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

by Michael C. Bender

  Brad could almost always reassure the boss in the moment, but it was only a matter of time before the tensions would erupt all over again. Inviting more attention to himself with divisive tweets seemed inadvisable even to Brad’s allies. But Brad would consistently wave off any concern about social media.

  “Dude,” he said to one colleague. “The person who likes me doing this is Trump.”

  And sure enough, the Twitter post that had prompted the intervention in the first place would inevitably be retweeted by Trump. Brad understood that a traditional campaign manager would never amplify the kind of incendiary memes and hot takes that poured out of his social media profile. But Trump was no traditional candidate.

  “Jared’s pissed,” Brad said as he scrolled through his phone at Mary Ann’s Diner, where he’d order a red velvet muffin—lightly grilled—and unsweetened iced tea. “He doesn’t want me pushing the Bloomberg video. But if a video like this came out about Trump, every one of those other campaign managers would be tweeting about it. Jared’s just a little more cautious than me. Obviously.”

  It was a rare admission of any daylight between the two. Brad viewed a significant portion of his job as managing his relationship with the Trump family as much as managing the Trump campaign. And Brad did his part to blur the line between family and business, willingly or otherwise. Born in Topeka, Kansas, on January 3, 1976, he was the eldest son of Dwight and Rita Parscale. Dwight, a former assistant attorney general, spent two decades practicing law, but left the field after getting so upset at a ruling, he told friends, he wanted to “beat the crap” out of the judge. Brad described his upbringing as “not overly redneck.”

  Dwight had also run, unsuccessfully, for a series of political offices, including a U.S. House seat before Brad was born, and Kansas attorney general in 1990. The two were close. When Brad accepted a scholarship to play basketball at the University of Texas at San Antonio, Dwight moved the family to be close to him.2 Dwight had hoped some of Brad’s political success in 2016 would help revive his own ambitions, and in 2018, he ran for Republican chairman of Bexar County, Texas. Dwight had been endorsed for the Bexar County position by the outgoing chairman, Robert Stovall, who vacated the seat after Brad endorsed him in a Republican primary for a congressional seat. Stovall and Dwight both lost. Dwight again appealed to Brad for work in 2020, asking his son to have Trump appoint him director of the FBI. When Brad refused, they stopped speaking for a stretch.

  Brad would repeatedly find similarities between his father and Trump: Both men were seventy-four years old, prone to conspiracy theories, and had businesses that went into bankruptcy3 and Brad maintained complicated relationships with each that were often knotted around money.

  Brad also had a tendency to view himself as another of the Trump kids. He took it as a sign that while he, Don Junior, Eric, and Jared were all born in different years, their birthdays fell within the same eleven-day stretch between December 31 and January 10.

  “That’s statistically very rare,” Brad told them when he first put it together. “I don’t know if it’s celestial, but if you’re born in the cold weather, it affects how you approach the rest of your life.”

  Don Junior and Jared were less amazed.

  “So what, Brad?” Jared said.

  When Brad showed up for work during the 2016 campaign, he didn’t own a suit. Eric stopped him before he could get into the elevator at Trump Tower.

  “No,” Eric told him. “You can’t go up and see him without a suit.”

  Brad walked to Men’s Warehouse but couldn’t find anything off the rack that fit his unusual six-foot-eight frame. He kept walking to Tom James Company, where he ordered a made-to-measure suit that he wore on his first day at the campaign. Brad eventually had all his suits made at the same shop, including the one he’d worn to campaign for Trump at New Hampshire eateries on the day of the primary.

  During the 2016 race, Brad grew close to Jared just as the son-in-law took tighter control of the campaign and showed more interest in exploring the digital side of electioneering. Jared leaned on Brad’s background in digital marketing, even though he’d never before worked on a political campaign. Trump asked him to create a webpage for his exploratory committee in 2015, and he was digital director by June 2016, creating and placing ads on social media platforms such as Facebook, developing the campaign’s website, and driving online fundraising efforts.

  By 2020, Brad viewed Jared like a brother. They had been speaking every day, sometimes multiple times a day, for years. Brad spoke to his own sister twice a year, at best. Jared could wink at Brad from across the room, and Brad would understand that he needed to take a break and not be so aggressive with Trump.

  “I don’t think I’m here without him, I don’t think he thinks he’s here without me,” Brad told me once heading into 2020. “We found each other. By the way, let me ask you a question. You’ve been around for a while. Are two people any closer than me and Jared? We’re tied at the hip. Who else has that? Nobody, right? I’m surprised no one has gone far enough to call me a Trump kid.”

  In the Manchester diner that morning, Brad introduced himself to one patron who showed polite interest, then turned his attention back to his breakfast. Brad glanced around the room, realized no one was trying to catch his attention, and turned to his team.

  “Okay, let’s get out of here,” he said. “I already said hi to all the people.”

  Later that morning outside Londonderry High School, where voting booths had been arranged inside the gymnasium, Brad dazzled the Republican volunteers, a half dozen senior citizens speakin’ in wicked N’Hampshah accents, sporting Patriots coats and MAGA hats. They knew who he was, and were ready for him. So he opened his phone and gave them a behind-the-scenes look.

  “You can find events near you, local or national. You can register to attend an event, either an RNC event or a campaign event, register to vote, invite your friends, or host a meet-up. It’s everything it takes to be a Trump supporter,” Brad told the group, huddled under a pop-up tent with a table of baked goods and Dunkin’ Donuts coffee.

  “Whoa! Really?” said Liz Thomas, a Londonderry resident on her shift at the polling place. “What’s the site?”

  “No,” Brad said. “It’s in beta. But it’s nice, right?”

  “Did you build that?” she asked.

  “Yep,” Brad said. “Well, it was my company. But it was my idea. I built Trump World in a lot of ways.”

  Brad turned to the next group of Republicans who walked up to see him. “Hey! How are you guys? Want a hat?”

  “I was in charge of Trump’s advertising,” Brad added when he was asked what he did before the campaign. “All the advertising and marketing and branding.”

  Trump would have been surprised to hear that description of Brad’s work. The president, when he was upset with Brad, would refer to him as “a guy who makes websites.”

  But Brad was in his element. He promised one elderly man a half dozen times that he would tell Trump—he would call him that night!—about the need to provide dental care for military vets. He confused one woman in Patriots garb by professing fealty to his beloved Kansas City Chiefs. After a slow start at the diner that morning, Brad was hitting his stride as a man-of-the-people.

  “Some people love this part of it—I don’t mind it,” Brad said as he wrapped up his day of campaigning. “I probably get more handshakes than anyone.”

  Then he ducked back into the leather interior of the fully loaded black Infiniti SUV escorting him around the Manchester metropolitan area.

  “I’m not running for office,” he said. “But I think I have it in me.”

  Brad was creative and hardworking, and loved little more than telling stories. When he thought about the campaign, it was in that context. He was the songwriter, and Jared was the conductor. Another time Brad was the director, and Trump was the artist. Eventually he decided Jared was the director, Brad was the producer, and Trump was the talent.

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bsp; Brad’s optimism and energy on this chilly day in early February was rooted in just how far the Trump campaign had come these past four years. In all of 2016, the campaign spent $42 million on ground game. They’d spent $80 million in 2019, and planned to invest another $492 million in 2020. Brad had worked to develop a close relationship with Ronna at the RNC, and despite Trump’s inherent distrust of the establishment of the party he professed to lead, the campaign’s partnership with the RNC was closer than it had been with any Republican presidential campaign for as long as anyone could remember. By mid-February it had resulted in more than 80 leadership sessions for volunteers, and 160 neighborhood gatherings for Trump supporters—known as MAGA meet-ups. Volunteers had knocked on 55,000 doors and made 70,000 phone calls. They’d brought out more Iowans to the 2020 caucuses than any campaign since Jimmy Carter.

  But Trump would never see Brad as anything more than the guy who made the website.

  Meanwhile, out in Los Angeles, Hope Hicks was miserable.

  Hope had joined Trump’s campaign in 2015 while she was working for Ivanka on her fashion brand. When Trump called her into his office and asked if she wanted to join the campaign, Hope had thought he was talking about a marketing campaign for one of his properties. But she agreed anyway, and became a constant presence at Trump’s side in the office, on the trail, on his private plane. In the White House, she was an indispensable aide, a calming presence in a West Wing rocked by one controversy after the next. She left the White House after a little more than a year, in March 2018 as the Mueller investigation was underway. When the investigation concluded the following year, she cried, and called her friends in the White House to tell them how happy she was it was over.

  But she also realized how much she missed the dysfunctional adrenaline of Trump’s orbit. The transition to Los Angeles, away from her family and friends on the East Coast, was harder than she’d imagined. Her contact with Trump had dropped off considerably when she left, but whenever they talked, Trump told her she was always welcome. Now she was ready to return.

  Trump was ready, too. He was admittedly superstitious, and as he looked around his West Wing, he saw that most of his 2016 team was gone. Derek Lyons, his staff secretary, had worked for Jeb Bush, not Trump, during the primary. Mark Meadows, who was effectively chief of staff but who wouldn’t formally be given the role for another month, was a late supporter. Jared had kept Corey mostly out of the White House, and always seemed to forget to invite Kellyanne to the political meetings.

  “Who was with me when I was there by myself?” Trump would ask.

  Hope agreed to come back, carving out a role as a White House counselor. Jared told others she would report to him, but Hope had a direct line to Trump and exerted her influence over the president’s schedule with an eye toward reelection. Trump had also just returned Johnny McEntee to the White House. His personal aide on the campaign had been expelled from the White House in 2018, when his growing gambling debts were deemed a security risk to the administration. McEntee was escorted out of the building so quickly that he’d left his suit jacket at his desk.

  David Bossie, Trump’s 2016 deputy campaign manager, had also returned to Trump World after a months-long exile. Bossie had been cast aside after news reports that one of his fundraising groups collected $18 million during Trump’s first two years on the promise to support Trump-aligned candidates, but spent nearly all of those proceeds on more fundraising, administration costs, and salary. Bossie had come into the White House and walked Trump through his expenditures, insisting he had not grifted off the president.

  Trump recalled the conversation in the final months of 2019 with his political team during a meeting in the White House Map Room to go over campaign ads. Trump had expected Bossie to spend some of the disputed money supporting Trump’s reelection, but complained to others in the room that he didn’t like Bossie’s political ads.

  “You know Bossie,” Trump told Larry Weitzner, his lead ad maker and the chief executive of Jamestown Associates, a consulting firm with roots in New Jersey Republican politics. “You should send him some of this footage.”

  Weitzner told Trump that coordinating with Bossie’s group might raise legal problems for the campaign. The president instead turned to Jared and asked him to help improve Bossie’s ads. Jared was noncommittal.

  “Well, you don’t like him,” Trump said to Jared.

  “I caught him stealing from the campaign,” Jared told Trump. “So, no. Typically that wouldn’t give me a very high opinion of somebody.”

  By early February, Trump had much of his old crew back in place and a new poll showing his political stock on the rise. A Gallup poll on February 12 showed that 61 percent of Americans said they were better off than they were three years earlier. That was more than any of the past four election cycles when an incumbent president was running. It put Trump in such a good mood that when he visited his campaign headquarters for the first time on February 13, he made only passing reference to how much the modern office must cost. Instead, he wanted to talk politics. He wanted to talk about which Democrat was going to win the nomination. Another favorite topic was the Alabama Senate primary, where his former attorney general, Jeff Sessions, was trying to mount a political comeback. The thought of it would ignite a flurry of F-bombs from Trump, who badly wanted to endorse one of the other two main Republican rivals in the race. It took everything in his political team’s power to hold him off until the race was down to two candidates.

  Trump was also interested in whether he should be meddling more directly in the Democratic primary. The campaign knew that if Trump focused on any particular Democratic candidate, it would drive media coverage and attention from voters. Internal polling showed that Trump performed best against Warren. Brad and others suggested to Trump that if he attacked her, it would convince Democrats to give her a second look and boost her poll numbers. Trump was intrigued, but could never stay on message long enough to make a difference.

  On February 15, Trump attended a rare South Florida fundraiser outside the confines of Mar-a-Lago. But the price tag was worth traveling a few miles north: The dinner at billionaire investor Nelson Peltz’s home raised $10 million for the reelection bid. While the stunning sum made news, attendees would remember it as the first time they’d heard clear warnings from the administration about the contagion in China that had been earning headlines for several weeks.

  “It’s worse than people think,” Robert O’Brien, the president’s national security adviser, told a small group of people at Peltz’s home. They should be careful where they traveled, he told them.

  The next day, Trump opened the Daytona 500 with a lap around the Florida racetrack in the presidential limousine, a first in presidential history.

  “So exciting,” Trump said.

  He then headed off to a four-day campaign swing out West, which may have been the best indication of how good he was feeling. Compared to his predecessors, Trump rarely traveled. When he did, he almost always returned home that night, preferring the comforts of his own bed. His post-impeachment tour would take him through Arizona, California, Colorado, and Nevada, with a pair of fundraisers and three rallies along the way. Each night he would return to his Las Vegas hotel.

  The highlight of the trip came on the second day when, after a campaign rally in Phoenix, Trump learned that Mike Bloomberg had been molly-whopped on the Democratic debate stage by Elizabeth Warren.

  Trump World was split over the Bloomberg candidacy. Brad dismissed Bloomberg as an unappealing candidate and mocked his strategy of skipping the early state primaries. But not all of Bloomberg’s campaign was ripe for ribbing: The New York billionaire was the only candidate besides Trump to spend eight figures for commercial time during the Super Bowl.

  Ronna thought Bloomberg’s ads were getting better, and his name ID was high. The RNC’s data wasn’t showing much movement, but no one wanted to discount him because of the huge checks he was writing his campaign.

  Pe
nce wasn’t so sure, either. Bloomberg had been successful in business, but not even New York politics compared to the national stage.

  “I just don’t see it,” he’d told others in the West Wing.

  John McLaughlin, one of Trump’s pollsters, and Jared thought Bloomberg could be dangerous. Trump was anxious about Bloomberg, too, and had to be constantly reassured.

  “What do you think of Bloomberg?” he’d ask Oval Office visitors.

  “Who are you most worried about?” Trump asked Tony Fabrizio in February.

  “Buttigieg,” Fabrizio said, referring to Pete Buttigieg, the former mayor from South Bend, Indiana, who had won Iowa and nearly pulled off an upset in New Hampshire.

  “Buttigieg? That fucking guy?” Trump said. “Nah.”

  By mid-January, Bloomberg was beating Trump by seven points in Michigan, according to a Detroit Free Press poll.

  The Democratic debate began while Trump was still onstage in Phoenix, but the president had been monitoring its progress, with aides providing updates. Now, back on Air Force One, Trump cued it up on TiVo. A giddy Trump walked back to the press cabin in the tail of the plane and invited reporters to come watch it with him in his personal cabin at the front.