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

by Michael C. Bender

  Trump would take more than four dozen questions over the next ninety minutes. The first one was why he didn’t want to wear a mask.

  “I just don’t want to wear one,” Trump said, and added again that it was a recommendation, not a requirement. “I think wearing a face mask as I greet presidents, prime ministers, dictators, kings, queens, I don’t know. Somehow, I don’t see it for myself. I just—I just don’t. Maybe I’ll change my mind, but this will pass and hopefully it’ll pass very quickly.”

  At the Ford plant in Michigan, the policy was that everyone on-site needed to wear personal protective equipment, including masks. The car company informed the White House of that requirement ahead of the president’s visit. But Trump remained reluctant. He sat behind the chevron-shaped desk in the president’s office on Air Force One and polled his aides, who were spread out along the leather couch that lined the wall and in the leather captain’s chairs on the other side of his desk. Meadows, Scavino, Hope, Derek Lyons, Johnny McEntee, and Kayleigh McEnany all urged him not to wear a mask.

  Jared said he thought the mask was a good idea. His daughter, Ivanka, and Melania, the first lady, had both made a point of wearing masks in public.

  Trump was intrigued, and he summoned Ronna, who was seated farther back in the plane.

  “Should I wear a mask?” Trump asked her.

  “Yeah,” Ronna told him. “I think you should wear a mask.”

  Meadows, Scavino, Hope, and McEntee immediately interjected, criticizing Trump for even considering the idea. Trump had made his decision not to wear a mask and, they argued, he could not reverse himself now just because of pressure from the media. They spoke as if the mask contained kryptonite and Trump would lose his superpower with his base as soon he looped one behind his ears.

  “The leader of the free world shouldn’t wear a mask,” Meadows said.

  “It’s embarrassing,” Scavino added.

  Ronna was startled. She was also planning the 2020 Republican National Convention, which meant she was closely reading coronavirus guidance and protocols from the Trump Administration and in the states. When she had fallen ill in March with Covid-like symptoms, she had alerted people she had been in contact with that she might have the virus. Testing at that time was not prevalent, and it could take weeks to receive the results. She told her team at the RNC that it was the responsible thing to do and asked for help to spread the word to the people with whom she’d met.

  Meadows called her at home. “Ronna, we think it’s wrong to share that you’re getting this test,” he told her.

  Now Ronna looked around the Air Force One cabin and saw mostly white men prepared to defend Trump to their last breath. Those voters were never going to leave Trump’s side.

  “Why?” Trump asked Ronna. “Why do you think that?”

  “I’m the exact voter you need to win over, and suburban women will love it,” she told Trump. “You’re going to a state with a high Covid rate, and it will set a good example. They’ve also asked you to do it.”

  Jared backed her up. “I think Ronna could be right,” he said.

  Trump was intrigued by the rare alignment between his son-in-law and the party chairwoman. “Bring me the mask,” he said.

  He had tried on a white mask before and didn’t like it. But the new White House masks were navy blue, with the presidential seal in the lower left corner. He looped the cloth straps around his ears and adjusted the mask over his nose and chin.

  “Well?” Trump said. “What do you think, Ronna?”

  “Yeah,” Ronna told him approvingly. “I think you should wear a mask.”

  Trump did put the mask on, but only once he was behind closed doors at the plant.

  Later, a reporter asked him why he didn’t wear the mask on the public part of the tour.

  “I didn’t want to give the press the pleasure of seeing it,” Trump said with the briefest of smirks.

  The next week, Richard Walters, the chief of staff at the Republican National Committee, sat in the lobby of Trump International Hotel griping into the iPhone pressed against his ear. It was the second month of lockdowns,3 and he was losing his mind over the havoc the pandemic was causing—especially to the Republican convention he was planning.

  The convention he and Ronna had spent the past two years planning was falling apart. Cooper’s administration in Raleigh had plenty of leverage to require Trump’s Republicans to meet every coronavirus protocol that the president was often willfully ignoring. As much as Walters and convention officials tried to negotiate, Cooper wouldn’t give an inch.

  Walters arrived at the hotel on May 27 for a meeting with Susie Wiles, who had been trying to rebuild a consulting business and was there to meet with Walters and some clients. She saw him on the phone, nodded, and stood off to the side.

  “Guys!” Walters yelled into his phone. “It’s never going to work in North Carolina. The governor doesn’t want us there. He’s told us point-blank that it’s not going to work.”

  Wiles knew an opportunity when she saw one.

  “You know,” she told Walters. “If things don’t work out in Charlotte, we’d love to have you in Jacksonville.”

  Walters scoffed. Trump didn’t want to change cities, and Walters didn’t particularly want to go to Jacksonville.

  But just a day later, the offer from Wiles didn’t seem so funny.

  On May 28, Ronna and Walters had reached their breaking point with Cooper. They had a convention meeting scheduled with Trump the next day and decided they needed to bring him some alternatives. The only way changing locations had a chance of working this late in the process was to find a city with a Republican mayor in a state with a Republican governor. They would have to grapple with the pandemic no matter what and wanted to eliminate any risk of partisan flare-ups. But that political calculation severely restricted where they could go. Ronna’s convention team considered Orlando, but Orange County mayor Jerry Demings wasn’t just a Democrat, he was married to Representative Val Demings, whom Biden was considering as a running mate. Tennessee governor Bill Lee wanted to help bring the convention to Nashville, but Mayor John Cooper was a Democrat. Texas governor Greg Abbott suggested Dallas. Same issue. The one city that they kept coming back to: Jacksonville. Walters called Wiles.

  “I know you were joking yesterday,” Walters said. “But… were you?”

  Wiles made a round of calls, and reported back nothing but optimism.

  Ronna and Walters brought the news to the president the next day.

  Trump, who had refused even to consider downsizing the convention just three weeks earlier, not only signed off on exploring Jacksonville, but floated the possibility of an even more drastic shift.

  “Maybe even something virtual?” he suggested.

  Walters felt dizzy. Trump’s extraordinary indecision seemed to trigger a momentary bout of vertigo. But the Republican operative collected himself, and booked a flight to Jacksonville for June 1. Ten days later, Trump announced plans to relocate the convention there.

  Footnotes

  1 One of Trump’s favorite rally stories was how Ronna repeatedly called him in 2016 to say he’d win Michigan, her home state, by making just a few more campaign stops there. It was a flattering story, but nary a word of it was true. Ronna had said that Trump could win Michigan, but aside from a brief encounter at a rally that year, the two had never spoken.

  2 Both dogs were named after San Antonio Spurs stars, Stephen Jackson and Tony Parker.

  3 Except at the Trump Hotel, which could always seem to find an open room for some friends of the president.

  8

  Law and Order

  “When the looting starts, the shooting starts. Thank you!”

  —Twitter, May 29, 2020

  The sun was setting on a clear and balmy Memorial Day when a forty-six-year-old Black man walked into Cup Foods market at the corner of Chicago Avenue and Thirty-eighth Street in South Minneapolis. He’d been out of work since March when stay-at-h
ome orders cost him his job as a bouncer. He’d been infected with the virus that had caused his restaurant to close. Now he was about to pay for a pack of smokes with a counterfeit $20 bill. And for the briefest of moments, George Perry Floyd Jr. was in the clear.

  But when the teenage clerk behind the register spotted the forgery, Floyd refused to return the cigarettes. Soon, four police officers were on the scene, including Derek Chauvin, a white cop with red flags spilling from his personnel file. Chauvin pinned Floyd chest down on the pavement, handcuffed his wrists behind his back, and knelt on the nape of his neck.

  “I can’t breathe,” Floyd pleaded more than twenty times.

  Chauvin wouldn’t budge.

  Less than ten minutes later, Floyd was dead.

  Witnesses with cell phones documented every agonizing moment of Floyd’s horrific death, from his desperate pleas for mercy to his final cries for his mama. The next day, Minneapolis police chief Medaria Arradondo fired all four officers, and criminal charges soon followed. But that was like bringing a water pail to a forest fire. The nation’s loathsome history on civil rights had no shortage of gruesome and tragic events, but it was quickly apparent that the sheer cruelty of Floyd’s murder, captured on video for the world to see, would be a breaking point.

  From the Oval Office, Trump struggled to calibrate a response to match the enormity of the moment. Few of his top advisers specifically represented—or even really understood—working-class Americans, much less Black Americans. In the White House, the closest Trump had to an adviser on regular Americans was probably Kellyanne, who was raised by her mother, grandmother, and two aunts in a New Jersey working-class home and worked for decades as a pollster for many of the Republican Party’s most populist candidates. But even she couldn’t come up with the full name of a single staffer when she was asked in 2018 on NBC’s Meet the Press to identify the seniormost Black official in the Trump White House.1

  Trump’s response was also impaired by his stunning disregard for history, particularly compared to most other modern presidents. Senior officials described his understanding of slavery, Jim Crow, or the Black experience in general post–Civil War as vague to nonexistent. But Trump’s indifference to Black history was similar to his disregard for the history of any race, religion, or creed.

  On his way to Paris to commemorate the hundredth anniversary of the First World War armistice, for example, Trump listened as John Kelly, his chief of staff at the time, reminded the president which countries were on which side during the conflict. Kelly continued the discussion by connecting the dots from the First World War to the Second World War and all of Hitler’s atrocities.

  “Well, Hitler did a lot of good things,” Trump told Kelly.

  When I asked Trump about the remark, he claimed the conversation had never happened, and he denied praising Hitler. But others said the remark stunned Kelly. The chief of staff told the president that he was wrong, but Trump was undeterred. Trump pointed to Germany’s economic gains once Hitler took over as chancellor. Kelly pushed back again and argued that the German people would have been better off poor than subjected to the Nazi genocide.

  “Even if it was true that he was solely responsible for rebuilding the economy, on balance, you cannot ever say anything supportive of Adolf Hitler,” Kelly told Trump. “You just can’t.”

  Even if Trump hadn’t internalized the lessons of history, much of the country seemed to understand the moment and viewed Floyd’s senseless killing as only the latest in a shameful series of Black deaths. In 2020 alone, twenty-five-year-old Ahmaud Arbery was killed during a jog near his South Georgia home by two white men, who said Arbery looked like a suspect in several break-ins in the area. Two weeks later, twenty-six-year-old Breonna Taylor was shot dead by Louisville police during a botched raid on her apartment. Floyd’s death was a reminder of those tragically avoidable killings, and the countless before them, as well as the painfully debasing racism to which Black Americans were regularly subjected. The frustration and anguish that had accrued after decades of daily racial indignities had been emphatically—finally—cracked open by Floyd’s death, and protesters poured into the streets of the nation’s capital and major municipalities.

  What was unique about the videos capturing Floyd’s death were that they also somehow awakened white Americans to what their fellow Black countrymen had long known. The Black Lives Matter protests were joined by large numbers of white men and women, too—young and old, city dwellers and suburban residents—and the demonstrations had support from the vast majority of Americans regardless of race, religion, or economic status. Corporate America rushed to adapt, as Quaker Oats Company canceled its Aunt Jemima brand, NASCAR banned the Confederate flag from its races, and the NFL’s Washington Redskins changed their name to the Washington Football Team until they had time to come up with an alternative.

  More than 15 million Americans attended protests in the first week. Black men wept on live television. Kaleth Wright, the top Black enlisted airman in the Air Force, spoke publicly about how the sight of blue police lights in his rearview mirror made his heart race “like most other Black men in America.”

  “Who am I?” Wright posted on Twitter. “I am a Black man who happens to be Chief Master Sergeant of the Air Force. I am George Floyd… I am Philando Castile, I am Michael Brown, I am Alton Sterling, I am Tamir Rice.”

  But Floyd’s death was more significant than even that grisly chronology. If it was racially motivated police brutality that killed him, it was the systemic racism of the nation’s economic and health systems that had pushed him—struggling with money and infected with Covid—to that street corner in the first place. Floyd also embodied the disproportionate toll exacted on Blacks from a historic economic collapse and deadly pandemic.

  Centuries of racial inequality in the job market meant that Black Americans were more likely to work in the hospitality, construction, and transportation fields, which suffered the highest layoffs during the pandemic. But Blacks were also more likely to be employed as Instacart shoppers, nursing assistants, and other undervalued jobs that were suddenly deemed “essential” to prop up the economy’s remains. Long-standing residential segregation and redlining policies meant Blacks were more likely to live in crowded conditions—a problematic situation when the federal government was urging people to stay six feet apart because the virus was so contagious.

  Blacks infected with Covid were more likely to experience harsher symptoms since they suffered a higher rate of diabetes, heart disease, and lung disease—three conditions present in a combined 90 percent of Covid-related hospitalizations. Their hospital costs were also less likely to be covered by health insurance. The health insurance gap between Blacks and whites had started to narrow under the Affordable Care Act. But those gains vanished as Trump made it a priority to dismantle his predecessor’s signature domestic legislative achievement.

  In 2020, Blacks were 2.6 times more likely than whites to be shot and killed by police and 2.5 times more likely to be impoverished. When it came to Covid, Blacks were 1.1 times more likely to be infected, 2.9 times more likely to be hospitalized, and 1.9 times more likely to die from it. For 46.8 million Black Americans, a life-threatening crisis seemed to lurk around every corner. Their deep frustrations over generations of racial tension now had a fresh layer of anxiety stemming from coronavirus.

  The country had turned into a tinderbox. And inside the Oval Office was a president who liked playing with matches.

  The groundwork for Trump’s response to Floyd’s death had been laid years earlier.

  Consider the Wednesday evening in North Carolina during the spring of 2016, when loathing and contempt swirled through the rowdy Trump rally crowd at Crown Coliseum, the 8,500-seat home of the Fayetteville Marksmen hockey club. The crowd’s candidate was center stage in a dark suit, the knot of his powder blue tie pushed tightly against the top button of his crisp white shirt, but their prolonged and resounding chorus of boos was aimed directly at Rakeem
Jones.

  A twenty-six-year-old Black man in a white T-shirt with long dreadlocks, Jones, who delivered pizzas for a living, raised his middle finger in the air and followed Cumberland County sheriff’s deputies as they escorted him out of his seat.

  But as Jones ascended the arena’s cement steps, he was blindsided in the right temple by the flying forearm from John McGraw, a seventy-eight-year-old white man in a fuchsia shirt, leather vest, and cowboy hat. Known to friends as “Quick Draw,” McGraw made leather gun holsters that he sold at flea markets and had been sitting a few rows behind Jones’s group. As they were leaving, McGraw quickly shuffle-stepped down his aisle, past a dozen or so Trump supporters, and reached the steps just in time to slam the stranger viciously in the face.

  The crowd gasped as Jones stumbled back. He stayed on his feet, only to be pinned to the ground by four officers once he reached the top of the stairs. McGraw, meanwhile, returned to his seat and watched the rest of the show. Police only arrested McGraw days later when cell phone videos posted online showed him bragging that he enjoyed “knocking the hell out of that big mouth.” Trump had used the same language a few weeks earlier in Cedar Rapids, Iowa, when he urged supporters to “just knock the hell” out of any protesters in their midst and promised to pay their legal fees.

  The night after Fayetteville, Trump traveled to Chicago, the city with the nation’s second-largest Black population, for a rally at the UIC Pavilion. Several progressive groups, including Black Lives Matter, had organized protests outside the arena and sent demonstrators into the event with anti-Trump signs hidden under their clothes. Skirmishes erupted, and Trump eventually canceled the event as security struggled to maintain order. But more violence flared up as protesters celebrated, and Trump supporters grew angry and frustrated. A bottle struck one officer in the head. Dozens were bloodied and bruised. Sopan Deb, an Indian American who had been covering Trump since the start of the campaign for CBS News, was slammed to the pavement and handcuffed without warning by two Chicago police officers as he recorded footage of the protests. When video emerged showing Deb had done nothing wrong, Chicago police dropped the charge of resisting arrest.