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

by Michael C. Bender

  Guests would be seated by 4:50 p.m. Five minutes later, Pence and his wife, Karen, would take their seats, front row and center. Then, at 5:00 p.m., the president’s military aide would announce the start of the event with the big reveal:1

  “Ladies and gentlemen, the president of the United States and Mrs. Trump, accompanied by Judge Amy Coney Barrett and family.”

  The Trump and Barrett families, who would be mingling inside the Oval Office, would emerge from the West Wing. Melania would walk the judge’s family to their seats. The president would take his place behind the lectern, deliver his remarks, and then step stage right as soon as he finished. That would be Barrett’s signal to deliver a few brief words. The speeches would wrap by 5:20 p.m.

  Most of the afternoon seemed to stay on script. Even Trump’s ad-libbing at the end, when he took the lectern back after Barrett had finished and thanked his guests for coming, had barely taken any time.

  “All of the senators—please, we really appreciate it,” Trump said. “I know you’re going to have a busy couple of weeks, but I think it’s going to be easier than you might think.”

  Just as planned, after the speeches, the Trumps and the Barretts exited the Rose Garden the same way they’d entered, but then turned away from the Oval Office and instead walked along the West Colonnade toward the Diplomatic Reception Room for a few clicks to commemorate the moment.

  When the Dip Room’s doors closed behind them, the press team was to escort reporters out of the Rose Garden, through the Palm Room, and back into the White House briefing room. The other 200 guests—lawmakers, conservative activists, Fox News personalities—would then be directed away from the White House, along the curved driveway past the South Lawn putting green, and down to the southwest gate at 17th Street and State Place NW.

  By 5:40 p.m., the event would conclude.

  But in the Trump White House, it was never quite that simple.

  Trump—always the maître d’ in chief—asked aides to invite in his Rose Garden guests for an impromptu after party as soon as he had entered the Dip Room. The past six months had been a parade of horribles—the nationwide death toll from Covid had just eclipsed 200,000 just a few days earlier—and this was a rare, big moment to enjoy.

  “Bring in the senators,” Trump said.

  Within minutes, a procession of conservative senators filed into the room. Mike Lee. Thom Tillis. Josh Hawley. Ben Sasse. Kelly Loeffler.

  Sasse and Tillis, who had worn masks in the Rose Garden, removed them inside.

  Attorney General Bill Barr invited himself in, as did Health and Human Services secretary Alex Azar, a key member of the White House Coronavirus Task Force. Trump’s Cabinet secretaries knew they didn’t need a special invitation in the White House—Trump always wanted things loose and doors open.

  Meadows brought in a few guests. Pat Cipollone walked in with his wife, Becky, and longtime family friend Laura Ingraham, the Fox News personality. Labor Secretary Eugene Scalia brought in his wife, Trish, and mother, Maureen, the widow of former Supreme Court justice Antonin Scalia.

  Former New Jersey governor Chris Christie had been at the White House that morning to help Trump prepare for his first debate with Biden—now three days away in Cleveland—and then stayed for the Rose Garden event. When he walked inside to retrieve the briefcase he’d left in the Map Room, Kellyanne, who had been helping with debate prep, too, flagged him down.

  “There’s a reception,” she told him. “You should at least stop by.”

  Christie stuck around.

  He spent a few minutes talking to Barrett and her family. He chatted with Melania, and he eventually said goodbye to Trump.

  The day after the Rose Garden event, Christie returned to the White House to continue preparations for the debate. It was a Sunday, but the first debate was now just two days away. It was a famously tricky moment for incumbents, who often assumed their day job over the past four years was preparation enough, but then found themselves to be rustier than their rivals, who had spent months honing their skills during the primary season.

  Trump had started his prep in mid-August, at his Bedminster golf club, and eventually endured a total of eleven practice sessions, with most of the meetings occurring in the White House. But Trump defined debate prep differently than any other major party’s presidential nominee.

  Even in 2016, when prep was mostly overseen by Stephen Miller, Trump’s debate meetings usually resembled bull sessions. Other presidential candidates often prepared by combing through a 300-page binder, reading and memorizing as much as possible. Then a typical candidate would find a political ally to play the role of the opponent to sharpen their verbal sparring and get a feel for how the evening might unfold. But that was too formal for Trump. He gave some of his advisers the impression that he was afraid to acknowledge he needed practice, and that it would make him look weak even inside his inner circle. Debate prep in 2016 was mostly an attempt to make Trump feel comfortable.

  That’s mostly how debate prep happened in 2020, too.

  His team prepared him a three-page packet of material, which included reminders of his accomplishments in office and what he planned to do with a second term.

  He didn’t want to stand behind a podium to familiarize himself with the setup and didn’t need anyone to play the part of Biden. Instead, he mostly wanted to talk through strategy and refresh himself on the issues. But sometimes he could barely be bothered to do that much.

  Trump took phone calls during some practice sessions, while Christie, Kellyanne, Stepien, and Jason Miller sat and waited. He ended one debate session by saying he wanted to save his voice for a rally that night. Another time he cut it short to prepare for the Barrett announcement.

  The prep team was constantly changing, too. Kellyanne, Christie, Stepien, and Miller formed the core, but Hope sat in on most sessions. Stephen Miller attended at least one, where he reminded everyone that Biden was willing to give illegal immigrants health care. Rush Limbaugh, the conservative radio shock jock, phoned Trump to offer pointers. Reince Priebus, the former Republican National Committee chairman and Trump’s first White House chief of staff, repeatedly lobbied to be a part of debate prep, but was shut out. For the final two debate prep sessions, Trump demanded Rudy Giuliani’s addition to the team.

  Others just happened to walk into the room. Kayleigh McEnany came in during one session and Trump engaged with her for so long that others assumed debate prep was over.

  The day after Barrett’s Rose Garden announcement, Trump had been in his 4:00 p.m. debate prep for less than an hour—after spending five hours at his Virginia golf course—when Derek Lyons, the White House staff secretary, interrupted to remind the president about a news conference at 5:00 p.m. Kellyanne and Jason Miller were furious with Lyons, and tried to convince Trump to skip the news conference. It was a Sunday evening, and few people would be watching. Plus, he could hold one the next day. Christie discouraged him, too. But Trump insisted.

  Trump wanted to avoid debate prep partly because he knew Christie was going to hammer him. Trump had a quick temper, but mostly preferred to avoid confrontation. And tussling with Christie felt like a chore. For Trump, it was another homework assignment to be avoided.

  But Trump was right in at least one sense: Christie absolutely blasted him behind closed doors. To others in the room, the heated exchanges seemed to trigger something interpersonal between the two of them. There were moments when Trump enjoyed the back-and-forth, but Christie was determined to rattle Trump, especially over his handling of coronavirus.

  “You messed up Covid—you killed people!” Christie shouted at Trump, trying to push him off balance. “All you think about is politics!”

  The gambit was to hurl tough questions at Trump, see how he would respond, and figure out where improvements were needed. While there were no formal roles, Christie had taken on the job of channeling Biden, while Kellyanne assumed the role of moderator, Fox News Sunday anchor Chris Wallace. And like Ch
ristie, Kellyanne charged at Trump with every bit of fire and fury she could muster.

  She fashioned a question by telling Trump that the audience included the mother of Heather Heyer. That was the woman, she told him, who was killed that Saturday afternoon in Charlottesville, where protesters were carrying Tiki torches, chanting racist mantras, and wearing MAGA hats.

  “And yet you say they’re fine people?” she asked him.

  “I didn’t see any MAGA hats!” Trump shot back. He had burrowed in on the minutiae and the team urged him to focus instead on the broader question.

  She hammered him over his claim that he hired only the best people. Then why, she asked, had so many of his campaign and White House advisers been indicted or jailed? Why were the four-star generals who had worked for him now supporting Biden?

  “Well, they didn’t give such good advice,” Trump responded.

  Kellyanne stared at him.

  “You’re not listening,” she said.

  She peppered him with abortion questions and attacked him over his struggle to address race relations. She told him to think thematically so that he’d have a three- or four-point answer waiting in the wings whenever race or abortion came up—regardless of what specific question had been asked.

  Kellyanne went after him on health care, too. She had sided with Attorney General Barr over the summer and urged Trump not to ask the Supreme Court to overturn Obamacare, which would have wiped out medical coverage for some 23 million Americans in an election year.

  “You’re taking away people’s health care in the middle of a pandemic,” Kellyanne told Trump.

  “No,” he argued. “I’m giving them better health care.”

  “Well, where is it?” she asked him.

  Her aggressiveness and sharply worded questions both inspired and deflated some of her colleagues.

  “When I hear the way you phrase things, I want to quit my job,” one staffer later told Kellyanne.

  Jason Miller and Giuliani warned Trump that Biden was going to interrupt him, as he had Paul Ryan in the 2012 vice presidential debate. They told him that was how Biden won the debate, and Trump shouldn’t let him do the same to him.

  But Kellyanne disagreed. She said Biden had won that debate by looking like the elder statesman schooling a young pupil—a dynamic that Biden wouldn’t be able to replicate against Trump. She also didn’t think Biden was as sharp or as witty as he had been during that race. She urged Trump to consider Biden’s 2008 vice presidential debate against Sarah Palin, who, like Trump, brought a unique approach to the debate stage and seemed to fluster Biden at times.

  On topics Trump was most passionate about, he would argue back angrily with his sparring partners. On subjects he cared less about, he would just shake his head and mutter retorts.

  “Wrong,” he would say.

  “Untrue,” he’d offer with a shrug.

  Trump also repeatedly turned questions back to the subject of Hunter Biden. But the attack was convoluted and hard to follow. Kellyanne urged him to keep it simple, and offered a pared-down rejoinder. “Joe Biden gives us Hunter Biden—Donald Trump gives us Amy Coney Barrett,” she said.

  They urged him to challenge each and every time Biden used a number, because the odds were that Biden had mixed it up. Kellyanne and Jason Miller both told Trump that Biden almost always confused thousands, millions, and billions. Christie, Kellyanne, and Miller also told Trump to be aggressive—but not to the point that it would overshadow Biden.

  “Let him speak, because that’s going to wear him down,” Kellyanne advised Trump. “Biden doesn’t do well when he has to speak at length.”

  Christie urged Trump to let Biden speak first. “When your adversaries are in the midst of committing suicide, there’s no reason to commit murder,” he said.

  Giuliani suggested he open the debate aggressively, believing it would rattle Biden. “We can live with a headline that you were too tough on him,” he told Trump. “We can’t live with a headline that he dominated the debate.”

  After one final practice on the morning of September 29—the day of the debate—Christie had some lunch, got into his car, and drove home to New Jersey feeling confident that Trump was in a good place.

  “He’s really ready,” Christie told a friend who called during the drive home. “He’s going to have a good night tonight.”

  When the debate commenced that evening, held in an auditorium at the Cleveland Clinic, strict health precautions meant that only about 100 people were in the audience, instead of the thousands that typically attend a presidential debate. Only one reserved seat went unused. Ronna had canceled at the last minute. She had flown home from Washington on Friday—a day before the Rose Garden event—when she learned that her teenage son was sick with coronavirus. Now she felt ill, too, and skipped the debate out of an abundance of caution.

  Trump’s side of the hall was filled with family, staff, and other guests—including local pastor Darrell Scott, U.S. Representative Jim Jordan, and UFC fighter Colby Covington in his red MAGA hat. Almost all of them had taken their seats in the hall without their masks on, which was against the Cleveland Clinic’s policy, including Trump’s family and White House staff who viewed wearing a mask as a sign of weakness.

  Because of Covid, the two candidates agreed not to shake hands at the start of the debate and to keep their distance. It was just as well. Any degree of decorum was out the window almost from the moderator’s introductions.

  The first question from Chris Wallace was about Trump’s decision to nominate a Supreme Court justice so close to an election. The president defended his right to make the pick—elections had consequences and Democrats would have done the same, he said, using only ninety seconds of the two minutes he was given.

  Biden used his entire time to argue that while elections had consequences, the 2020 decision was already under way—tens of thousands of people had already cast their ballots, and the nomination should wait until everyone had their say. Biden then pivoted and said that Barrett’s confirmation would almost surely mean the end of Obamacare since Trump had tried to have the health care policy repealed in the middle of a pandemic.

  Trump shot back that Biden had misstated the number of Americans with preexisting conditions—but Biden had the number right. Trump accused his rival of supporting a health plan that had been pushed by his Democratic primary rivals that would end the private health insurance market.

  “You’re going to socialist medicine,” Trump said.

  “He knows what I proposed,” Biden said. “What I proposed is that we expand Obamacare and we increase it.”

  “It’s not what your party is saying,” Trump shot back.

  “That is simply a lie,” Biden said.

  “Your party wants to go socialist medicine and socialist health care,” Trump continued.

  “The party is me,” Biden interjected. “Right now, I am the Democratic Party.”

  “And they’re going to dominate you, Joe. You know that.”

  Biden pointed out 200,000 Americans had died of Covid since Trump had been president—“On his watch,” he said—and again questioned the wisdom of repealing Obamacare during a pandemic.

  Trump said two million people would have been dead from Covid had Biden been president.

  Wallace tried to get control, but Trump—who scowled, sneered, and wagged his finger for most of the debate—talked over him.

  “You’re not going to be able to shut him up,” Biden told Wallace. The jab triggered another back-and-forth between Trump and Biden.

  Biden insisted that Roe v. Wade “was on the ballot” in the race. It was a simple turn of phrase that both sides of the abortion debate tended to agree with every election year. But Trump argued even that point. Biden tried to explain what he meant, but Trump seemed to sense this was an opportunity to land a knockout punch. He wouldn’t relent.

  “You don’t know what’s on the ballot,” Trump said. “Why is it on the ballot? Why is it on the ball
ot? It’s not on the ballot. I don’t think so. There’s nothing happening there.”

  “Donald, would you just be quiet for a minute,” Biden said.

  “You don’t know her view on Roe v. Wade,” Trump said about Barrett. “You don’t know her view.”

  Wallace tried to ask his second question, which was about what Trump planned to do if the Supreme Court struck down Obamacare. But Trump interrupted before he could get the words out. Wallace admonished him, but then Biden interjected.

  Wallace reset himself and tried to ask his question again as Trump started to talk over him once more. Now it was an argument between Trump and Wallace.

  “Sir,” Wallace said. “You’re debating him, not me. Let me ask my question.”

  “Well, I’ll ask Joe,” Trump said.

  “No!” Wallace said.

  “The individual mandate was the most unpopular aspect of Obamacare…” Trump said to Biden.

  “Mr. President, I’d like you to…” Wallace said. “Mr. President!”

  “I got rid of it, and we will protect people with preexisting conditions,” Trump said.

  “Mr. President!” Wallace said again, a noticeable quiver in his voice. He was losing his patience. “I’m the moderator of this debate, and I would like you to let me ask my question and then you can answer.”

  Trump paused.

  “Go ahead, Chris,” he said.

  “You, in the course of these four years, have never come up with a comprehensive plan to replace Obamacare,” Wallace said. “And just this last Thursday you signed a largely symbolic executive order to protect people with preexisting conditions five days before this debate. So my question, sir, is what is the Trump health care plan?”

  “Well, first of all, I guess I’m debating you,” Trump said. “But that’s okay, I’m not surprised.”