Castillo insisted on hiring outside advertising firms to produce the TV spots for Hispanic markets—one for ads in the diverse Latino market in Florida and another for Mexican American voters in the Southwest. She formed advisory boards for the coalitions, but insisted that those spots be given to people who actually wanted to work. Board members were required to raise money, become media surrogates for the campaign, or help recruit volunteers for the grassroots army of ground troops the campaign was building with the Republican National Committee. The coalitions department quickly raised hundreds of thousands of dollars and created contact lists with more than 100,000 emails.
Katrina Pierson, a veteran of the Tea Party movement and Trump’s 2016 campaign, had returned to the 2020 campaign as a senior adviser and took an active role in Castillo’s “Black Voices for Trump” coalition. The two women believed the president could make inroads with Black voters if the campaign actively reached out and respectfully explained the president’s record.
“There’s a brand of Black Republican who thinks demeaning Black people by calling them brainwashed by Democrats or stuck on the plantation will somehow resonate—but it doesn’t,” Pierson told Jared. “It only resonates with white people because it’s shit they can’t say.”
Jared was impressed and in 2019 set up a meeting with Pierson, Castillo, and the administration staff involved in outreach to the Black community. That group included Ja’Ron Smith, the West Wing aide Kellyanne had claimed was the White House’s most senior Black employee (Smith also worked in Jared’s Office of American Innovation); Nicole Frazier, the White House director for African American outreach; Henry Childs, the Commerce Department’s director of minority business development; and Ashley Bell in the Small Business Administration. In the meeting, Jared criticized the White House press shop for what he viewed as a failure to communicate the First Step Act’s successful passage. He wanted the group to develop a campaign message for Black voters and assemble a specific and tactical plan to deliver it.
Castillo redoubled efforts on Black Voices, while continuing to roll out other coalitions. The first to be unveiled was Latinos for Trump. For a campaign often fueled on hype, the group’s premiere in Miami on June 25, 2019, was something of a plot twist—it exceeded everyone’s expectations. Vice President Pence was sent to the launch in Miami, and his team initially questioned the campaign’s decision to rent a ballroom in the DoubleTree hotel that could fit 600 people. That was much bigger than the crowds Pence was drawing at his usual stops in Michigan and Wisconsin. But the campaign had already started targeting Latinos, and they had noticed a strong response from South Florida to videos from John Pence, the vice president’s nephew and a fluent Spanish speaker. John Pence, who majored in Hispanic Studies and studied abroad in Nicaragua while at William & Mary, had cut so many Spanish-language videos for social media that some on the campaign nicknamed him “Juan Pence.”
The Pence team could only shake their heads when they arrived at the Miami airport hotel and found the place packed with an enthusiastic and rowdy crowd decked out in red hats, wrapped in American flags, and wearing bedazzled Trump jewelry pinned to their clothes.
“Mike Pence! Mike Pence!” the crowd chanted.
The sober vice president usually drew older, more milquetoast crowds. His staff was unaccustomed to hearing their boss’s name turned into a chorus.
“This is actually happening,” one Pence aide uttered.
The event created a buzz inside the Trump campaign and made kickoff events for new coalition groups a high-profile ticket for the campaign’s top-shelf surrogates, even attracting Trump family members. Lara, Eric’s wife, scheduled meetings with Castillo whenever she was in Washington and set up a biweekly call for progress updates. Lara frequently asked where she could be helpful and made sure that enough resources were available for coalition activities. When the campaign launched its second coalition, Women for Trump, with an event in Pennsylvania—at Valley Forge Casino Resort in King of Prussia—Lara Trump was the headliner. Brad and Pierson showed up, as did Kimberly Guilfoyle, Ronna, RNC chairwoman Ronna McDaniel, and Kayleigh McEnany, the campaign’s press secretary at the time.
That event also impressively drew about 1,000 people. But the costs were considerable. The campaign spent tens of thousands of dollars on advertising and even more on building the stage and sound system. Then there were the travel costs and salaries for the senior campaign staff in attendance. It underscored an unusual level of commitment from a Republican presidential campaign—but also raised eyebrows. It wasn’t how traditional operatives—like Bill Stepien or Justin Clark, both senior advisers at the time—would have allocated those kinds of campaign resources. Still, no one openly objected.
Campaign officials rolled their eyes whenever Jared would ask about the possibility of collecting 20 percent of the Black vote—no Republican presidential candidate had even broken double digits with Black voters since George W. Bush in 2004. But there was plenty of money to experiment, and Jared’s optimism could be infectious. Plus, the coalitions program had become a priority for the family, who jockeyed to launch new groups.
But the splashy blowouts started to drain the coalition budget. When Brad created the coalitions department in March 2019, he set aside $5 million to last until Election Day.
They’d spent it all before the calendar flipped to 2020.
In the early months of the pandemic—before Floyd’s death—Trump’s team had started picking up positive signals from Black leaders that they interpreted as potential softening on the incumbent president.
The reduction in sentences for crack cocaine offenses, which had disproportionately and unfairly targeted Black offenders, reduced prison time by an average of six years for more than 2,000 prisoners. Of those, 91 percent were Black. Trump’s tax-cut bill included specific incentives for investments in poverty-stricken areas, known as opportunity zones. And those incentives were starting to work, according to a study from the Urban Institute. The administration had also made some inroads with historically Black colleges and universities when it canceled repayment of more than $300 million in federal relief loans and made permanent more than $250 million in annual funding.
Al Sharpton, the MSNBC host and civil rights activist, had been secretly calling Trump, promising that his staff would work with the president’s team in the White House—even though he’d later ignore the follow-up calls from Jared’s team. Jesse Jackson, the Baptist minister and civil rights activist, had phoned a few times, too. White House staffers set up calls with Jackson, ministers, and other groups to provide technical assistance for those seeking coronavirus aid from the Paycheck Protection Program, the package of $350 billion in small business loans that Congress had passed in April. They organized a similar call with Surgeon General Jerome Adams to walk through Covid issues for Black community leaders. And more than 600 Black leaders joined a call as White House aides strategized over a push to codify in federal statutes the opportunity zone revitalization council that Trump had created by executive order.
But none of Jared’s efforts to repair Trump’s image with the Black community would matter after May 26, 2020, when the video of George Floyd’s murder began spreading online.
It was the Tuesday after Memorial Day, and senior White House staff gathered inside the West Wing for a prescheduled meeting about coronavirus. The death toll was approaching 100,000 in the United States, and the administration was scrambling to address a shortage of remdesivir, the antiviral used to treat Covid. The mixed messaging coming from the West Wing as aides touted social distancing guidelines while mocking Democratic governors for not reopening their states faster had created its own problem as local and national news showed horrifying scenes of large Memorial Day crowds gathered on Florida beaches and inside East Coast bars.
“We’re getting crushed on Covid,” said Alyssa Farah, the communications director.
Jared, who seemed distracted and more aloof than usual in the meeting, interrupted
her.
“I’m just going to stop you,” he said. “There is going to be one story that dominates absolutely everything for the foreseeable future. I’m already hearing from African American leaders about the death of George Floyd in Minnesota.”
Mark Meadows, the White House chief of staff, brushed it off.
“Nobody is going to care about that,” Meadows told him.
Meadows disputed that he’d responded that way, but it took another day for Trump to watch the devastating video. By then, protests had spilled across multiple U.S. cities. The first demonstrators had gathered just hours after Jared’s warning on Tuesday, creating a makeshift memorial for Floyd outside the convenience store where he’d been pinned to the ground. The crowd of hundreds turned into thousands by that night. They marched two miles from the memorial to the Minneapolis Police Department’s third precinct station. Violence erupted as protesters hurled rocks and water bottles, and law enforcement outfitted in riot gear fired flash-bangs and tear gas canisters. Similar scenes were unfolding on Wednesday in Kentucky, Georgia, and California by the time Scavino loaded the Floyd video on his phone and handed it to Trump on Air Force One.
Trump sat in the president’s suite near the front of the plane. He was returning from Florida, where poor weather had scrubbed SpaceX’s attempt at becoming the first private company to launch a human crew into orbit. It was an outing for the whole Family Trump: Melania, Jared and Ivanka, Don Junior and Kim, Eric and Lara, and a collection of grandkids had all come. As Trump pressed Play on the video, he was surrounded by Jared, Scavino, National Security Adviser Robert O’Brien, and his media team.
Trump contorted his face as he watched. He looked repulsed, then turned away, and handed the phone back to his aides without finishing.
“This is fucking terrible,” he blurted out.
Trump said he wanted to speak immediately with Attorney General Bill Barr, and dictated a tweet to Scavino, which Trump posted after Air Force One landed.
“My heart goes out to George’s family and friends,” Trump said in the post. “Justice will be served!”
Trump was still shaken by the video the next afternoon when Barr arrived in the Oval Office on Thursday to brief the president about Floyd’s death, now three days later. Trump had tweeted the night before that he planned to expedite the probe from the Justice Department. The only effect of the tweet, however, was to politicize the issue and infuriate Barr, who hated the suggestion that his interest in the case was political or the idea that anybody was his boss. It was the opening fissure in the relationship between the irascible and stubborn septuagenarians.
“This is fucked up,” Trump told Barr about Floyd’s death in a meeting that included Jeffrey Rosen, the deputy attorney general, and a room full of other aides.
Barr pointed to some potential complications, but Trump didn’t want to hear them.
“I know these fucking cops,” Trump said, recalling stories he’d heard growing up in Queens about savage police tactics. “They can get out of control sometimes. They can be rough.”
Trump’s assessment struck some in the room as surprisingly critical of police, and the president showed a level of empathy for Floyd behind closed doors that he would never fully reveal in public. Had he tried, it might have helped dial down the tension. But Trump didn’t see it as part of his job to show empathy, and he worried that such a display would signal weakness to his base.
After his briefing with Barr, Trump told reporters in the Oval Office that afternoon that he didn’t like watching the video. When they asked him if he’d spoken to Floyd’s family yet, Trump said he hadn’t.
“That was a very bad thing that I saw,” the president said. “I saw it last night, and I didn’t like it.”
But Trump’s compassion quickly evaporated that night as he watched demonstrators torch a Minneapolis police station and the protests spread to New York City; Denver; Phoenix; Columbus, Ohio; and Memphis, Tennessee.
At nearly 1:00 a.m. on Friday, May 29, Trump made a dramatic pivot from empathy for Floyd’s family as he posted a racially charged threat of violence against the protesters.
“These THUGS are dishonoring the memory of George Floyd,” he wrote on Twitter. “When the looting starts, the shooting starts. Thank you!”
The tweet mortified staff inside the White House and at the campaign. The phrase dated back to the 1960s and the hardline Miami police chief Walter Headley, who aimed it at “Negro hoodlums.”
Twitter executives took action. They determined that Trump’s post glorified violence, which was a violation of the site’s terms of service, and for the first time blocked a message on Trump’s Twitter page. That meant other users were prevented from replying to it, liking it, or sharing it with others. The tech company’s drastic action was becoming a trend. Just days earlier, Twitter had applied a fact-checking notice to Trump’s false claim about voter fraud.
Trump either saw no difference between the peaceful protesters and the rioters or simply didn’t care. Inside the White House, Meadows had been chief of staff for just six weeks and a new communications team had been ushered in with him. They frantically tried to convince Trump to walk back his tweet. But there was an art to convincing Trump to reverse himself. He would never admit he’d been wrong, so a different approach was needed. Farah tried to appeal to his political interests, describing herself as the kind of educated female voter who was open to supporting Trump but needed to be convinced.
Trump wasn’t persuaded.
McEnany, meanwhile, seemed to have an instinct for communicating with Trump. She framed the fix as merely explaining why the liberal media had either misunderstood or deliberately misconstrued Trump’s post. Trump finally sent a second tweet more than thirteen hours after the first.
“Looting leads to shooting,” Trump wrote in the post, as he claimed that the first tweet wasn’t a threat—it was merely a considerate warning that sometimes lootings are violent.
It wasn’t convincing, but at least it was a walk-back.
Trump finally called Floyd’s family that day.
“Terrific people,” he told reporters Friday afternoon.
But the family remembered the call a little differently. Philonise Floyd, George Floyd’s brother, told MSNBC that the call was “so fast” and that Trump “didn’t give me an opportunity to even speak.”
“I was trying to talk to him,” Philonise said during an interview on Sharpton’s program. “But he just kept, like, pushing me off, like, ‘I don’t want to hear what you’re talking about.’”
That night, protests erupted for the fourth consecutive time since Floyd’s death.
In Georgia, Republican governor Brian Kemp declared an emergency after demonstrators poured into Atlanta’s Centennial Olympic Park and smashed windows. Others climbed on top of the large red CNN logo outside the company’s headquarters, spray-painted it, and raised a Black Lives Matter flag. In Richmond, Virginia, a police cruiser and a city bus downtown were both set on fire. Violence flared in New York, injuring protesters and law enforcement.
Violence was escalating, but not in a way that Trump World had expected. In Oakland, California, a gunman shot and killed Dave Underwood, a fifty-three-year-old federal security officer guarding a federal courthouse. At a news conference about the murder, Chad Wolf, Trump’s acting homeland security secretary, and Ken Cuccinelli, who was Wolf’s deputy secretary, talked about Antifa and connected it to the Black Lives Matter protests. But the two men eventually arrested for the killing had ties to the far-right extremist “Boogaloo” movement that sought to instigate a second Civil War. Steven Carrillo, a thirty-two-year-old Air Force staff sergeant, was charged with murder, and Robert Justus Jr., a thirty-year-old he’d met just a few hours earlier, was charged with aiding and abetting.
But Trump had no time for nuance. Crowds were also closing in on the White House, and a burst of violence erupted Friday evening near Lafayette Square, the historic seven-acre park just north of the White
House. The park featured President Andrew Jackson’s statue on horseback—the world’s first equestrian statue balanced solely on the horse’s hind legs—and had been used at various points as a graveyard, a zoo, and an encampment for slaves who built the White House.
Law enforcement in riot gear sprayed chemical irritants at protesters in the park who threw water bottles and rocks and tugged at the police barricades. One demonstrator climbed a window ledge at Freedman’s Bank Building—a historic building on the edge of the park—and gripped the protective iron bars with one hand while using the other to write “Fuck Trump” in purple spray paint.
When a group of protesters breached a barricade along the Treasury Department fence and the White House lawn at about 7:00 p.m., Secret Service locked down the White House. The president, his wife, and his youngest son, fourteen-year-old Barron, were hurried into a secure underground bunker under the East Wing of the White House—the same shelter that Vice President Dick Cheney had used on September 11, 2001, when authorities feared a plane hijacked by Al Qaeda might be heading toward the White House.
The Trumps remained in the basement bunker for about an hour.
On Saturday morning, Trump tweeted that he’d never felt unsafe. He insisted that he’d watched “every move” of the protests. He never mentioned his retreat to the bunker.
Jared and Brad had been suggesting all week that Trump address Floyd’s death with a speech. They wanted to feed him lines that would make him appear more empathetic for the families involved in the senseless deaths and leaven the overly aggressive law-and-order message. But Trump’s error-filled Oval Office address about coronavirus a few months earlier was still painfully fresh for too many other White House aides. Trump’s advisers also had no new policy proposals to pitch to address the crisis. And ultimately, Trump had no interest in delivering a message of unity.
“Frankly, We Did Win This Election”: The Inside Story of How Trump Lost Page 18
