Trump had staked nearly his entire campaign in 2016 around a law-and-order image, and now groaned that the criminal justice reform that Kushner had persuaded him to support made him look weak and—even worse—hadn’t earned him any goodwill among Black voters.
“I’ve done all this stuff for the Blacks—it’s always Jared telling me to do this,” Trump said to one confidante on Father’s Day. “And they all f—— hate me, and none of them are going to vote for me.”
The weekend after Father’s Day, Trump canceled a trip to Bedminster at the last minute—after Kushner had already left for the New Jersey golf club—and instead scheduled a round of political meetings at the White House without him.
A month after the murder of Floyd, Trump was dumping on his son-in-law, and he was also abandoning the chance to improve his relationship with Black leaders and Black voters during a particularly tumultuous moment in U.S. race relations and the presidential campaign. The story of this month, from the murder of Floyd to Trump’s assertion that his outreach to Black voters wasn’t working, is one of missed opportunities and bungled messaging, even in the eyes of some of Trump’s closest advisers, who described their firsthand accounts with me during the past year. Many of the sources spoke to me on the condition of deep background, an agreement that meant I could share their stories without direct attribution.
Trump had long struggled with addressing the nation’s racial issues, and his senior staff hadn’t included a single Black staffer since he’d fired Omarosa Manigault Newman—a former contestant on his reality television show—at the end of 2017. In August 2018, White House counselor Kellyanne Conway had been asked on NBC’s Meet the Press to name the top Black official in the Trump White House and could only come up with his first name: Ja’Ron.
But Ja’Ron Smith was two pay grades below the top ranks. After Conway’s interview, Smith asked for a promotion to formalize his role as the West Wing’s senior-most Black official and close the $ 50,000 salary gap. Kushner agreed but then put him off for the next two years.
Still, Smith remained in the White House, where he continued to work on Kushner’s criminal justice issues and played a crucial role in outreach to Black community leaders. In June 2020, Smith was writing a proposal for Trump to make Juneteenth a federal holiday. But the outcry over Trump’s rally on the day that commemorated the end of slavery convinced Smith to shelve the plan.
Trump hadn’t thought to ask his seniormost Black official about holding a rally on Juneteenth.
Trump’s first test at addressing the country’s racial tensions came in the summer of 2017. On a Saturday in August, 32-year-old Heather Heyer was killed, and 19 others injured, when a 22-old neo-Nazi drove his souped-up 2010 Dodge Challenger at about 30 miles per hour into a crowd in Charlottesville, Virginia. Heyer, who was white, and the others were protesting a white supremacist rally organized to oppose the removal of a statue of Robert E. Lee, a Virginian who commanded the Confederate States Army during the Civil War. Trump had been golfing at his Bedminster club that morning. It had been about two hours since Heyer’s death, and Trump said he wanted to “put out a comment as to what’s going on in Charlottesville.”
“We condemn in the strongest possible terms this egregious display of hatred, bigotry, and violence on many sides—on many sides,” Trump said.
The White House tried in vain to focus cable networks and newspaper reporters on the first words of his statement instead of the final phrase—“on many sides”—that he’d ad-libbed and then repeated. But the obvious question they couldn’t answer was how the president could put any blame on the peaceful counter-protesters. His remarks seemed to justify the white supremacist violence, and Trump’s silence over the next 24 hours unnerved even those around him.
Back at Trump Tower in New York two days later, Trump had a news conference scheduled to discuss the nation’s infrastructure. Responding to questions about Charlottesville, he again blamed the counterprotesters.
“You had some very bad people in that group, but you also had people that were very fine people, on both sides,” Trump said.
The next day, Stephen Schwarzman, a longtime friend of Trump’s and chief executive of Blackstone Group, called the president and told him he had disbanded the White House Strategic and Policy Forum, a coalition of businesses chaired by Schwarzman that Trump had convened in February 2017 to advise him on economic issues. There weren’t enough executives left who would stand by Trump after his repeated failures to adequately address Charlottesville, Schwarzman said. Trump hung up and beat his friend to the punch by quickly tweeting that he was shutting down the panel.
Gary Cohn, the president’s top economic adviser—and a registered Democrat—was even more despondent. Raised Jewish on the East Side of Cleveland and a longtime New York resident, he stood next to Trump for the infrastructure news conference and grew increasingly alarmed and uncomfortable. Later, in a private meeting inside the Oval Office, Cohn unloaded on the president.
Cohn told Trump that his lack of clarity had been harmful to the country and that he’d put an incredible amount of pressure on people working in the White House. He told Trump that he might have to quit. No one backed Cohn up. Others in the room, including Pence, remained quiet.
Cohn returned to his office after the meeting broke up. Following a few minutes behind, Pence climbed the flight of stairs and appeared at the threshold of Cohn’s door.
“I’m proud of you,” Pence told him, safely out of earshot of the president.
An even bigger test for Trump came on May 26, 2020.
Ironically, in the early months of the COVID-19 pandemic in 2020, Trump’s team had started picking up positive signals from some 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 him, which left the president with the impression that their staffs should work together. But the follow-up calls from Kushner’s team would go unanswered. Jesse Jackson, the Baptist minister and civil rights activist and one-time presidential candidate, had phoned a few times, too.
And more than 600 Black leaders joined a call as White House aides strategized over a push to codify the opportunity zone revitalization council that Trump had created by executive order.
But none of Kushner’s efforts to repair Trump’s image with the Black community would matter when the video of George Floyd’s murder began spreading online.
The morning after Memorial Day, 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.
“We’re getting crushed on Covid,” said Alyssa Farah, the communications director.
Kushner, 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, according to officials in the room. Meadows disputed this version of events.
It took another day for Trump to watch the devastating video of Floyd’s murder aboard Air Force One, where he was returning to Washington from Florida. Trump sat in the president’s suite near the front of the plane. As Trump pressed “play” on the video, he was surrounded by Kushner, social media director and deputy White House chief of staff Dan Scavino, National Security Adviser Robert O’Brien and his media team. Trump contorted his face as he watched. He looked repulsed, then turned away. He handed the phone back to his aides without finishing.
“This is f—— terrible,” he exclaimed.
Trump said he wanted to speak immediately with Attorney General Bill Barr.
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 prickly and stubborn septuagenarians.
“I know these f—— 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.
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.
“These THUGS are dishonoring the memory of George Floyd,” he wrote on Twitter. “When the looting starts, the shooting starts. Thank you!”
Later, Jackson said during one of his calls with Trump that the president said he was considering attending Floyd’s funeral. Jackson dissuaded him from that idea, telling the president that he had barely spoken to the family after Floyd died. Trump had reached out to the Floyd family four days after his death in a call that relatives later criticized as brief and one-sided. Jackson told Trump that it would have been disrespectful to then turn up to the memorial service.
Trump agreed—and it was the last time he and Jackson spoke for the rest of the year.
As Trump stewed amid negative coverage of the worsening pandemic, the deepening recession and now the racial justice protests, it was clear to campaign aides that they needed to get their candidate back on the road again, and soon.
In early June, Trump gathered a dozen of his top White House staffers and campaign aides—plus Mike Lindell, the MyPillow company founder and a vocal Trump supporter—to discuss the campaign’s television advertising strategy and a return to the campaign trail. Trump admired the success Lindell had selling pillows with infomercials, and Brad Parscale, his campaign manager, cornered Lindell before the meeting and urged him to attest to the brilliance of the advertising campaign.
Parscale’s prep work paid off. Trump turned to Lindell as soon as campaign staffers finished their presentation on the advertising strategy.
“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 Parscale presented 11 potential locations in six different states: Arizona, Florida, Michigan, Oklahoma, Pennsylvania, and Wisconsin. Nearly all of the sites were outdoors.
But Florida was off the table. Parscale suggested a drive-in-style rally in Central Florida, but Trump said Governor Ron DeSantis didn’t want a big crowd in his state during the pandemic. Parscale urged Trump to call DeSantis and tell him it was safe, but Trump refused.
No one liked the options in Arizona—the weather was too hot for an outdoor rally, and a spike in Covid cases precluded indoor venues—and Pennsylvania, Michigan and Wisconsin were all governed by Democrats. That left Tulsa, Oklahoma, which had landed on Parscale’s list after he asked Pence earlier that week about which state, governed by a Trump-friendly Republican, had the fewest Covid restrictions in the nation. The Mabee Center—the 11,300-seat arena Parscale proposed that day—had been the location of a Trump rally during the 2016 campaign. Trump was sold. (Parscale moved the venue to the 19,000-seat Bank of America Center after ticket requests shot through the roof, a result of both a prank from TikTok teens and a campaign decision to blast the announcement out to supporters across the country.)
Parscale recommended holding the Tulsa rally on June 19. No one on Parscale’s team flagged that day—or that combination of time and place—as potentially problematic. Had Parscale bothered to ask Katrina Pierson, the highest-ranking Black staffer on the campaign and a close friend of Parscale’s, she would have told him that June 19 was Juneteenth, a significant holiday for Black Americans that commemorated the end of slavery. She also would have said to 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.
When staffers inside the Republican National Committee heard about the plans, they immediately pushed back.
“Don’t do this,” Ronna McDaniel, the RNC chairwoman, told Parscale. “The media is not going to give us the benefit of the doubt, especially now.”
There still 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 Parscale dug in. Parscale’s only previous campaign had been Trump’s 2016 bid. Still, what the marketing and advertising veteran lacked in political experience, he filled in with overconfidence in what he viewed as his unlimited ability to win hearts and change minds.
On 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 Kushner and, as Trump described them, “friends of mine and members of the African American community.” 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.
Trump said the meeting had been called to address law enforcement, education and healthcare issues. But for the next half-hour, Trump didn’t articulate any particular policy that would address any of those issues. The one thing Trump did talk about most extensively that afternoon: his return to rallies.
“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 planned to be in Tulsa.
“It will be Friday,” Trump said. “Friday night. Next week.”
Democrats went on the warpath. Trump, they said, couldn’t be more insensitive to the world erupting all around him. 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. Now, the rally on Juneteenth threatened to exacerbate the racial fissures further.
The backlash shocked Trump. He started quizzing everyone around him.
“Do you know what it is?” Trump would ask.
Two days after announcing his rally, 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.
The following week, on the afternoon of June 17, my phone vibrated with a call from the White House. It was a few days before Trump’s Tulsa rally, and the president wanted to see me.
In our interview, one year ago this week, Trump tried to put a spin on the controversy. He told me that he had made Juneteenth a day to remember.
“Nobody had heard of it,” Trump told me.
He was surprised to find out that his 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.
But such details were irrelevant to him. Instead, he insisted, “I did something good.”
“I made Juneteenth very famous,” he said.
Trump would arrive in Tulsa to a half-filled arena. Parscale had hightailed it out of the backstage area when he saw Trump and the White House entourage approaching—no one had told the president that the BOK Center wasn’t anywhere close to capacity.
Before rallies, White House aides usually inflated crowd sizes for Trump once they were told a capacity crowd was inside the building. On the way to Tulsa, no one knew how to break the disappointing news to Trump. It wasn’t until he was backstage and turned on the television that he realized the arena was two-thirds empty.
When Trump finally took the stage that night, he urged his latest audience to forget the past several months. From the rally stage in Tulsa, Trump sought a fresh start for his reelection bid.
“So we begin, Oklahoma,” the president would tell them. “We begin. We begin our campaign.”
But the truth was the campaign had begun long ago. What was actually beginning now, for Trump, was the end.
Adapted from ‘Frankly We Did Win This Election’: The Inside Story of How Donald Trump Lost by Michael C. Bender.
Author: Michael C. Bender
This post originally appeared on Politics, Policy, Political News Top Stories