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

by Michael C. Bender

  The week before the Republican convention was set to start, Trump paid close attention to the Democratic show. He was not a fan of what he saw. He was bored by the pace of the evening and the speeches he watched, and on the third night—just five nights before the opening of his own convention—he ordered across-the-board cuts to the lengths of all the speeches. No one objected, except for Trump’s own children. Don Junior had already finished his speech. Ivanka was not about to be treated like all the rest. Hope agreed to increase time for them both, under one condition: They couldn’t tell anyone else in the family, or then everyone would want more time.

  But most of the speechwriting hadn’t been finished anyway. Many drafts weren’t finalized until the day they were supposed to be delivered. While speeches for Trump, Melania, and Pence were left to their own teams, Sims and his team handled nearly all the rest. Jason Miller had given him specific but broad guidance.

  “Ramp up the economic populism and the foreign policy nationalism in everything we’ve done,” Miller said. “Throughout everything.”

  By the third day of the Democratic convention, and with five days until the start of Trump’s convention, Mike Pompeo still hadn’t been asked to be included as a speaker. That wasn’t unusual. The sitting secretary of state rarely spoke at a party’s political conventions, a decision rooted in a tradition of keeping the country’s top diplomat out of domestic politics to maintain a semblance of nonpartisanship. Earlier in the year, the State Department had disseminated several legal memos that put limitations on the political activity for those working in the agency. “Senate-confirmed Presidential appointees may not even attend a political party convention or convention-related event,” read one. Not only did that sentence seem to apply to Pompeo, but it was one of the few in the memo that was bolded.

  But Pompeo had let it be known in Republican circles that he was interested in running for president someday, and he wasn’t about to cede the stage to other potential 2024 contenders, like Mike Pence, Tim Scott, and Nikki Haley. Pompeo suggested taping his speech from Jerusalem. It wasn’t public yet, but Pompeo was traveling to the Middle East on a five-day tour intended to discuss regional peace and security. In his estimation, that would give him a perfect backdrop to espouse the president’s foreign policy accomplishments and maybe squeeze in a bit of back-patting for himself, too. Trump didn’t give it a second thought, and by that Friday, Pompeo was locked in.

  The success of a party’s convention rests on the final speech from the nominee. Not only did Biden exceed the expectations set by Trump World—which were so low that no one would have been surprised if the former vice president stopped his speech to start eating the paper the words were written on—but was actually good enough that it worried the Trump campaign team.

  “That son of a bitch cleared the bar,” Stepien told his team. “Now our convention matters a lot more than it did before that speech.”

  Trump’s team had convinced themselves that the Democratic convention would be so boring and such a disaster that it almost didn’t matter what their own would look like. When they saw that Biden could in fact string more than three sentences together, there was sudden interest and concern about their own programming. Sayegh’s phone started buzzing with messages from Hope and Scavino from inside the White House, and Stepien and Justin Clark at the campaign. Ronna wanted assurances. The messages ranged from gentle “Hey, what’s going on with our convention?” texts to more aggressive demands that it better be good.

  On Friday, the day after the Democrats wrapped, Sayegh called his team together. “We’ve got to put everybody at ease,” he told them. Kennedy and Sims pulled an all-nighter preparing a memo, with details on all the speakers they’d lined up and key quotes from their remarks. Sadoux Kim focused his aides’ efforts on assembling the opening video and highlight reel.

  First thing Saturday morning, in an office on the fifteenth floor of the campaign headquarters, all the senior political aides sat around a table: Jared, Ivanka, Lara, Eric, Hope, Stepien, and Scavino. There was no talking. They all fixed their gaze on Tony. He cued up a video and pressed Play.

  The video was narrated by Jon Voight, a Trump favorite and Mar-a-Lago member, and included snippets from Cardinal Timothy Dolan’s opening prayer and speeches that were already in the hopper. The video was well produced, and the Mellon Auditorium in Washington, where speakers would address the nation beneath brass chandeliers and gold leaf bracket lamps, popped onto the screen. A sense of relief washed over the room. Heads nodded as they paged through the list of speakers and speech highlights. The campaign had initially demanded final approval over every speech. After that meeting, no one ever asked to see anything else.

  One of the prime-time speakers lined up for night three, “Land of Heroes,” was Dan Crenshaw, the thirty-six-year-old former Navy SEAL, who’d lost his right eye in Afghanistan. Crenshaw, a Republican, was elected to the U.S. House in 2018 to represent a suburban Houston district that Trump had won by nine points. During the 2016 race, Crenshaw posted on social media that Trump was an idiot, insane, and ignorant. But in his first eighteen months in Washington, Crenshaw voted against both articles of impeachment against Trump, then after the coronavirus lockdowns were about a month old, Trump retweeted a video Crenshaw recorded blaming China for the contagion instead of the president.

  “BRILLIANT,” Trump wrote.

  By the time the convention rolled around, Crenshaw’s past criticisms of Trump were forgotten. But maybe they shouldn’t have been.

  This freaking guy, Sims thought to himself after reading Crenshaw’s prepared remarks.

  Sims had read thousands of words of convention speeches at that point, and written just as many. Surely his eyes must just be getting tired. He must have just missed it. Sims pressed Command+F on his iMac and searched for the word “Trump.”

  Nothing.

  He erased that, and searched for the word “president.”

  Nothing.

  Sims had had to Trumpify a handful of convention speeches—adding some of the president’s accomplishments and additional superlatives. For Crenshaw, Sims added a few mentions of Trump to fit the military veteran’s remarks, including one that would credit Trump for taking out ISIS and a final line that endorsed Trump: “And by voting for Donald Trump on November third, you can be sure it will continue to be protected by the president as well.”

  Sims attached the revised remarks to an email, noted that he’d made a few edits, and hit Send.

  “Hey, Cliff,” came a reply from Justin Discigil, Crenshaw’s communications director, a few hours later. “Just spoke with my boss. He feels very strongly about the speech. The speech is written in his words, and he drafted it completely himself.”

  Sims called Discigil.

  “Dude. What is going on?” Sims asked as soon as the aide answered. “If you think your guy is going to speak at the president’s convention without mentioning him and no one is going to notice, you’re crazy.”

  The speech was in the middle of a political convention, but Crenshaw wanted to keep his remarks free from partisanship. The campaign had asked him to speak about military heroes. He’d had friends killed in action and didn’t view their valor at the province of Republicans or Democrats. Crenshaw was ready to walk if Trump World tried to take over his speech.

  But there was also a political calculation on the part of the Texas Republican.

  “The president is the biggest liability to our reelection,” Discigil said.

  Sims lost his mind. Why would Crenshaw agree to speak at the convention? Why would he think he could have it both ways?

  Crenshaw eventually agreed to credit “the president” for supporting the military but never mentioned Trump by name. Inside the campaign, Miller and Clark decided not to elevate the issue to Trump, and instead bumped Crenshaw out of a prime-time slot without informing the congressman about the change.

  After the speech aired, Sims texted Discigil the links to every tweet he saw menti
oning the conspicuous lack of Trump mentions in the congressman’s speech.

  Discigil never responded.

  Trump focused on his speech to close out the final night with unusual attention. During the week, he repeatedly practiced the address in the Map Room of the White House with Jared, Hope, Jason Miller, and his two speechwriters, Haley and Worthington. Trump rarely reviewed speeches—let alone practiced them—before the words were fed into the teleprompter for him to read in front of the cameras. His investment of time into his own convention address explained to some aides why he remained largely glued to the script for the hour-long address.

  Trump attacked Biden, promoted his baseless theory that the Obama administration had spied on his campaign, and portrayed himself as the defender of working Americans. He made little mention of the civil rights protests, other than to tick through a list of cities he said had been overrun by street violence. And he made exaggerated claims about coronavirus as he bragged about his handling of the pandemic to a large audience that was mostly unmasked—despite sitting shoulder-to-shoulder for the speech.

  “Everything we’ve achieved is now in danger,” Trump said. “This election will decide whether we will defend the American way of life or allow a radical movement to completely dismantle and destroy it.”

  Trump’s speech was followed by a brilliant fireworks display.

  He’d asked for it only after seeing what the Democrats had done for Biden on the last night of his convention.

  At the first light on the last Friday in August, temperatures in the capital were in the low 80s, humidity was rising but not yet uncomfortable, and a bed of cottonlike clouds had for the moment blocked out the oppressive heat beating down from the midsummer sun. A punishing downpour was in the forecast, but the morning was gorgeous and Trump woke up feeling better than he had in months. He had just wrapped up the Republican National Convention by accepting his party’s presidential nomination for the second consecutive election in a beautiful setting on the South Lawn of the White House. He didn’t even tweet until almost 10:00 a.m. that morning, and even then it was only to say thank you for the great ratings and reviews from the night before. Sure, ratings were lower than they were for Biden’s speech the week before, but from where Trump stood that evening, it had been a pretty spectacular event.

  Waiting in the Rose Garden the morning after his speech was the merry and buoyant band of Trumpsters largely responsible for the convention success: a group of little-known outcasts, misfits, and retreads who had all traveled different paths into Trump World.

  Sadoux Kim, Adam Kennedy, and Sayegh were there, as was Jason Miller, and of course, Sims. This motley crew—their nasal passages freshly swabbed for Covid—stood outside making awkward small talk, hands in their pockets or otherwise picking at their fingernails with an energy that seesawed between nervousness and excitement.

  Finally, the Oval Office doors swung open.

  “My team!” Trump bellowed, smiling as he descended down six steps from the colonnade, over the newly laid limestone paving that framed the lawn—another Melania-approved update!—and into the garden. “These are the people!”

  Trump had gathered them to toast their success, reveling in the moment the only way he knew how: reserving credit for himself, and roasting his guests.

  “We should do those South Lawn events every single week,” Trump said. Nervous laughter rippled from his brigade. He was kidding, right? No one really ever knew for sure. Trump barreled on. He talked for a few more minutes about his convention address, made sure everyone had loved it as much as he had. Everyone would remember later how much time he spent talking about the testimonial from Herschel Walker, the former football star who asserted that his love for Trump was greater than all the friendships he’d lost over it.

  Then Trump spotted Sims.

  It had been two years since Trump had laid eyes on the thirty-six-year-old Alabamian.

  “There he is—we always loved him,” Trump said, pointing at Sims and suddenly speaking as if he were the narrator reminding viewers about scenes from last season.

  The peanut gallery in the Rose Garden had been anticipating this moment and they were eating it up.

  “Then I had to sue his ass off,” Trump continued. “But I won, and now I’ve brought him back, because I’m such a nice guy.”

  Inside, Trump wanted to hand out small souvenirs, mostly little tchotchkes with the White House seal. Trump had turned the private dining room just off the Oval Office into a gift shop where he kept tote bags, mugs, cheesy faux crystal plates, and red MAGA hats—tons of them—to hand out to visitors. Everyone who crossed the threshold also heard the only historical fact about the White House that Trump ever consistently repeated: This was a room where President Clinton would bring Monica Lewinsky and, well, you know.

  Trump tried to make these Oval Office moments for visitors feel larger than life, because what he really wanted was to be talked about: He wanted his guests to tell their friends how gracious he’d been, remember how much fun they’d had, and reaffirm that, yes, he definitely deserved the job. There was something touching about Trump’s little room of cheap knickknacks, but also kind of tragic. The harder Trump tried to make the experience feel majestic, the more he made it feel smaller. The gifts he was so excited to hand out weren’t all that different from Washington Monument snow globes or the “Trump-Pence 2020” coffee mugs at the gift shops trying to snag tourists walking through Reagan National Airport. His jokes were crude but, to be fair, often memorable—and no one in the Oval Office that Friday morning would forget anytime soon the show he was putting on for them.

  Trump turned to Sayegh and motioned to the elementary-school-age son he’d brought with him to the White House.

  “Give him one of the ashtrays,” Trump instructed, then told the boy, “You can put it on eBay tonight.”

  Trump next called Jason Miller up for a photo.

  “You must have the most patient wife in the world,” Trump said.

  It was a dig at Miller’s well-publicized extramarital affairs. Cheung felt tears welling in his eyes and turned his back and walked to the other side of the office to keep from bursting into laughter. Others couldn’t look away as Trump needled Miller.

  “What she puts up with I don’t understand. She puts up with a lot, doesn’t she?” Trump said. “I don’t know how he keeps her. That’s why he’s good at his job, I guess.”

  If Miller was tempted to return fire on the thrice-married Trump, he kept it to himself.

  “You’re very right sir,” Miller said through a half smile. “She’s fantastic. She’s very patient.”

  “Why don’t you take one of the ashtrays for her,” Trump told him.

  14

  Hell Week and a Half

  “This was a blessing from God that I caught it.”

  —Recorded video, Rose Garden, October 7, 2020

  The main entrance from the south side of the White House is a set of doors that open into the Diplomatic Reception Room—one of four similarly sized oval-shaped suites in the building. But the Dip Room, as the locals call it, holds its own unique history. In the 1830s, slaves used the space to polish silver. In the 1930s, FDR sat near the open hearth and delivered his popular fireside radio chats. In 1961, First Lady Jackie Kennedy redecorated and hung striking hand-painted wallpaper depicting panoramic views of American landscapes and entertained ambassadors and visiting diplomats who were welcomed there for much of the twentieth century.

  On September 26, 2020, President Trump used the room to host a Covid-19 superspreader.

  Just like so many other key moments in the Trump White House, the superspreader was a spur-of-the-moment thing. And just like a long list of Trump’s self-inflicted troubles, this one arose from a willful disregard for traditional protocols.

  The moment, from a legacy perspective, was monumental. No president since Reagan had more than two Supreme Court nominees confirmed. No one had three in their first four years since Nixon
, who had four. But more important, Trump’s third pick would tip the political balance of the court toward conservatives. For all those reasons, he wanted to play up the drama of the unveiling of his chosen justice as much as he had for his first two nominees.

  In 2017, the White House counsel’s office had Neil Gorsuch wait at a friend’s house in Denver in order to avoid reporters who might have been staking out his own home for signs ahead of Trump’s announcement. In 2018, Trump was so pleased that his selection hadn’t leaked that he teased the audience in the East Room for nearly five minutes before introducing Brett Kavanaugh, who then emerged from behind a closed door with his family.

  For Amy Coney Barrett, the White House sent one of the Air Force’s newest purchases—a $64 million Gulfstream business jet designed to chauffeur government VIPs around the globe—to pick her up in South Bend, Indiana. The day of Barrett’s announcement was scripted down to the last minute. Republican senators and Cabinet members would be tested for coronavirus in the Eisenhower Executive Office Building next door to the White House, and then escorted to the Cabinet Room in the West Wing to wait until it was time to take their seats. At 4:45 p.m., the gates would close at the visitor’s entrance at 15th Street and E Street NW, and reporters would be directed to a patch of grass roped off behind a couple hundred seats on the Rose Garden lawn.