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

by Michael C. Bender

  The second target was Wisconsin, which had been called for Biden the day after Election Day. Trump’s lawsuit there alleged ballots had been mishandled. The petition was ultimately rejected in the state supreme court, where it had arrived on December 1—the same day Attorney General Bill Barr announced that there was no evidence of widespread voter fraud in the election.

  Their third state was Arizona, which had been correctly called for Biden on Election Day by the AP and Fox. The campaign sought to invalidate ballots in Phoenix that they alleged had been mishandled. The suit was dismissed, but the strategy never had a chance: The votes in question ultimately weren’t enough to close Biden’s margin of victory.

  The team had walked through the plan for about an hour when Trump left the room to take a call. Stepien used the moment to gather the crew and again urged them to keep repeating the long odds.

  “We want to be super clear,” Stepien said. “We want to make sure there’s no mistake he misheard something.”

  After the meeting, Stepien and Clark agreed that their message had been well received by Trump, and they left the White House feeling like they were all on the same page. But Jason Miller wasn’t so sure. To Miller, Trump seemed more willing to keep fighting than he was to accept the low probability for success.

  “I always thought we had much better odds,” Trump told me during an interview after the election at Mar-a-Lago. “It was much higher than five or ten percent.”

  In many ways, it was a simple yet systematic failure of imagination in Trump World that prevented anyone from anticipating that the Oval Office was about to be overtaken by Rudy Giuliani; that the president would rush to install a band of sycophants across the administration; and that the repeated misuse and abuse of the bully pulpit from the world’s most powerful political office would foment a revolution in the heart of the nation’s capital.

  Trump had spent four years insisting that anything negative about his brand was fake news. The media was lying, no other elected officials should be believed, and the courts weren’t to be trusted. It was a lie that he repeated most consistently when it came to his standing among American voters. Positive polls were accurate, negative polls were wrong, and the only possible explanation for any electoral defeat—the 2020 presidential race, the 2016 Iowa caucuses, or even the 2004 Emmys—was the predictable, if false, claim of cheating and fraud. Each repetition of rigged elections was its own jackhammer to the foundation of the country’s democratic principles.

  But despite all the years and all the tweets and all the baseless claims of voter fraud, Trump World mostly assumed that the president, at the end of the day, would behave rationally—or at least reasonably. Ronna and Pence both had separately described that theory to others in Trump World—that Trump would find his own natural exit ramp from the fictional freeway down which he’d been barrelling for a month. Cipollone told other administration officials that Trump was in a good frame of mind. Ivanka told some White House officials she thought her father might invite Biden to the White House, as Obama had done for him. Even Mark Milley—the chairman of the Joint Chiefs of Staff who had battled with Trump all summer over the president’s instinct to advance his own political goals by deploying uniformed soldiers on the streets of major American cities—conveyed some optimism inside the Pentagon after Trump had spoken about an agenda item in a meeting and momentarily acknowledged reality.

  “We’ll leave that for the next guy,” Trump said.

  During the first two weeks of November, the prevailing theory among campaign officials, political operatives, and White House aides was that Trump just needed the time and space to process the defeat, and that he would eventually come to terms with his grief and do the right thing. Few believed he had it in him to acknowledge defeat and concede the race—a troubling fact that everyone seemed to take for granted. Let Trump be Trump, as Corey and Bossie liked to say. The focus instead was on the agreed upon belief that after a bit of pouting to protect his image, Trump would roll up his extra long ties, take down from the wall that bizarre painting of Trump himself sitting around a table with Lincoln, Nixon, and a half-dozen other Republican presidents, collect his supermodel wife and teenage son, and peacefully leave office.

  One senior Republican official told the Washington Post less than a week after Election Day that there was little downside to “humoring” Trump for a little while.

  “He went golfing this weekend. It’s not like he’s plotting how to prevent Joe Biden from taking power on January 20,” the official said. “He’s tweeting about filing some lawsuits, those lawsuits will fail, then he’ll tweet some more about how the election was stolen, and then he’ll leave.”

  Pence, Stepien, and Ronna told themselves that they were being respectful of the president and giving him the kind of space he required to blow off steam after an undoubtedly crushing defeat on the biggest stage in politics. But they were also unwittingly creating an opening for Giuliani and the most dangerous elements inside Trump World—a horrifying nexus of flunkeys and fawners who were willing to say and do anything to keep Trump in power, and their own feet in the door.

  There was a corner of Trump World that had, however briefly, at least considered telling Trump he’d lost.

  While Trump had been golfing that Saturday morning, a small circle of advisers had been sitting inside campaign headquarters around the table in a glass-encased conference room considering their options. They watched with alarm as Giuliani turned in a news conference performance so absurd that its location attained instant iconic status: Four Seasons Total Landscaping. Standing in a local landscaping company’s parking lot, Giuliani had intended to highlight his allegations of voter fraud in Philadelphia, but the story out of the event was a flub over the location; Trump had initially tweeted out that the news conference would be held at the luxury Four Seasons hotel, only to have to clarify that the event was, in fact, at Four Seasons Total Landscaping. It was an embarrassing development for the campaign’s skilled advance team that had been grounded in Washington because of budget concerns. As Giuliani stood in the northeast Philly parking lot of the cement block building—next to a sex shop and a crematorium—the Associated Press and all of the major cable news networks called the election. Even Corey was smart enough to stay out of that shot.

  Giuliani mocked the news that the race was over, but back in Washington, the bungled news conference crystallized the finality of the moment for some of Trump World’s most loyal lieutenants.

  Hope articulated what several were thinking and suggested the team tell Trump that the election was over. If the president could find a way to begrudgingly concede, then he—and his team—could enjoy the final months of the presidency, she said. Trump could take one of the foreign trips he’d been planning for after the election. He could push through executive orders that he’d been told were too controversial to sign before the election.

  “Let’s do all the things we didn’t get to do because of all of the distractions, and have fun,” Hope said.

  Bossie agreed. Herschmann endorsed the plan.

  Then Eric and Don Junior shot it down.

  Two days prior, Don Junior had posted encouragement on Twitter for his father to “go to total war over this election.”

  “Expose all of the fraud, cheating, dead/no longer in state voters,” Don Junior wrote.

  There was no easing up now.

  “What you’re talking about isn’t even an option,” he told Hope.

  The two sons channeled their father’s reaction. They warned he would never go for it and said it wasn’t worth broaching.

  “It’s a nonstarter,” Eric said.

  The motion was tabled, and that was as close as Trump’s family and some of his longest-serving aides would get to finding a way to tell the president the one thing they knew he couldn’t handle: that he’d lost.

  The group talked themselves into the 5 to 10 percent approach by saying that any president deserved to have his legal options pursued. Mos
t believed that once those challenges were exhausted, Trump would downshift out of attack mode. Or, if not, certainly Trump would get himself there by December 14, when the Electoral College met in Washington to cast their votes in the presidential race.

  Except that had never been Trump’s plan. Stepien and Clark left their meeting with Trump on Saturday confident that the president would behave in a relatively realistic way when it came to his legal options. But they had barely made it off White House grounds when Trump signaled a very different approach on a phone call with Chris Christie.

  Christie had lost his share of elections—he’d been voted out of the first office he ever held as a Morris County, New Jersey, freeholder and barely lasted two states in the 2016 Republican presidential primary. The pain of losing the White House, Christie understood, must be exponentially worse. Christie tried to empathize with Trump, and he told the president he should be proud of what he’d accomplished. Christie suggested a whirlwind domestic tour to take a final bow.

  “But to do that, you have to say to people that you understand you lost,” Christie said.

  “Is that all you got?” Trump said.

  “Yes,” Christie told him. “Because that’s all there is.”

  Trump didn’t want to hear any of it.

  “I can still win this thing,” Trump said.

  Trump wasn’t untangling himself from the fraud accusations. He was pulling the knot tighter.

  Most political campaigns end on election night with the team gathered in a hotel ballroom or campaign office with families and supporters. The moment of finality and closure provides candidates and their staff an opportunity to celebrate a hard-fought victory or, perhaps more importantly, grieve together over a loss. Trump’s election night stretched over four days and much of Trump World had scattered by the time the race was called. One senior staffer was sipping coffee on her couch watching CNN when the news broke. Another had brought his son to a flag football game for the first time in months when Fox News alerted the result. Another was away at his sister’s wedding.

  Many of those who remained would be repulsed by Trump’s actions over the days and weeks to come—an exodus that started when Trump fired his defense secretary, Mark Esper, by tweet.

  The move broke a promise Trump and his team had made a few weeks earlier to David Urban, the Trump adviser who was friends with Esper. Urban was livid and immediately called Jared. Jared didn’t want Esper fired, but he told Urban that Trump’s promise was to keep him through the election. Urban already seemed to be teetering on the edge of Trump World—he was the campaign’s top consultant for Pennsylvania, but he rarely left Florida during the pandemic and had become the top lobbyist at TikTok, the Chinese company that America-First Trumpians believed was a national security risk to the United States.

  “I’m fucking done,” Urban told Jared. “It’s a dick move, and it looks like he’s out of control.”

  But Trump was just getting started. Within days of firing Esper, Trump had replaced veteran defense and intelligence officials with inexperienced loyalists hungry to appease the new boss.

  Administration officials like Pompeo and Milley believed some of Trump’s new hires were conspiracy theorists and discussed whether others might have links to neo-Nazi groups. Senior administration officials weren’t completely sure what Trump was up to, and they started hitting the panic button.

  “The crazies have taken over,” Pompeo warned a colleague about the White House.

  Pompeo worried that foreign adversaries might view the domestic instability from the electoral uncertainty being fanned by Trump as an opportunity to exploit. Pompeo left one senior administration official with the impression that he was also concerned about the possibility that Trump might engage in a foreign conflict as a way to strengthen his political argument for remaining in office. Pompeo suggested a daily call with Meadows and Milley to all stay on the same page when it came to hot spots overseas.

  But publicly, Pompeo played a cynical political hand and fed into the fraud conspiracy when, during a State Department news conference on November 10, he said he anticipated a second Trump term.

  “There will be a smooth transition to a second Trump Administration,” Pompeo said, adding that “there is a process—the Constitution lays it out pretty clearly.”

  Milley, meanwhile, took a more direct approach and started sending clear signals to the White House that, whatever Trump’s plan, he should leave the military out of it.

  “We do not take an oath to a king or a queen, a tyrant or a dictator,” Milley said at the opening of the U.S. Army’s museum on November 11 as Chris Miller, the acting defense secretary who had replaced Esper, sat nearby.

  “We do not take an oath to an individual,” Milley said.

  Less than a week after Stepien and Clark had walked Trump through their legal plan, Giuliani was blowing it up—and pushing his way further into the Oval Office. On November 13, Trump summoned Clark into the Oval Office as Giuliani, on speakerphone, claimed the campaign had been too slow to contest election results in Georgia. Clark explained that state law required results to be certified before a recount could be requested, which hadn’t yet happened.

  “They’re lying to you, sir!” Giuliani shouted.

  Clark denied anyone was lying. Suddenly, the two men were shouting loud enough that it startled people waiting outside the Oval Office.

  “You’re a fucking asshole, Rudy!” Clark said.

  Clark had been the campaign’s top attorney for the past year. He’d spent most of 2019 in the weeds of state and national party rulebooks ensuring that it was virtually impossible for any Republican to challenge Trump in a primary. During Trump’s first two years, he ground out long hours as a White House aide. Now, after one phone call from Giuliani, the president was entertaining nonsensical attacks on his ability to read Georgia election code and to give an honest answer to a simple question to the president he’d spent four years trying to reelect.

  Clark stopped going to the White House.

  Meanwhile, Bossie was sidelined with Covid—testing positive one day after he’d been put in charge of the campaign’s legal team. Meadows had tested positive for Covid just before the election had been called, and he was out until mid-November. Hope had been consistently rebuffed when she pitched Trump on scheduling almost anything that didn’t have to do with election fraud—and she had started to pare back her work schedule, as well.

  Senior officials who remained in the West Wing avoided the Oval Office and engaged in gallows humor, coming up with titles for their tell-all memoirs about the final days in office, like Series Finale: The Ugliest Transition.

  Jared considered stepping in to help Clark but saw only the downside. He knew his father-in-law had lost—he and Ivanka had started talking about moving to Miami before the race was even officially called. But he couldn’t bring himself to tell the president to end the fight. Trump was the grandfather of his children. Jared didn’t want to hear his father-in-law complain at every family gathering that a second term might have happened—if only Jared hadn’t gone soft.

  Instead, Jared wanted to avoid the Oval Office at all costs, too, and he left the country entirely. He saw an opportunity for more progress in the Middle East on peace deals, which he thought could potentially be among the lasting legacies of the administration. But Trump wanted him to skip the Gulf Coast Council summit in Saudi Arabia, stay in Washington, and fight alongside him.

  Jared argued to make the trip.

  “I’m probably going to disagree—you’re going to be yelling at me,” Jared said. “We’ve got to have a good relationship going forward. Let me go.”

  “Ok, fine,” Trump said. “Go do it.”

  The same fight between Clark and Giuliani that was attracting eavesdroppers around the White House was also unfolding down in Georgia. Six hundred miles separated the two battles, but both were technically over Georgia election law, pitted Republicans against one another, and Trump was the provoca
teur at the center of each one.

  In Georgia, the campaign had set up a team tasked with finding legal challenges that would improve Trump’s margins. There had been barely any litigation filed during the first two weeks after the campaign’s legal team gathered research and intelligence on what had happened as election officials continued to count ballots. But meanwhile, a parallel track was underway from the Oval Office where Giuliani and Meadows, who was just returning to work after being sidelined by Covid, started bringing in their own people.

  Within days, the parallel teams, both launched at Trump’s request, started converging in Georgia.

  “We’re from the White House,” one attorney said after arriving in Georgia the day after the Giuliani-Clark fight.

  “Well, if you were from the White House I’d know, because I’m from the White House,” said another attorney who had been in Georgia for two weeks.

  Meanwhile, panic was ripping through the Georgia Republican Party and the Republican Senate majority in Washington. Both of the state’s senators—David Perdue and Kelly Loeffler—had failed to win a majority on November 3 and were facing runoff elections on January 5. Republicans needed to win at least one of the two seats to maintain their advantage over Democrats in the Senate.

  For several weeks, Republicans in Georgia—and Washington—had been giving Trump space to process the loss. Now Trump was tweeting about electronic bugs that were changing counts in voting machines. But Trump’s Georgia Legal Team No. 1 had worked the angles in Atlanta to secure recounts that allowed them to trace individual votes to machines. Not a single machine had changed a single vote.