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

by Michael C. Bender

  Several hours after Saundra and her friends had taken their places in the front row, President Trump was pacing backstage. Back in Washington, Democrats on the floor of the U.S. House of Representatives were preparing to saddle Trump with the historic and profoundly unpleasant epithet of an impeached president—what for months Trump could only bring himself to utter as “the I-word.” But in the Midwestern arena 600 miles from the U.S. Capitol, behind the twenty-foot-tall black velvet curtains and inside a large private room with matte gray walls and a drop ceiling of textured square tiles, the president and Trump World’s top lieutenants plotted the path forward. Election Day was less than eleven months away, and his campaign team knew impeachment had some political upside. The first step was to leverage the fortuitous timing of his “Merry Christmas” rally by producing a made-for-TV moment that would steal some of the spotlight from Democrats.

  After the House scheduled its impeachment vote for the night of the rally, the plan had been for Trump to burst onto the stage in a defiant display of showmanship, emerging from backstage through a redbrick fireplace—like a MAGA Santa who had come to inspire deplorable boys and girls and put coal in the stockings of every Democrat and disloyal Republican. But once again, Congress was ruining everything. House lawmakers were still yapping, the vote was running late, and it was already a half-hour past the rally’s 7:00 p.m. scheduled start.

  Inside the hold room, Trump, in his standard blue suit and red tie, grew impatient and snapped about the relatively small size of the Kellogg Arena. With just 6,200 seats, the venue was about half the size of his typical rally.

  Michael Glassner, who oversaw production of Trump’s mega-rallies as the campaign’s chief operating officer, defended the choice as data-driven and strategic. Ronna McDaniel, the head of the Republican National Committee and a former Michigan Republican chairwoman, chimed in that she had warned everyone that the arena was too small. Brad Parscale, the campaign manager, reassured Trump that impeachment was going to help him win reelection. On the other side of the room, White House deputy chief of staff Dan Scavino, the president’s longtime aide and social media adviser, scrolled through his phone. Stephen Miller, the White House’s senior policy adviser, huddled with Jared Kushner, the president’s son-in-law and senior adviser, about how to respond to the impeachment vote.

  Trump turned his attention back to the television tuned to Fox News. He’d been in contact with House Republican leader Kevin McCarthy and didn’t want to start the rally until the California lawmaker had delivered his party’s final speech before the vote. But Trump also wanted to avoid walking out onstage too close to 8:00 p.m., when Fox News host Tucker Carlson was unlikely to cut away from the opening monologue of his show to feature Trump’s rally.

  He leaned toward Vice President Mike Pence, who stood nearby waiting for the go-ahead to introduce the president. They discussed their options, and finally Trump decided he’d waited long enough.

  “Fuck it,” he said. “It’s going to happen while I’m up there. We’re going.”

  Pence headed to the stage, and Trump pointed a finger at Hogan Gidley, a White House press assistant. He instructed Gidley to make a sign with the final vote and show it to him while he was onstage. Then Trump immediately reconsidered his plan and told Gidley to have Kayleigh McEnany bring him the results. It was a campaign event and McEnany was the campaign’s press secretary. Plus, she was wearing a bright orange dress that Trump knew he would be sure to spot from the stage.

  At 8:03 p.m., just minutes after McCarthy had finished his speech on the House floor back in Washington, Scavino introduced Trump from the backstage microphone wired into the arena’s loudspeakers.

  “Ladies and gentlemen, please welcome the forty-fifth president of the United States, Donald J. Trump!”

  Lee Greenwood’s patriotic anthem “God Bless the USA” boomed through the public address system as Trump waited a beat and then made his grand entrance, smiling and clapping his way through the mock fireplace.1 The crowd erupted in applause and cheers so loud that the cresting roar startled several staffers backstage. Trump basked in the moment. He slowly shuffled along the catwalk, and only stopped clapping long enough to pump his fist or point into the crowd as Greenwood’s crooning filled the room. Finally, he reached the lectern, flanked on each side by Christmas trees adorned with glossy gold ball ornaments and crowned with a red “Keep America Great” cap.

  “It does not feel like we are being impeached,” Trump told his devoted followers. “We did nothing wrong.”

  One of Trump’s first actions as president—just hours after he was inaugurated on January 20, 2017—was to file paperwork for his reelection. After just thirteen months in office, he hired Brad to manage the campaign. No president had announced a reelection bid that early. That meant Trump never really stopped campaigning. It allowed him to perpetually raise money for his political operation and schedule a rally whenever he needed an injection of adulation or to divert attention from controversy in Washington. Jared, Brad, and Ronna struck a deal that braided the campaign and the White House with RNC operations and enabled them to share resources, including staff and office space. Trump had held his ceremonial campaign kickoff at a rally on June 18, 2019, in Orlando, an event that was indistinguishable from every other rally he’d had: nursing grievances, reliving the glory from the 2016 campaign, and never bothering to outline what a second term might entail.

  It was a month after that Orlando rally, on July 25, when Trump picked up the phone and repeatedly pressured Ukrainian president Volodymyr Zelensky to help smear his political rivals. Trump wanted Zelensky to spread misinformation about Russian attempts to influence the 2016 election and investigate Joe Biden, the former Democratic vice president who had opened his campaign to unseat Trump just three months earlier. That phone call—paired with Trump’s attempt to force Zelensky’s hand by blocking $400 million in military aid for Kyiv—sparked the impeachment inquiry in late September.

  The impeachment inquiry, in many ways, marked the actual start of the campaign. It provided purpose and mission to Trump World and offered a desperately needed reason for a fractured Republican Party to unite around the president. Trump always intended to treat his reelection in 2020 as a continuation of his campaign in 2016, even though an incumbent running as a change agent was a tricky feat to pull off. The impeachment allowed the president once again to cast himself as a victim and Washington outsider.

  But the prospect of impeachment left him deeply rattled.

  Whenever Trump thought about impeachment—which was often—he would swirl through a narrow range of unhappy emotions: frustration over his helplessness to derail the proceedings in the House; anger that his first three years as president had been almost entirely overshadowed by the Russian election meddling investigation and now eclipsed by impeachment; and bewilderment that his “perfect phone call” with Ukraine had backfired so resoundingly. He said he simply wanted the newly elected Ukrainian president to investigate the political corruption of Joe Biden and his son, Hunter Biden. He never explicitly said it was about the presidential campaign. He constantly peppered aides with questions about whether House Democrats would actually go through with the impeachment proceedings.

  “Are they really going to impeach me?” he asked an aide on the morning of the impeachment vote.

  If his staff answered affirmatively—and usually that was only Mick Mulvaney, who was the third White House chief of staff by the third year of the presidency—Trump would unspool a furious diatribe complaining that he was always mistreated.

  “They’ve got nothing on me!” he would complain.

  Trump’s political team, however, recognized the opportunity impeachment provided and tried to contain the emotional fallout from Trump and his family.

  “This is terrible,” Eric Trump, the president’s middle child, complained during a lunch at the family hotel in Washington with several members of Trump World. “They’re going to impeach my father.”


  “If they impeach the president, it will be awful and it will be a stain on his record,” said Richard Walters, the Republican National Committee chief of staff. “But it will nearly guarantee he gets reelected.”

  When Democratic House Speaker Nancy Pelosi finally stood behind her mahogany lectern and announced opening a formal impeachment investigation into Trump on the evening of September 24, 2019, electricity seemed to pulse through campaign headquarters.

  “The president must be held accountable,” Pelosi said in the hall outside her third-floor Capitol office. “No one is above the law.”

  Campaign staffers had congregated around the multiple flat-screen TVs mounted on the dark gray walls behind the communication team’s cubicles. When Pelosi finished her speech, Brad turned to Tim Murtaugh, the campaign’s communication director. Murtaugh, a slim and serious political veteran, shook his head in disbelief as he watched the screen.

  “Okay,” Brad said. “Go.”

  Murtaugh’s team of about a dozen aides—his staff would ultimately grow to more than 100—leaped to action. They blasted out a video, prepped weeks earlier, that mocked the Democrats’ obsession with impeachment. A small army of Trump World surrogates and social media influencers were armed with talking points that had been prepared for days. Brad put his name on an official statement from the campaign that predicted Pelosi’s move would only encourage and energize Trump’s supporters and lead to a landslide victory in 2020.

  Gary Coby, the campaign’s digital director, pushed his team’s already aggressive fundraising operation. Their first email after Pelosi’s announcement played off a promise from Trump earlier in the day to declassify a rough transcript of his phone call with Zelensky. The email subject line was “Call Transcript” and included a paperclip emoji that suggested an attachment awaited inside. But the only thing included in the email was a link to a donation page.

  From Howard Dean to Ron Paul to Barack Obama, online fundraising has always been driven by supporters’ passion and small-dollar donations. High-dollar, in-person fundraisers, meanwhile, tended to have a more transactional nature as deep-pocketed donors and corporate executives treated contributions as business decisions. And if emotion was the propellant of online fundraising, impeachment proved to be high-octane fuel for Trump’s fiercely loyal tribe that viewed any criticism of him in deeply personal terms. In the first three hours after the House investigation was announced, the campaign raised $1 million. Within twenty-four hours, the number ballooned to $5 million. Over the final three months of 2019, the Trump team’s impeachment-themed fundraising appeals helped collect nearly $155 million, one-third of their fundraising haul for the year.

  When it came to impeachment strategy, the biggest wild card was Trump himself, and whether he could avoid the self-inflicted wounds that would repel potential allies in Congress. Trump would never win over the Democratic majority in the House, but his team could find a political victory in the defeat by keeping the 196 Republicans unified in opposition. It wouldn’t save Trump from impeachment. But losing any Republicans in the House threatened to impede momentum for the White House heading into a Senate trial and undermine Trump’s case with voters that the prosecution was a partisan political charade. It was no easy task. More than two dozen House Republicans were retiring in 2020, which meant they couldn’t be strong-armed with the kind of political tools that Republican leadership would typically deploy: campaign cash, threats of primary challengers, or a little good old-fashioned online Twitter bullying from the wicked thumbs of @realdonaldtrump.2 Several outgoing lawmakers in the House, including Will Hurd of Texas and Francis Rooney of Florida, had made their disapproval of Trump well known.

  Still, plenty of high-ranking officials in Trump World were privately horrified at what Trump had said on that call with Zelensky. They could convince themselves that it wasn’t impeachable, but few could justify how Trump had so casually put so much at risk over such a long-shot scheme to discredit Biden. Inside campaign headquarters in September, Brad and his team tried to puzzle together the logic of what seemed to be a completely separate political operation being run out of the West Wing that had encouraged Trump to bring up Biden with Zelensky. The campaign’s instinct was to blame the people around the president. And the name that kept coming up was Rudy Giuliani, the former New York mayor with a decades-long relationship with Trump, who was now employed as his attorney.

  “This is crazy shit,” Justin Clark, the campaign’s top attorney, griped about Giuliani’s ploy.

  But politically, the reelection team couldn’t believe their good luck. Two months of Democratic hearings and witness testimony—from members of Trump’s own administration—had done nothing to sway public opinion. Even Trump’s reliably self-destructive behavior hadn’t hurt. But the president wasn’t making it easy.

  He had broken decades of international precedent when he released a rough transcript of his call with Zelensky the day after Pelosi announced the impeachment inquiry. His West Wing was divided over the decision, and he hadn’t even bothered to check with Brad. But Trump pushed ahead, certain that the transcript would convince Democrats to call off the impeachment proceedings. It was the kind of grand, inside-Washington political miscalculation that was proving to be a major weakness of the outsider president. The content of the conversation only emboldened his rivals.

  In October, the president publicly called on another foreign power (China) to investigate the Bidens, impeachment proceedings for members of Congress (no such thing), and refused to comply with a single subpoena from the coequal branch of government just a couple of miles down Pennsylvania Avenue (sparking concerns of a constitutional crisis).

  In mid-October, Mulvaney openly admitted that Trump wanted to block military aid for Ukraine in exchange for political investigations into his political rivals.

  “That’s why we held up the money,” Mulvaney said in a disastrous news conference. The White House immediately tried to walk back Mulvaney’s candor.3 But none of the gaffes seemed to matter.

  Just 49 percent of Americans said they thought Trump should be impeached, according to a Wall Street Journal/NBC News poll taken after Mulvaney’s stunning news conference confessional. Two months later, the same survey showed 48 percent supported the move.

  As the inquiry unfolded, Brad hadn’t been able to contain his enthusiasm over the thought of a split-screen image on the cable networks featuring, on one side, out-of-touch Washington symbolized by the typical and somewhat tedious C-SPAN shot of lawmakers milling about on the House floor, while, on the other half of the screen, Trump absorbed the adoration from the cheering arena crowd that surrounded him.

  Brad’s anticipation of the potential political boost from impeachment constantly irritated Trump. But the eager campaign manager was in charge of his first political race, and Trump rallies weren’t the sideshow—they were the entire campaign. As chance would have it, Trump was standing onstage the very night of the impeachment vote.

  There was no better place for Trump to absorb the impact from the crushing blow over which he’d spent months agonizing than right there in the center of his beloved rally stage. Just him, his pulpit, and the gooseneck-thin microphone he’d reflexively grab at the start of every speech and yank back and forth a few times, as if testing its ability to withstand the flurry of grievances, gossip, putdowns, pranks, understatements, oversimplifications, misrepresentations, deceptions, attacks, counterattacks, self-affirmations, reassurances, promises, hopes, and dreams that he was about to pour into it.

  Brad was always on the lookout for signs in the stars and listening for what the universe might be whispering. The House’s decision to schedule the vote on the night of a campaign rally had to be more than a mere coincidence.

  “A happy coincidence,” Glassner told him.

  Trump was still resisting his fate on the morning of his impeachment when he flipped on Fox & Friends and launched his first tweet of the day, inspired by Brian Kilmeade, one of the anchors of his f
avorite breakfast program. Kilmeade had just lamented that Democrats would impeach Trump over something so trivial.

  “Well said, Brian!” Trump typed into his phone.

  Twenty-three minutes later, he posted another.

  “Can you believe that I will be impeached today by the Radical Left, Do Nothing Democrats, AND I DID NOTHING WRONG!”

  And then another.

  “A terrible thing. Read the Transcripts. This should never happen to another President again. Say a PRAYER!”

  Trump posted forty-three more tweets over the first three hours that morning. As House lawmakers opened the formal debate at 9:00 a.m., Trump was on Twitter interacting with Fox personalities, praising conservative media columnists, and attacking his critics.

  When Trump hadn’t emerged from behind closed doors by lunchtime, White House reporters started asking what he was doing on that historic day.

  “The president will be working all day,” said Stephanie Grisham, the sixth of seven White House communications directors during Trump’s four years. “He will be briefed by staff throughout that day and could catch some of the proceedings between meetings.”

  Nine minutes after the statement went out, Trump was back on Twitter.

  “SUCH ATROCIOUS LIES BY THE RADICAL LEFT, DO NOTHING DEMOCRATS. THIS IS AN ASSAULT ON AMERICA, AND AN ASSAULT ON THE REPUBLICAN PARTY!!!!”

  As Trump prepared to leave the White House for Battle Creek that afternoon, he phoned Tony Sayegh, a communications adviser who was walking out of the White House, for some last-minute feedback on what he’d be saying.

  Trump would remain unrepentant. That was never in doubt. But if his vote-counters were right, and House Republicans remained unified in their opposition, he would celebrate that as a win for the party and his movement and a sign of momentum heading into the Senate trial. He just needed to wait for the vote.