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

by Michael C. Bender

  The irony was that Stepien had always trusted Fabrizio’s polling. In Stepien’s first days as campaign manager, the veteran pollster had been one of few campaign hands he had asked for help. But then Stepien found out how much the campaign was paying for Fabrizio’s expertise, and he couldn’t get past the price. Fabrizio’s rates were no secret—he was widely known as an expensive pollster. But Stepien had become obsessed with trying to watch every cent, even to the point of irritating campaign aides by putting a stop to catered lunch meetings.2 Stepien exploded in a flurry of expletives over a monthly $25,000 fee Brad had approved to secure the services of Fabrizio’s firm.

  “Holy shit!” Stepien said when he learned about it. “I’ve never heard of a pollster having a monthly retainer!”

  Stepien never asked Fabrizio about the retainer. He just mostly stopped speaking with him. During the first week of September, Fabrizio gave a lengthy state-by-state presentation that walked the campaign through a deep dive into which voters the campaign needed to target, what the messages should be, and which markets required the biggest investment of advertising dollars. Fabrizio was hoarse by the end of the call. But Stepien hadn’t said a word.

  A few weeks later, Fabrizio sent around results from a “brushfire” survey that skimmed the battleground states to measure trends. The poll showed Trump’s numbers had sharply fallen off a cliff. It was a confusing twist for an already angry campaign manager, and Stepien could barely conceal his frustration when he confronted Fabrizio over the data.

  “You give me these numbers—what do they mean?” Stepien snapped. “Why did this happen?”

  The poll was an average of the seventeen battleground states, Fabrizio told him. It was only a snapshot of the current landscape and was not intended to show why it looked that way. But Stepien wasn’t satisfied, and the two men argued back and forth until Fabrizio was finally as angry as the campaign manager.

  “You know what the problem is here? The problem is we can’t control the White House message! And coronavirus cases keep going up!” Fabrizio shot back.

  The campaign didn’t ask Fabrizio for another in-depth poll for the final two months of the race. Instead, Stepien quietly brought in another pollster, Brock McCleary. McCleary was a former New Jersey Republican Party operative who had worked on several races with Stepien. Stepien explained the change around campaign headquarters by saying he had just as much confidence in McCleary, but at half the price of Fabrizio. McCleary’s firm, Cygnal, billed the Trump campaign for $1.8 million in polling services over the final two months of the race. Fabrizio’s firm had charged $4.5 million—over the previous two years.

  In addition to McCleary and Skelly, the last addition to Stepien’s rebuilt data team was also the most unusual: Kevin Hassett, a Penn-trained economist with ginger hair, a wide, boyish grin, and a long list of admirers in the White House. Hassett had been chairman of the White House Council of Economic Advisers for most of Trump’s first three years in office and was known inside the West Wing for his sharp mind, endless optimism, and policy views that didn’t fit neatly into political orthodoxy, including an openness to a carbon tax and reducing levies on corporate income.

  Hassett had become close to Jared, who admired the economist’s rosy outlook and brought him back into the White House at the start of the pandemic to assist with the administration’s response to Covid. Hassett had no experience in public health or any background in infectious diseases, but neither did Jared. Hassett’s optimism—he had authored a book in 1999 based on the argument that stocks were so undervalued that the Dow would soon surpass the 36,000 marker (it passed 27,000 on Election Day)—reigned supreme again. Back in the White House, he helped build a model that suggested the daily death count would peak in mid-April and then come to a halt by mid-May. Even a year after that prediction—in May 2021—there were still about 700 Americans dying each day from Covid.3

  To the surprise of some colleagues, including Stepien, who had worked for two years in the White House with Hassett, Hassett’s interests also included partisan politics. He’d been an economic adviser to John McCain in 2008 and Mitt Romney in 2012, but Jared brought him into the Trump campaign to try his hand at modeling political data. During the final month of the race, Hassett was part of a weekly call with Jared, Stepien, and others, advising on where his models showed opportunities for Trump. By the final week, the call had become daily.

  Inside the campaign, Hassett’s sunny analysis was identified as the spark for a brief, internal battle over whether Trump should visit New Mexico in the final week of the race. The push came from Jared, who felt upbeat about Trump’s surge at the end of the race—and his own decisions to replace Brad, elevate Katie Walsh inside Trump World, and build a reservoir of cash inside campaign coffers.

  The campaign’s key man in Ohio, Bob Paduchik, had told Jared the race was all but over there in mid-October. In Florida, Susie Wiles had been touting strong trends in unlikely demographics for Trump: Hispanic men and Black men. Meadows was confident North Carolina was done and dusted. The Midwest looked close—the surge of absentee ballots flipped the advantage in Pennsylvania back and forth every day—but Jared had seen the same show back in 2016.

  Stepien and Oczkowski told Jared that Arizona looked close, but the margins from early voting were in their favor. And in Georgia, the campaign was predicting a victory with a 4 percent margin, surpassing Trump’s victory there in 2016.

  Jared pointed to that data when Trump asked about a final stop in Georgia.

  “You’ll be fine,” Jared told the president.

  But Trump wanted to go.

  “If David is saying we need to go, then let’s go,” Trump said.

  Trump World sent word to Perdue’s campaign on October 29 that the president had agreed to a rally in Rome on November 1, just as the senator had requested. To fit the Georgia stop into the schedule, which already included five rallies on each of the final two days, the Trump campaign scratched one of two North Carolina events that day. But Trump had waited so long to commit to visiting Georgia that Perdue had to drop out of the final debate—which had already been scheduled for that night—with his Democratic opponent, Jon Ossoff, in order to attend the rally with the president.

  At the rally, Trump donned a red campaign hat and repeatedly praised Perdue, talking about how wonderful and happy he felt to be on the campaign trail.

  “I shouldn’t even be here,” Trump told the crowd at the start of the rally. “They say I have Georgia made, but you know what? I said, ‘I promised we have to be here.’ They said, ‘Sir, you don’t have to come to Georgia. We have it made. It’s won, it’s well.’

  “But you’ve got to go vote,” Trump added a few minutes later. “You never know. It’s called politics. You never know. Got to be careful. Get out and vote.”

  Days until Election: 1

  On November 2, Trump opened the final day of the campaign convinced that victory was his. He wasn’t relying on his gut or his Twitter mentions. His campaign team had told him. Stepien’s reconfigured data operation showed that Trump had been methodically closing the gap with Biden for weeks and that turnout would be abysmally low, which was a dynamic that had favored Trump in 2016 and would benefit him again in 2020. Trump heard from Stepien and Miller that he would win Arizona by a nose and capture Georgia by a comfortable four-point margin. Neither would happen.

  But there was no denying the energy on the ground. Even public polls during the final stretch showed Trump closing in on Biden. With three weeks to go in the race, Trump trailed Biden by more than ten percentage points, according to the RealClearPolitics average of national polls, and that average dropped by about one point each week. Trump was in a good mood, mocking rivals and laughing out loud at a supercut of Biden’s verbal stumbles that the campaign had spliced together and started playing at rallies. He finished each performance with a wide smile and an endearingly awful hip-twist and fist-shake—to call it a dance would only sully the word—to the 1978 disc
o anthem “Y.M.C.A.,” from The Village People.

  Trump, who had been sidelined with Covid until October 12, was competing with an energy that few even in his inner circle could believe. He would relax at night by watching a UFC fight on the flight home and flipping through the cable networks to find footage of the Biden rallies so he could laugh and make fun of the honking cars—a Biden campaign nod to Covid protocols. He’d walk through the plane to check on his team on the flight home—telling them to enjoy their meal and asking if they were tired yet. Ronna had campaigned with Trump for a few days and told him she was exhausted.

  “I want Regeneron next time!” she told him.

  The campaign team felt the gap closing, but the atmosphere inside Air Force One was beyond cautious optimism for a strong finish. There seemed to be a metaphysical certainty about a second term for Trump. Robert O’Brien, Trump’s national security adviser who frequently traveled for campaign stops, told the president that he might win 340 electoral votes. Eric Trump carried a map with even more electoral votes. Jason Miller told reporters that the campaign felt more confident now than it had at the same point in 2016.

  “We’re going to win it, we’re winning all over,” Trump said in Traverse City, Michigan, on the last day of campaigning. “We see the real numbers.”

  But the reality was that it had been more than three decades since a Republican had won with the kinds of numbers Eric and O’Brien were touting. And the problems that the Stepien regime had been complaining about for months—too much superfluous spending under Brad, too many outside voices influencing decisions, and too many messages coming from the president—had never been fully addressed.

  Instead, all three concerns were epitomized in a single campaign TV spot that aired in the last weeks of the race—including on the final day. “The one that Hannity wrote,” as it was known inside the campaign.

  In 2016, Hannity had appeared in a promotional video for Trump in which he touted the Republican nominee and pledged his personal support. And even though the Fox News star often described himself as a talk show host and not a reporter, the video crossed a line inside corporate headquarters, which billed the network as a journalistic outlet. Fox issued an unsigned statement at the time claiming that Hannity hadn’t told anyone about the video in advance and that “he will not be doing anything along these lines for the remainder of the election season.”

  Now, four years later, Hannity told me that he had nothing do with the spot known inside the campaign as “the Hannity ad,” and disputed that he wrote any commercials for Trump. He said he hadn’t suggested ideas or offered any advice when it came to the president’s campaign spots. Hannity said he had merely raised concerns with the campaign during the final months of the race about why they were being outspent by Biden on television in key swing states.

  “The world knows that Sean Hannity supports Donald Trump. But my involvement specifically in the campaign—no. I was not involved that much,” Hannity told me, when I asked him about the commercial. “Anybody who said that is full of shit.”

  If Hannity had written the ad—as campaign officials privately said he did and as Trump didn’t dispute it—it would likely have set off similar alarms once again inside the network.

  But even if Hannity had nothing to do with the spot, that would represent its own remarkable twist. The only reason the ad aired was because campaign officials were told Hannity wrote it with Trump’s blessing; if Hannity had nothing to do with the commercial, that would raise significant questions about the decision-making process inside the campaign.

  It was a memorable ad inside campaign headquarters. The Trump campaign aired more than 100 different TV spots in 2020, and this was one of just eight that were sixty-seconds long. Nearly all of the other commercials were thirty seconds.

  Multiple internal campaign emails referred to the spot simply as “Hannity.” Another referred to it as the “Hannity-written” spot.

  “POTUS has not yet approved, but Hannity has,” read one internal email.

  “Hannity said this is our best spot yet,” another campaign aide wrote.

  But inside the campaign, the spot was mocked mercilessly—mostly because of the dramatic, over-the-top language and a message that seemed to value quantity over quality. The script that circulated in mid-September leveled almost two-dozen different attacks at Biden in a single minute—roughly one attack every two-and-a-half seconds.

  “Everyone hated it,” a Trump campaign official said. “It was so ridiculous.”

  The original script also included language that Hannity often used on his show during the final two months of the race. Biden was a “forty-seven-year swamp creature” who had “accomplished nothing” and supported a “radical, socialist Green New Deal.” The Democratic nominee was partnering with “socialist Bernie Sanders,” and Biden himself was “radical, socialist, extreme.” It accused Biden of wanting to raise trillions in new taxes, supporting amnesty for undocumented immigrants, turning his back on law enforcement, and lacking the courage to denounce violence.

  The campaign’s legal team wouldn’t allow the term “socialist” to be used so loosely, but the production team leaned into the absurdity. The spot was narrated with a deep, sinister male voice and included a series of outlandish images, including one with Biden rising out of a swamp.4

  The final thirty seconds abruptly shifted to positive messages about how Trump was fighting for every American.

  “Vote Donald Trump 2020 for you and your family’s safety and security,” the narrator said in the final line of the ad.

  Campaign officials didn’t think the spot would win Trump any new voters and deemed it so useless that they limited it to exactly one show: Hannity. The calculation was that running the spot in that hour of primetime on Fox News would ensure that both Trump and Hannity saw it. If the two men watched the spot on television—and were satisfied enough to stop asking about the commercial—that seemed to be the best result of the ad.

  The total investment: $1.5 million to air on Hannity’s show from October 12 to November 2. The spot aired on six of the sixteen primetime episodes of Hannity during that time, and on three of the network’s daytime programs on the final day of campaigning. For a campaign that had pulled down its ads in August and cut the size of its advertising buys in some Midwest battlegrounds in mid-September—both partly out of Stepien’s concern they wouldn’t have enough cash for the stretch run—it was a heavy price to pay.

  Trump approved every TV spot before it aired, and “the one that Hannity wrote” was no different. But Trump’s pollsters had showed him data that his own disjointed messaging—which the “Hannity” ad seemed to underscore—was hurting him against Biden.

  One way the campaign tested messaging was an open-ended question that asked respondents to recall anything they could remember from the past week that Trump and Biden either said or did.

  In late September, voters remembered ten different items about Biden. Several memories involed Supreme Court Justice Ruth Bader Ginsburg, who had just died. But the next five most frequent answers were centered around Biden’s singular issue of the race: Covid. Some remembered that he’d said Trump had mishandled the pandemic. Others recalled Biden had said too many had died from the contagion. Still more remembered Biden saying that Trump’s response showed he was unfit for office.

  For Trump, voters remembered fifteen different topics—a list of issues that was as profuse as it was diffuse. Ginsburg’s passing. Covid going away. Lies about Covid. He’d disparaged the military. The improving economy. Fighting with Fauci. Racist remarks. Something about the president being nominated for the Nobel Peace Prize. Voters recalled both of Trump’s campaign slogans: Keep America Great and Make America Great.

  Few things encapsulated Trump’s mixed messaging in 2020 like his inability to decide between two different slogans. He had been vacillating between the two for much of 2019 and the first months of 2020, but hadn’t used “Keep America Great” since the pan
demic started. The switch back to his 2016 slogan seemed to just underscore a country—and a campaign—in regression.

  Trump’s campaign in 2016 was chaotic, crude, and reductive. But it was also consistent. His candidacy was defined by promises to build a wall, rewrite trade deals, and beat Crooked Hillary. He seemed to instinctively know where to needle opponents, and when he succeeded, he cruelly refused to let up. It was often elemental and painful to watch, but it was almost always effective.

  In 2020, Trump’s messaging strategy was less visceral and more accidental. In the summer, his campaign had aired TV ads with no less than a half dozen different messages. Depending on which spots were in rotation, Biden was too cozy with China, too eager to raise taxes, too liberal, or too cognitively impaired to be president. In some ads, Biden was too soft on crime. In others, he was too tough.

  Trump had made derisive nicknames his hallmark but couldn’t find the handle in 2020. He tried at least ten different times to rename the former vice president. “Sleepy Joe” was one of the first and most common, but that didn’t sound like a villain so much as someone who needed to go to bed at 9:00 p.m. And, well, that sounded nice, especially after four years of Trump. He tried “China Joe,” “Corrupt Joe,” “Quid Pro Joe.” At another point it was “O’Biden” when he tried to tie his challenger to Obama, which was another ill-advised strategy since the former president had remained widely popular across the country.

  On his last day of campaigning, Trump hit the trail with the energy of a candidate who was about to pull off another improbable come-from-behind victory. But he spoke like one who didn’t know what job he was seeking. With final-day rallies in North Carolina, Pennsylvania, Wisconsin, and two in Michigan, Trump criticized Fauci, Beyoncé and Jay-Z, Jon Bon Jovi, and Lady Gaga.

  His crowd in Scranton started a “LeBron James sucks” chant. In Fayetteville, they reprised the 2016 anti-Clinton favorite, “Lock her up.”