“Frankly, We Did Win This Election”: The Inside Story of How Trump Lost

by Michael C. Bender

  “Those are the real people,” Trump said about the Enquirer’s readers during one interview with the New York Times.

  Stone, who was sitting across the desk, put an even finer point on it.

  “That is the Trump constituency,” Stone said.

  While Trump resented the lampooning of his hypothetical candidacy, there were also signs in 1999 that Trump’s gift for creating sensational headlines would help conceal the blemishes of his abrasive personal style and unorthodox political positions.

  Sean Hannity, then in his third year of cohosting the Hannity & Colmes program on Fox News, was particularly fascinated. In one episode shortly after Trump launched his exploratory committee, Hannity repeatedly tried to focus a panel discussion on Trump’s interview with Howard Stern a few days earlier when Trump spoke at length about his sex life with his then-girlfriend, Melania Knavs.

  “I want to go back to Donald Trump,” Hannity said during the show. “He did refer to his girlfriend as a potential first lady, and claimed that he mentally feels her up in public…”

  “I don’t understand all this shock talk,” Russell Varney, the outgoing chairman of the Reform Party, told Hannity.

  The panel moved on.

  A few months later, Trump declined to run and blamed the unraveling of the Reform Party. The group’s most prominent member, Minnesota governor Jesse “The Body” Ventura, had just quit and his exit opened a leadership battle between—as Trump described them—“a Klansman,” “a neo-Nazi,” and “a communist.”

  “This is not company I wish to keep,” Trump said.

  Trump tested the water a third time during the 2012 election cycle as President Obama was seeking a second term. This time, Trump was almost completely brushed off as a sideshow. But once again, there were signals of his resonance.

  Trump was in his eleventh season as host of NBC’s The Apprentice when he arrived in Washington, D.C., on February 10, 2011, to give a speech to the Conservative Political Action Conference. He walked out onstage to the same theme music as his popular reality show, the 1970s soul tune “For the Love of Money.”6 The crowd went bonkers—and remained in that state for the thirteen-minute speech that followed.

  Trump mocked Ron Paul—the Texas Republican and two-time winner of CPAC’s straw poll—as having no chance to win a presidential election. He accused China of manipulating its currency. He ripped American leaders as weak. He bragged about his wealth and the beatdowns he claimed to have put on any people or companies who stood in his way.

  “I’ve won many wars,” Trump said.

  Baited by repeated rounds of applause and laughter from his audience, Trump soaked up the cheers and waded into the already debunked conspiracy and racist lie that Obama hadn’t been born in America.

  “Our current president came out of nowhere, came out of nowhere,” Trump said. “In fact, I’ll go a step further: The people who went to school with him, they never saw him—they don’t know who he is.”

  The crowd erupted in applause.

  “Nobody knew who the hell he was,” Trump said as the crowd grew louder. “He’s now our president!”

  Birtherism had bubbled up in 2008, when multiple lawsuits challenged Obama’s August 4, 1961, birth at Kapiolani Maternity and Gynecological Hospital in Hawaii. The state health director issued a statement that she had seen the original birth certificate. Both of Honolulu’s major newspapers, the Advertiser and the Star Bulletin, found Obama’s birth announcement in their archives. Every lawsuit was dismissed.

  Behind the scenes in Trump Tower, the birther issue was too controversial even for Stone. He had warned Trump that he would be viewed as a racist.

  “The established media is going to destroy you, because it’s going to look like race baiting,” Stone told him.

  “It’s not race baiting,” Trump objected. “He’s either eligible, or he’s not eligible.”

  A month later, Trump was the proud face of the birtherism conspiracy.

  “Do you think it’s an important subject?” Bill O’Reilly asked Trump about Obama’s birth certificate during an interview on his Fox News program on March 30.

  “Maybe it says he is a Muslim,” Trump said. “I don’t know.”

  Hannity, meanwhile, ran with the issue. He used his prime-time Fox News program to discuss birtherism again on April 5, April 7, April 11, and April 13, and in an interview with Trump on April 14 and again in part two of the Trump interview on April 15.

  Hannity featured Trump and the birtherism controversy on April 18, and in four blocks of his show on April 19, including his interview with Sarah Palin, the Republican vice presidential nominee in 2008. Hannity returned to it the following night on April 20 and again on April 21, April 25, and April 26. He discussed it again on April 27, the day Obama presented a copy of his long-form birth certificate at the White House.

  By then, a CNN poll showed Trump tied for first in a hypothetical Republican primary, and trouncing Mitt Romney, the eventual Republican nominee. But in mid-May, NBC renewed The Celebrity Apprentice for another season and said it would find a new host if Trump ran for president. The following day, Trump ended the speculation and said he wouldn’t run.

  “Business is my greatest passion, and I’m not ready to leave the private sector,” he said.

  The polls that put Trump at the top of the race seemed to be long forgotten four years later when he finally announced a formal campaign for president of the United States.

  The day of Trump’s announcement in New York, Hannity asked Jeb Bush, the front-runner for the party’s nomination at the time, about the new entry to the race.

  Bush laughed.

  And then apologized.

  “I’m sorry,” Bush said with a smile. “I shouldn’t have done that.”

  Each of Trump’s successive flirtations with a presidential campaign had taught him something different about how he would run for the White House. In 1988, the considerable overlap between promotional marketing and politicking played to his natural skills as a showman. The exploratory bid in 2000 signaled that he could exploit the gaping maw between the fragile sensibilities of the media and the underdog pragmatism of the downtrodden to conceal his own blemished character. In the 2012 cycle, he experienced the raw animal magnetism that drew some quarters of the country—and certain corners of Fox News—to a message that the country’s racial and cultural identity was under attack.

  But Trump’s interest was always in running. He thrilled at how the mere act of declaring himself a presidential contender would catapult him into the upper echelons of establishment respectability, and squarely into the state where he was always most comfortable: the center of attention. By the time he finally announced a formal presidential campaign on June 16, 2015, he knew he wanted to win, but he still had never given much thought to exactly how to win—let alone how to govern.

  On February 1, 2016, Trump’s son-in-law and eldest daughter arrived at the DoubleTree Hilton in Cedar Rapids, Iowa, for the nation’s first presidential nominating contest.

  They looked around and were appalled.

  Trump was one of a dozen major candidates seeking the Republican nomination, and all the other candidates seemed to have hordes of volunteers in color-coordinated shirts standing behind tables with piles of literature about their candidate. The Trump campaign had nothing.

  Jared and Ivanka, who was seven months pregnant with her third child, picked up a folding table, carried it across the room, and placed it in the middle of the caucus site. As Iowans approached and asked about caucusing for Trump, the two New Yorkers traded blank stares. Ivanka had recorded a how-to-caucus video for the campaign a few days earlier, but she’d read the instructions from a script. She asked Jared if he knew what to do.

  “I have no idea,” Jared told his wife.

  He pulled out his phone, opened a web browser, and typed out one letter at a time: H-o-w d-o y-o-u c-a-u-c-u-s?

  Ivanka delivered an off-the-cuff speech to the caucus goers and pro
mised that “my father will make America great again.” Then, she walked a few steps away and called him.

  “There’s nobody here!” she told her father. “Like, there’s no swag. There’s no volunteers!”

  Jared was furious. Any faith he had left in Corey Lewandowski, the campaign manager, had evaporated. He cursed Chuck Laudner, the director of the Trump campaign in Iowa.

  “This is a shit operation,” Jared told Ivanka, and vowed to assume the burden of reorganizing his father-in-law’s campaign.

  But to blame Corey was to forgive Trump for his remarkable lack of preparedness.

  Trump had been floating the idea of running for president off and on for thirty years by the time he finally asked Iowans for the Republican Party nomination in 2016. But he had paid little attention to the mechanics of politics, like what a caucus even was or how previous candidates had won. He wanted to win the job without really having to work for it. In an interview after he declined to run in 2000, Trump said his biggest takeaway was how hard it would be to actually campaign for president.

  “The other night, I was sitting at Mar-a-Lago in Palm Beach, Florida, watching television and I was watching Gore on a freezing evening knocking on a door saying, ‘Hi, I’m the vice president. I’d love your vote.’ And he’s freezing!” Trump said. “And I’m watching McCain, and I’m watching Bush. And they were all working so hard. And I said, ‘You know, it’s not such an easy life they have,’ as I’m sitting, you know, in 75-degree weather.”

  But then he made his decision with little actual preparation. He offered Corey, at the time an obscure New Hampshire political operative, the campaign manager’s job at their very first meeting, in 2015.

  Trump told Corey about his fleet of helicopters and jets, and he asked what his odds were of winning the White House.

  “Five percent,” Corey told him.

  “I think it’s ten percent,” Trump said. “Let’s split the difference.”

  “Sounds good to me,” Corey said.

  Trump asked how much it would cost him to run in the first three states to hold presidential nominating contests: Iowa, New Hampshire, and South Carolina. Not how much it would cost to win—just to run.

  Corey said that would set him back about $25 million, a fraction of what Mitt Romney had spent in 2012.

  “I don’t need $200 million for this campaign,” he said.

  Stone thought Corey was nuts. Stone didn’t think anyone could win a presidential campaign by spending next to nothing on television advertising and relying solely on free media from an endless barrage of TV and newspaper interviews. Jeb Bush’s political machine was building a $156 million war chest. No way, Stone told them, that anyone could punch their way out of that with one interview after another.

  But Stone was wrong. The presidential contest awaiting Trump was as unpleasant as it was unpredictable.

  Trump lost the Iowa caucuses, but he won the next primary contest in New Hampshire and never again relinquished front-runner status. He upended the Republican Party, scythed the base from its Washington leadership, and left conservatives at war with themselves—but won the nomination. The political veterans on his team urged him to find ways to unite the party. He would need the entire party’s help, they told him, to take down Hillary Clinton, the Democratic presidential nominee who had more money, more political infrastructure, and a more traditionally relevant résumé. But Trump would never atone. Instead, he amplified the divisive intensity.

  The general election was a series of dumpster fires and car crashes followed by car crashes into dumpster fires. Trump generated a perpetual news cycle of outrageous statements, vicious political brawls, and previously unthinkable policy positions. And no one could look away.

  Not even a scandalous Access Hollywood videotape that showed Trump grotesquely bragging about sexually assaulting women proved fatal. The tape from 2005 had surfaced in the Washington Post just four weeks before Election Day, and a stream of Republicans immediately rescinded their endorsements or called on him to quit the race. But the next day Trump sat in his Manhattan penthouse and shrugged it off during an interview with the Wall Street Journal.

  “I never, ever give up,” he said.

  And Trump won again—a victory that shocked the Trump campaign every bit as much as the rest of the country.

  The 5 to 10 percent strategy that he and Corey had sketched out the previous year had worked. Voters said they were horrified by Trump’s coarseness and quick temper, but they liked Clinton even less.

  Inside the White House, Trump’s surroundings had changed, but the game plan did not. Allies and critics alike, who had predicted Trump would mature into the job—and that the staggering weight of the office would mold him into a more presidential form—were repeatedly proven wrong. Instead, Trump remained in attack mode and paid little mind to repairing an American electorate riven by a brutally divisive 2016 campaign. That neglect extended to his own team, which had also been shattered by the experience.

  While the new president was preoccupied with his baseless claims that widespread election fraud had cost him the popular vote, the tectonic plates in Trump World had shifted violently. He had compiled a bevy of political consultants after a seventeen-month presidential campaign in which he’d cycled through three separate leadership teams, none of which were ever completely eliminated and instead mostly just layered over. He also maintained a wide circle of familial advisers, which most often included his three eldest children plus their spouses and significant others. By the start of 2017, the team was already crawling over each other to take credit for the historic victory—they all claimed possession of a playbook that had never actually existed—and jockey for proximity to President Trump.

  Jared viewed himself as one of Trump World’s gatekeepers and was often a calming presence who kept Trump—and the team around him—focused on a specific task. He quickly emerged as one of the few Trump advisers whose personal buy-in could help deliver results in an otherwise chaotic West Wing.

  But he was also blamed, in part, for the rocky start. He took credit around Washington for the campaign’s heavy reliance on digital advertising and social media, a program whose importance he understood much better than the strategy or details that underpinned it. He isolated Corey and David Bossie, the 2016 deputy campaign manager and longtime conservative activist, making sure neither had roles in the administration. He led the charge to oust White House chief strategist Steve Bannon, who had been chief executive of the 2016 campaign and could articulate Trump’s brand of populism better than anyone—including even Trump himself. And he retroactively cast himself as the de facto campaign manager, diminishing the role played by White House counselor Kellyanne Conway, a fellow New Jersey native who was installed as campaign manager in the final months of the race and became the first woman in America to hold that title for a winning U.S. presidential campaign.

  In fact, Jared hadn’t paid much attention to his father-in-law’s presidential campaign as Trump and Corey had puzzled it together in 2015. But this time he wanted his hands on the levers of the reelection bid. Jared started laying groundwork in the early days of the new administration to box out Kellyanne, Corey, Bossie, and anyone else whom Trump might suddenly decide to put in charge. Jared described his role to others as protecting Trump from “overconfident idiots.” Trump often made decisions in the moment, sometimes based on little more than reading the faces in the room and making a gut call. Jared was concerned that management style left him vulnerable to brash promoters, especially on television.

  “You get to run one more time,” Jared had told Trump. “So just let me know what you want to do. This is your campaign, but I’m not going to let you hire any idiots.”

  After just thirteen months as president, Trump announced Brad Parscale as his 2020 campaign manager at Jared’s urging. Brad had been digital director for the 2016 campaign, which was the only political race in which he’d ever been involved. Brad had been living in San Antonio in 20
11 when he low-balled a bid to build a website for the Trump Organization to get his foot in the door. His ploy worked and the Trumps remained clients until 2015, when Eric asked him to build a website for his father’s presidential campaign.

  Brad designed a campaign strategy around a digital marketing funnel aimed at white working-class voters in the Midwest in much the same way that the New York Times targeted coastal elites. But instead of subscribing to a digital newspaper, Brad’s flood of Facebook ads pushed his targets to go out and vote for Trump. The digital effort helped Trump overcome a huge cash disadvantage and become the first Republican since Ronald Reagan in 1984 to win Pennsylvania, Michigan, and Wisconsin all in the same election.

  Brad had never run a campaign on his own, but inexperience was often viewed as an asset in Trump World. Jared knew Brad’s inexperience would make him easier to control—he would later describe him as a mere placeholder—but Brad viewed the promotion as a sign of strength in their relationship. Meanwhile, his elevation infuriated much of the 2016 team, who were blindsided by a move they perceived to be a power grab by Jared. Even Brad didn’t know Trump would offer him the job when he arrived in the Oval Office for a meeting on February 27, 2018.

  “Do you think you can do this?” Trump asked him. “I heard you were the most valuable player in 2016.”

  Brad accepted and was immediately shuttled down the street from the White House to a meeting at Trump International Hotel where Jared, Eric, and the president’s oldest child, Donald Trump Jr., laid out the rules: Brad needed to divest from any other business, stay in constant contact with them, and remain 100 percent committed to the family. Brad agreed. He asked how they wanted to handle the public announcement, but Jared had already leaked the news to the Drudge Report. Text messages poured into Brad’s phone, everything from warm congratulations for landing the high-profile gig to unsettling warnings from friends cautioning that the job would destroy his life.