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

by Michael C. Bender

  The dividing lines quickly hardened between Trump’s two campaign teams as Brad spent the next year publicly describing the reelection bid as bigger, better, and more disciplined than the ragtag effort in 2016. No more campaign aides having to work on the fifth floor of Trump Tower, where The Apprentice had once been taped and sheetrock fell from the walls in 2016.Version 2.0 would be spread across the fourteenth floor of a modern office building just across the Potomac River in Arlington, Virginia, complete with glass-walled conference rooms overlooking the symbols of American democracy that formed the Washington skyline.

  The reelection campaign quickly assembled a thick, corporate-style binder with guidelines that covered design minutiae such as font size, spacing, and preapproved colors. Trump Red and Trump Blue were for logos, Trump Gold for special occasions. The detailed book—“Branding Guidelines for the Trump Presidential Campaign”—underscored the new regime’s rejection of the seat-of-the-pants style of electioneering that had characterized the first campaign. It specified which images of Trump best conveyed compassion, which showed strength, and, in the case of a photo of the president pointing into the camera, which ones let online donors know they urgently needed to boost contributions.

  Corey and Bossie scoffed. They hadn’t needed a branding book to win the presidency.

  “It’s very Trumpian to be understaffed, underfunded, and underestimated as an underdog,” Kellyanne told me in June of 2019.

  By the start of 2020, the two-year-old reelection bid had a sleek new look and a more professional feel from the outside. But on the inside, the campaign facelift masked the internal tension that had been festering since 2016 as Trump toggled between ignoring the rivalries and encouraging them.

  “They’re fighting over who loves me the most,” Trump told me during a 2017 Oval Office interview when I had asked about the backbiting inside his team.

  Also concealed from public view was the unresolved conflict inherent in the setup of the campaign management. Trump put Brad’s hand on the wheel, but with Jared steering from the backseat. Each represented competing parts of Trump’s own personality.

  The thirty-nine-year-old Jared, with dimpled cheeks, a baby-smooth face, and a fondness for slim-fitting suits and skinny ties, was calculating and ruthless and shared his father-in-law’s totalitarian approach to business. Jared was married to Ivanka, the president’s favorite and most commercially marketable child, and descended from the kind of wealthy Jewish real estate family that Trump admired during his own rise in the industry and even long after he’d transformed his company into a licensing business.7

  The forty-four-year-old Brad, meanwhile, was a towering six-foot-eight Kansan with a long, bushy beard and an internal compass that consistently led him to the center of the action. He channeled the more primitive pieces of the Trumpian id. Both were restless, truth-stretching salesmen who valued a well-told story over the preciseness of the facts. They shared an instinct for viral branding and understood how to tap into the zeitgeist with merchandising and memes that raised money and generated energy for the campaign. More than 12 million Americans in 2016 said Trump wasn’t qualified to be president but voted for him anyway—a data point that reaffirmed for Brad that a well-liked brand could prove more important than a well-liked candidate.

  By the end of 2019, the campaign had raised more than $20 million just by selling branded merchandise timed to social media trends and cable news headlines. The campaign pushed Trump-branded plastic straws as Americans complained about environmentally friendly paper straws that always seemed to dissolve upon contact with a cold drink. They promoted a Christmas tree ornament shaped like a red Make America Great Again hat, albeit finished with 24-karat gold as a special treat for the holidays. And when Trump referred to House Intelligence chairman Adam Schiff, the California Democrat leading the impeachment charge, as a “little pencil neck,” the campaign quickly printed shirts that lampooned Schiff with a red clown nose and a No. 2 pencil in place of his neck.

  But Trump’s inability to reconcile his conflicting impulses left his campaign team without a clear roadmap to follow from the very start of the race. Instead, the unresolved questions about control of the campaign and long-simmering internal feuds were carried into the start of 2020, but masked—at least for the moment—by the shiny new campaign operation and an artificial bubble in Trump’s poll numbers that had been inflated as his Democratic rivals leaned into impeachment.

  “I hit my highest poll numbers since I got elected because the American people and, frankly, people all over the world, know it’s a hoax,” Trump said at a campaign rally in the opening weeks of the new year. “The Democrats are trying to overturn the last election—we will make sure they face another crushing defeat in 2020. November third—mark it off.”

  Footnotes

  1 John Barron’s first appearance, incidentally, was an attempt to stall a New York Times story about why he’d razed a Midtown Manhattan building to make way for Trump Tower. Trump had jackhammered two art deco relief sculptures instead of donating them to the Metropolitan Museum of Art, which he had promised to do after the museum expressed interest in the pieces.

  2 The national debt, incidentally, increased by $7.8 trillion during Trump’s four years in office.

  3 Yes, that Matt Lauer.

  4 Trump and Beatty had spent the better part of a decade competing for space in the tabloids, and the Hollywood leading man had also just floated the possibility of his own presidential campaign.

  5 Trump stated in the Times , “I’ve been out with lots of beautiful women, OK? I guess we all have our Achilles’ heel.”

  6 Fun fact: The show glorified the dramatic cutthroat competition of capitalism, but the name of the song came from a Bible verse that warned about that very thing: “For the love of money is the root of all evil” (1 Timothy 6:10).

  7 Trump’s fascination was less about race or religion, and more about capitalism and recognition. The Rose family, among the oldest real estate families in the city, were on Trump’s short list of true heroes. He was close with Richard LeFrak, one of the largest developers in the New York area. These were people who took huge risks building on some of the world’s most expensive real estate. Trump wanted to impress them his entire adult life.

  3

  Momentum

  “The great USMCA Trade Deal has been sitting on Nancy Pelosi’s desk for 8 months. She doesn’t even know what it says.”

  —Twitter, December 19, 2019

  The Battle Creek rally had lifted Trump’s spirits, but not enough to completely shake the torment of impeachment. He was more convinced than ever that there was nothing illegal about his call to Ukraine, and that Democrats were only trying to embarrass him. The day after the rally, he barely even noted the moment when the House approved his administration’s rewrite of the North American Free Trade Agreement. It wasn’t just a major campaign promise: It was one of his only unshakable policy views, the principles of which he had articulated since his very first national TV interview—an October 1980 discussion with talk show host Rona Barrett at the height of the Iran hostage crisis.

  “We just sit back and take everybody’s abuse,” the thirty-four-year-old Trump said at the time.

  The revised pact was one of the biggest bipartisan achievements of Trump’s term. It passed Congress with more support than his administration’s criminal justice reform legislation, which eliminated mandatory minimum prison sentences, and far more than his 2017 tax cut, which about a dozen Republicans voted against. The practical significance of the new trade policy was debatable. The law created more incentives to manufacture car parts in the United States and improved access to the Canadian dairy market, but the changes were also largely a branding exercise that renamed the pact the US-Mexico-Canada Agreement. Still, the opportunity for a political impact was clear.

  Trump’s hard line on trade helped explain the unusual appeal for a Republican in the Rust Belt, and his path to a second term started with defendin
g those states, where the new trade law was hugely popular. In 1993, the congressional delegations in Pennsylvania, Wisconsin, and Michigan had opposed the original NAFTA deal, 28–17. Twenty-six years later, House members from the three states—nineteen Democrats, nineteen Republicans, and one independent—backed Trump’s US-Mexico-Canada Agreement, 35–4.

  But Trump’s attention was elsewhere. He posted sixty-eight messages on Twitter that day. Just one mentioned the trade deal, and he used that to criticize Pelosi for not pursuing it sooner. Nearly all the other social media posts focused on impeachment.

  “PRESIDENTIAL HARASSMENT!” he wrote.

  The next day, Trump and his family bundled up in their winter coats to depart the White House for a two-week vacation at Mar-a-Lago, his winter retreat in Palm Beach, Florida. Trump and his teenage son, Barron, wore matching black overcoats, dark suits, and silk ties—power red for dad, icy blue for son—while Melania attired herself in taupe: a knee-length camel-hair winter coat that matched her cashmere sweater and beige ankle-length dress pants. Her parents, Viktor and Amalija Knavs, who had effectively moved to Washington with their daughter, were on their way, too. The rest of the Trump kids and their families would join everyone in the South Florida sunshine.

  The thick, salty South Florida air was good medicine for Trump. He golfed that first morning in Florida and spent fourteen of his sixteen vacation days on the course. He loved to play. There was little else he could think of that was more fun and more relaxing than golfing at one of his eponymous courses, but he hated to admit it. On one hand, he should have been embarrassed; he had relentlessly mocked then-President Obama for the 306 days the Democrat spent golfing over eight years in office—and then Trump nearly matched that total in half the time.

  But Trump’s shamelessness was his political superpower.

  One of the first things Jared realized during the 2016 campaign was the colossal value of his father-in-law’s willingness to say and do things other candidates would never dare. There was obvious risk, of course, but every time he thought Trump had finally suffered a fatal self-inflicted wound, his father-in-law would bounce back. And yet admitting a love for golf—or often, that he even played the game—was where Trump drew the line.

  I remember being struck by this from the very beginning, in April 2017, when I and a few other colleagues at the Wall Street Journal landed the first newspaper interview with Trump in the Oval Office. Trump wanted to memorialize the occasion with some pictures, and as we loitered around the Resolute Desk, Jerry Seib, the executive Washington editor for the newspaper, asked a seemingly casual question.

  “How’s the golf game?” Seib asked.

  “You know, I go to these places, but I don’t play very much,” Trump said, suggesting that while he was already a frequent visitor to his golf clubs as president, he wasn’t actually hitting the links.

  Trump’s travel between the White House and his courses was a well-documented matter of public record, but the president wouldn’t admit he was really playing. At that point—twelve weeks into his presidency—Trump had been golfing nineteen times. Obama, at the three-month mark, hadn’t played at all.

  Two years and eight months later, during a Christmas Eve call with the troops during the fourth day of his 2019 break, Trump wouldn’t even level with Brigadier General David L. Odom, the deputy commanding general of a Marine amphibious force, who asked how he planned to spend his Christmas.

  “I really pretty much work,” Trump said. “That’s what I like to do.”

  An hour later, Trump climbed out of the black presidential limousine known as The Beast—a specially designed $1.5 million Cadillac that can put out a smokescreen, electrify its exterior handles, and hermetically seal itself to protect the passengers from biochemical attacks—and walked into Trump International Golf Club in West Palm Beach.

  On January 2, 2020, the start of what would be one of the most tumultuous years in modern American history, Trump’s calendar included some work, some play, and some campaigning.

  After a round of golf that Thursday morning, Trump visited with Jared, Brad, and Coby. The small crew walked Trump through some early planning for the new year, including potential rally sites, new merchandise in the pipeline, and the latest campaign ads they were working on—most notably the hugely expensive Super Bowl ad they were planning. The $5 million thirty-second spot was roughly 500 times as expensive as a typical national commercial. The ad would later become a flashpoint amid the already vicious internal backbiting of Trump World. Was the Super Bowl ad—the reelection bid’s largest single expenditure—a sign of profligate spending and undisciplined strategy? Or was the purchase—less than 1 percent of the $1.5 billion spent on his election—an investment in the president’s brand and the kind of outside-the-box thinking needed to reelect an unorthodox candidate?1 The most forceful opponent of the Super Bowl spot was Tony Fabrizio, the campaign’s chief pollster. The sixty-year-old Fabrizio had been in and out of Trump World for the past decade and involved in politics far longer, ever since working as an eighteen-year-old on a Long Island congressional race in 1978. Barrel-chested, bald-headed, and squat, Fabrizio had a reputation for delivering unvarnished truth to his clients. Raised in an Italian family in Long Island, he could be a crotchety old bull who was also at turns playful and mischievous. It was sometimes tough to tell the difference between arguments and affection with Fabrizio. He drove a powder blue Aston Martin convertible at home in South Florida and leaned into his reputation as a political brawler. Inside Senator Bob Dole’s 1996 presidential campaign headquarters, where he was chief pollster, Fabrizio taped his nickname, “The Rat,” onto his office nameplate.

  Fabrizio had studied the art of applied politics at the foot of legendary New York Republican Arthur Finkelstein, who groomed a generation of the party’s most well-known operatives, including Roger Stone, whom Finkelstein introduced to Fabrizio in 1978. One of Finkelstein’s rules was that it was always a more effective play to focus on your opponent than on your own candidate. And when it came to the Super Bowl ad, Trump didn’t even have an opponent yet. The football game was set for February 2, but the first nominating contest in Iowa wasn’t until February 3. Even inside the campaign no one was sure which Democrat they might face. The one thing everyone seemed to agree on in January was that Senator Bernie Sanders was going to win Iowa, which was actually won by Pete Buttigieg, the former South Bend mayor. Brad thought Senator Elizabeth Warren was coming on strong. Ronna said Senator Kamala Harris looked like a formidable contender. John McLaughlin, another Trump campaign pollster, and Dick Morris, a former Clinton political strategist who had been quietly advising Trump, warned that former New York mayor Michael Bloomberg could surge to the nomination. Bill Stepien, a senior campaign adviser at the time, pointed to polling that showed Biden was Trump’s biggest threat.

  But what spooked Fabrizio most was the cost. Inside campaign headquarters in December, Brad had been watching the commercial when he hurriedly gathered in his office senior members of his team to play them a rough cut. Fabrizio, McLaughlin, and Murtaugh watched the chilling spot. Shot in black and white and set to slow, sentimental piano chords, the ad showed Alice Johnson, a sixty-three-year-old Black woman, walking—and then running—out of the federal prison from which she’d just been released and into the open arms of her friends and family. After more than twenty years in prison, Trump had commuted the life sentence she’d received for her role as the kingpin of a Memphis-based cocaine ring. The ad described her crime as “a nonviolent drug offense.”

  “What do you think?” Brad had asked the room.

  “Yeah,” Fabrizio said nonchalantly. “It’s a good ad.”

  Brad questioned the pollster’s lack of enthusiasm.

  “That’s a lot of money,” Fabrizio said. “Do you know how far that will go at the end of the election?”

  Brad waved off the concern. “No,” he assured the group. “We’re going to have plenty of money.”

  The fact tha
t the Trump campaign was swimming in cash proved to be the deciding factor. An aggressive, cutting-edge, and boundary-pushing online fundraising operation run by Gary Coby, and a more traditional though equally prodigious fundraising effort by Ronna aimed at high-end donors from the RNC, had together raised more than $460 million in 2019 for Trump’s reelection, and the team ended the year with nearly $200 million in the bank. By the end of January, the campaign collected another $60 million. Brad had studied how Obama’s reelection campaign collected and spent money in the 2012 race and had adjusted budget projections so that they never had more than $120 million on hand at a time.

  “Just think we should keep this around as a quick snapshot of Obama spending,” Brad wrote in an email to Jared in December 2019 that included a spreadsheet of how much the Obama team had raised, spent, and had in the bank for each month of 2012. “They matched their spending to what was raised each month after they had a nominee, then released their cash stockpile with any final money raised in the last thirty days. Makes a ton of sense.”

  At the start of February, just before the Super Bowl ad aired, the Trump campaign had already spent more than $50 million on ads, including $35 million on digital ads on Facebook and Google and another $17 million on broadcast and cable television ads.

  Trump was discussing the Super Bowl ad at Mar-a-Lago with Jared, Brad, and Coby when national security officials pulled Trump out of the room.

  “Watch your Twitter,” he told them. “It’s going to get interesting.”

  Trump disappeared into a secured room in the resort, tuned into a military video feed, and watched as American MQ-9 Reaper drones fired multiple supersonic, laser-guided Hellfire missiles at a pair of cars leaving Baghdad International Airport. Moments later, Qassem Soleimani, the commander of Iran’s elite Quds Force, was dead.