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

by Michael C. Bender

  Once Trump took office, Urban proved to be a pipeline for critical positions in the new administration. Two of his recommendations were fellow cadets from his West Point class of 1986, both Esper and Pompeo, who became Trump’s first CIA director and spent the final thirty-three months of the administration as secretary of state.

  For Urban, removing the monuments was a guaranteed political win. Other than the Confederate officers, no other bases were named after military leaders who attacked the United States. Urban framed it to Trump as a rebranding opportunity. Use the bases, he said, to memorialize Medal of Honor recipients instead of insurrectionists. The change would give him a political tailwind and help cool the temperature of an already overheated racial debate.

  “That’s a pretty good idea, actually,” Trump said.

  “It’s a great fucking idea,” Urban responded.

  Esper also signaled his willingness to change the base names, the first time the military had opened the door on the conversation. Then Trump slammed it shut. He’d heard from other aides, including Meadows, that changing the base names would hurt him with his base.

  “Our people hate this,” Trump told two Cabinet officials. “Changing the names? We’re not doing that.”

  After the Senate Armed Services Committee, with bipartisan support, approved a measure that would strip Confederate names from the bases, Trump posted on Twitter that he would veto the military spending bill if lawmakers included the action.

  In 2016, Trump built his law-and-order message on three main pillars: stopping illegal immigration, confronting China to bring high-end manufacturing jobs back to the United States, and pulling the plug on endless wars.

  It was a powerful pitch for military voters and particularly persuasive for the families, friends, and loved ones of soldiers who died fighting in Afghanistan and Iraq, and it may well have tipped the balance to Trump in 2016. In a little-noticed research paper seven months after that election, two university professors, who had spent a decade studying the socioeconomic gap between military families and the rest of the country, showed that Trump dramatically overperformed in disadvantaged communities where voters have shouldered a disproportionate burden of the human cost of national security.

  Bannon told me after the 2016 race that the campaign had targeted blue-collar communities with a high rate of combat casualties, using social media advertising and Trump political rallies.

  “It was one of the most important things we did,” he said.

  Trump had kept the country out of any new armed conflicts. Still, he’d insisted on bringing 1,600 active-duty troops to Washington to fight his political battles—and that number would have been closer to 10,000 had it not been for the pushback from Milley, Esper, and Barr. In the days after St. John’s, Mattis, Trump’s former defense secretary, loudly criticized the scene as an abuse of executive authority, and he accused Trump of creating a “false conflict between the military and civilian society.” Two days later, John Kelly—by then out of the White House and a vocal critic of Trump—said he agreed with Mattis. Kelly said there was no “mature leadership” in the White House and that Trump wasn’t even trying to pretend to unite the country.

  “The partisanship has gotten out of hand—the tribal thing has gotten out of hand,” Kelly said at the time.

  Military veterans still preferred Trump over Biden, but not by the margins Trump needed to win reelection. Exit polls ultimately showed that his seven-point margin against Biden in 2020 was down from twenty-seven points against Clinton in 2016 among veterans.

  Footnotes

  1 Trump’s fury burned for days, and he repeatedly asked Meadows if he’d found the leaker. Meadows, in turn, obsessed over tracking down the source. It was the lasting memory of the ordeal for many West Wing aides.

  2 Morrison quickly called for an investigation. Park Police never identified the two officers and said their investigation was still ongoing a year later.

  10

  Juneteenth, Observed

  “I did something good—I made Juneteenth very famous.”

  —Interview with author, Oval Office, June 17, 2020

  By early June, as Trump stewed amid negative coverage of the worsening pandemic and deepening recession, it was clear to campaign aides that they needed to get their candidate back on the road again, and soon. Brad had suggested a drive-in rally in Florida, but Trump hated the idea. Brad then pushed for an outdoor event in the state, but Trump told him that Florida Governor Ron DeSantis didn’t want to host a rally at that point in the pandemic.

  Brad had been scheduled to present the campaign’s plans for TV advertising on June 9, and Trump said he wanted the meeting to also include an update on potential rally locations. The discussion in the White House Map Room included about a dozen aides, plus Trump, Pence, and Mike Lindell, the Minnesota entrepreneur who had overcome a crack cocaine addiction, founded the MyPillow company, and been a vocal Trump supporter in 2016. He’d become a close adviser to Trump heading into the reelection.1 Trump admired the success Lindell had selling pillows with infomercials, and Brad wanted Lindell there to attest to the brilliance of the advertising campaign.

  “You need to go in there and you need to tell the president that the TV team is doing a good job,” Brad told Lindell before the meeting.

  Brad’s prep work paid off. Trump turned to Lindell as soon as the presentation had finished.

  “Mike, are they doing a good job?” Trump asked.

  “Yes, they’re doing great!” Lindell said. “I’ve talked to them before, and they’re talking to my team.”

  The meeting then turned to a discussion about rallies, and Brad presented a list of eleven potential locations in six different states: Arizona, Florida, Michigan, Oklahoma, Pennsylvania, and Wisconsin. Nearly all of the sites were outdoors. Brad pushed again for Pensacola. He told Trump that he’d spoken to DeSantis, and that the governor would back down if the president called him again. But Trump didn’t want to make the call. Florida was off the table.

  Pennsylvania, Michigan, and Wisconsin were all governed by Democrats and Trump World didn’t want to repeat the problems they’d had planning the party’s convention in Charlotte. They didn’t blame Covid for their convention issues. They blamed Roy Cooper, the state’s Democratic governor.

  Trump and his team were convinced that Democratic governors in battleground states were playing politics with social distancing guidelines, refusing to loosen protocols in a way that would let him hold the kind of mega-rallies that had become a physical manifestation of his political strength.

  But waiting until the pandemic was under control was simply not an option.

  Scale back rallies? Hope would tell him he’d be mocked for capitulating to critics in the media. Models from the scientists showing Covid deaths increasing would draw sneers from Meadows. “You look weak in a mask”—that was the refrain from Johnny McEntee.

  That left Tulsa, Oklahoma, which had landed on Brad’s list after he asked Pence earlier that week about which state, governed by a Trump-friendly Republican, had the fewest Covid restrictions.

  Tulsa also had the smallest coronavirus caseload of any of the options, reopening efforts were the furthest along, and the Mabee Center—the 11,300-seat arena Brad proposed that day—had been the location of a Trump rally during the 2016 campaign.

  Trump was sold.

  An indoor rally, however, immediately raised the question of face masks. There was debate about whether they would require masks, and Brad suggested printing a few thousand face masks with campaign branding. Trump rejected both ideas.

  “No, we don’t need to give out masks to everyone,” he said.

  Brad recommended holding the rally on June 19. He loved Friday night events, but rallies those nights were rare because the campaign often had to find open days between concerts, basketball games, and other traveling road shows that had been booked months in advance. Brad floated the date inside the campaign, but not to an extensive circle. No one o
n Brad’s team flagged that day—or that combination of time and place—as potentially problematic. Had Brad bothered to ask Katrina Pierson, the highest-ranking Black staffer on the campaign and a close friend of Brad’s, she could have told him that June 19 was Juneteenth, a significant holiday for Black Americans that commemorated the end of slavery.

  She also would have told him that Tulsa, as most Black Americans are well aware, had been home to one of the bloodiest outbreaks of racial violence in the nation’s history. She’d have explained that it had only been two weeks since Floyd had been killed, that protests over police brutality, which disproportionately had fatal consequences for Blacks were still boiling over across the country every night, and that holding a rally in the middle of a civil rights crisis on Juneteenth in the same city as the 1921 Tulsa Race Massacre was unwise.

  Meanwhile, in the White House, Ja’Ron Smith—the West Wing’s senior-most Black official—had been working on an executive order for Trump to declare Juneteenth a federal holiday. But no one had thought to ask him, either.

  When Richard Walters heard about the plans on a conference call that day with the campaign, the Republican National Committee’s chief of staff’s eyes widened. Walters, who started out with a low-level job at the party as a twenty-three-year-old out of college, grew up in the Deep South, about fifteen miles east of the Mississippi state capitol and some three hours south of Oxford, where he attended the University of Mississippi. He wrote his college thesis on the effect of systemic racism on education policy, and he knew what the Juneteenth holiday meant to Black Americans. And he didn’t need Wikipedia to know that some 300 people were killed in Tulsa—and an entire Black neighborhood, including 1,200 homes, destroyed. He urged the campaign to reconsider immediately, and Ronna, as she often did, had his back.

  “Don’t do this,” Ronna told Brad. “The media is not going to give us the benefit of the doubt, especially now.”

  There was time to change the date, or reconsider plans entirely. The campaign hadn’t yet signed contracts with vendors or the arena, or even publicly announced the event. But Brad dug in. What he lacked in campaign experience, he filled in with overconfidence in what he viewed as his own unlimited ability to win hearts and change minds. If Juneteenth was such an important holiday, Brad reasoned, then Trump should be at the center of the festivities.

  “This is a holiday that’s supposed to be about celebration and acknowledging that slavery is over,” Brad said. “I’m not going to let the media frame that narrative.”

  Brad discussed it later with Jared. Neither one told Trump.

  The next day, June 10, Trump had a single item on his public schedule: a 12:30 p.m. intelligence briefing. But, as was often the case with the Trump White House, that changed suddenly without any significant notice. At 3:30 p.m., the White House summoned whichever reporters hadn’t wandered too far from their briefing room desks and quickly ushered them into the Cabinet Room, where Trump sat with Jared and, as Trump described them, Black friends of his. That included Ben Carson, Trump’s housing secretary; Darrell Scott and Kareem Lanier, the founders of the Urban Revitalization Coalition; and Republican gadfly Raynard Jackson, who had sued the party over the trademark for “Black Republican Trailblazer Awards Luncheon,” which he believed that he, not the GOP, owned.

  “We’re with friends of mine and members of the African American community,” Trump said. “And we’re going to be talking about law enforcement, education, business, health, and various other things.”

  For the next half hour, Trump didn’t articulate any particular policy that would address any of those issues. He condemned the “defund the police” movement growing out of the Black Lives Matter protests but said little else that would indicate any consideration of future policymaking.

  The one thing Trump did talk about most extensively that afternoon: his return to rallies. It’s where he turned the conversation immediately after introducing the group as his Black friends, but before mentioning a single one of their names.

  “We’re going to start our rallies back up now,” Trump informed the press. “The first one, we believe, will be probably—we’re just starting to call up—will be in Oklahoma.”

  As reporters were ushered out of the room, one journalist asked Trump when he was going to Tulsa.

  “It will be Friday,” Trump said. “Friday night. Next week.”

  Juneteenth.

  Trump’s pronouncement put the campaign on high alert but, at least initially, not because of the date. They hadn’t signed the contract for the arena yet or finalized a slew of other details. But that drama would soon be overtaken when Democrats went on the warpath. Trump, they said, couldn’t be more insensitive to the world erupting all around him. If you weren’t hunkered down inside your own home hiding from Covid, you were probably out on the streets protesting police brutality. Trump seemed to be thumbing his nose at both with a campaign rally on Juneteenth.

  The backlash shocked Trump. He started quizzing everyone around him.

  “Do you know what it is?” Trump would ask.

  He didn’t have a single Black senior adviser around him to ask.

  “Nobody had heard of it,” Trump told me in an interview just days before the rally.

  During the interview, he was surprised to find out that his own administration had put out statements in each of his first three years in office commemorating Juneteenth.

  “Oh really?” he said. “We put out a statement? The Trump White House put out a statement?”

  Each statement, put out in his name, included a description of the holiday.

  The day after announcing his Juneteenth rally, Trump escaped Washington and flew to Dallas for a fundraiser with about two-dozen attendees, collecting about $10 million for the reelection effort. He woke up in Bedminster the following morning as the cable networks continued hammering him for the Juneteenth rally. That night, Trump turned to a Secret Service agent, who was Black, and asked him about Juneteenth.

  “Yes,” the agent told Trump. “I know what it is. And it’s very offensive to me that you’re having this rally on Juneteenth.”

  At 11:23 p.m. that night, Trump posted on Twitter that he wanted to change the date. In the tweet, and later to me during our Oval Office interview, Trump would exaggerate the number of people who’d personally asked him to reconsider.

  “Many of my African American friends and supporters have reached out to suggest that we consider changing the date out,” he posted on Twitter.

  Trump moved the rally back a day, to Saturday, June 20, but never considered canceling it.

  The electric, capacity-crowd Trump rallies had become the signature events of his conservative movement. And the potential to bring even hundreds of thousands of people to Tulsa—at a time when there were no baseball games, no concerts, no large gatherings of any kind—would serve as a potent reminder of the fervor and passion that Trump commanded across America.

  On the afternoon of June 17, the Wednesday before the Tulsa rally, my phone vibrated with a call from the White House. By the third month of work-from-home orders, I was healthy, but fully ensconced in lockdown mode. Face unshaven for two months and hair unsheared for twice as long, I wore a pair of grungy khaki shorts and a tattered orange T-shirt from a long-ago family reunion. My afternoon cup of coffee almost finished, I was hustling to file a front-page story for the Wall Street Journal from my bedroom. The room my wife and I had once used almost exclusively for sleep now doubled as our cramped home office during the day, as well as a sort of clandestine cafeteria where we regularly ate lunch in order to escape the grabby fingers of a toddler in our nanny share on the first floor, and to not disturb my nine-year-old on the second floor, who was spending much of her summer synchronizing iPad games and FaceTiming with her friends.2 The White House call pierced the sanctuary of my bedroom-turned-workspace.

  “Any chance you could get to the White House, like, now?” asked White House communications director Alyssa Farah. “The
president just asked for you.”

  I quickly showered, slipped on a dark suit, and knotted a tie around my neck for the first time since March 10, my last day in the office. Within thirty minutes I arrived at the north gate of the White House where a staffer from the medical unit awaited visitors from inside a canvas tent. He checked my temperature, inquired about any experiences I may have had with a list of symptoms, and waved me through. Inside the West Wing, the crew of young, unmasked White House press assistants mocked my long hair and bearded face. A military paramedic asked me to sign a consent form, explained the pros and cons of the Abbott testing machine approved under the Emergency Use Authorization, and told me a positive test, God forbid, would be relayed “all the way up to POTUS.”

  He held up a swab. I held my breath.

  As the machine that resembled a cross between a photo printer and a hand-held credit card reader analyzed my nasal secretions, I sat in the West Wing lobby frantically scribbling questions for the most powerful man in the world.

  After twenty minutes, White House press secretary Kayleigh McEnany appeared and flashed me a warm, wide, and toothy smile.

  “You saved the day,” she told me.

  At the time, I wasn’t sure what she meant. I interpreted her comment simply as appreciation that I’d rushed over to the White House on a moment’s notice, which was, in fact, the one thing I’d asked them not to do to me. Two months earlier, when the president and Kellyanne had called to dissect one of my articles, Trump had invited me to the White House for an interview. That sparked weeks of back and forth with McEnany and Farah over schedules, my request to bring other Wall Street Journal reporters with me, and whether we could have cameras in the room. But after more than a month of struggling to get straight answers on any of those questions, I ultimately retreated to a single plea: Please just don’t call me in the middle of my work-from-home nightmare and give me a five-minute notice. Yes, Farah had assured me, that’s a completely reasonable request.