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

by Michael C. Bender

  “I hear what you’re saying,” Trump told Mulvaney. “But Pat and these guys say they won’t do it, and I need these guys.”

  In a moment of serendipity for the counsel’s office, Pence walked into the meeting. Trump asked for his opinion on whether they should bring in the outside attorneys Mulvaney had requested.

  “Well, we have some problems with that,” Pence said. “We don’t think that’s the right idea.”

  Cipollone successfully wrested control of the impeachment strategy from Mulvaney and contained much of the decision-making to his team of attorneys and advisers. Cipollone cared most about acquittal and worked to keep Trump focused on that goal. But Trump was intrigued by the idea of calling witnesses in the Senate trial. Brad told the president that a lengthy trial with a long list of salacious witnesses would motivate his base, propel fundraising efforts, and, come November, boost voter turnout. Giuliani wanted to put Hunter Biden on the stand. Trump not only went back and forth over the question of calling witnesses, but he also equivocated over the lineup of lawyers who would mount his defense. He’d deliberated over his roster since October, and still wanted to include Giuliani. That arrangement would have been a massive conflict for Trump’s legal team.

  “Rudy can’t do this,” Sekulow told Trump. “He’s a witness. He’s at the center of this whole thing!”

  But Trump viewed Giuliani’s appearances on TV on his behalf as purely beneficial. The rest of Trump World was perplexed, viewing Giuliani as either problematic or entertaining—but almost always in a purely unintentional way. Officials inside the campaign and White House knew that Giuliani had a direct line to Trump and, with just a quick phone call, could derail any plans they had put in place. Cipollone had an uncomfortable front-row seat as Giuliani moved in and out of the White House during the past year, spinning Trump on convoluted Ukraine conspiracies. But the reserved Cipollone limited his concerns to his team.

  “I have a very high regard for Rudy Giuliani as a fellow New Yorker,” Cipollone told Trump, then pushed for other high-profile lawyers to avoid adding Giuliani.

  Cipollone instead leaned internally on a pair of White House attorneys, Patrick Philbin and Mike Purpura. For Trump’s outside legal team, led by Jay Sekulow, Trump selected familiar faces from Fox News with household name recognition and TV experience—the most controversial selections of which were Alan Dershowitz and Ken Starr. Dershowitz, a constitutional-law professor who famously helped defend O. J. Simpson during his trial on murder charges in the 1990s, was fighting a defamation suit filed by a victim of financier Jeffrey Epstein, who claimed she was forced to have sex with Epstein’s friends, including Dershowitz, who had worked on Epstein’s 2007 legal team. Starr, also a member of Epstein’s 2007 defense, was best known for leading investigations of President Bill Clinton during the 1990s. He had resigned as chancellor of Baylor University in 2016 amid allegations the school mishandled sexual-assault allegations aimed at its football team.

  Trump also added Robert Ray, who succeeded Starr as special counsel in the Clinton investigation; Jane Raskin, a veteran of Trump’s private legal team during Mueller’s probe; and Pam Bondi, a former Florida attorney general. One last-minute addition from Trump was Eric Herschmann, a partner at the firm founded by Marc Kasowitz, who had represented Trump in divorce proceedings, bankruptcy cases, sexual misconduct allegations during the 2016 campaign, and briefly during the Mueller investigation. Attorneys in the counsel’s office viewed Herschmann’s arrival skeptically, and several believed he was Jared’s cousin. It wasn’t true, but the misconception lasted for all of 2020 inside the West Wing, fueled by the fact that Jared had brought Herschmann into the White House, and the two were close, both Jewish, and Jared came from a wealthy family and Hershmann drove a Rolls Royce to work. When he arrived in the White House, Herschmann put so many questions to the counsel’s office staff that Cipollone soon assigned him a West Wing staffer in order to contain the inquiries. As Trump increased pressure to pursue witnesses, Cipollone handed Herschmann the Hunter portfolio. Herschmann prepared for the possibility that he might examine Hunter Biden with such vigor that he endeared himself to the other attorneys in the office, who didn’t want to be bothered with the task.

  With the legal team finally in place, an unusual sense of relative calm radiated from all corners of Trump World. The campaign had been using impeachment to attack Democrats with TV ads for two months and to fuel an aggressive digital operation that delivered its best fundraising quarter to date, dwarfing all of the Democratic challengers. Public polls showed that two-thirds of Democrats were worried about the November election, while Republican excitement outpaced Democrats’—and was growing.

  The White House wasn’t without its internal rivalries. Cipollone had lost confidence in Mulvaney after the news conference gaffe, and he was at war with Grisham, the White House communications director who was furious the attorney was calling his own plays with the media. But the Trump White House was also in a brief period of productivity just before heading into one of the most tumultuous ten-month stretches that any president faced ahead of a reelection.

  There were two types of national stories that tended to have the most impact on the public perception of Trump, and neither were in play in those months. As Brad often told the president, his approval only seemed to dip when he was perceived as overly coarse and insensitive, and nothing highlighted those negative traits like his handling of racial issues and the embarrassing chaos created by constant backbiting and turnover in the White House. But for the moment, the pin was in both of those grenades.

  A second factor at play was an abiding sense throughout Trump World that they knew what they were doing. That confidence was born out of survival instead of accomplishment. The Mueller investigation, and its daily—often hourly—news cycle that drummed on and drowned out almost everything else for twenty-three of Trump’s first twenty-six months in office was over. On one hand, the Mueller investigation netted almost 200 criminal charges, three dozen indictments or guilty pleas, and five prison sentences. But for this White House, it was a resounding victory that Trump was still standing—an outcome that had started to feel inevitable regardless of the size or intensity of the crisis.

  During the 2016 campaign, Washington’s political class predicted Trump’s immediate demise when he misrepresented Republican Senator John McCain’s war record and then criticized him over it.

  “He’s a war hero because he was captured,” Trump said at the time. “I like people that weren’t captured.”2

  But nothing happened.

  Trump belittled Khizr and Ghazala Khan, the Gold Star parents of a slain Muslim soldier. He criticized U.S. Judge Gonzalo Curiel for ruling against him in a fraud case against Trump University, accusing the Indiana-born judge of political bias because he was “Hispanic” and “Mexican” and probably didn’t like that Trump wanted to build a border wall. Former Miss Universe Alicia Machado said Trump—who owned the beauty pageant—called her Miss Piggy because she’d gained weight and Miss Housekeeping because of her Hispanic heritage. His fellow Republicans wanted him to quit the race after the Access Hollywood tape.

  He won the election despite all of it.

  By the time the White House was heading into the Senate impeachment vote—where the only question about the outcome in a Republican-controlled chamber was how large Trump’s victory would be—they were starting to feel invincible.

  “We’ve been through this before,” Jared told White House staffers during an impeachment planning meeting.

  The biggest reason for optimism was that Mitch McConnell was in charge of the Senate, which would ultimately decide Trump’s fate. The fastidious and opportunistic Kentuckian, with pillowy jowls and an inscrutable smirk, had methodically swatted away all of Trump’s probing questions about a lengthy trial with a parade of witnesses. Trump repeatedly asked about calling Hunter Biden as a witness, hoping to raise doubts about his father. But McConnell was having none of it.

 
; Trump and McConnell were both white Republican men in their seventies who had avoided serving in Vietnam thanks to medical deferrals. But their personalities and political styles couldn’t have been more different. McConnell was born in Alabama at the back end of the Silent Generation and was taciturn and goal-oriented. Trump, born four years later in New York at the start of the Baby Boomer generation, was a loud talker focused on the moment. Trump’s first political job was president. McConnell’s introduction to Washington was in 1968 as a congressional aide. McConnell endured Trump’s frivolity. Trump complained that McConnell wouldn’t even crack a smile at his jokes.

  In 2017, when the two men struggled to lock down enough votes to repeal the Affordable Care Act, a frustrated McConnell went silent as Trump started chitchatting about a television program he had watched the previous night.

  “Mitch?” Trump said. “Are you there?”

  McConnell waited another beat.

  “Yes, Mr. President,” he responded. “Back to the bill…”

  McConnell was also frustrated by Trump’s refusal to focus on the details of legislation. In one White House meeting, after the president asked for another explaination about a health care provision that McConnell had repeatedly explained at length, the Senate leader’s only response was to slowly turn his head and glare at Reince Priebus, then the White House chief of staff.

  But by the start of 2020, the two men had forged an odd alliance. McConnell was grateful for Trump’s help keeping the Republican majority in the 2018 midterms, and Trump had come to respect McConnell as a hardball tactician. During the three-day government shutdown in 2018—the first of two during Trump’s four years in office—the president was considering concessions with Democrats, who had refused to fund the government without changes to his immigration policy. McConnell advised Trump that the Democrats had backed themselves into a corner and would have to cave. Trump took the advice, and the Democrats buckled.

  The two also teamed up to install a record number of federal judges, including a particularly acrimonious battle over Brett Kavanaugh’s nomination to the Supreme Court. After the opening of Kavanaugh’s confirmation hearing, Trump grew alarmed that the moving testimony from Christine Blasey Ford, who had accused Kavanaugh of sexually assaulting her when they were teenagers, would sink the nomination.

  “We’re only at halftime here,” McConnell said, pointing out that Kavanaugh would have a chance to respond to the accusations after the break. “Let’s see how Brett does and make an evaluation then.”

  The nomination was approved by the committee and Kavanaugh was confirmed by the Senate with the Republican majority carrying the day on a largely party-line vote.

  On the impeachment trial, McConnell repeatedly pointed to that Republican majority as the most important factor for Trump to keep in mind. Republicans would have enough votes to acquit him, and infusing other variables into that equation created risk, even if it might also provide Trump a chance to embarrass his political rivals.

  The roughest stretch of the trial came the night of January 26, when the New York Times obtained a key passage from the unreleased memoir of John Bolton, who was Trump’s national security adviser at the time of his call to Ukraine. The information ran counter to a key Trump defense that he had held up the aid because of broad corruption concerns—not to try to hinder a political rival—and it turned up the heat on some Republicans to extend the trial by calling witnesses.

  As White House aides scrambled to figure out how to respond, Trump groused about how Bolton had wanted to be his national security adviser only because he couldn’t win the Senate confirmation required for many other senior jobs.

  “I should have seen that as a red flag,” Trump said. “But instead, I did the guy a favor, took him at his word that this was a good fit, and this is what he did to me?”

  For the first time, McConnell’s plans for a quick Senate impeachment trial were under threat of derailment. McConnell and his office had been directing the Trump legal team, pointing out which arguments would be important to make during the trial and what would resonate with certain undecided senators. Now the Senate leader exercised a behind-the-scenes campaign in the chamber to keep his members from panicking and breaking en masse from Trump. McConnell told Trump that fence-sitting Republican senators were wary both of crossing the president and of appearing browbeaten by him. They needed to be seen as having made their own decisions. So Trump stayed on the sidelines.

  A couple days later, I crossed paths with Trump as he strolled the halls of the West Wing. He was calm and collected, almost bored with talk about witnesses.

  “Whatever it is, it is,” he said.

  The result of the final vote on acquittal, on February 5, was as expected. The details were not. White House officials believed they had all the Republicans locked down—and talked openly about which Democrats would join them.

  “Oh yeah, we’ve got Manchin locked in,” Tony Sayegh, one of the communications advisers for the legal team, told associates. “Sinema is 50–50. But Manchin is locked in, 100 percent.”

  Later that day, every Democrat voted against Trump, as did Romney, keeping Trump from his coveted talking point that every Republican in Congress had opposed his impeachment.

  The Romney vote infuriated Trump World, including Don Junior, who was having lunch in Washington. He started gaming out tweets that called on Romney to leave the party, aimed at nothing more than trolling the GOP’s 2012 presidential nominee.

  “Mitt Romney is forever bitter that he will never be POTUS,” Don Junior wrote on Twitter. “He was too weak to beat the Democrats then so he’s joining them now. He’s now officially a member of the resistance & should be expelled from the GOP.”

  Instead, the Twitter missive triggered an immediate backlash. Reporters started calling about whether there was a movement afoot to expel Romney. Don Junior also took a call from Ronna, who was Romney’s niece.

  “You know I can’t just kick him out of the party, right?” the Republican Party chairwoman said.

  “I’m just fucking with him,” Don Junior replied. “This is not some thought-out strategy coordinated with the Republican caucus.”

  The next morning, the president unloaded on his rivals as “dishonest and corrupt”—doing so at the National Prayer Breakfast, a customarily nonpartisan event in Washington.

  There, Trump held up a pair of newspapers with the headline ACQUITTED, and questioned remarks from the previous speaker, Harvard professor Arthur Brooks, who warned of the increasing polarization of the country and urged the audience to “love your enemies.” The president took swipes at Pelosi and Romney, the latter a practicing Mormon, who had cited his faith as the deciding factor in his vote for Trump’s removal.

  “I don’t like people who use their faith as justification for doing what they know is wrong,” Trump said. “So many people have been hurt, and we can’t let that go on.”

  A new Gallup poll showed a personal best job approval rating of 49 percent, including 94 percent among Republicans, and half of all registered voters saying the president deserved to be reelected.

  On the other side of the aisle, Democrats were in disarray. The Iowa caucuses were two days earlier, but they were still another two days away from knowing the results thanks to an embarrassing meltdown in the caucus count, and Biden was six days away from getting trounced in the second consecutive nominating contest.

  Trump World felt indestructible.

  Footnotes

  1 The expression dates back to 1998, when William H. Ginsburg—the lawyer representing Monica Lewinsky during her sex scandal with President Clinton—became the first person to be interviewed on all five Sunday shows on the same day. Other Trump World denizens who accomplished this feat include Jay Sekulow, a Trump attorney tapped in 2017 to explain the meeting Don Junior and Jared took with a Russian operative, and Secretary of State Mike Pompeo, who did it twice: in 2019 to discuss Trump’s attempt to invite the Taliban to Camp David, and in 2020
about Soleimani’s killing.

  2 McCain wasn’t universally acknowledged as a war hero simply because he was taken prisoner. The Vietnamese tried to release him when they learned he was the son of a prominent Navy officer, but McCain refused to violate the military’s Code of Conduct for Prisoners of War and insisted soldiers be released in the order they’d been captured. That decision resulted in an extra five years of torture and imprisonment for McCain.

  5

  Victory Lap

  “A full, complete, and absolute, total acquittal. And it wasn’t even close.”

  —Campaign rally, Manchester, New Hampshire, February 10, 2020

  On the afternoon of February 10, Trump opened the east door of the Oval Office, stuck out his hand, and checked for rain. He laughed—it was a covered patio—and an aide scurried to grab Trump’s black umbrella. With the umbrella extended overhead, Trump shuffled through the wet grass of the South Lawn, waved to reporters who shouted questions from the other side of the grass, and climbed the few steps into an idling Marine One, the president’s four-blade, twin-engine helicopter painted military green with a white top. The president was heading to New Hampshire for the first campaign rally since being cleared of impeachment charges, and all of Trump World was primed for the victory lap.