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

by Michael C. Bender

  Ronna also viewed the project in personal terms and had put her foot down. She hadn’t decided whether to seek a second two-year term as RNC chairwoman and viewed the WinRed deal as a legacy project that could benefit the party for years to come. Keeping the new company as a nonprofit, she told Jared, would make sure it remained as an arm of the RNC.

  Jared wasn’t interested. “I don’t give a fuck about the future of the Republican Party!” he told Ronna inside the hotel meeting room.

  “Good to know,” Ronna shot back. “I will be running for chair for a second term, and I will make sure you don’t come anywhere near this!”

  The eventual agreement formed WinRed. It was a for-profit company but built on Revv’s existing fundraising software and anchored inside the Republican ecosystem. Revv owned 60 percent of the company and the other 40 percent stake was for Data Trust, an information warehouse the party had created the previous decade. Data Trust oversaw a treasure trove of information on the voting patterns and consumer habits of tens of millions of Americans that was easily the RNC’s most valuable resource.

  By early May, Brad finally had Trump’s approval to open fire on the Joe Biden candidacy. He was headed to the White House for a round of meetings on May 7, his first face-to-face with the boss in more than six weeks, when he enthusiastically teased his battle plans on social media and compared the campaign to the moon-sized space station equipped with a planet-destroying laser from Star Wars—ignoring that the weapon had failed to stop the Rebel Alliance and the station had exploded.

  “For nearly three years we have been building a juggernaut campaign (Death Star). It is firing on all cylinders. Data, Digital, TV, Political, Surrogates, Coalitions, etc,” Brad tweeted. “In a few days we start pressing FIRE for the first time.”

  Brad was mocked on social media, but inside the White House, the focus was on what to do about Trump’s convention in Charlotte, North Carolina.

  Ronna wanted Charlotte to work. They had raised about $40 million for the event, money that would have to stay in the city if the party pulled out. Ronna and the city’s Democratic mayor, Vi Lyles, had developed a strong rapport. Their teams had integrated, and more than sixty Republican convention staffers had been living in Charlotte for more than a year making preparations. But Ronna told the president that it was becoming increasingly difficult to raise the final $20 million they needed for the event. Donors weren’t convinced a convention could be planned in the middle of a pandemic, and corporations that were furloughing workers couldn’t justify cutting a seven-figure check. Plus, the party needed at least another $1 million to cover the masks and other personal protective equipment they hadn’t anticipated.

  To Brad, that sounded like a green light to start downsizing. He opposed even asking companies for money during the pandemic—he didn’t think it was a good look. And the truth was he would have happily canceled those first few days of the convention. He wanted to start building the event around the president’s speech, which was the only piece of the convention that he believed would give the campaign a boost.

  But Meadows, the newly installed chief of staff, had been in Trump’s ear, warning him that North Carolina governor Roy Cooper, a Democrat, would try to use the pandemic as an excuse to shut down the convention. Meadows had represented western North Carolina in the U.S. House for seven years before joining Trump’s White House. A sandwich shop owner turned real estate developer, Meadows had shared the ballot during his first race in 2012 with Cooper, who ran unopposed that year for a fourth term as state attorney general.

  “Cooper’s going to screw you,” Meadows told Trump. “He’s a bad actor, and he’s going to be awful.”

  Trump didn’t want a scaled-down convention. This was his moment, and he wanted the full glory of the coronation that hadn’t been afforded to him four years earlier when the four-day convention in Cleveland featured an emotional, public screaming match among several thousand Republican activists over Trump’s nomination, Trump distracting from the festivities when he phoned in to Fox News to trash Ohio governor John Kasich, and Melania Trump plagiarizing from Michelle Obama. And that was just day one.

  At the meeting with Brad in the White House, Ronna told Trump she would continue pushing Cooper’s administration for an agreement on the convention. Brad still had a few items on the agenda, but Trump’s schedule was running late, and the campaign manager offered to let Justin Clark jump ahead of him to go through legal issues over Election Day voting. But instead of waiting around, Brad left the White House, hopped on a plane, and flew home. Flight options were limited during the pandemic, and Brad wanted to spend the night in his own bed.

  Brad knew the six-week stretch without seeing Trump had been too long. But he figured if he came back to Washington once a week—maybe once every two weeks—that would be enough.

  But the ground was shifting underneath him.

  On May 21, a group of anti-Trump Republicans known as the Lincoln Project released a political ad focused not on Trump but on Brad. It was unusual, if not unprecedented, for a political advertisement to attack a presidential candidate’s campaign manager. But by highlighting reports of Brad’s personal spending—and insinuating that he could afford new cars and houses because he was ripping off Trump—the ad had an audience of one: Trump himself. Trump had been second-guessing his decision to slot Brad in as the campaign manager for the past two and a half years. And his anxiety was almost always about the money, just as it had been in their first fight in 2016 when Trump stormed out of his penthouse on the twenty-sixth floor of Trump Tower, took the elevator down to his campaign offices on the fourteenth floor, and steamrolled past cubicles while wildly waving the printout of a story claiming that Brad’s company had collected $96 million from the campaign. But now Trump never came down to the fourteenth floor. He had no idea who was in what office. So he just barked Brad’s name as he stomped across the hall.

  “Brad!” Trump boomed as he walked right past Brad’s office. “Brad Parscale!”

  Brad had never before had Trump rip his face from his skull and made the mistake of quickly closing his laptop and running out to meet the boss. Trump unleashed a stream of insults, accusations, and expletives that seemed to defy basic laws of human biology that state every man must at some point pause to take a breath.

  “That’s my money!” Trump screamed.

  Bossie rushed out of his office and directed the two men into the nearby kitchenette to give them at least a modicum of privacy.

  “Hey!” Bossie yelled back at Trump, trying to interrupt him.

  Kellyanne had now joined the rumpus in the pantry, and she and Bossie explained that Brad’s company was paying for the advertising and marketing. That monstrous sum included some profit, but the cash was almost entirely for expenses that were documented on invoices but not in campaign finance reports.

  Trump’s suspicion that Brad was ripping him off stirred up again in 2019 when a news story surfaced that Brad had been on a shopping spree of South Florida waterfront homes and luxury cars. Trump immediately summoned his campaign manager to his office. Trump hated even the suggestion that someone might be taking advantage of him.

  “What the fuck?” he yelled at Brad, again waving a printed-out news story.

  He told the president that he and his wife, Candice, had suffered a devastating loss in 2015. Candice had been pregnant with their twins, but the babies were born prematurely—almost three months early—and died after only a few days. Brad had spent much of the following year in New York working on the race, and when he finally went home to Texas, his marriage was strained from the pressure of their overwhelming grief.

  What happened, he told Trump, was that he and Candice eventually decided to stay together. Their plan was to sell everything they had—companies, cars, and homes with the furniture, tools, clothes, and everything else in it—and, like so many Americans before them, move to Florida to start over.

  Trump sighed.

  “I just hate thes
e fucking stories,” he told Brad.

  Jared spoke up and vouched for Brad. Brad wasn’t ripping off the president, Jared explained. If anything, he said, it was the other way around.

  “Brad can make a million fucking dollars a month with his marketing skills, and by the way, I’d be the first person to hire him,” Jared told Trump. “You’re getting him for $30,000 a month. So you need to just calm down.”

  Trump relented and Brad survived the moment, but the damage was done. Trump would move on, but not from the suspicion that Brad was ripping him off—the only thing he ever forgot was Brad’s defense. Trump rarely let an opportunity slip by to let his campaign manager know he was on thin ice. The president constantly asked other Republicans if he’d picked the right guy and tortured Brad with a slightly different, but equally consistent, query.

  “What color is that Ferrari again?” he would ask.

  The Lincoln Project knew the Ferrari was a pressure point for Trump. Their intent was to rile him to the point of triggering the kind of chaos that turned off voters. Brad was worried it might work.

  The group had already put out a series of ads that had captured Trump’s attention. Their first spot in March painted the Trump family as profiteers leveraging the presidency for their personal benefit, and highlighted a “billion-dollar bailout” Kushner received from a Qatar-backed investment company to help him pay off a notoriously bad real estate deal. In the first week of May, Trump unleashed a round of furious tweets at nearly 1:00 a.m. after he saw another Lincoln Project spot—this one criticizing his own response to the pandemic—that aired during the Fox News program he had been watching on TiVo. He complained about the spot on social media again later that day, and complained to reporters about it at Andrews Air Force Base.

  “They should not call it the Lincoln Project,” Trump said. “They should call it the Losers Project.”

  Before the president arrived for the meeting in the Cabinet Room, Brad had pulled Pence aside to discuss the Lincoln Project spot attacking him. He addressed the vice president by his first name—a striking informality that immediately raised eyebrows.

  “Mike, if the president believes this stuff about me, then he better believe what’s coming out about Jared,” Brad said.

  Pence stared silently back at Brad as other aides arrived in the room.

  The meeting that morning was with operatives from Trump World and McConnell’s team, part of an effort to keep the two sides on the same page in battleground states for both the presidential contest and Senate races. But Trump was more interested in getting to the bottom of a question he’d been asking for months:

  Why couldn’t anyone tell him where his most crucial staffer in the largest battleground state had been for the past eight months?

  Where was Susie Wiles?

  Wiles was among the few experienced political hands around Trump who had compiled a record of success before 2016. But Brad—at the urging of Ron DeSantis, the Florida governor—had sidelined her without telling Trump.

  Trump credited Wiles for his victory in Florida in 2016, and winning his adopted home state again in 2020 was always at the top of his priority list. The daughter of legendary NFL play-by-play man Pat Summerall, Wiles had soft blue eyes and short, side-parted silver hair, and she had been a guiding hand in the Republican Party’s most important victories during the past decade.

  She managed Rick Scott’s campaign for governor in 2010—when almost no other operatives in the state would work for him. Scott’s hospital chain had paid the nation’s largest Medicare fraud fine—and now he wanted to run for governor in the state with the largest share of Medicare recipients in the country.

  Wiles helped keep the governor’s office in Republican hands in 2018 when she took over DeSantis’s bid for governor with six weeks left in the race. Public polls showed him trailing by 5 percentage points, but DeSantis squeaked by Democrat Andrew Gillum by a margin of 0.4 percent.

  In 2016, Wiles was in charge of Florida for Trump, but their relationship before the victory had been tense. Less than two weeks before Election Day, Trump was in Florida when Wiles told him they were out of money in the state. She needed him to write a personal check for $900,000 to finish their voter turnout program. Trump was furious, and—as they say in Trump World—he ripped her face off her skull. Every insult he could imagine he hurled at her. Wiles was shaken and repeatedly tried to call Brian Ballard, one of the state’s top Republican fundraisers who also ran the lobbying firm where she worked, but he didn’t answer. More shouting. She tried to hold back the tears. And finally, she got the check.

  The next day, Trump was still steaming at a fundraiser at Mar-a-Lago that Ballard had organized. When Ballard arrived, Trump was waiting for him.

  “Your girl doesn’t have it,” Trump said, skipping any pleasantries. “She’s fucking this thing up. We’re going to lose.”

  Ballard chastised him for being such a jerk to Wiles. “You’re going to win if you do what she says,” he told Trump. “And what are you going to do? We’re ten days out. You’re going to fold it up?”

  “If I lose, it’s your fucking ass,” Trump said as he poked his index finger into Ballard’s shoulder.

  Ballard and Trump walked into a ballroom where donors, some of whom had given more than $1 million, had been left waiting for two hours. Trump told Ballard to introduce him quickly—as in seconds.

  “Hey, how are you doing?” Trump said to the donors. “We’re doing good. We’re going to win. But I’ve got to get back on the plane. I’ve got to get out of here and go campaign. Anyone have any questions?”

  Hands shot into the air.

  “No?” Trump said. “Okay. Thanks.”

  Trump walked out, and the donors asked for their money back. Ten days later, Trump won Florida, and all was forgiven.

  Wiles had returned to lead Trump’s reelection effort in Florida, but in September 2019, DeSantis and Brad had teamed up to ice her out. DeSantis’s team blamed Wiles for a story in the Tampa Bay Times that suggested he was trying to sell access to the governor’s office. She denied it, and even some of DeSantis’s allies couldn’t figure out why he’d think Wiles was behind the story. But DeSantis was at the height of his powers as a newly elected governor, and widely expected to seek the presidency after Trump. He leaned on Brad to remove her from the campaign, and he put similar pressure on Ballard to fire her from his lobbying firm. Brad had already openly discussed with others the possibility that he might team up with DeSantis for a 2024 race for the White House. Brad notified Trump World that Wiles had been banished.

  “We’re done with Susie,” Brad told Ronna. “She’s out.”

  Brad never told Trump, but the president asked about Wiles anytime Florida was discussed. When he forgot, Bossie reminded him. When Trump traveled to Florida to visit The Villages retirement community, he asked state lawmakers if they knew where she was. They mostly mumbled.

  He called Ronna.

  “Why isn’t Susie on the ground here?” Trump asked her. “Why don’t you have her here?”

  Trump’s visit wasn’t an RNC event, and Wiles wasn’t an RNC employee—she had worked for him at the campaign.

  “That’s not me,” Ronna told him. “That’s a question for Brad and Governor DeSantis. Because if it was up to me, I’d have her there in a heartbeat.”

  Eight months later, during the campaign meeting in the Cabinet Room, Pence finally spoke up and said that Wiles had been collateral damage in some of the early jockeying for the 2024 presidential race and internal Florida Republican backbiting. Wiles had worked for DeSantis, but she was closer with Scott, who was also regularly mentioned as a potential presidential candidate. DeSantis may have been trying to clip Wiles and, by extension, Scott. Trump seemed satisfied with the explanation, but he still demanded her return.

  “I want her back,” Trump said.

  As the meeting broke up, Stepien sidled up to Trump.

  “I know you’re concerned that Brad has been making m
oney off you,” Stepien told him. “I want you to know I would never do that to you.”

  A few days later, Stepien would be promoted to deputy campaign manager. It was a move that Brad supported—he’d tried to make Stepien deputy campaign manager more than a year earlier—and was designed to help build out some infrastructure underneath the campaign manager for the final five months of the race.

  But it was also a move that foreshadowed greater implications, both for Brad and the campaign.

  That afternoon, Trump was aboard Air Force One on his way to Michigan again. He’d barely left the White House grounds for two months because of the pandemic, and had been growing restless. The Michigan trip, where he would observe a Ford plant producing ventilators instead of car parts, was one of several strategic trips aimed at highlighting his administration’s efforts to respond to the pandemic in key states in the presidential race. As his flight approached the crucial Midwestern battleground, he faced a decision: Should he wear a face mask?

  His administration had already reversed itself on mask guidelines. Early in the pandemic, when high-end N95 masks were in short supply, public health officials said masks weren’t necessary—a statement designed, in part, to prevent a run on the already hard-to-find N95 masks that frontline workers desperately needed.

  “Seriously people—STOP BUYING MASKS!” Surgeon General Jerome Adams had posted on Twitter on February 29.

  That recommendation changed as it became clear the virus could be spread through asymptomatic carriers and that simple cloth face coverings, along with social distancing, could slow transmission. Trump announced the the new mask recommendations at his daily coronavirus news conference on April 3, but made clear that he would personally resist the change.

  “You don’t have to do it,” Trump said, undercutting his own administration’s message even as he announced it himself. “I’m choosing not to do it.”