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

by Michael C. Bender

  13 Dollman was named operations director of Trump’s reelection in 2017 and became chief financial officer of the 2020 campaign.

  13

  The Trump TV Convention

  “With a heart full of gratitude and boundless optimism, I profoundly accept this nomination for president of the United States.”

  —Convention speech, South Lawn, August 27

  After Pence had explained to Trump that the smothering of Susie Wiles was a vicious opening salvo of the 2024 presidential race, Ronna had revealed that Wiles had been secretly helping the party with convention planning in Jacksonville. Wiles agreed to provide her help free of charge, which let the party keep the arrangement off the books and out of public campaign finance reports that DeSantis and his team might have seen.

  In early July, Trump finally called the Florida governor.

  “What’s the deal with Susie?” Trump said on the call. “She won Florida for me.”

  “Well, that’s just like saying the batboy won the World Series for you,” DeSantis responded.

  But Trump had had enough, and he decided to hire her back. On July 2, he dictated a tweet from inside the Oval Office that his team posted on the campaign’s social media account. The tweet was unsigned but the author’s voice was unmistakable.

  “Susie Wiles (@susie57) was a very important part of how we Made Florida Great Again with @realDonaldTrump in 2016 and it’s tremendous to welcome her back to the team. We will win Florida again going away!”

  DeSantis was furious when he saw the news back in Florida and immediately phoned Trump, who ignored three consecutive calls and finally answered on the fourth. The conversation quickly grew heated.

  “This isn’t your fucking decision,” Trump told DeSantis. “Stay out of it.”

  Amidst all the tumult inside the campaign and surrounding the convention, Trump finally wore a mask in public.

  The moment came during a July 11 visit to the Walter Reed National Military Medical Center, where he met with wounded soldiers and health care workers caring for Covid patients. The virus had infected more than 3.2 million Americans and killed at least 134,000 by the time Trump slipped around his ears the bands of the navy blue face covering that matched his dark suit and was embossed with a gold presidential seal in the bottom left corner. He walked the halls of the hospital with his trademark squint, giving his best Clint Eastwood impression but with his mouth shielded for medical purposes instead of clenching a cigar.

  Polling showed that as many as 80 percent of Americans supported wearing masks outdoors, and Trump’s political team celebrated the victory over White House advisers who had repeatedly urged him not to cover his face. Few voters had blamed Trump when coronavirus started to spread. But his refusal to remain focused on the deadly pandemic had put his polling in free fall for two months—a 4.4 point deficit with Biden in May in the RealClearPolitics national poll average had nearly doubled to 8.6 points on the day Stepien was promoted in July.

  Yet Trump was proud of how he looked in the mask and sought feedback from aides in the days that followed. About a week after his visit to the military hospital, Trump asked Tony Fabrizio, his chief pollster, if he’d seen the public images of the mask-clad president. Fabrizio had repeatedly pushed Trump to don a mask and support a national mask mandate that would demonstrate his seriousness when it came to stemming the contagion.

  “A lot of people said maybe it looked weak,” Trump said.

  “It didn’t make you look weak, it made you look strong,” Fabrizio said.

  Trump nodded and walked toward the White House briefing room for a news conference. But he paused and turned back to offer his pollster one more concession.

  “I promise I won’t call it the Kung Flu,” Trump said. “Because I know you don’t like that.”

  “It’s not about my personal opinion,” Fabrizio said. “When you call it the Kung Flu, you’re demeaning people who take it seriously. And it makes it sound like you’re not taking it seriously.”

  “Yeah, I’ll just call it the China virus,” Trump said.

  “Well,” Fabrizio said, “that’s not good, either.”

  Jason Miller, Trump’s communications strategist, asked Fabrizio how quickly Trump’s polling would improve now that he’d publicly worn a mask. Fabrizio chortled at Miller’s optimism.

  “This is like a guy who smoked for twenty-five years, suddenly stopped, and then wants a lung X-ray and asks if it’s all clear now,” Fabrizio said. “It doesn’t work that way.”

  “We’re the fucking doctors,” Miller shot back. “So we gotta prescribe something.”

  “The prescription stays the same: Stick with it,” Fabrizio said.

  But Trump wouldn’t take his medicine. After a political meeting ended inside the Oval Office at the end of the month, Trump introduced his team to Dr. Scott Atlas, a radiologist who had been chief of neuroradiology at Stanford University Medical Center and had advised Giuliani during his 2008 presidential bid. Atlas had denounced lockdowns and embraced the idea of herd immunity, which would let the virus spread freely under the assumption that most of the population would quickly build resistance to the contagion. His persistent criticism of Dr. Anthony Fauci, the administration’s top epidemiologist who had been a vocal advocate for masks and social distancing, earned him frequent appearances on Fox News.

  Trump asked Atlas to share his Covid prediction with the campaign team.

  “Coronavirus is going to be gone by September,” Atlas said. “By the end of September, it will be a memory.”

  “See?” Trump said. “What did I tell you?”

  “With all due respect, Mr. President, I don’t think that’s correct,” Fabrizio said.

  “This guy’s an expert!” Trump said.

  Trump hired Atlas as a coronavirus adviser in the White House a month later. Atlas’s controversial theories and aggressive behavior quickly became one of the few things that could unite Trump World.

  Fauci complained to colleagues that Atlas was a “total nutcase.” Even Kayleigh McEnany, the White House press secretary, who had her own casual relationship with the truth, had been reluctant to cite him.

  “I’m worried he’s a little fast and loose with the facts,” she told her team.

  Inside the White House, much of Atlas’s hostility was directed at Dr. Deborah Birx, a global health expert on immunology and vaccine research whom Trump had brought into the White House earlier in the year to help coordinate the administration’s Covid response. Atlas attacked her suggestions on social distancing guidelines in emails he would blast across the administration, and shouted at her in private meetings.

  In one meeting inside the West Wing in late August, Birx expressed concern about the upcoming Labor Day holiday weekend and suggested that the White House remind the American people to practice social distancing. She wanted to prevent a spike in Covid cases heading into the fall.

  “You just want to shut down the country!” Atlas shouted. “I speak for the president, and we are not shutting down the country!”

  Birx glared back at him. “That’s fine, but just know that you are killing people,” she said.

  The rest of the room sat in stunned silence.

  “Well,” Jared said. “It’s good to have a robust debate.”

  Despite Trump’s battle with DeSantis over Wiles’s return to the campaign, convention planning had been coasting along in Jacksonville. One of the biggest questions early on from the RNC was whether there would be enough lodging to accommodate all the visitors. The city had hosted a Super Bowl in 2005 and immediately suggested the same solution they had used that year: seven massive cruise ships docked along the St. Johns River.

  But there had been too many headlines about cruise ships infected with Covid in 2020—and no one wanted to live through a rehashing of Trump’s hostile refusal to care for sick passengers in a callous attempt to keep a lid on the number of Covid cases in the country.

  “Absolutely not,” said Walters, the
RNC chief of staff. “It’s a nonstarter.”

  Ultimately, the hotel issue had mostly solved itself as it became quickly apparent that a full convention would be impossible. The risks seemed to be growing, and Ronna was alarmed. There was no escaping the urgency of the situation when she traveled to Jacksonville in mid-July for a walk-through of venues the party wanted to use for the convention. When she and her team pulled into the parking lot of TIAA Bank Field, the 67,000-seat pro football stadium Republicans were considering for the convention, they were greeted by an hours-long line of cars waiting for drive-through Covid tests.

  “Holy crap,” Ronna said.

  She felt responsibility for her party’s activists. The average age of their convention delegates was over sixty-five, which increased the odds of severe illness from the virus. Some had told her they were nervous about traveling. But others were ready to risk it all to give Trump the show of support they knew he desperately wanted, and to make sure he wasn’t embarrassed again like he had been in Tulsa. One delegate pledged his attendance despite a medical condition that made him susceptible to Covid’s most dangerous symptoms, and told Ronna that he considered his participation to be on par with going to war.

  “No!” Ronna said. “This is not going to war. And we don’t want you to die going to the convention and fighting for our president.”

  Ronna had regretted not acting more forcefully with Trump about the Juneteenth rally. She could have taken her concerns about the date directly to him, but instead stayed in her lane and everyone got burned. The convention was clearly her jurisdiction and she wouldn’t make the same mistake again.

  Ronna called Trump. “We can give you the best speech—we can build the best stage,” she said. “But if one person leaves and dies, it will overwhelm anything we do.”

  Trump paused. He’d been strident and unequivocal in public about reopening the country, but the surge of sickness in Florida had spooked him.

  “It’s not the right time,” he said. “We should not be doing this.”

  Stepien, Meadows, and Jason Miller were patched into the call. The decision was made to cancel the in-person convention in Jacksonville. Trump said he’d make the announcement the next day at the Coronavirus Task Force news conference.

  Still, there were doubts within Trump’s inner circle about whether he’d go through with it. He’d been anticipating the convention for months and was known for making last-minute reversals.

  The next day, about a half hour before the news conference, Stepien called his team with an update: “This is actually happening.”

  Trump stood behind the lectern in the White House briefing room and described his reluctant decision. His political team, he claimed, had practically begged him to hold the convention online.

  “I have to protect the American people,” he said. “That’s what I’ve always done. That’s what I always will do. That’s what I’m about.”

  Trump’s announcement that he was pulling the convention from Jacksonville—made at the top of a White House press briefing—was news to the rest of the convention team and just about everyone else involved in the planning in Jacksonville.

  As attention moved to where they would hold the now virtual convention—now just weeks away—Trump floated the possibility of giving his speech at Gettysburg, and privately inquired about other national monuments. But there was no time for the kind of prep work and security measures that would be needed for those locations.

  By the end of July, less than four weeks from the convention, the Trump campaign still had no program for four nights of a prime-time, made-for-TV convention featuring the nation’s first reality TV star turned president. No pressure.

  The campaign needed to slot in people who were up for the job, but the president was also a prickly pear, and they knew they needed people who made Trump feel comfortable, knew his voice, and understood his politics. The answer, as it almost always was for personnel decisions in Trump World, was to hire people with previous experience—good or bad—working for Trump. That meant bringing in Sadoux Kim, a former co–executive producer of The Celebrity Apprentice, to oversee production and logistics from a war room/control room set up inside Trump International Hotel, but also Cliff Sims, the former White House director of message strategy—whom Trump had sued the year before—to handle speechwriting duties for almost all of the ten-plus hours of programming.

  To assemble the programming, Jared tapped forty-four-year-old Tony Sayegh. The son of politically attuned Lebanese immigrants, he had long ears, brown eyes, and dark black hair turning gray at the temples. Sayegh was a vice president at Jamestown Associates when the Trump campaign landed in his portfolio in 2016. After a good word from Judge Jeanine, who had once employed him on her Fox News show, he joined the Treasury Department as an assistant secretary and returned to the White House in 2019—taking a brief absence from a consulting gig at Teneo—to assist the White House during impeachment proceedings. Sayegh earned high marks from both Bannon and Jared, which was no easy task, and was generally well liked by the people who worked under him. He was also extremely competitive with his peers. The race to replace Hope as White House communications director in 2018 grew so vicious that Sayegh and the other contender were both eventually disqualified and the job went to Stephanie Grisham, whom he then tussled with during impeachment proceedings. The Sayegh-Grisham rivalry played itself out again during convention planning as events in the East Wing, controlled by the first lady’s office, where Grisham had returned, were canceled and rescheduled without any explanation. No one bothered to ask for one, either.

  Sayegh assembled a convention team of some of the most capable hands to find their way into the Trump White House. Despite well-earned headlines about record West Wing turnover and woefully miscast roles—six national security advisers in three years, an explosive eleven-day run as White House communications director for Anthony Scaramucci—some corners of the West Wing had been quietly populated by steady hands, who, behind the scenes, worked to keep the trains running. One of those was Adam Kennedy.

  Kennedy joined the White House as a deputy research director and left in the spring of 2020, just before coronavirus lockdowns set in, as the No. 2 official in the communications office. He avoided the TV cameras while supervising a rapid response team of thirteen people he’d assembled during the Mueller hearings, and put back together for the Senate impeachment trial. His work earned high marks from Republicans in Congress, who were constantly frustrated by their struggle to extract any guidance or game plan from the White House. Sayegh took notice and reached out to Kennedy, who had joined an outside conservative firm.

  Sayegh also brought in Steven Cheung, who had worked in PR for the Ultimate Fighting Championship before finding his way to the Trump campaign in 2016. Cheung followed Trump to Washington, where he kept a low profile in the communications shop, while playing a key role in some of Trump’s most notable successes, including the confirmation of Supreme Court justice Neil Gorsuch and the overhaul of the tax code, where he worked closely with Sayegh.

  And then there was Cliff Sims, whose return to Trump World was surprising, but not shocking. One of the few aides with access to Trump both during the campaign and at the White House, Sims left the administration in 2018 after John Kelly, then the chief of staff, accused him of secretly recording the president. Sims denied it, then wrote a tell-all memoir of his time with Trump that brought a seven-figure payday—and a lawsuit from the Trump campaign. Trump accused him of violating a nondisclosure agreement and Sims sued Trump, accusing him of improperly blocking former employees from invoking their First Amendment rights. The two sides eventually settled.

  A teetotaling Southerner who used expressions like “Oh my gosh” and “Golly,” Sims remained in contact with Jared and Hope. They told Trump that Sims’s book wasn’t an attack on him; it was a critique of the infighting around him. When Kellyanne learned Sims was back in the fold, she asked Trump if that was such a good idea after what had ha
ppened the first time.

  “I heard it wasn’t so bad for me as it was for you,” Trump shot back.

  With a convention team in place, Sayegh’s first task was a meeting with Vince Haley and Ross Worthington, the two main White House speechwriters. Much of Washington associated Stephen Miller, the steely-eyed anti-immigration provocateur, with the wordcraft behind the president’s teleprompter. White House flacks like Hogan Gidley insisted that every speech was 100 percent Trump’s own words. But the truth was that Trump rarely wrote anything longer than a few words scribbled with a black Sharpie on a printout of a news article he would then sign and send to whichever aide, Cabinet member, or journalist he was either praising or blaming for the story. In reality, from the very start of the administration, Trump’s speeches were being written by two Newt Gingrich acolytes: the fifty-three-year-old Vince Haley, who had managed the former House Speaker’s 2012 presidential campaign, and Ross Worthington, who was deputy communications director on that presidential bid and, two years later, coauthored the former speaker’s book Breakout: Pioneers of the Future, Prison Guards of the Past, and the Epic Battle That Will Decide America’s Fate.

  It wasn’t just the Washington press corps that missed the rise of Haley and Worthington. It was a well-guarded secret inside the West Wing and, for months, kept even from the president himself. Miller had indeed penned Trump’s speeches during the final months of the 2016 campaign, and the two spent so much time together that Miller knew the president would throw a fit if he tried to phase himself out of the speechwriting. Trump viewed himself as a complex personality and intricate thinker whose worldview couldn’t be easily shoehorned into traditional definitions of conservative and liberal. But Trump was a creature of comfort, immensely more at ease with the devils he knew. Nothing tasted as good as dinner at a Trump hotel restaurant. No bed was as restful as his own. And he didn’t know Haley, and he didn’t know Worthington. So even though the two men were clearly identified as the highest-paid speechwriters on the White House payroll from Day One, Miller kept the arrangement from Trump so he could continue to free himself up to focus on his true passion—immigration policy. The plan was to slowly introduce Trump to Haley and Worthington. They started attending meetings, then started traveling, and eventually, Trump got to know them and trust them.