Trump’s campaign said the bar was doing the Trump Foundation a favor by “storing” the painting on its wall. When Fahrenthold relayed that explanation to a tax expert, he said, “It’s hard to make an IRS auditor laugh, but this would do it.”
In response to Fahrenthold’s stories, the New York attorney general opened an investigation into the Trump Foundation. Then, in early October, Fahrenthold reported that the Trump Foundation had been soliciting donations without obtaining the required New York State license. The next day, the state attorney general ordered the foundation to cease all fund-raising. The Trump campaign questioned the attorney general’s “political motives,” but said the foundation would cooperate with the investigation.
Then, on October 9, Fahrenthold got a call from a source. This was not about taxes, not about charity. Instead, the source provided a copy of a videotape shot eleven years earlier, during Trump’s visit to a Hollywood backlot to film a cameo appearance on the Days of Our Lives TV soap. Trump was being shadowed by a crew from Access Hollywood, and the show had recorded their conversation. In the first minute of the tape, Trump and the show’s host, Billy Bush, are together inside the Access Hollywood bus, wearing hot microphones, having an extremely lewd conversation. Trump told Bush about his efforts to seduce a married woman: “I moved on her, and I failed. I’ll admit it. . . . I did try and fuck her. She was married.” The tape was recorded several months after Trump married his third wife, Melania.
Later in the tape, as the two men prepared to meet a soap-opera actress on the studio lot, Trump confided to Bush that “I’ve got to use some Tic Tacs, just in case I start kissing her. You know, I’m automatically attracted to beautiful— I just start kissing them. It’s like a magnet. Just kiss. I don’t even wait. . . . And when you’re a star, they let you do it. You can do anything.”
Bush egged him on: “Whatever you want.”
“Grab them by the pussy,” Trump said. “You can do anything.”
The Post got the tape shortly after 11:00 a.m. Fahrenthold sent a transcript of the lewdest parts of the tape to the campaign, seeking a comment. Trump and his senior aides—including Conway, New Jersey governor Chris Christie, Republican National Committee chairman Reince Priebus, campaign chief executive Stephen Bannon, and deputy campaign manager David Bossie—were on the twenty-fifth floor of Trump Tower, preparing for the first debate, when Fahrenthold’s request arrived. Bossie looked at his phone and saw a message. “We have a problem,” it said. He gave his phone to Bannon, who read the transcript, and then to Conway. Trump looked at the transcript and told the group not to worry: it doesn’t sound like me.
Campaign spokesman Hope Hicks asked to see the video. The Post sent it along, requesting a comment by 4:00 p.m. Now Trump heard his own voice; there could be no denial. The question was how to respond. Conway thought of herself as Rapunzel, locked in Trump Tower, as she struggled to find a way out of this latest crisis. Trump provided the solution: he would film an apology, and the networks would feel obliged to run it.
First, the campaign answered Fahrenthold, sending him a statement from Trump: “This was locker room banter, a private conversation that took place many years ago. Bill Clinton has said far worse to me on the golf course—not even close. I apologize if anyone was offended.” At 4:02 p.m., the Post published Fahrenthold’s story, which quickly became the most-read account in the history of washingtonpost.com. At one point, more than one hundred thousand people read it simultaneously, briefly crashing the newspaper’s internal tracking system.
That evening, Trump put his regrets on video. “I said it, I was wrong, and I apologize,” he said, but then he immediately pivoted to attack mode: “I’ve said some foolish things, but there’s a big difference between the words and actions of other people. Bill Clinton has actually abused women and Hillary has bullied, attacked, shamed, and intimidated his victims.” The late-night video did nothing to stem a tidal wave of criticism. Some Republicans withdrew their endorsements. Others called for him to step down and be replaced by his running mate, Mike Pence. But campaign advisers concluded that in the end, the tape would not change many votes. Most supporters found Trump’s attitudes on the tape appalling, but they still wanted him to Make America Great Again.
• • •
THE FLOOD OF BAD news kept rising. But with more than a month to go before the vote, there was still time for the troubled waters to recede. Trump may have avoided paying federal taxes for eighteen straight years, the New York Times reported after it obtained tax records showing that Trump had declared a $916 million loss on his 1995 returns. A parade of women from Trump’s past accused him of groping them. But in the weeks that followed, Trump’s poll numbers crept back up again, and then, eleven days before the election, when Comey announced that the FBI had resumed its inquiry into the email controversy, it became Clinton’s turn to struggle in the spotlight of painfully damaging news. As awful as his casual banter about sexual assault had been, this bombshell, Trump’s advisers believed, would depress turnout among Clinton supporters and reinvigorate Trump backers. “It was like looking at the lottery ticket and saying, ‘I think these are the winning numbers, but I’m going to go confirm them again,’ ” said Republican National Committee strategist Sean Spicer, who was working closely with Trump.
Former House Speaker Newt Gingrich, who was advising Trump, called the candidate, elated, and told him, “It is better to be lucky than smart, although it’s good to be both.”
Trump, who rarely declined a media request, realized he should not step on the Clinton investigation story. “I don’t think I should do any more interviews, do you?” Trump asked Gingrich.
“No, I think nine days of the teleprompter will be just fine,” Gingrich replied. The final strategy was set. Trump would remain on the attack the rest of the way, staying on script. His top advisers even took steps to separate the boss from his Twitter account.
• • •
ON THE FRIDAY BEFORE Election Day, Brad Parscale, Trump’s digital director, sat in his office in Trump Tower and stared in delight at his computer screen. This was not only Parscale’s first presidential race, it was his first political campaign of any kind. Before this, he had been an obscure Trump Organization employee, charged with finding foreign customers for the mogul’s real estate business. He had impressed Trump’s children, and they recommended him for the campaign’s top digital job.
For months, Parscale and his team had been collecting information about tens of millions of voters, working with files prepared both by the Republican National Committee and a firm called Cambridge Analytica, which was, not incidentally, largely owned by one of Trump’s most generous supporters, Robert Mercer, who had given $14 million to a political action committee that initially supported Ted Cruz and then morphed into the Defeat Crooked Hillary PAC. The company had made an audacious claim: using demographic and consumer data, along with psychological surveys, it claimed it could predict how every voter in the land would behave.
Parscale’s job was to figure out where every potential Trump voter was located, and therefore where the campaign should focus its effort. The campaign’s strategy had been based on boosting turnout among rural white voters, while doing what they could to diminish the pro-Clinton turnout among minorities. Parscale and his staff developed a two-minute TV ad that promised to replace a “corrupt” government with one controlled “by you, the American people”; his data allowed the campaign to air the ad in the battleground state markets where it might best expand turnout. Now, four days before the vote, Parscale saw the results of his work on his computer screen. He called Eric Trump and told him, “If this holds until Sunday, we are going to win this thing.”
Most pundits predicted a Clinton vi
ctory. But Parscale’s confidence only grew with each day’s report of absentee ballots and early-voting figures. The data showed that the kind of people Trump most needed were voting precisely where he needed them. Parscale was all but certain Trump would be president. The polling that news outlets were reporting had underestimated the hidden Trump voters in key states, people who hadn’t come out to vote in recent elections. “We weren’t playing for the popular vote,” Parscale said; he was fine with losing that to Clinton, as Trump did. The election was about winning the Electoral College, winning in states such as Pennsylvania, Michigan, and Ohio, stripping away what the Democrats had thought of as their structural advantage in traditionally blue states. In the end, a flip of only 107,000 votes in Michigan, Wisconsin, and Pennsylvania would have turned the election to Clinton. Clinton never set foot in Wisconsin during the fall campaign.
The Clinton campaign was so confident that it had pumped resources into states it didn’t need to win, such as Arizona and Nebraska, and neglected traditional Democratic strongholds such as Michigan and Wisconsin. Although Clinton’s campaign ran three times as many TV ads as Trump during the general election, she aired almost no ads in Wisconsin and Michigan in the second half of October. Trump flooded the zone and won both states.
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