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

by Michael C. Bender

  But the campaign still wasn’t sure what its message was for Trump, or which voters to target. Stepien was swamped. His team was also telling him that the campaign was on pace to spend $200 million more than they were projected to raise, so pulled down almost all of the campaign’s advertising from television. Stepien also halted the campaign’s use of Deep Root to target campaign spots (despite the company’s contract already having been paid) and went about rebuilding the data operation—with just three months left in the race.

  When Stepien took over, he had to move quickly to install his team, because Trump—who insisted he was his own best chief of staff, communications director, and military adviser—had also been moving personnel like pawns across a chessboard. He’d grown frustrated with Jared as the situation with Brad had worsened, but the only punishment he’d inflicted upon his son-in-law was to take matters into his own hands.

  Trump had opened frequent communication with Dick Morris, the former Clinton political strategist whose father had been Trump’s real estate lawyer and was a cousin of Roy Cohn, the hard-charging anticommunist who was also Trump’s mentor. Morris started providing friendly advice to Trump in April, but it picked up in the summer and the two men were in daily contact for the last two months of the race.

  Morris was soon emailing Stepien’s inner circle and campaign pollsters with suggested survey questions and pointed critiques. Jared had also started sharing polling with Morris, as well as with Meadows and former House Speaker Newt Gingrich, but had failed to mention it to Stepien.

  Morris, Meadows, and others, including White House policy adviser Stephen Miller, had also started suggesting their own poll questions. The queries ranged from testing transgender issues to questions about expelling Chinese students from the country after the Covid outbreak, which was one of Morris’s pet issues. There were so many poll questions being proposed from outside the campaign that they were assembled into what the political team referred to as the “peanut gallery survey.” The questions then would be polled through an “IVR” poll, which was a relatively short automated call that carried little weight with top campaign officials—but it helped to placate the president and the people around him and bought Stepien a little more time to try to get the operation under control.

  Another consequential personnel move by Trump that summer was to bring back Jeff DeWit, who had been a part of the 2016 campaign and later served in the administration as NASA’s chief financial officer. DeWit was the Arizona state treasurer in 2015 when he met Trump at a South Carolina conference. After the two chatted, DeWit offered to endorse Trump’s presidential bid. Although the burgeoning campaign wasn’t ready to roll out endorsements, DeWit became an unofficial adviser to Corey, and raised his profile with Trump when he helped organize what became one of Trump’s biggest early campaign rallies: more than 4,000 people at the Phoenix Convention Center.

  In May 2016, DeWit was in his office in Phoenix reading the news that Corey had just been fired as Trump’s campaign manager when his phone rang with a call from Jared.

  “How soon can you get to New York?” Jared asked.

  DeWit told him he needed just a day, even though he was working as Arizona state treasurer, a job he’d been elected to in 2014. He arrived at Jared’s New York office having been told little else other than they had a 9:00 a.m. meeting inside Trump Tower, about three blocks away. DeWit had been in and out of Trump Tower for much of the past year and had pitched Jared on an unpaid job as chief operating officer. He’d noticed that phones weren’t being answered and mail had gone unopened and wanted to help make the campaign more efficient. But when they arrived in Trump Tower, DeWit was brought to a small conference room outside the office of Allen Weisselberg, the chief financial officer of the Trump Organization. When Jared and DeWit walked into the conference room, Weisselberg was grilling Rick Gates, a senior campaign adviser who would later be sentenced to 45 days in jail as part of Mueller’s Russia probe.

  “Where’s the fucking money, Rick!” Weisselberg barked at Gates.

  The money in question was more than $730,000 that had been transferred from the campaign to a new Delaware-based company called Left Hand Enterprises. Gates denied any wrongdoing, and said the money had been spent printing and mailing campaign flyers to voters. Weisselberg wanted to know what he knew about the new LLC—who was running it, what his connection was to it, and where it had come from. They went back and forth for nearly an hour until an exasperated Gates threw up his hands and asked his interrogators what exactly they wanted him to do.

  “Well, that’s why he’s here,” Jared said, pointing to DeWit. “He’s the new CFO and you’re not touching the money again.”

  DeWit seemed confused, and finally spoke up to tell Jared that he had wanted to be chief operating officer, not chief financial officer.

  “Oh, sorry,” Jared corrected himself. “He’s the CFO and COO.”

  DeWit walked out of the meeting unsure about what had just happened. Jared’s advice was to go run the campaign. “It’s down on the fifth floor,” he told him. “You know where it is.”

  On the fifth floor, DeWit announced himself as the new COO/CFO and looked for a desk. The only one he could find was in the office that Corey had just vacated. He went in, sat down, and almost immediately staffers started funneling through asking for his input on decisions. A couple of months later, DeWit was headed to the Republican National Convention in Cleveland and asked Sean Dollman, his chief deputy back in the Arizona treasurer’s office, to come out to New York to cover for him.

  “Here’s what you do—just sit at that desk and people will run in and ask questions,” DeWit told Dollman. “Just choose the best option, and it will all work out—and you’ll get to know everybody.”

  Dollman thought his boss was crazy. But it worked, and he was soon named deputy chief of operations for the Trump 2016 campaign.13

  DeWit, meanwhile, had been asked by Jared to travel to San Antonio to negotiate a contract for Brad. He had been earning a 12.5 percent commission on the campaign’s digital advertising, and costs were starting to accumulate. DeWit returned to New York with a contract that reduced Brad’s commission to 1.5 percent.

  But DeWit was suspicious of Brad’s invoices. Brad’s company was charging the campaign for use of the staff back in Texas, but DeWit wasn’t sure those staffers existed. With approval from both Trump and Jared, DeWit began preparing to travel back down to San Antonio to audit Brad’s team.

  A few days after the election, Brad stormed into DeWit’s office screaming about the 1.5 percent commission. He felt he’d been ripped off. He had earned about $900,000, but insisted that the digital director of a winning presidential campaign should have made more than ten times that. DeWit pointed out that he’d been working without a salary the entire time, and offered to switch places.

  Shortly after, DeWit took a phone call from Rick Dearborn, who had been named executive director of Trump’s transition team. Trump and his family had just won the White House. Any interest in DeWit’s audit was gone.

  They were curious again in the summer of 2020.

  As part of Trump’s attempt to get a handle on his own campaign after Tulsa, he made it clear that he wanted DeWit back in the fold. DeWit flew in from Arizona to meet with Trump at the White House, and then was taken to Jared’s office, where, along with Brad, they discussed a new role for DeWit.

  Brad would later tell people that DeWit was desperate for the chief operations officer title, even though it had been held by Michael Glassner—who had been working for Trump for five consecutive years. DeWit would tell Glassner that the idea came from Brad, who wanted to shift blame for the Tulsa rally to Glassner, who had been in charge of campaign rallies for years. Regardless of whose idea it was, Brad, Jared, and DeWit all agreed: Glassner would be demoted to a role overseeing the campaign legal bills, and DeWit would break the news to him.

  Glassner, eating lunch at his desk inside the campaign, knew what was coming when DeWit wa
lked into his office.

  “I’m out, aren’t I?” he asked.

  “Yes and no,” DeWit told him.

  “Fuck,” Glassner replied.

  They agreed that Glassner would move his belongings out of the office that night, after the other staffers had left for the day. When campaign aides arrived the next morning, DeWit was seated at the desk, ready to weigh in on any decisions that needed to be made.

  DeWit got to work analyzing the campaign budget, and within ten days provided Jared documents that showed the reelection campaign was trending into debt: between $100 and $200 million in the hole by Election Day. Jared was upset about the finding, and initially blamed DeWit, ordering him to run the numbers again. When DeWit came back, he told Jared the problem was that the campaign was underestimating the costs of fundraising—and was spending too much money trying to raise more. Brad was out a few days later.

  DeWit turned next to a review of Brad’s campaign income, which he believed was a duty that fell to him as chief operating officer. But the blowback turned on him first.

  After Brad was demoted, news leaked from Business Insider that DeWit’s real job had been to perform an internal review of the campaign spending. The story set off alarm bells around Trump World.

  Pointed questions about Brad’s income had always been most useful as an internal cudgel to help undermine him, then sideline him, and—in the final months of the race—try to pin the blame on him for the loss. But now Trump World staff worried that DeWit had misunderstood his mandate and was actually going to investigate all aspects of campaign spending—a swampy mess of potential misconduct that few of them actually wanted waded through.

  One major change under Stepien was the campaign’s relationship with the Republican National Committee. Friction remained from the 2016 race between Stepien and much of Ronna’s senior leadership team. Ronna was running the Michigan Republican Party during that race, but Stepien disapproved of her decision to keep many of those same players in her orbit. Katie Walsh had become one of Ronna’s top advisers. Ronna elevated Richard Walters, who had been the party’s top finance director the year before.

  Walters had worked his way up inside at the RNC to become its top staffer. But that was part of the problem for Stepien. Not only had the RNC been a reluctant partner for Trump in 2016—and continued to be influenced by many of the same people in 2020—but he viewed the party as an organ of the presidency that should remain fluid and scrappy, staffed with young operatives devoted to the party’s leader instead of their own bank accounts. Walters had obscured exactly how much he was being paid by the RNC, and the party was embarrassed by a February 2020 report from ProPublica showing that in addition to his salary of $238,200 Walters also earned $135,000 through his company Red Wave Strategies. But the RNC wasn’t merely an extension of the Trump campaign. The deal with Brad had effectively turned them into a full partner, and Ronna had become one of the president’s closest advisers. The RNC was paying for the field staff. They were covering costs for state directors who couldn’t get calls returned from campaign headquarters. Even the lease for the campaign headquarters was being paid for by the RNC.

  But that level of investment elevated the RNC’s expectations for the relationship. Ronna and her team wanted their opinions to be considered. Jared had always tried to limit Ronna’s influence with Trump in order to protect his own, but Brad viewed the RNC as a crucial partner. Under Stepien, however, Ronna was often left on the outside looking in—sometimes literally. In June, she had arrived at the White House for a political meeting, but waited in the lobby for more than an hour before she was brought into the Oval. When she walked in, the president asked why she was so late.

  “They don’t want me sitting in the meetings with you,” Ronna told him.

  Beyond the power struggle between Jared and Ronna and the philosophical differences between the new campaign manager and the head of the RNC, Stepien was correct to question the loyalty and dedication of Ronna’s staff to Trump. The president’s handling of Covid and the White House’s treatment of Ronna had top staffers inside the RNC openly musing—for the first time in their lives—about not voting for the Republican nominee for president. Ultimately, some did not cast their Election Day ballot for Trump.

  Stepien spent much of his first weeks on the job on a very un-Stepien pursuit: relationship building. He met with Ivanka to talk about the travel schedule she wanted to ramp up and her portfolio of promoting skills-based training and women’s and working family issues. He praised Lara for how hard she was working, telling her how effective he thought she’d been.

  “Every time I look up, you’re on TV,” he told her. “You’re killing it.”

  He knew he had work to do with the Trump family, and he went out of his way to tell them how much he appreciated what Brad had done and how he’d built the campaign.

  “I hope he knows I was never gunning for him,” Stepien would tell Brad’s allies.

  Stepien also reached out to Brad’s enemies. Brad had spent most of 2019 describing how wonderfully the reelection campaign was running, how much money had been raised, how much groundwork had been laid, and how gorgeous the new office was. All generally true. But Brad’s only point of comparison was the 2016 race, which infuriated Kellyanne, Bossie, and Corey. They all had leadership roles steering that secondhand clunker down the street, siphoning gas from the neighbors just to get the old beater full of back-biters and gossipmongers over the finish line. But they had finished first—a fact Brad barely bothered to mention—and now they were determined to finish him. Stepien was not about to repeat that mistake. He praised Kellyanne to the president. He made sure to show Bossie respect. He was on the phone multiple times a day with Corey, who, just four short years earlier, had tried to keep the New Jersey operative out of the campaign.

  Stepien gave stilted pep talks to the staff and dialed into a conference call with grassroots groups asking them to stay in the fight. He reluctantly engaged in a conference call with reporters, walking them through a battleground map state by state.

  Trump would overcome polling deficits in Pennsylvania by running up margins in the smallest, most rural counties in the state, Stepien said on the call. Their Wisconsin team had spent the past year finding new Trump supporters and registering them to vote, he added. He noted that public polls—the same ones he had criticized to start the call—showed Trump exceeding his 2016 margins with certain key demographics. He identified Minnesota, Nevada, and New Hampshire as possible pickups.

  “I would advise we not get stuck in that 2004 mindset of viewing Minnesota through an old, outdated political lens,” Stepien said. “Look at the pathway exposed by the president in 2016, the playbook. There are enough votes in Minnesota to win. Now we have the resources to go get them.”

  Stepien opened the July 16 conference call for questions and scoffed when a reporter asked about Georgia, where polls showed that Biden was starting to break through.

  “I invite Democrats to spend a lot of money in the expensive media market of Atlanta and keep thinking it’s for real—because we had the same conversation in 2016,” Stepien said.

  Stepien felt good about Georgia, and several other states, too. But he was largely running on his gut at that point, because the various data he was getting at the campaign was starting to conflict with itself. And he didn’t know what to believe.

  Footnotes

  1 If Stepien had been paying attention to politics in high school, he no doubt would have noticed a wild local race for Morris County freeholder his junior year that ended with the election of a brash young Republican named Chris Christie.

  2 Stepien earned all-American honors from the club league in both his junior and his senior years.

  3 Mobbed-up Jersey vernacular for what most other Americans would simply call a driver.

  4 The losing streak for New Jersey Republican Senate candidates now stands at sixteen consecutive races over forty-two years after Cory Booker was comfortably reelected
in 2020.

  5 Baroni caught some breaks that year, too. When his opponent attacked him over a false claim that he was a Hamilton native, Baroni admitted he’d been born in another state—but adopted by Hamilton residents. The silver-tongued Republican lobbyist was suddenly transformed into a sympathetic orphan.

  6 “Wally Edge” helped launch the careers of some widely respected political journalists, including MSNBC’s Steve Kornacki, Politico’s Alex Isenstadt, and the Boston Globe’s James Pindell.

  7 The three Republicans helped “Wally Edge” rank the state’s top operatives, which also just happened to always include their names. A decade later, DuHaime’s bio page at Mercury Public Affairs—the global consulting firm where he’s a partner—still notes that he’s been named to every annual power list put out by PoliticsNJ.

  8 Stepien surprised some friends that year when they found out that not only was he engaged, but that his fiancée was Stacy Schuster, with whom he’d sparred during Baroni’s 2003 campaign.

  9 The goodwill would be returned when Stepien successfully lobbied Trump to pardon Gilmore for felony convictions over falsifying a loan application and failure to pay taxes. Trump issued the pardon on his last day in office.

  10 Jared was dazzled by Stepien’s mastery of analytics and had tried to hire him at Kushner Companies in 2016 when Corey and Trump blocked Jared’s first attempt to bring Stepien into the campaign.

  11 “So it’s ‘Person, woman, man, camera, TV.’ Okay, that’s very good,” Trump boasted during a Fox News interview, explaining how he’d passed the cognitive test by repeating back five words. “If you get it in order, you get extra points.”

  12 Marital fidelity was one thing Trump admired about Pence. And he had an amusing, Trumpian way of describing it—as if it hadn’t occurred to him to be faithful until Pence mentioned it. “He was like thirty years ahead of his time on the woman thing,” Trump told one friend. “If the rest of us had listened, we would have had a lot less problems.”