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

by Michael C. Bender

  By that point, Jared had decided that Stepien’s attempt to rebuild the campaign’s polling and data operation had backfired. Jared thought the strategy Stepien and Jason Miller implemented to purchase TV ads wasn’t precise enough in its targets, and he was concerned about the corrosiveness between the campaign and the Republican National Committee. Those were all areas on which he and Brad had been aligned for years.

  In his diminished role, Brad had started to engage with the campaign again and sent an email to Jared, Stepien, and Miller at the end of August that analyzed the Biden campaign’s TV buys for September and October, compared them to the Trump campaign’s plans, and determined that Biden was acting more like the 2016 Trump campaign, while Trump’s reelection bid more closely resembled Hillary Clinton’s four years prior. Brad also sent his memo to Eric and Lara Trump, Don Junior, and Ken Kurson, the New Jersey strategist and Kushner family friend—and separately forwarded it to Ronna later.

  Brad praised Biden’s team for “buying deep.” The Democrat would have ads in seventy-five media markets by the fall, and those buys would be complemented with spots on national networks that skewed toward female and Black viewers. Brad complimented the Biden team for running spots—thirty-six unique ads by his count—that focused on the same theme but varied in length and imagery based on which voters they were targeting.

  Brad noted that Biden had been uncontested on local radio for weeks, except for a small buy the Trump campaign had made in New Mexico. The Biden team was also targeting addressable television, which was one of the under-the-radar Trump campaign tactics in 2016. The emergence of televisions and cable boxes with their own IP addresses had enabled campaigns and other advertisers to direct specific messages to specific types of viewers, and that kind of surgical marketing was still developing ahead of the 2020 campaign; in 2019, Gary Coby, Trump’s digital director, had met with executives from some cable providers to help build their advertising tools—but the campaign halted those purchases once Brad was demoted.

  “Biden’s buying team is significantly ahead of Clinton’s at this point in 2016 in terms of TV buying execution,” Brad wrote in his email. “It actually looks a lot like what we did in Sept/Oct of 2016, and they seem to be executing many of the ideas that we had been working on for the last 18+ months.”

  Brad suggested changes that would make Trump’s advertising more efficient by targeting individual voters instead of broader media markets, and he strongly recommended starting a radio advertising campaign focused on Black and Hispanic stations.

  A few weeks later, Jared brought him to Washington for a campaign-wide media summit.

  Everyone seated around the conference table on September 22 inside campaign headquarters theoretically played for the same team. But there was no denying the competitive atmosphere as tension rippled through the room.

  Jared and Hope were there from the White House. Larry Weitzner, the campaign’s lead ad maker, was at the table, along with representatives from National Media, a Virginia-based media-buying company that helped the campaign place its ads. Gary Coby was in attendance, as was Stepien, who left partway through the meeting.

  Brad brought a high level of energy. He’d stayed up late the night before with his team focusing on things that excited him: integrated marketing strategies, and incorporating connected TV and video-on-demand. He and Coby geeked out like they had in the good old days. His pitch was high-level, with lots of the corporate jargon that Jared liked. Jason Miller’s presentation was detailed, but focused on how many gross ratings points he would buy on specific days. Brad talked about being more efficient by targeting audiences instead of media markets and about increasing flexibility by setting aside pots of money for last-minute openings that networks often tried to unload at discounted rates. After the meeting, Jared asked Brad to come back and oversee the campaign’s digital and TV advertising operation. Brad didn’t know whether to punch him or hug him. He felt vindicated, but also like he was being asked to do the exact job he’d had taken away from him—but without the campaign manager title.

  Candice’s reaction wasn’t quite as nuanced when Brad returned home and told her the news.

  “Why the fuck would you go do this after they did this to you?” she shouted at him. “They’re going to use you, throw you out again, you’re gonna be more depressed.”

  They argued and drank and shouted until police arrived at their Fort Lauderdale home on September 27, a Sunday evening. The next day, Brad sat in the psychiatric ward of Broward Health Medical Center—an involuntary three-night stay and evaluation required under Florida law. He watched the video of himself getting leveled by the cop playing on a loop on national television. He had an iced tea, an antidepressant pill, and no telephone. Some of the other patients recognized him.

  In some ways, it felt like a nice and needed vacation.

  Days until Election: 19

  With Brad out of commission, the campaign had made some adjustments to the ad-buying operation, but gaping holes still existed. Stepien could barely bring himself to speak with Ronna, who was openly resented by campaign aides and White House staffers jealous of her access to Trump. The campaign’s data operation was still having problems, and Gary Coby complained to other senior members of the team that he couldn’t get a clear direction on where to spend tens of millions in digital advertising.

  “I’ve got $65 million to spend on digital, and I don’t know whether to put it in Pennsylvania, Michigan, Wisconsin, and at what levels,” Coby said. “What’s our first path, what’s our second path, what’s our third path?”

  The campaign was complaining about money problems, but declined $55 million from the RNC to spend on television. The cash was the maximum amount the party could spend directly on behalf of Trump. Ronna thought the campaign’s advertising was overly aggressive and too loud to win the kind of suburban moms and senior citizens whom Trump needed to bring back into the fold. If they were going to hand over that kind of money, she wanted to help shape the new spot. When the campaign said no thanks, she called Trump and told him she was going to do it herself.

  The next day, Jared called Katie Walsh and asked her to take over the role he’d wanted for Brad.

  “Bill is locked in decision paralysis,” Jared told her.

  One of Jared’s go-to moves for moments of high stress was often to throw bodies at the problem, but choosing Walsh showed just how limited his options were. Walsh was a veteran and well-connected Republican operative, but her relationship with Trump had corroded so badly that she was forbidden from ever being in the same room with him. She and Stepien had been rivals since their blowout fights during the 2016 campaign.

  But in the Reagan Room of the party headquarters, Jared ordered Stepien to start working with her.

  Walsh’s first move was to bring in Deep Root, a Virginia analytics company that had been crossing the RNC’s voter scores with their own audience files to create a path for the campaign to reach the voters they were seeking. But Stepien had no faith in the RNC voter scores or in Deep Root, which the campaign had previously stopped using.

  He didn’t trust Ronna. And he didn’t trust much of anything Brad had built before he left. The skepticism was warranted, but the RNC complained that none of the new regime ever asked for help. Instead, Stepien, Clark, and Jason Miller mostly kept their own counsel. The result was blunt-force advertising. Instead of targeting spots where they could find persuadable voters—Latino men thirty-five and older, for instance, or rural white men who rarely voted but liked Trump’s message—ads were aimed at all voters, eighteen years and older, across entire media markets. Several Trump ads ended up airing on Gunsmoke and Bonanza.

  “We needed to call time out to figure out how we were going to target people,” one campaign official said. “Targeting them with bad data is worse than targeting them in a more old-school way.”

  The result was that the campaign started buying a certain number of ads per week—requesting, for example, forty-nine
spots on Fox News in a single week with no explanation. The amount of money spent on Washington, D.C. cable increased, which seemed to others on the team an obvious attempt to catch Trump’s attention instead of the district’s voters, who in 2016 had overwhelmingly supported Clinton.

  Other ad buys were influenced by media coverage. The campaign wanted to avoid any stories that they were pulling ads from states.

  The RNC’s spot, aimed at winning back seniors, struck a soft tone more akin to a pharmaceutical commercial than the campaign’s more aggressive ads, and targeted Arizona, Michigan, and three other states. The party also put up another ad in the final days of the campaign that highlighted the pandemic, and featured a woman wearing a face mask standing at a voting machine as she mulled her ballot.

  Days until Election: 15

  In the summer of 2016, Randal Thom went into cardiac arrest at his home in southwestern Minnesota. The prostitute who was with him at the time seized the opportunity to steal his van. But whenever Randal would retell the story, he’d always smile wide and make sure to emphasize that at least she called 911 before she snatched his keys.

  Trouble always seemed to follow Randal, but that was also part of his charm. In high school, he was student council president, a star on the football team, homecoming king—and arguably the biggest pot dealer in Windom, Minnesota. His beloved Alaskan malamute, whom he’d named after the president, was shot dead by a neighbor. The gunman claimed self-defense, having reached his limit from the terror campaign Randal’s dogs had unleashed on the neighborhood—killing a local goat, disappearing multiple chickens, and once biting a passerby badly enough to require medical attention. Randal remained convinced his malamute’s death was an assassination.

  He’d also paid steep prices for his decisions. Randal had survived a plane crash about twenty years earlier that had killed one of his brothers, who had been piloting the aircraft. The accident had landed him an insurance payout—but he then spent much of the money on drugs, increasingly neglecting his family. His wife and two small children left him. Except for a few instances, they never spoke to Randal again. He was repeatedly arrested for theft and drug possession. He spent time behind bars.

  Randal seemed to turn a corner in 2015 when he moved out to the country. He raised his dogs in peace and picked up some odd jobs from older siblings and their spouses. When he came home from his first Trump event that year, he seemed to find a new purpose.

  “He had never really been politically active, so I remember him coming home very excited about Trump and telling everyone he’s going to be the next president,” said Randal’s older brother Stan.

  Randal started bumping into the same crew in line at Trump’s campaign events in Iowa, and it was Randal who dubbed them the Front Row Joes. The rallies became the organizing principle in his life, and Trump fans loved him for it. Like Trump himself, all of Randal’s past mistakes didn’t matter to them. He hadn’t impaired their lives with his bad decisions, and everyone liked his optimism. Randal’s bedside manner wouldn’t fit any typical definition of Midwestern Nice. He was loud. He was gruff. He had stories that never seemed to end. If female friends were annoyed with him, he’d ask if they were “on the rag” and erupt in a savage laugh at his joke. But he also instinctively welcomed newcomers like they were long-lost friends and was always the first to offer a warm smile and a cold beer. He took to social media like a Millennial, regularly sending links to Trump friends, posting updates on the Front Row Joes Facebook page, and checking in with people if he hadn’t heard from them for too long. When Cindy Hoffman’s mother died in 2017, she arrived at the gravesite to find Randal’s red, white, and blue cowboy hat and a note: In memory of your sweet mama. Love you Cindy, love the Front Row Joes.

  Cindy turned around, and—even though few people had attended the funeral—there was Randal, waiting for her at the burial. She started crying. And then she started laughing when Randal told her the first note he’d written before anyone had arrived had blown off the grass, under the casket, and into the six-foot hole below.

  By 2020, family and friends were so encouraged by Randal’s turnaround that they started helping finance his travel to Trump events. When the pandemic halted the campaign rallies, he went instead to the Trump boat parades that formed along the coast of Florida. The parades invigorated Randal, and the president. As Trump struggled to respond to the pandemic and close the gap with Biden, his aides made sure to route the president’s Mar-a-Lago motorcade past the Trumpian armadas terrorizing the libs with loud country music and oversized Trump flags. Behind closed doors, too, Trump asked advisers if they had seen his followers’ flotillas crowding waterways from the Great Lakes to the Gulf of Mexico. The president planned to attend a boat parade in southeastern Florida the second-to-last weekend of October with an elaborate display of showmanship even by Trump’s standards. His campaign had drawn up plans for a floating landing pad for Marine One, but ultimately pulled the plug over Palm Beach County permitting issues.

  The boat parade floated on. But it was the last Trump event Randal would attend.

  On the afternoon of October 19, Randal had flown back to Minneapolis from Florida and was driving his Toyota minivan south on Highway 169. He was going too fast and started to swerve in and out of traffic. He clipped the back end of a 1994 Ford pickup, which then spun off the left side of the road, rolled over the guardrail, and landed on its roof. The sixty-seven-year-old driver was taken to the hospital, but he’d been wearing a seat belt and was released the next day. However, Randal refused to wear a seat belt, just like he had refused to wear a mask. The collision ejected him from the driver’s seat and onto the highway, where he was crushed to death under his own minivan.

  Alcohol was suspected, based on a witness’s account of Randal’s driving and the beer cans collected from the accident scene. But after an autopsy report didn’t mention any alcohol in his blood, friends said the cans were probably from the cooler of beer he always kept in the van. Randal had also been in crippling back pain, long overdue for surgery related to a lingering injury from the plane crash, and he’d been given intravenous painkillers the previous day in Florida when the torment sent him to the hospital. But a friend didn’t think he’d been given a prescription, and no pills were recovered on the scene. Some friends and family wondered if Randal had been texting and driving.

  When police arrived on the scene, the battery-operated megaphone Randal used for his cheerleading routines for Trump crowds outside rallies had been powered on from the impact of the crash. It was blaring Lee Greenwood’s patriotic country anthem “God Bless the USA,” a staple of Trump rallies.

  Hundreds of Trump flags had also burst from the minivan and fluttered down like confetti—shiny shades of red and white and blue—that now lay strewn across the highway. A patrolman picked up one of the flags and draped it over Randal.

  Days until Election: 10

  On October 24, Trump cast an early ballot at the Palm Beach County Library.

  Trump had mailed in his primary ballot in August, but that wasn’t an option after he’d spent the entire year warning about the dangers of voting by mail.

  In May, he accused the “rogue” Michigan secretary of state of illegally sending millions of voters mail-in ballots for which they hadn’t asked, but he was completely wrong. In June, he claimed that unnamed foreign countries would print millions of fraudulent mail ballots, without any evidence. In July, he promised that voting by mail would result in the “most inaccurate and fraudulent election in history”—and he called for the country to delay the election.

  In August, he said on Fox News that Democrats were already “trying to steal the election” and that he planned to dispatch sheriffs, U.S. attorneys, and attorneys general to polling places—despite not possessing those powers. At his debate with Biden in September, Trump launched an extensive attack on mail-in voting that was teeming with falsehoods and misrepresentations.

  From the debate stage in Cleveland, he accused Phila
delphia election officials of improperly blocking his team from monitoring voters filling out mail ballots, even though state law gave his team no legal right to do so. He said a West Virginia mailman was selling ballots, without explaining that the case involved a postal worker—who pleaded guilty in July—switching several absentee ballot requests from Democrat to Republican.

  “This is going to be a fraud like you’ve never seen,” Trump said that night.

  His team had begged him to stop. All of the claims were either baseless or wildly inaccurate. Plus, Republican state parties had spent years honing their vote-by-mail programs—including in Florida in 2016 when Wiles’s hard-fought personal check from Trump paid for a program to remind voters to return their mail-in ballots. But Trump wouldn’t budge on his plan to demonize mail voting, so instead the campaign hoped a very public trip to an early voting location would help convince Republicans who had abandoned their mail ballots to start showing up at the polls.

  The TV cameras captured Trump heading into the library but weren’t allowed to follow him into the voting booth. Only his team and a few poll workers were inside when Trump arrived.

  The president showed identification, received a ballot, and walked over to a plastic, pop-up voting booth. In the tiny booth, he spread his legs wide, hunched over with his elbows on the booth, and slipped a cheat sheet out from the inside pocket of his suit jacket to help him vote. The Palm Beach County ballot was multiple pages. Trump didn’t want to be accused of taking too long to vote, but he also didn’t want to leave any questions blank. As Meadows circled the room and Stepien hovered nearby, Trump made his pick in each race, from president to sheriff to the Palm Beach Soil and Water Conservation District Board of Supervisors.

  Trump finally finished, slid his ballot into the privacy sleeve, and walked over to the voting machine. He fed the first page into the machine—the president who had very seriously and carefully filled out his ballot now wore a proud look on his face. He fed the second page into the machine.