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

by Michael C. Bender

  Just like 2016, the final rally in 2020 was in Grand Rapids, Michigan, and Trump was hoarse by the time he landed at Gerald R. Ford International Airport.

  Trump was wrapped in a full-length black overcoat and a red campaign hat and black gloves as the temperature dipped into the 40s. His family joined him onstage. He and Pence tossed red hats into the crowd.

  During his speech, he attacked Biden as “Sleepy Joe” and “One Percent Joe.” He twice referred to “Barack Hussein Obama.” He complained about witch hunts, fake news, the deep state, and Hunter Biden.

  But in those final seventy-five minutes on a 2020 campaign rally stage, Trump mostly wanted to talk about what happened in 2016. He asked the crowd a dozen times to “remember four years ago.” He reminded his fans what it had been like that night to win Michigan and Ohio. He reminisced about how they had watched news anchors crying over his victory. And he confidently predicted—no fewer than fifteen times—that he would repeat his success again the next day.

  “We made history together four years ago,” Trump said, “and tomorrow, we’re going to make history once again.”

  Footnotes

  1 The presidential candidates are usually the main driver of turnout in an election year, and 2020 was no different. In contested Senate races that year, Republican candidates who received more total votes than Trump almost all lost while those who underperformed him nearly all won.

  2 “It was like Bill didn’t understand the size of this thing,” one senior campaign official said. “We were close to being a multi-billion-dollar operation. Buy lunch for the team.”

  3 Hassett shrugged off the criticism at the time and said his model wasn’t meant to be predictive, but it was widely reported that White House aides had interpreted it that way and used it to influence their decision to quickly reopen the economy.

  4 The Trump campaign already had an illustration of a Chuck Schumer swamp creature, and they simply clipped Biden’s head and pasted it on the Senate Democratic leader’s body for the spot.

  17

  Election Day

  “Frankly, we did win this election.”

  —Election night remarks, East Room, November 4, 2020

  Marine One touched down on the South Lawn of the White House just before 3:00 a.m. on Election Day. Trump gingerly walked down the six steps. He was an hour and a half late returning home, and exhausted. He’d hosted forty-five rallies in the twenty-one days since recovering from Covid. Four years earlier, he’d held fifty-one rallies over that same three-week span. Once again, Trump had run through the tape. His final seventeen hours of campaigning had included more than 3,000 miles of flights and motorcades, 367 minutes of rally speechifying, and five awkward and hilarious stage dances to “Y.M.C.A.”

  What was different this time was that he was confident he was going to win.

  In 2016, Trump had told Melania—just days before the election—that his plan was to make sure his private jet was gassed up before the votes were counted.

  “If I do lose, I’m coming out, we’re going to leave everyone else behind, and fly right to Monte Carlo,” Trump said.

  He described a scene in which he’d arrive in Monaco like a high-roller dressed to kill—an older and heavier (but wealthier) James Bond.

  Melania erupted in laughter.

  “Donald,” she said. “Nobody goes to Monte Carlo in November.”

  On his final day of campaigning in 2016, his tplane was about an hour from New York when Trump turned to Steve Bannon, his campaign’s chief executive and one of the only other passengers still awake on the flight.

  “Hey,” Trump said, getting Bannon’s attention. “How does this thing end?”

  A tiny chortle escaped from Bannon. “How do you mean?” he asked. “We’ll get the exit polls around four, and we’ll have a data room where they watch all that shit. We’ll be giving you updates on how people are turning out.”

  “No,” Trump said. “The victory speech or the concession speech. Are those requirements? Like, legally?”

  “No, no, there’s no legal requirement,” Bannon said.

  “I don’t want to give a concession,” Trump said. “Fuck them.”

  Bannon laughed.

  When Trump awoke later that morning, the first Election Day polls had already opened, and, once again, an unscalable fence had been installed around the White House out of concern for riots. He was running late for an interview with Fox & Friends, and his wife, Melania, was 1,000 miles away, absorbing the heavy ocean air surrounding the crown jewel in his series of sprawling South Florida holdings, Mar-a-Lago.

  Melania, who preferred herbal remedies and natural healing over evidence-based medicine, was convinced of the therapeutic qualities of that salty South Florida sea breeze. She loved it at Mar-a-Lago, and made it obvious to everyone how much she preferred it to her life in Washington. She dreaded that return flight back to Andrews Air Force Base, and never more so than now, the long-awaited Judgment Day for her husband.

  The source of her anxiety wasn’t so much the result of the race. She wasn’t sure how she’d react, win or lose. She’d feel excited and proud later that night at that tantalizing, but ultimately cruel, first taste of victory. A day before, she’d forcefully defended her husband at her own rally in Huntersville, North Carolina, a Charlotte suburb, where she took the stage to Tom Jones’s swinging, sexist seventies tune “She’s a Lady.”

  But the next night, election night, she seemed to betray the slightest signs of relief as the momentum shifted to Biden. The only thing she was sure of was that after four years, she mostly felt tired. No one would blame her for that. Plenty of White House aides felt the same.

  In 2016, she and Trump voted together in New York. Four years later, the Trumps became the first president and first lady to cast ballots in Florida, albeit ten days apart. Trump had already voted early, but Melania wanted to vote on Election Day. It was sunny and in the mid-70s by the time she slipped on a $3,200 Gucci dress to cast her ballot at the Morton and Barbara Mandel Recreation Center. She pulled on a pair of tan Christian Louboutin stilettos, some square-framed sunglasses with a dark brown leopard print, and grabbed a $30,000 Hermès handbag.

  If she had to go back to Washington after casting her vote, she was going to look sharp doing it.

  What irritated her most about the trip back to the White House was what awaited her there. Hundreds of people were coming to the White House that night for an election party she’d tried to stop, but in the process had been trampled by Meadows, Jared, and ultimately her own husband. If it was up to her, there would be no White House parties during the pandemic. Technically, social events in the White House were the purview of the first lady’s office. But it was a fight in which she was never successful. Even after her husband lost, she couldn’t stop the holiday parties. Melania successfully cut the invite lists down from 1,000 or so to around 200. But that just seemed to make the invites all the more desirable. When South Dakota governor Kristi Noem wanted to attend multiple Christmas parties and refused to take no for an answer, Melania gave in to that, too.

  “Fine,” Melania said. “You know what? If she wants to get Covid that bad, that’s up to her.”

  The constant use of the White House for blatantly political purposes also made her uncomfortable. She had tried to stop the campaign from using it for the convention, too. Her office had slow-walked several requests from the campaign ahead of the Republican National Convention, when she’d deliver her speech from the Rose Garden and the president would accept his party’s nomination on the South Lawn.

  Three times she’d rejected the request from Meadows to use the White House on election night. The campaign was supposed to use Trump International Hotel, just five blocks down the street, which had been sold out for the evening since January. Washington’s regulations prohibited public gatherings of more than fifty people, but Trump didn’t want to move his festivities. Nine days before the election, the campaign emailed supporters that they were
still planning a party at the hotel. But Washington mayor Muriel Bowser, who had been a loud critic of the White House over the Rose Garden superspreader, signaled she was ready to play hardball.

  “We’ll be talking to our licensee, which is the hotel,” Bowser said.

  That day, Meadows called Melania to speak with her about holding the event at the White House. They really had no other choice, he told her. The hotel would face fines or other penalties that the White House, which was exempt from local regulations, would not. But still she said no.

  “I’m not comfortable with it,” she told him, and asked for more time to discuss it with her staff.

  The regulations made sense to Melania. She didn’t want all those people at the White House, and she wasn’t sure how long the night would last. Timothy Harleth, who as the White House’s chief usher was a de facto general manager of the residence, agreed with her. Stephanie Grisham, her chief of staff, warned about how long the party might last.

  “Win or lose, there are going to be protests that night,” Grisham told her. “Are we going to end up with a 300-person slumber party at the White House if these people can’t get out?”

  Melania sent word back to Meadows that they’d have to look elsewhere. Meadows brought the verdict to Jared, who raised it with the president. Four days from the election, Trump called his wife from Air Force One as he flew from a rally in Michigan to another in Wisconsin.

  “This is your night—do what you’re going to do,” Melania told her husband. “You’re going to do it anyway.”

  Melania would at least protect herself. She would stay in the residence with Barron and her parents, and only come if Trump needed her to stand next to him for a public speech.

  The quick turnaround led to some tense negotiations between the campaign and the East Wing. Competing visions for the evening presented the main friction point. The campaign wanted to go Full Trump: big and loud, extravagant and celebratory. Winners. But the East Wing preferred something with the pandemic in mind.

  “Let’s not overdo it,” Grisham said when the campaign presented plans for an elaborate and grand stage in the East Room.

  But as always, there was a little more backstory. One corner of Trump World could never quite trust another. Adding to the heat of these talks was that the main point of contact for these discussions was Grisham and the campaign’s chief advance man, Max Miller. The two had dated for much of Trump’s presidency but were now broken up. Initial arguments in the negotiations over the party focused on Miller’s plans for a giant stage with extensive lighting and televisions everywhere. Grisham argued that the White House was effectively a museum and should be treated as such. The East Wing initially declined requests to use the White House’s caterers and social aides, then relented.

  “It was a huge pissing match,” said one White House official.

  The campaign wanted to create a war room for their number crunchers in the Map Room, a small ground-floor room off the Diplomatic Room that earned its name during World War II when Franklin Roosevelt used it as a situation room. They wanted a smaller, more exclusive war room for Stepien, Clark, and Jason Miller in the Old Family Dining Room, an intimate space in the northwestern corner of the first floor, where they could meet in private with Trump. Presidents had taken meals with their families in the space for 130 years, until the Kennedys moved the family dining quarters into the private residence. For election night, the White House had extra couches brought in along with television sets. But the senior campaign team barely left the Map Room, and the dining room ended up being used mostly as an escape room for senior White House staff, like Hope and Scavino, to avoid the crowds, and for Katie Miller—the vice president’s press secretary and wife of Stephen Miller, who would give birth two weeks later—to rest her feet.

  Max Miller got his team into the White House to begin setting up with less than forty-eight hours before guests would start arriving. The next night, it was after midnight when the Secret Service told the advance staffers they needed to wrap up. But they still weren’t finished. Miller called Grisham to have their time extended.

  “They’re kicking the team out, and we’re still building the stage and finishing the lighting!” Miller said.

  Miller and his team were just leaving the White House by the time the president landed at 3:00 a.m. They returned a few hours later for the final touches.

  Trump’s late night on his final day of campaigning caught up with him the next morning. He was forty-five minutes late calling in to a 7:00 a.m. interview on Fox & Friends, and just before he did, Hogan Gidley, the campaign’s press secretary, posted a tweet asking if Biden had packed it in for the day.

  Biden was, at that moment, at church. He’d started his day by visiting the grave of his older son.

  But Biden’s team wasn’t relying on prayer to win. The campaigns for both candidates believed the race would end with either Biden in a landslide, or Trump by an even narrower margin than his 2016 victory. But Trump thought he was primed for a blowout, and predicted as much on Fox & Friends that morning. He sounded groggy and hoarse. Steve Doocy, the friendliest of the three hosts, speculated that Trump had had only a few minutes of sleep the previous night because he’d campaigned so long the day before. He asked the president if he was serious when he’d said at his last event that he might start crying when the crowd chanted, “We love you.”

  “Were you a little emotional right then because that could have been the last rally of your political life?” Doocy asked.

  “Well,” Trump said, “I was kidding, actually.”

  Ainsley Earhardt told Trump that she just liked that he said it. “When you love someone, that’s always nice to hear back,” she told him.

  Brian Kilmeade stepped in and asked about a quote from Obama, who had accused Trump of caring more about drawing big crowds than keeping people safe during a pandemic. Trump answered by complaining about his coverage on Fox News, specifically the amount of time the network gave Democrats in 2020 compared to 2016.

  “It’s one of the biggest differences, this season compared to last,” he said, the former Apprentice host slipping into TV lingo to refer to his two campaigns.

  Trump started his day airing grievances about Fox on Fox. He’d end it in a fit of anger at the conservative network and a flurry of phone calls threatening to wipe them out.

  Boosting Trump’s confidence that morning were gains in U.S. stock markets, which, paired with rally attendance, he believed was an even better indicator of his political fortunes than the polling his campaign had spent millions to produce. After he hung up with Fox News, he called a conservative radio show host in Pennsylvania.

  “The ultimate poll is not some guy that makes a million dollars to go and talk to 213 people, which I’ve always felt was weak,” Trump told R. J. Harris in Harrisburg. “The ultimate poll are these massive crowds that are showing up to rallies. Nobody’s seen anything like it ever. There has never been anything like it.”

  “Tonight will be a landslide,” White House press secretary Kayleigh McEnany told Fox News late Tuesday morning.

  By lunchtime, Trump was on his way to campaign headquarters in Virginia, just his second visit to the offices that now included two full floors and parts of a third in the Arlington office building. The event was designed for him to show some appreciation for the hundreds of people who’d been working for the campaign, a few minutes that would help get them through the rest of the day. Nearly all the staffers, standing at their cubicles and waiting in their office doorways, wore masks. When Trump entered the office, he wore a blue suit, a purple tie, and no mask, nor did much of his entourage. Meadows, who’d escaped a few close calls with Covid already, hugged several staffers. Kushner, in blue jeans and a black cashmere sweater, didn’t bother with a mask. Nor did Kayleigh, or Stepien, who shuffled awkwardly next to the president, his gray Patagonia fleece vest zipped all the way up to his Adam’s apple.

  The campaign staff welcomed Trump with a long ovat
ion that brought a smile to the president’s face, as if he was there to have his spirits lifted instead of the other way around.

  Trump told the room that he thought he’d finished strong, and pointed to the rally and the debates, but then corrected himself.

  “Certainly the second debate and the rallies, it was a good combination,” he said. “I think we took off.”

  Asked if he thought there would be a result that night, Trump said he did, as Stepien nodded aggressively behind him. When another reporter asked if he’d written acceptance and concession speeches, Meadows repeatedly shook his head as he stood behind the president.

  “Hopefully, we’ll be only doing one of those two and, you know, winning is easy,” Trump said. “Losing is never easy—not for me, it’s not.”

  Trump returned to his motorcade, bringing several campaign staffers back to the White House complex with him. But on the way into the White House, Nick Trainer tested positive for Covid. At 3:00 p.m. that afternoon, the campaign had its first nightmare of the day.

  Trainer was sent home and his close contacts were retested, including Clark, who had traveled from campaign offices to the White House with Trainer. Clark again tested negative, so Sean Conley, the White House physician, let him stay as long as he wore a mask and returned to the medical unit that evening to be tested again.

  The campaign would keep Trainer’s positive test under wraps for several days, and say nothing when he didn’t show up for a scheduled call with reporters at 5:30 p.m. on Election Day. “Everybody on the Trump team, the president included, feels better and more confident about our positioning in 2020 than we did at this exact moment in 2016,” Jason Miller told reporters on the call, only a couple hours after Trainer’s test.