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At the end of June, in the afterglow of a debate performance that would ultimately prompt President Joe Biden to end his campaign for reelection, Donald Trump startled his aides by announcing that he’d come up with a new nickname for his opponent.
“The guy’s a retard. He’s retarded. I think that’s what I’ll start calling him,” Trump declared aboard his campaign plane, en route to a rally that evening, according to three people who heard him make the remarks: “Retarded Joe Biden.”
The staffers present—and, within hours, others who’d heard about the epithet secondhand—pleaded with Trump not to say this publicly. They warned him that it would antagonize the moderate voters who’d been breaking in their direction, while engendering sympathy for a politician who, at that moment, was the subject of widespread ridicule. As Trump demurred, musing that he might debut the nickname at that night’s event, his staffers puzzled over the timing. Biden was on the ropes. Polls showed Trump jumping out to the biggest lead he’d enjoyed in any of his three campaigns for the presidency. Everything was going right for the Republican Party and its nominee. Why would he jeopardize that for the sake of slinging a juvenile insult? (A campaign spokesperson, Steven Cheung, said the nickname “was never discussed and this is materially false.”)
Over the next several days—as Trump’s aides held their breath, convinced he would debut this latest slur at any moment—they came to realize something about Trump: He was restless, unhappy, and, yes, tired of winning. For the previous 20 months, he’d been hemmed in by a campaign built on the principles of restraint and competence. The former president’s ugliest impulses were regularly curbed by his top advisers; his most obnoxious allies and most outlandish ideas were sidelined. These guardrails had produced a professional campaign—a campaign that was headed for victory. But now, like a predator toying with its wounded catch, Trump had become bored. It reminded some allies of his havoc-making decisions in the White House. Trump never had much use for calm and quiet. He didn’t appreciate normalcy. Above all, he couldn’t stand being babysat.
“People are calling this the most disciplined campaign they’ve ever seen,” Trump remarked to friends at a fundraiser this summer, according to someone who heard the conversation. He smirked at the compliment. “What’s discipline got to do with winning?”
Trump never did deploy the nickname against Biden in public. Yet the restiveness he felt during that stretch of the race foretold a dramatic shift in the tone and tenor of his campaign. Within weeks, Trump would survive an assassination attempt, Biden would abandon his candidacy, Vice President Kamala Harris would replace him atop the Democratic ticket, and polls would show an election that once appeared finished suddenly reverting to coin-flip status. All the while, Trump became more agitated with what he saw as the trust-the-plan, run-out-the-clock strategy of his campaign—and more convinced that this cautious approach was going to cost him a second term.
In conversations with nearly a dozen of the former president’s aides, advisers, and friends, it became apparent that Trump’s feeling of midsummer tedium marked a crucial moment in his political career, setting off a chain reaction that nearly destroyed his campaign and continues to threaten his chances of victory. Even as they battled Democrats in a race that refuses to move outside the margin of error, some of Trump’s closest allies spent the closing months of the campaign at war with one another: planting damaging stories, rallying to the defense of wronged colleagues, and preemptively pointing fingers in the event of an electoral defeat.
At the center of this tumult, people close to Trump agreed, is a candidate whose appetite for chaos has only grown—and serves as a reminder of what awaits should he win on November 5.
Trump decided it was time to take matters into his own hands.
For the first 10 days following Biden’s departure from the race, Trump had listened dutifully as his campaign co-managers—a pair of longtime GOP consultants named Susie Wiles and Chris LaCivita—explained that the fundamentals of their strategy remained solid. Nothing dramatic needed to change with Harris taking over the ticket, they told Trump, because she was inheriting the vulnerabilities they had exploited so successfully against Biden. They argued that whatever burst of money and enthusiasm had accompanied her entry into the race would prove short-lived—and warned him against overreacting. Staying the course, they told Trump, was the surest recipe for electoral success.
He went along with their plan—for a while. But every hour his campaign spent attacking Harris as if she were a credible opponent—rather than bludgeoning her as the airheaded, unqualified, empty pantsuit Trump was sure she was—gnawed at the former president. Finally, he ran out of patience. On July 31, during an onstage interview with the National Association of Black Journalists, Trump publicly unloaded the sort of race-baiting barbs that his aides had, up until that point, succeeded in containing to his private diatribes.
“I didn’t know she was Black until a number of years ago when she happened to turn Black,” Trump told the journalists onstage, eliciting gasps from the audience. “I don’t know, is she Indian or is she Black?”
In the days after his NABJ appearance—as staffers scrambled to satisfy their boss’s appetite for pugilism without indulging his racist and misogynistic impulses—Trump began to lose confidence in his team. He had long dismissed the warnings from certain friends, such as his former acting director of national intelligence, Richard Grenell, that Wiles and LaCivita weren’t up to the job. But now he had reason to wonder. With Harris climbing rapidly in the polls and his own favorability numbers slipping, Trump was pondering, for the first time, a shake-up of his team. (Cheung said Trump never considered a change to his campaign leadership.)
In early August, Trump started courting two of his longtime allies and former campaign managers from 2016, Kellyanne Conway and Corey Lewandowski, discussing what it might look like if they rejoined his political operation in a formal capacity. Trump told Lewandowski—who promptly agreed to come aboard—that he missed the “fun,” freewheeling nature of that first run for the White House. He told Conway, meanwhile, that he worried he was being overly “managed” by his current team.
Trump’s conversations with Conway troubled Wiles and LaCivita. They knew that she and Trump were talking more and more frequently; they also knew she loved to take credit for electing him in 2016, and wouldn’t be eager to share accolades with her successors. Conway’s back-channeled criticisms of the 2024 campaign had been subtle but pointed; in an effort to placate her, LaCivita increased her monthly retainer at the Republican National Committee from $20,000 a month to $30,000. But in private conversations, Conway continued to point out the campaign’s shortcomings—especially, in her view, the mistaken selection of Ohio’s Senator J. D. Vance as Trump’s running mate. When Wiles and LaCivita met Trump at a fundraiser in the Hamptons the evening of August 2—having been tipped off that their boss just spent the day talking strategy with Conway at his Bedminster club in New Jersey—the campaign’s top advisers fretted that their days running the show might be numbered. (As The New York Times was reporting on Conway’s visit to Bedminster, Trump called reporter Maggie Haberman and angrily denied that changes were afoot, saying he was “thrilled” with Wiles and LaCivita.)
In truth, the real threat was Lewandowski.
A tough-talking operative who had famously accosted a female reporter in 2016 and later allegedly made unwanted sexual advances toward a Republican donor’s wife, Lewandowski had promised Trump a return to the “killer” vibes of 2016. But the details of his new role were left open to interpretation. Lewandowski believed—and told anyone who would listen—that he would outrank the existing campaign leadership. Trump himself, meanwhile, assured Wiles and LaCivita that Lewandowski would be a utility man, serving as a key surrogate while helping organize election-security efforts and field operations in swing states.
The honeymoon period was nonexistent. Before Lewandowski worked a single day on behalf of the campaign, he complained to friends that Wiles and LaCivita had leaked the news of his hiring in an unflattering light that downplayed his role—and timed it to coincide with when he was traveling and off the grid, unable to speak for himself.
Determined to assert himself, Lewandowski arrived at Palm Beach headquarters in mid-August with designs on running the place. Wiles accompanies Trump nearly everywhere on the trail, and LaCivita, when not joining them, often works from his home in Virginia, leaving Lewandowski with a free hand in Florida. He began taking aside junior staffers and department heads alike, one at a time, informing them that he spoke for Trump himself. He made it known that he would be in charge of all spending, and that he needed people to tell him what wasn’t working so he could fix it. Meanwhile, he began calling the campaign’s key operatives in the battleground states, probing for weaknesses in Trump’s ground game and assuring them that a strategy shift was in the works.
Even as colleagues grew tired of hearing Lewandowski describe himself as the former president’s personal proxy, they realized he wasn’t wrong. His arrival coincided with a marked shift in Trump’s mood and behavior. Gone, suddenly, was the candidate of 2024, who despite all the inevitable outbursts was at least receptive to direction and aware of consequences; in his place, as the summer progressed, was the alter ego of 2016, the candidate who did and said whatever he wanted and ignored anyone who sought to rein him in.
During the week of the Democratic National Convention, the former president shared a social-media post suggesting that Harris had performed oral sex in exchange for career advancement. He denigrated the Medal of Honor, the nation’s top award for military personnel, as less impressive than the civilian Medal of Freedom. He accused Harris of leading a “vicious, violent overthrow of a president of the United States.” He called into Fox News’s coverage of the convention and rambled so incoherently that the anchors cut his line 10 minutes into the interview. (Trump promptly dialed Newsmax to continue talking.) At a rally in North Carolina, after polling the audience about whether he should “get personal” with his attacks on Harris—the crowd responding rowdily to encourage his invective—Trump mused about firing his campaign advisers.
Around that time, Trump was asked by reporters about the tone of his candidacy. “I think I’m doing a very calm campaign,” he replied. “I have to do it my way.”
As Trump was settling on Vance as his vice-presidential pick, one of the arguments he found most persuasive centered on an injection of youthful verve: The freshman senator, then just 39 years old, could complement a running mate four decades his elder with a style and media savvy that broadened the campaign’s appeal. With that promise, however, came a certain peril. Vance maintained an entourage of Very Online influencers who had little experience winning campaigns but lots of owned libs in their social-media mentions. Now some of those right-wing agitators would be joining an operation that was already struggling to keep its principal on message.
Vance’s first two months on the ticket were largely uneventful. His awkward, halting appearances fueled a sense of buyer’s remorse among some Trump confidants, but he made no mistakes of any real consequence. (The talk of “childless cat ladies” preceded his appointment to the GOP ticket, as did his remarks that he “would like abortion to be illegal nationally.”) And then came September 9. It was one day before Trump would meet Harris in Philadelphia for their first and only debate, and Vance, according to people familiar with the situation, was feeling punchy. Over the past several days, the young senator had marinated in right-wing agitprop stemming from Springfield, Ohio, where it was rumored that Haitian migrants were stealing and eating pets. When Vance’s allies on the campaign learned that he’d already spoken out about related issues in Springfield—how the influx of thousands of Haitian migrants who came legally to fill jobs had stressed the city—they urged him to seize on this conspiracist catnip and turn it into a crusade for the Trump campaign.
One staffer in particular—a young activist named Alex Bruesewitz—helped convince Vance and his team that this was an opportunity to put his stamp on the campaign. Vance agreed. “Reports now show that people have had their pets abducted and eaten by people who shouldn’t be in this country,” the senator posted on X, catching the Trump campaign’s leaders entirely off guard. Figuring there was no use in half measures, Bruesewitz led Vance’s minions in blasting the social-media post around their networks and urging officials on other GOP campaigns, as well as at the Republican National Committee, to join Vance’s assault on the migrant community of Springfield. (Bruesewitz did not respond to a request for comment about this story.)
Most Republicans refused to go along. But Trump himself found the shtick irresistible. Even as he was sequestered in debate prep, word reached him that Vance had amplified the sensational claims about Springfield. The former president’s advisers were bewildered by Vance’s post. Though they went out of their way to avoid any talk of Springfield for the duration of the debate prep, there was an ominous feeling that Trump wouldn’t be able to help himself.
Yet somehow, by the time Trump charged ahead onstage the following night—“They’re eating the dogs; the people that came in, they’re eating the cats”—his campaign was facing a more serious crisis.
Several days earlier, Trump had fielded a phone call from one of his superfans: Laura Loomer. A right-wing agitator best known for racist and conspiracist bombast—she has celebrated the deaths of migrants and called school shootings fake events put on by crisis actors—Loomer had remained one of Trump’s most loyal and vocal supporters even in the darkest moments of his post–January 6 exile at Mar-a-Lago. That loyalty gave her a direct line to the former president. After she had joined the candidate aboard his plane during crucial trips to Iowa and New Hampshire early in the year, campaign officials discussed ways to sideline Loomer without causing a scene. They neutralized a volatile situation at the convention this summer, for example, by providing Loomer with a front-row seat for Trump’s acceptance speech—putting her in close physical proximity to her idol while keeping her far from the VIP area that cameras would be shooting live.
But now, in the first week of September, Loomer was getting antsy. She called Trump and demanded to know why the campaign had been keeping her at bay; why she hadn’t been allowed back on the plane as the Republican nominee toured the country. Trump told Loomer not to worry: He would personally see to it that she was invited aboard the plane for his next trip. Later that day, when Trump relayed this request to Wiles—who, since the beginning of the campaign, had controlled the flight manifest—she registered disbelief. “Sir, our next trip is to Philadelphia for the debate,” Wiles told Trump, according to two people familiar with the conversation. “Are you sure that’s a good idea?”
Trump shrugged. “I don’t know,” he said. “Just stick her in the back of the plane.”
Wiles knew that nothing good could come of this. Still, after one more round of gentle pushback, she acquiesced. (Even people like Wiles, who have a track record of talking Trump out of certain reckless ideas, learn that you cannot retain a seat at the table if you tell the man “no” one time too many.) Wiles decided that allowing Loomer on the trip was not a hill to die on. Perhaps, she would later remark to friends, it should have been.
When Trump’s jet touched down in Philadelphia on September 10, and photographers captured Loomer disembarking, some of the former president’s allies were apoplectic. Republican elected officials began texting campaign aides demanding to know why she was traveling with Trump. But outside of Wiles and LaCivita, Trump’s own staffers hadn’t known she was on the manifest. They were as bewildered—and furious—as everyone else. (Why Trump’s employees find Loomer uniquely noxious, when their boss consorts with known racists and trafficks in cruel conspiracy theories himself, is a separate question.)
As the night unfolded, with Loomer watching the debate backstage and then joining other GOP surrogates in the spin room, campaign leaders weighed their next move. Yanking her from the plane risked turning the story into something bigger and messier: a jilted Loomer lashing out against corrupt RINO deep-state simps in the aftermath of Trump’s miserable debate performance. Wiles decided that Trump’s special guest would remain on the manifest for the duration of the itinerary. The only problem? They were headed straight from Philadelphia to New York City for a memorial ceremony the next morning, honoring victims of 9/11—which Loomer, naturally, had described as an inside job.
After the cameras showed Loomer standing near Trump at Ground Zero, the former president’s own phone lit up. For the rest of the day, friends and associates and donors dialed his number with a manic urgency. Some read him old tweets that Loomer had sent; others demanded that whoever let this woman aboard the plane be fired. Senator Lindsey Graham asked Trump if he was trying to lose the election. To all of this Trump pleaded ignorance. He began complaining to aides that nobody had ever explained to him, specifically, why Loomer was so toxic. They responded by pulling up Loomer’s most incendiary posts and showing them to the boss. Trump winced at some and seemed unaffected by others. But he agreed, by the end of the trip, that Loomer needed to go. What sealed Loomer’s fate, according to two people who were part of these conversations, wasn’t just her racist diatribes but also her appearance: Trump, who is generally appalled by plastic surgery, was disgusted to learn about the apparent extent of Loomer’s facial alterations. (When asked for comment, Cheung told me, “Laura was a hard worker in the primaries and President Trump appreciates a fighter.”)
Trump regarded the Loomer episode as a one-off nuisance. His advisers, however, feared that something more fundamental had gone amiss. The past month had seen the campaign spiral into a free-for-all. Lewandowski was going rogue. Morale was plummeting among the rank-and-file staff. And Trump himself seemed intent on sabotaging a message—curbing immigration, fighting inflation, projecting strength on the world stage—that had been engineered to win him the election. Privately, Wiles confided to friends that she and LaCivita felt they’d lost control of the campaign.
When she and LaCivita sat down with Trump in the middle of September, Wiles urged her boss to realize just how badly things were going. These recent mistakes could not be repeated; this current path was unsustainable. “We need to step back and think hard about what we’re doing,” Wiles told him, according to several people familiar with the conversation. “Because this can’t go on.”
Trump doesn’t take well to admonishment. Yet the only other time he’d heard Wiles address him like this was in late 2022, shortly after he’d announced his candidacy, when he’d dined with Nick Fuentes, a white supremacist, at Mar-a-Lago. Trump seemed to recognize now, as he had then, that he was engaging in self-sabotage. He told Wiles that he agreed: It was time to tighten things up.
Trump thought the conversation was over. But there was one more thing on Wiles’s mind.
Days before departing for that doomed East Coast swing through Philadelphia and Lower Manhattan, Lewandowski had told Trump that they needed to talk. There was information, he said, that the candidate deserved to know.
When they met at Mar-a-Lago, Lewandowski laid it all out. He’d spent several weeks digging into the finances of the campaign, he told Trump, and things weren’t adding up. Far too much money was being spent on programs insignificant to his electoral success, and there had been no apparent oversight of contracts and arrangements that created a windfall for certain campaign employees. Lewandowski told Trump that he’d taken the liberty of bringing in a private consultant—personally escorting this outsider into the campaign’s offices—to study the books. This person’s conclusion, Lewandowski said, was: “Your people are either completely incompetent, or they’re stealing from you.”
Trump seemed conflicted. Nothing angered him more than the idea of being taken advantage of. Then again, if there was one person in politics he’d come to rely upon—one person who, he believed, would never steal from him—it was Wiles. Ultimately, Trump instructed Lewandowski to take his concerns to her.
When Lewandowski did so, on a plane ride that same week, things quickly went sideways. He made no accusations about specific individuals, but shared his belief that certain tactical decisions had been made with big paydays in mind. Wiles told him that she took offense at such conjecture—and that she didn’t need to justify anything to him. Still, Wiles spent the next hour walking Lewandowski through the choices made about vendors, contracts, and costs. When he continued to suggest that things weren’t on the level, Wiles ended the conversation, preferring to focus on preparing Trump for the upcoming debate.
Once the debate was behind them—and with many on the inside fearing that the campaign was falling apart—Wiles sensed that Lewandowski was about to make a move. He had repeatedly gone back to Trump, asking for control over hiring and firing as well as veto power over all spending decisions, which would effectively put him in charge of the campaign. Now he was going all in, telling Trump that Wiles and LaCivita had invested tens of millions of dollars in direct-mail outreach aimed at mobilizing supporters during the early-voting period—money that just so happened to line the pockets of certain campaign staffers, including LaCivita, and that could have been spent instead on television advertising. Lewandowski understood that the only tactical component of campaigning that Trump cared about was TV ads. He was telling Trump not just that he was being stolen from, but that the money in question would have made him ubiquitous on TV.
On September 12, when Wiles told Trump, “This can’t go on,” she added that she wasn’t just talking about Loomer and Springfield. Lewandowski had parachuted into a well-run campaign and rolled grenades into every department, Wiles told Trump, sowing distrust and spreading rumors and making it impossible for her to do her job. “If there’s something you’re skeptical of, something you want answers to, let’s talk about it,” Wiles told her boss. “But if you don’t have confidence in me and Chris, just say so.”
It was an ultimatum. And if Trump struggled with the decision before him—fire Wiles and LaCivita, or keep them and banish Lewandowski—he didn’t let on. Then and there he gave Wiles a vote of confidence. The next day, on the campaign plane, Trump convened Wiles, LaCivita, and Lewandowski around a table in the front cabin, in a meeting first reported on by Puck. He spoke directly to Lewandowski. “We can’t afford to lose these guys,” Trump said, motioning toward Wiles and LaCivita. “They’re in charge.”
Lewandowski knew the fight was lost. “Sir, I’m the only fucking person on this plane who isn’t getting paid to be here right now,” he grumbled, according to multiple people familiar with the meeting. “I’m happy to go back to fucking New Hampshire.”
“No, I want you on TV for me every day,” Trump said. He paused. “And go win me New Hampshire, while you’re at it.”
Lewandowski slapped the table. “You’re not going to win New Hampshire,” he said. “But okay.”
When passengers reboarded the plane for the next leg of their trip, Lewandowski was not on it. Being evicted from the plane is a signature insult in Trump’s political sphere. Lewandowski told friends that he’d planned all along to fly commercial to his next destination; the former president told his traveling aides that Lewandowski’s absence was meant to send the message that dissent would no longer be tolerated. Trump had lost a lot of ground to Harris over the previous month, and victory was possible only if everyone on the campaign fell back in line.
Things appeared to stabilize from there. As September gave way to October, and Harris launched a major media offensive aimed at connecting with voters who still felt no familiarity with her, Trump’s campaign was delighted to cede the spotlight. Wiles and LaCivita believed that every moment Harris spent in front of live cameras translated to more Republican votes. Instead of trying to book Trump onto major networks, where his comments might produce negative news cycles, his team arranged a tour of podcasts, most of them aimed at young men. The effort was led by Bruesewitz, the impulsive young Vance sycophant who maintained an impressive network of right-wing influencers. The strategy appeared to work: For the first three weeks of October, Trump’s internal polling showed Harris’s momentum stalled—measured in both net favorability and vote share—while Trump’s numbers inched upward.
By the middle of October, Trump was being hounded with requests from Republican candidates for joint appearances—requests that had been conspicuously few and far between just a month earlier. Even vulnerable incumbents, such as Representative Ken Calvert of California, tried to grab ahold of Trump’s coattails, campaigning with him in his decidedly purple district. Surveying the narrative shift, Trump’s allies marveled at how simple it had all been. Keeping voters’ attention on Harris—while, to the extent they could, keeping Trump out of his own way—had produced the most significant movement in his direction since her entry into the race.
Not that Trump wasn’t doing his best to muck things up. The 40 minutes he spent onstage in Pennsylvania swaying silently to music prompted aides to exchange frenzied messages wondering whether the audio could be cut to get him off the stage. (Ultimately, they decided, letting him dance was less dangerous than letting him rant.) A week later, back in the all-important commonwealth for another event, he left aides slack-jawed by marveling at the ample genitalia of the late golf legend Arnold Palmer.
Even as the political class settled on Trump as the betting favorite, his allies couldn’t shake a pair of very bad feelings. The first was about ground game: With much of their party’s resources being diverted to legal efforts, the GOP’s field operation was struggling to keep pace with the Democrats. The patchwork strategy left Republicans heavily dependent on outside help. But good help is hard to find. Elon Musk’s canvassing program was fast becoming a punch line in Republican circles. Several GOP consulting firms saw young staffers take short leaves to knock doors for Musk, lured by the enormous commissions he offered. His new system proved easy to game, allowing workers to inflate the number of contacts they reported, and to pocket the rewards. (Musk’s political entity, America PAC, did not respond to a request for comment.)
The more urgent concern, however, was the acrimony that had fractured the Republican nominee’s political operation. Lewandowski had, within a month of his defenestration at 30,000 feet, worked his way back into Trump’s inner circle—and even, at times, onto the plane itself. Wiles had, around the time of their showdown with Lewandowski, told LaCivita that she could no longer deal with the headache of handling the manifest. She charged him with the thankless duty for the remainder of the campaign, making for awkward encounters whenever Trump announced he wanted Lewandowski to accompany him somewhere.
Even when Lewandowski wasn’t around, his presence was felt. In one instance, South Dakota Governor Kristi Noem—with whom Lewandowski was reported to have carried on a romantic relationship (they have both denied this)—boarded the Trump plane after an event and joined the former president for a strategy briefing with his aides. As the candidate received a series of positive updates from the ground—early-voting metrics, state-based internal polling—Noem interrupted to say that the campaign was lagging behind the Democrats in terms of voter-registration numbers. Trump’s aides were stunned: Not only was she contradicting their own data, but those present were convinced that Lewandowski had put her up to it in order to make Wiles and LaCivita look bad. (Noem, through a spokesperson, denied this and took offense at the notion that “she needs a man to put her up to anything.”)
As the race moved toward its conclusion—and as the constellation of helpers and hangers-on surrounding Trump began positioning themselves to take credit or deflect blame—more than a few people close to the candidate were shopping dirt on their internal rivals. A sense of foreboding settled in over the campaign. There was so much bad blood, several aides told me, that something was bound to spill out into the open.
Sure enough, on October 15, the Daily Beast published an explosive story alleging that LaCivita had skimmed huge amounts off the top of TV ads, direct mail, and other expenditures, netting him some $22 million from his work on behalf of the campaign and a pair of related super PACs. Multiple campaign sources told me that the nature of these arrangements was exaggerated, and that although LaCivita had made plenty of money—and perhaps more than some people were comfortable with—it was nowhere near that amount. (“Not only is the $22 million number manufactured out of thin air,” LaCivita told me in a statement, “but it’s defamatory.”) His objections hardly mattered: Trump was livid. Even when Wiles tried to calm him down, arguing that Lewandowski had planted the story to eliminate LaCivita, the former president kept fuming, saying the story made him look like a fool and demanding to know why the campaign hadn’t stopped it from being published.
With everyone in the campaign watching to see how their boss would respond to the article, Trump made it known that LaCivita was not welcome on the plane for a planned trip to Georgia that evening. Trump was still beside himself a day later, ranting about the article and telling friends that he’d fire LaCivita—and possibly his entire team—if it weren’t for the PR hit that would cause just weeks out from Election Day. (Cheung denied that Trump was upset by the Daily Beast report, saying “everyone recognized it came from disgruntled individuals.”)
LaCivita was abruptly summoned to Trump Tower on the morning of Friday, October 18. There, he found himself climbing into the lead car of the former president’s motorcade, a limousine in which Trump often rides alone to recharge between events. On this occasion, there was another passenger, the businessman Howard Lutnick, who had recently been named a co-chair of Trump’s White House transition team. The three of them made small talk all the way to LaGuardia Airport, as LaCivita waited for the hammer to drop. It felt, LaCivita would later tell several friends, like an episode of The Apprentice: beckoned by the boss, shoved into the limo with a spectator on hand, only to ride in suspense for what seemed like an eternity, believing that at any moment Trump would turn and say, “You’re fired.”
Instead, when they arrived at LaGuardia and boarded the campaign plane, Trump signaled for LaCivita to join him in the cramped, four-seat office at the front of the cabin. As they settled across from each other, Trump reached for a small stack of paper: a printout of the Daily Beast story. LaCivita, in turn, produced a much thicker stack of paper. These were the exhibits for the defense: Federal Election Commission reports, bank-account statements, pay stubs, vendor agreements, and more. For the next half hour, according to several sources with knowledge of the exchange, the two men had it out—profanities flying but voices kept intentionally low—as LaCivita insisted to Trump that he wasn’t ripping the candidate off. Trump, the sources said, seemed to vacillate between believing his employee and seething over the dollar figure, wondering how something so specific could be wrong. Finally, after a couple of concluding f-bombs, Trump seemed satisfied. “Okay, I get it, I get it,” he told LaCivita, holding up his hands as if requesting that the defense rest. He added: “You should sue those bastards.”
The air was more or less cleared: Trump has not raised the issue of LaCivita’s pay since, aides told me, save for several episodes of the candidate teasingly—but conspicuously—calling LaCivita “my $22 million man!” Nevertheless, the alliance remains fragile. Less than a week after the détente, CNN unearthed LaCivita’s Twitter activity from January 6, 2021, including his having liked a tweet that called for Trump to be removed via the Twenty-Fifth Amendment. At that point, Trump told several people that LaCivita was dead to him—that he would ride out the remainder of the campaign, but would have no place in his administration or political operation going forward.
That was just fine by LaCivita; he had always viewed himself as a hired gun, and his reservations about working for Trump weren’t exactly a secret. Still, the word that Trump had iced one of his two key lieutenants sent a shiver through the rest of the staff. Many had noticed new faces popping into the building, poking around, asking questions about finances and compliance. With Trump’s suspicions piqued, every staffer, as well as every decision, would be under the microscope through Election Day.
Entering the final weekend of October, I noticed something in conversations with numerous Trump staffers: resignation. They had long since become accustomed to working in the high-intensity, zero-margin-for-error environment created by Wiles and LaCivita. But this home stretch of the campaign hadn’t just been hard and stressful; it had been disillusioning. Several campaign officials had told me, throughout the spring and summer, how excited they were about working in the next Trump White House. Now those same people were telling me—as paperwork was being distributed internally to begin the process of placing personnel in the transition team and in the prospective administration—that they’d had a change of heart. The past three months had been the most unpleasant of their careers. Win or lose, they said, they were done with the chaos of Donald Trump—even if the nation was not.
Standing in the bowels of Madison Square Garden on the evening of Sunday, October 27, an irate group of Trump staffers, family members, and loyalists was looking for someone to blame.
The prime-time show playing out just beyond their corridor had been eight years in the making. Trump, hailed as “the man who built New York’s skyline” by a roster of celebrity speakers, would stage an elaborate homecoming to celebrate his conquest of the American political psyche. It seemed that nothing—not even the $1 million price tag for producing such an event—could put a damper on the occasion.
And then, before some in the audience had even found their seats, the party was over.
The first presenter, a shock comedian named Tony Hinchcliffe, told a sequence of jokes that earned little laughter but managed to antagonize constituencies Trump had spent months courting. One was about Black people carving watermelons for Halloween; another portrayed Jews as money-hungry and Arabs as primitive. The worst line turned out to be the most destructive. “I don’t know if you guys know this, but there’s literally a floating island of garbage in the middle of the ocean right now,” Hinchcliffe said. “I think it’s called Puerto Rico.”
The blowback was instantaneous. Elected officials—Democrats, and, before long, Republicans too—blasted the comedian’s remarks. Headlines from the world’s leading news organizations described the event as every bit the hate-fest Republicans had promised it wouldn’t be. Trump aides were blitzed with text messages from lawmakers and donors and lobbyists wanting to know who, exactly, had the bright idea of inviting a comic to kick off the most consequential event of the fall campaign.
In truth, some of Trump’s senior staff hadn’t actually watched Hinchcliffe’s set. The Garden was a labyrinth of security checkpoints and political processions, and the event had barely been under way when he spoke. Now they were racing to catch up with the damage—and rewinding the clock to figure out how Hinchcliffe had ended up onstage in the first place.
It didn’t take long to get to the answer: Alex Bruesewitz.
Technically a mid-level staffer—formally a liaison to right-wing media, informally a terminally online troll and perpetual devil on the campaign’s shoulder—Bruesewitz had grown his profile inside of Trump’s orbit. The candidate’s appearances on various bro-themed podcasts were hailed as acts of strategic genius. But there was one guest booking Bruesewitz couldn’t secure: He wanted Trump to talk with Hinchcliffe on his show, Kill Tony. When word got around that Trump was looking for opening acts at the Garden, Bruesewitz made the introductions. Trump’s head of planning and production, Justin Caporale, ran with the idea. No senior staff ever bothered to vet Hinchcliffe themselves.
Now, with their grand celebration quickly morphing into a public-relations nightmare, Trump’s allies stewed. Two decisions needed to be made, and quickly: whether to inform the man of the hour about this disaster before he took the stage, and whether to issue a statement rebuking Hinchcliffe and his remarks. Some staffers feared throwing Trump off his game at such a crucial moment, and others argued that showing any weakness would just make things worse. But LaCivita dictated a short statement to the communications team that was blasted out to reporters across the arena, distancing the campaign from Hinchcliffe, while Wiles pulled the former president aside and explained the situation. (Trump, aides told me, was merely annoyed at the time; only after watching television coverage the next morning would he rage about how Wiles, LaCivita, and Caporale had “fucked this up.”)
Backstage at the Garden, in the blur of debate and indecision over damage control, it was Stephen Miller who pondered the bigger picture. (Miller did not respond to a request for comment.) According to two people who were present, Miller, the Trump policy adviser whose own nativist impulses are well documented, was not offended by Hinchcliffe’s racist jokes. Yet he was angered by them all the same: He knew the campaign had just committed a huge unforced error. He believed that Bruesewitz had done profound damage to Trump’s electoral prospects. And, in that moment, he seethed at what this lack of discipline portended for Trump should he return to power.
The irony, apparently, was lost on Miller. He and his colleagues would spend the coming days savaging Bruesewitz for his recklessness when really—as ever—the culprit was a man whose addiction to mayhem creates the conditions in which a comedian who was once dropped by his talent agency for using racial slurs onstage could be invited to kick off the closing event of the election without a single objection being raised.
“If we can’t trust this kid with a campaign,” Miller said to the group, according to one of the people present, “how can we trust him in the White House?”
