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

by Michael C. Bender

  “What? No, wait—I mean, yes, but stall for me for a minute, Molly,” I said. “I need to find a pen. Um, how are things at the White House today?”

  “Everything is fine,” Michaels said. “The president is waiting. May I put you through?”

  I was patched through and Trump’s distant voice was a clear signal that I was on speaker. Trump told me that he’d just been informed of an article I’d written a few days earlier in the Wall Street Journal about his strategizing with White House and campaign aides over how to respond to criticism of his administration’s handling of the crisis. Kellyanne had been cut out of many of those meetings by Jared and Brad and had used my story as payback. She’d directed his attention to the tenth paragraph, which explained that Trump’s advisers had concluded that a strong counterargument was that no world leader had been exceptionally well prepared to respond. Kellyanne had countered that this was a ridiculous argument because it acknowledged the original criticism and she had urged the president to call and set me straight. Trump explained this all to me as Kellyanne sat next to him in the Oval Office.

  The president’s message, he said, was that he’d handled the pandemic perfectly.

  “I’ve saved hundreds, I’ve saved thousands, actually, they say I’ve saved tens of thousands of lives,” Trump said.

  I wasn’t very interested in litigating a three-day-old story, and I pressed Trump on other topics in search of some news. But Trump mostly wanted to chat. He asked if I’d watched a video he’d posted to Twitter. He mocked a “crazy Charles Blow story” in the New York Times. He asked why he hadn’t seen me at any of his Covid task force news briefings, and if I needed his help getting in. I viewed it as a generous gesture, but one that made him sound like the bouncer at a club instead of the president of the United States.

  But that’s how Trump had been thinking about the news conferences.

  “The number one show on television,” he told me.

  He viewed the news conferences as ratings bonanzas, not a crucial public service to impart critical health information to the American people. Trump laughed that the Fox News show Special Report had become the top-rated program on the network since he started his news conferences, which Fox carried live and often began at about the same time as Bret Baier’s 6:00 p.m. show. Trump asked me what I thought was better: his coronavirus news conferences or his campaign rallies. Then he answered his own question.

  “I have a feeling we reach more people this way than the rallies,” he said.

  “Well,” he said, drawing the conversation to a close, “I’m going out there in about fifteen minutes. I took all my time to study. If I do a lousy job, it’s your fault, because I didn’t have time to read anything.”

  He laughed and hung up.

  After I phoned my editor, I turned my Vespa toward home. A few minutes down the road, my phone rang again with a White House number. I pulled over. It was Kellyanne.

  “That’s how we roll!” she said.

  Two days later, Trump’s political team presented him with a troubling round of new polling. The president trailed Biden in fifteen of the campaign’s seventeen battleground states, including Texas and Iowa. In the other two states, Ohio and Nevada, he and Biden were tied.

  The blitz of attack ads from Democratic super-PACs had barely registered with voters. The data showed instead that Trump’s news conferences were killing him, especially among seniors. Older voters weren’t just an attentive voting bloc, they were also the most at risk for severe health risks from Covid. They were tuning in for up-to-the-minute information about a confusing contagion and instead watching as Trump provided conflicting updates, attacked his opponents, and sparred with the press.

  “They’re not tuning in for you, sir,” Ronna told him. “They want to see their leader. You’ve said you are a wartime president, and now you have to prove it.”

  Ronna was among the few in Trump World willing to consistently level with Trump. She and Trump barely knew each other when he backed her bid for party chairwoman in 2017.1 But she used her influence sparingly and had become one of the president’s longest-running political advisers, particularly among those who didn’t inhabit a branch of the family tree. Her own lineage had prepared her perfectly for the job. When Ronna was twenty-one years old, she worked on the U.S. Senate campaign of her mother, Ronna Romney, who was divorced from her father, the son of former Michigan governor George Romney. But the elder Romney, himself a former presidential candidate, endorsed her mother’s primary challenger. Ronna’s mother lost.

  “There’s nothing I’ve dealt with, even since I’ve been chair, that was as difficult as that experience,” Ronna said.

  The family split still manifested itself two decades later. Her mom’s side of the family was largely supportive of Trump, and the Romney side less so. Senator Mitt Romney, her uncle and the party’s 2012 presidential nominee, said he hadn’t voted for Trump in 2016 and wouldn’t again in 2020, either. Ronna, who had used her Romney maiden name while campaigning for Michigan state party chair, dropped it when she took the party post in Washington.

  Ronna told the president that the news conferences had become less useful and were now hurting him politically. Others on the call, including Jared and Brad, agreed.

  But Trump dismissed their concerns and changed the subject.

  Three days later, Trump used his news conference to suggest that injecting bleach or other disinfectants might cure Covid. “Is there a way we can do something like that by injection inside, or almost a cleaning?” he wondered aloud. The moment was humiliating and became an instant late-night comedy show punch line. But to the relief of many White House and campaign aides, it effectively ended Trump’s daily appearances in the briefing room.

  As April drew to a close, Fabrizio grew more frustrated. He sent a three-page memo to Brad that outlined his case for a sustained attack on Biden. The campaign was at its lowest point in a year. While Trump had been hammered by a “triple whammy” of economic collapse, Covid, and his own handling of the contagion, Biden had largely avoided national media scrutiny and taken his message to local markets. The result was that Biden had rehabilitated his image across the board, but particularly with key voting groups, including white independents, suburban women, and Black and Hispanic voters. More than 50 percent of voters said they had a positive image of Biden, according to internal polling, which was up 20 points in just two months. In February, Biden trailed Trump by five points in the campaign’s target states. Now the Democrat was up eight.

  “We have seen the enemy and the enemy is us,” Fabrizio wrote.

  “There is little chance that we will find ourselves back in the position we were in February without a full-throated engagement of Biden,” Fabrizio wrote. “And there is NO guarantee that in this new post-Covid world, we climb back to where we were.”

  One reason for optimism for Trump World was that huge swings in Biden’s polling during the primary showed that voters could change their opinions about him. But voters had steadfast views about Trump. His approval rating fluctuated, but in a much narrower range than Biden’s, a sign that there was little the campaign could tell voters about Trump that they didn’t already know or suspect.

  For Fabrizio, that meant positive messages about Trump weren’t going to move the needle with voters enough to close the gap. The only way to accomplish that was an advertising campaign on television and online that would put their “do or die” states—Florida, Michigan, Wisconsin, and Pennsylvania—safely into their column, and close the gap in the “must win” states of Arizona, Georgia, North Carolina, Ohio, Iowa, and Texas.

  Brad agreed and told Fabrizio he’d authorize a few million on TV and a few million for digital.

  “Do you have any fear that if I spend too much early, I will be in trouble later?” Brad asked.

  Fabrizio told him the job would only get harder the longer they waited. And if the advertising messaging didn’t work, they would still have time to adjust. But to kn
ow for sure the campaign needed to spend tens of millions on the effort.

  “If you’re convinced that the campaign will conservatively raise $500–$600 million alone and most all of our ground game costs are paid for by the RNC, what are we waiting for?” Fabrizio asked. “If you don’t think we can match Biden dollar for dollar in the final stretch of the campaign, then that might give me pause. But if you think we can, then what is the holdup?”

  Stepien, who would be named deputy campaign manager in a few weeks, weighed in with his support, too. He said Trump would have lost in 2016 if that race had been about him instead of Clinton. Right now, Stepien said, the race was entirely about Trump.

  “It’s not late, but it’s not early either,” Stepien said. “The White House can’t make it a choice and we know the media won’t. It has to come from the campaign. I’m with you.”

  Fabrizio devoted nearly an entire page of his memo to debunking a conspiracy theory that had bubbled up inside Trump World, including with the president, that Democrats were going to steal Biden’s nomination at the convention. The rumor had been discussed to the point that Trump had cited it as a reason to hold off on heavy spending against Biden earlier in the month.

  Dick Morris told Trump that Biden was too old and too prone to gaffes to be the nominee. McLaughlin agreed it was a possibility. Others said Fox News anchor Sean Hannity expressed concern that Biden would collapse under a sustained attack from Trump. The president, meanwhile, had often complained that his early attack on Warren had damaged her presidential bid, which he regretted because he viewed her as an easier opponent than Biden. Now he worried that a heavy blitz of attack ads would hasten the secret plot being hatched by Democrats, and his mind raced with who they might select in Biden’s place.

  “They’re going to realize he’s old, and they’re going to give it to somebody else,” Trump said during a meeting in April with political advisers. “They’re going to give it to Hillary, or they’re going to give it to Michelle Obama.”

  Fabrizio aimed to debunk the theory by outlining the remaining Democratic primaries, in which Biden had no significant challenger, and the delegate math to secure the nomination. Biden would have enough delegates to secure the nomination in just three weeks, Fabrizio explained, and it would be mathematically impossible to steal it in four weeks.

  “I know that there is some concern (which I strenuously disagree with) that if we go after Biden too soon, we can collapse him, and the Dems will replace him at their convention,” Fabrizio wrote in the April 27 memo. “I know POTUS tends to share this opinion. But whether or not they can steal it from Biden is quickly becoming a moot point. And perhaps, POTUS needs to see and understand the timeline.”

  Brad had been waiting for two years to unleash the campaign’s artillery on an opponent, and he used Fabrizio’s memo to start assembling a new presentation for the president as he sat poolside in South Florida. He loved working from home. He’d already been home for three weeks when he officially sent the campaign staff home in mid-March. Brad had an apartment near campaign headquarters in Virginia, but he preferred Fort Lauderdale. He took calls from the pool and laughed when the other person on the line could hear him splashing. His daughter, Alexis, came home from college. And he could spend more time with Candice, his wife, and their two Australian Labradoodles, Jackson and Parker.2

  But back in Washington, Brad’s rivals inside Trump World had started a whisper campaign that used his absence to portray him as disconnected and indolent. Nearly every top lieutenant in Trump World had fought to stay within a few feet of their leader, wary of who might influence Trump in their absence—or shiv them when they weren’t looking. But Brad viewed himself as more than just a staffer. He had a strong working relationship with Ronna. He’d nurtured relationships with Trump’s children and the in-laws. He told Trump that Ivana Trump and Marla Maples, the president’s ex-wives, often phoned to check-in and sometimes share a secret or two about him. Brad described the president to others not as a boss, but as a friend.

  The campaign manager missed the growing coup against him in part because he didn’t think there was anything to complain about. Trump’s numbers were in the tank, but Brad viewed that as a direct result of the president’s pandemic response and a problem for the White House. Brad viewed the pandemic as, theoretically, a political advantage for Trump. The lockdowns should have been a much bigger problem for Biden, who was more reliant on in-person fundraisers that the shutdowns made more difficult. He didn’t take the Democratic National Committee very seriously, and Biden didn’t seem to have any political infrastructure ready. But when it came to Trump’s political operations, Brad’s feelings matched those sunny South Florida afternoons.

  The Trump campaign and the Republican National Committee had spent the past several years and invested tens of millions of dollars in collecting email addresses and cell phone numbers from voters. That kind of information was a commodity for almost any private business by 2020, but it was the lifeblood for the Trump reelection effort, and its digital operation was the beating heart pumping information to every corner of the campaign.

  While Trump himself struggled with how to handle Covid, the campaign had transitioned quite smoothly. That was largely due to the handiwork of Gary Coby, the digital director. In the first weeks of the pandemic, Coby’s team of about 100 people extended their already long tentacles even further into all aspects of the campaign. When the Trump kids and other surrogates stopped holding rallies or traveling on bus tours, Coby’s team made sure their online events attracted millions of eyeballs. The digital team fed new targets and information to Chris Carr, who was overseeing thousands of Republican ground troops across the country. But the most important metric was money, and Coby’s team—which was blasting more than a million texts and email solicitations every day—was crushing it. They collected a little less than $30 million in March, cleared $36 million, then $47 million in May.

  The results exceeded expectations partly because of the makeup of Coby’s team, mostly young and hardworking staffers who had moved back home during the pandemic and, without children or any other responsibilities, worked around the clock. Coby, meanwhile, was a thoughtful and hard-charging boss. He was fastidious and goal-oriented, which ran counter to the self-promotional ideals valued inside Trump World. But he was also ultra-aggressive—he’d left the business for a short time in his twenties to play professional poker—and in the wheelhouse of the Trump demo: a thirty-five-year-old white male with a high school diploma and a blue-collar upbringing.

  Coby’s first break in politics came when he was twenty years old and a member of his church in Bowie, Maryland, a well-known Republican operative named Curt Anderson, helped him land an internship in the U.S. House. Coby worked for various campaigns and private companies until he found himself at the Republican National Committee in 2016. When his boss, RNC chief digital officer Gerrit Lansing, asked if anyone on the team wanted to fly to San Antonio to meet Brad and see the campaign’s digital operation, Coby jumped at the chance.

  Coby was only thirty in 2016, but when it came to digital advertising, he’d had as much experience as anyone in the business. His résumé dovetailed with Brad’s expertise on the creative side of advertising, website building, and digital marketing. The two men dorked out as they dove into the weeds of the digital operations. The next day, Brad was discussing some details with Lansing when he looked up from his computer as if he’d just remembered something.

  “Oh,” he said. “Gary works for me now. I took him.”

  “Okay,” Lansing said.

  Brad never had that discussion with Coby, who just laughed when he heard Brad claim him as an employee. Coby remained on the RNC payroll for the rest of the year, and in San Antonio for much of the next two months. Even when the party’s staff was recalled from that city when negotiations broke down over a joint fundraising agreement between the RNC and Trump, Coby remained. The gesture was meaningful to Brad, and negotiations were settle
d within a couple of days.

  The deal divided proceeds from the text messages and digital ads. The RNC agreed to cover the costs and mandated that the party be the permanent home for Trump’s growing donor file. The Trump campaign also agreed to use Revv, a private company Lansing had started, to process online payments.

  By 2020, Lansing and Coby were partners in multiple companies hired by the Trump campaign. Opn Sesame, which provided text messaging services, sent more than 500 million texts in the final four months, which raised the campaign and the RNC more than $600 million. The company, which earned between seven cents and eight cents per text, was paid about $35 million in those four months, according to internal campaign documents.

  The second company was Revv, which Coby invested in after the 2016 race and by 2020 had been folded into WinRed—the Republican Party’s exclusive online fundraising program. The creation of the potentially lucrative endeavor launched a battle that pitted Republican data geeks against each other, sparked a year of intraparty legal bickering, and exposed tensions at the highest level of Trump World that finally exploded into an intense argument between Ronna and Jared inside the Trump Hotel.

  Jared didn’t think the RNC could pull off the new operation and considered doing it himself. He discussed starting a new company with Brad and Gabriel Leydon, the founder of a California video game company who had informally advised Jared since the 2016 race. Brad said no, and it became increasingly clear that Jared would have to blow up the party to do it.