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

by Michael C. Bender

  Trump had already ousted two key impeachment witnesses: He fired European Union ambassador Gordon Sondland and removed Lieutenant Colonel Alexander Vindman, a Ukraine expert, from the White House National Security Council, along with his twin brother for good measure. He mocked the lone Republican who had dared vote against him during a meeting with U.S. governors just before departing for New Hampshire.

  “How’s Mitt Romney?” Trump asked Gary Herbert, who was governor of Utah, Romney’s home state.

  Herbert said they hadn’t spoken and continued with his question about the national debt.

  “You keep him,” Trump said. “We don’t want him.”

  But the rally in New Hampshire was where he could truly revel in his triumph, an endorphin-fueled jamboree with his most entrenched supporters whom he’d been telling for months that were the real targets of impeachment. Trump had been accused of abusing the power of the presidency, but he insisted that what Pelosi and the Democrats in Washington were really trying to do was nullify the 2016 election. The man who had spent fourteen years creating an alternate reality on television had now done the same from the rally stage. Impeachment, Trump argued, was nothing more than the latest attempt from liberals and socialists to shake down Americans for more taxes, take away Christmas, and turn the country into something different than what their parents had wanted for them and what they wanted for their children.

  In the biting cold of midwinter in New England, rallygoers started lining up two days early. The first to set up her chair on the icy sidewalk surrounded by piles of newly plowed snow was a founding member of the Front Row Joes, Libby DePiero. Long silver hair sprouted from underneath the hood of her black parka while her black gloves with faux fur trim gripped a sign that read TRUMP’S FRONT ROW JOES. The poster included a picture of her pal Randal Thom’s Alaskan malamute, an energetic little pup named Donald Trump.

  Libby, a sixty-four-year-old retiree who enjoyed sparkly nail polish, leopard prints, and selfies with Trump campaign officials, had once driven her Ford Focus so far to attend a Trump campaign rally—about 1,000 miles from her home in Connecticut to Indiana—that when she stretched out in bed that night, she thought the twitching in her driving leg was coming from an animal under the mattress.

  Front Row Joes maintain instant recall of a particular set of details that effectively establishes their membership in the group and, to a certain extent, determines the internal hierarchy: the number of rallies attended, the farthest they ever traveled for an event, and an excruciatingly detailed story about their first time meeting The Donald. Most of the original Front Row Joes met Trump early in the 2016 campaign during quotidian encounters that became indelible memories to be recounted forevermore with endearing levels of earnestness and pride.

  “My first rally was in Nashua, at the Radisson. That was the first time I spoke to him, and I still remember what I said,” Libby told me outside a 2019 rally in Orlando as she sat in her aluminum-frame folding lawn chair. A bed pillow softened the seat of webbed nylon straps—red, white, and blue, of course. She wore loose-fitting pants with a snakeskin print, and her black New Balance sneakers bounced with nervous energy.

  “It’s such an honor to meet you,” Libby told Trump.

  “What did you say?” Trump asked her.

  “I said it’s such an honor,” she said.

  “Thank you,” Trump replied.

  Libby recalled the memory with a wide smile.

  “That’s what he said!” she told me.

  She’d been to almost sixty rallies by the time she’d lined up in Manchester, returning in part because of the network of friends she’d created at the rallies and in part because she only trusted the president to deliver her the news.

  “How else would I know what’s going on?” she said.

  The next night, as temperatures dropped to 10 degrees, Libby was joined by dozens of other devotees camping out to save their place in line.

  The reelection campaign planned to flex its muscle in Manchester, a show of strength heading into New Hampshire’s first-in-the-nation primary. A swarm of surrogates from Congress and both Trump campaigns attended the rally and would be deployed to polling places on primary day, where they would encourage campaign volunteers and greet voters.

  “Getting the band back together!” Louisiana congressman Steve Scalise told Trump on the flight to New Hampshire aboard Air Force One.

  The remark signaled Trump’s strengthening grip on the party. Four years earlier, Scalise had endorsed Trump only after all of his major Republican challengers had left the race.

  The splashy display in New Hampshire was designed to run up the score as much as possible on the last remaining Republican primary challenger, former Massachusetts governor William Weld,1 who lacked the money and the support to mount much of a campaign. But the bigger obstacle was that the rules of the game had changed. Bill Stepien and Justin Clark had spent much of the past year working to make it as difficult as possible for any potential primary challenger. They had calculated that one of the biggest reasons George H. W. Bush and Jimmy Carter had been one-term presidents was that each had been weakened by difficult primaries.

  Stepien and Clark started by holding a national conference call with state party chairs to inform them of the vetting they wanted for convention delegates. Stepien repeatedly told party leaders that there was going to be no drama at the convention. It was a clear message to expel any Never Trumpers where they could. Pro-Trump Republicans were elevated in the ranks in liberal states like Massachusetts. Ken Buck, a U.S. House member and fierce Trump supporter, took over the Republican Party in Colorado, where Trump’s unpopularity had splintered the party and resulted in big losses in the midterms. Brad endorsed Laura Cox, a former Michigan state legislator, to take over the state party there. And the Republican National Committee approved a symbolic yet unusual resolution that President Trump had their “undivided support.”

  It was the kind of backroom arm twisting that Trump had repeatedly criticized the political establishment for doing to insurgents. But one candidate’s rigged system was another president’s advantage of incumbency. With his nomination all but assured, the only thing left to accomplish during primary season was to deliver historic victory margins, drive up Republican turnout, and unleash a shock-and-awe campaign that would leave little doubt who the favorite would be heading into November.

  The effort came with huge costs. In New Hampshire, the campaign chartered its own planes and planned a massive primary night party at Murphy’s Taproom in Bedford for a victory that was never in doubt. Brad had boxes of red campaign hats specially made for New Hampshire: KEEP NH GREAT—2020 PRIMARY TEAM. Earlier in the month, the campaign had brought everyone to Iowa for a similar showing. In addition to Air Force One, they chartered a plane with a manifest so deep that Bossie and Corey, two of the original Trump campaign operatives, didn’t know most of the names on the list.

  But those expenses didn’t matter much at that moment. Trump seemed to be running against all eight of the major Democratic candidates at once, and his team was enjoying the consequence-free campaigning: the adrenaline rush of the fight, but none of the anticipation of an uncertain outcome. Brad intentionally planned to put the rally in Manchester, hoping the president’s extensive security precautions would snarl traffic in the state’s largest city and frustrate rival campaigns in the final hours before the polls opened. Traffic was so backed up that my own fifteen-minute drive from the airport to the arena took nearly an hour. It was well past the press deadline to get in when I finally jumped out of the taxi about a mile away and navigated my way through various blockades to the arena, where Emily Novotny, an advance staffer on the campaign, helped me make it past the last few security checkpoints while I was heckled for the last few feet by Corey and Bossie, who seemed quite delighted by the whole spectacle.

  Even if the primary result was certain, the outcome in November was very much in doubt in New Hampshire. Trump had lost the state in 2
016 by a margin of 0.37 percent, his smallest margin of defeat. But in 2020, Trump had an argument to make: Unemployment in the state was below 3 percent. Wages, which had stagnated during the Great Recession, had been growing under Trump.

  The president and his team still hadn’t settled on a messaging strategy, partly because they expected Trump to find his secret sauce once Democrats picked their nominee. But Trump was struggling to decide whether to stick with his 2016 theme, “Make America Great Again,” or update it to “Keep America Great.” Brad urged him to stick with the 2016 MAGA branding, which he argued was now the name of the movement more than anything else. Trump worried that it sounded like he hadn’t done the job.

  “I made America great,” Trump said. “I don’t have to make it anymore.”

  But when it came time to approve the new Keep America Great hats, Trump stalled. He relentlessly tinkered with the flatness of the brim, the size of the font, and the shape of the front panel. At a fundraiser in September 2019 in the Beverly Hills mansion of Geoffrey Palmer, Trump considered several prototypes as he sat behind the desk of the billionaire builder’s large study, which was wrapped in gold and maroon floor-to-ceiling curtains and lit by a gold chandelier. Brian Kennedy, the president of Cali-Fame, the Southern California company that had been making the caps since the 2016 race, dripped with sweat as he nervously watched Trump finger the different prototypes while Brad, Jared, Don Junior, Kimberly Guilfoyle, and Treasury Secretary Steven Mnuchin looked on. Kennedy’s nerves made Brad overly anxious, and he worried that Kennedy’s profuse sweating would distract Trump and further delay a decision about the hats. Brad repeatedly interjected, trying to pinpoint what the president liked and didn’t like, but his meddling in the conversation irritated Jared.

  “Will you shut up and let him do his job,” Jared finally blurted out.

  Trump eventually picked one. A week later, he asked for another slight tweak to the font. The repeated changes resulted in multiple “Keep America Great” hats that Trump signed with his name and memorialized by adding “#1” with his black Sharpie.

  The changes were unusual for Trump. His superstition and paranoia usually meant never changing anything that worked, and he and his team spent much of 2020 trying to re-create the 2016 dynamics. That included holding a rally in the same New Hampshire arena on the same night—the eve of the presidential primary.

  It was in New Hampshire four years earlier where Trump had turned his primary campaign around and, the night before, delivered a rally performance that encapsulated the strange chemistry between the performer and his audience that on occasion surprised even him.

  “She just said a terrible thing!” Trump had said in SNHU Arena, pointing to a woman in the crowd who had yelled an expletive.

  Trump asked the crowd if they’d heard what she called Senator Ted Cruz, his chief rival in the Republican race, and told her to shout it out again. The woman tried, but her tiny voice was hard to discern in the 12,000-seat arena. So Trump amplified it for her.

  “She said he’s a pussy!” Trump said as he feigned dismay.

  The crowd erupted in a deafening roar of approval as Trump surveyed the scene.

  “What kind of people do I have here?” He smiled. “What do I have?”

  Four years later, Air Force One was packed with the president’s political aides and allies when it touched down at Manchester-Boston Regional Airport about an hour before the rally. Waiting on the tarmac to greet him was Corey, his first campaign manager, who was based in New Hampshire.

  “Welcome home, sir,” he said.

  Inside SNHU Arena, Representative Matt Gaetz mingled with the crowd, signed hats, and posed for pictures. Onstage, Kimberly Guilfoyle, the former Fox News personality now dating Don Junior, warmed up the crowd. She shouted into the microphone that Trump was “the best president this country has ever seen,” pumping her fist into the air with every syllable. The crowd cheered in agreement.

  “That felt good, didn’t it?” she said, adding, “Gimme some Trump, Trump, Trump!”

  Guilfoyle, wearing dark-framed reading glasses with her chestnut brown hair layered over her shoulders, introduced Don Junior as the next speaker. She avoided the kind of vivid descriptions of Don Junior she often used at private fundraisers to give donors an unwanted glimpse into their private lives—how he liked when she wore a cheerleading outfit and was a “naughty boy” when she “let him out of his cage.” Instead, she described him as “Braveheart meets honey badger.” They greeted each other onstage with a warm embrace and quick kiss.

  Don Junior wore a dark blue suit, an open-collared shirt, and a wide smile as he whirled red campaign hats into the audience. The crowd showed their appreciation by breaking into a chant of “Forty-six! Forty-six!”

  Trump’s son kept chumming the waters with the lumpy red discs in a sea of fervid MAGA fans. When the “Forty-six!” chant broke out again fifteen minutes into his remarks, Don Junior tried to tamp it down with his hands.

  His head tilted to the side, and he grimaced. “Wow,” he said, briefly letting it pick up momentum. “One step at a time.”

  He continued, holding his hands in the air. “Let’s worry about 2020. That’s all we’ve got to focus on, right? Let’s keep winning.”

  In his next breath, Don Junior started his energetic introduction for Pence, who was warmly received. But there was no special chant for the silver-haired, straitlaced son of Indiana.

  Backstage, Marc Short, Pence’s chief of staff, and Katie Miller, the vice president’s communications director, exchanged a glance.

  “That’s funny,” Miller said.

  After Pence walked offstage, he made an awkward joke about the moment to Don Junior and Kimberly. Later that week, Marty Obst, Pence’s longtime political strategist, made it known back at campaign headquarters that Pence was never again to follow Don Junior onstage.

  “He’s just a hard act to follow,” Obst said.

  The morning after the rally, Brad pulled up to a cinnamon-colored brick building—weathered and water-stained from the dependably cold and wet New Hampshire winters—that housed the nearly century-old Red Arrow Diner in downtown Manchester. Inside, grizzled old white men, some in puffy winter coats and others in shirtsleeves, were bellied up to the curved, fire-engine-red breakfast counter, sitting on one-legged red vinyl bar stools. The plastic-covered menus had previously been considered by a perfectly adequate roster of celebrity gourmands, including favorite son Adam Sandler, the Barenaked Ladies, and former host of The Apprentice and future U.S. president Donald J. Trump.

  The diner was a required stop on any candidate’s swing through Manchester. But in February 2020, the campaign instead dispersed a group of surrogates, including Brad, on the morning of the primary because Trump was already back at the White House. The president preferred large crowds and cable networks instead of diner stops and local news. He’d made an exception for the Red Arrow back in January 2016 when he slid into a booth and signed autographs. In a dark suit, white shirt, and blue striped tie, he ordered a Diet Coke and a Newton Burger—a ground beef patty with all the traditional burger trimmings, plus a scoop of deep-fried mac and cheese, a grilled cheese sandwich in place of a bottom bun, and a second grilled cheese sandwich as the top bun. It would be immediately rebranded as the Trump Tower.

  “Enjoy your burger, racist!” a woman had yelled as she was halfway out the diner door.

  Trump had betrayed no reaction and continued the conversation in his booth. But four years later, he sent Brad.

  When Brad entered the tiny cafe, it was already cramped at 8:45 in the morning. The tight quarters made him appear even larger as he walked in wearing a dark blue three-piece suit, a fresh New Hampshire–edition campaign cap perched on his head, and his blondish-brown beard neatly combed and styled like an upside-down mohawk. His entourage pushed into the diner and crowded around him: a full camera crew; two young, long-legged assistants; a retired Army special forces soldier now working as a bodyguard; and a
press minder. Brad surveyed the scene, his cell phone pressed to the side of his face. It was already his third call that morning from Jared, who would call once more before lunch and send repeated texts. The constant contact was mostly to micromanage Brad’s social media profile but also to weigh in on the major political stories.

  That morning, the big story was Mike Bloomberg, the tech billionaire and would-be Trump challenger—and father of one of Ivanka’s best friends—who was trending on Twitter. An old recording had surfaced of Bloomberg using racial terms to describe the controversial stop-and-frisk policing practice he presided over as New York City mayor. Bloomberg apologized for the policy, but that did little to keep it from ricocheting around the Internet and catching the attention of the president, Don Junior, and Brad, all three of whom did their best to escalate Bloomberg’s embarrassment. At 8:00 a.m., Brad tweeted that Bloomberg was “a complete racist” and retweeted another post adding only the hashtag #BloombergIsARacist. But Jared didn’t think the campaign manager for the president of the United States should concern himself with juvenile horseplay in the sandbox of social media. Jared wanted the tweets taken down, and told Brad to change the new banner on his Twitter page, which was an old picture of the diminutive Bloomberg standing between Jared and the president. It was cropped so that the heads of Trump and Jared were at the top of the banner, while Bloomberg could barely see over the bottom of the frame. It made Brad chuckle every time he looked at it. He changed the picture, but left the tweets up.

  Others in Brad’s orbit had warned him to dial down the heat radiating from his social media presence. There were plenty of others around Trump World who would willingly post those kinds of tweets. Don Junior had essentially turned Twitter-flamethrowing into his personal brand. Plus, the campaign already had a network of social media influencers whom they’d blast with text messages suggesting tweets and Facebook posts. The mainstream media had come down hard on Brad the past few years, digging into nearly $100 million in campaign cash that had been paid to his marketing company during the 2016 campaign and millions more when he was named campaign manager in 2018. There was never any evidence of wrongdoing, but that was only half the problem. He’d also bought a pair of million-dollar condos, a $400,000 boat, and another half million in luxury cars, including a Range Rover and a Ferrari. For Trump, who was already prone to conspiracies and triggered by the very thought of people making money off him, the perception that Brad had gotten rich off the back of Trump’s political ambitions had fueled a years-long fight between the two men.