The Aug. 2 dinner at the Bridgehampton, New York, home of Howard Lutnick, the Cantor Fitzgerald CEO, was a high-powered affair. Among the roughly 130 people who dined under an air-conditioned tent were some of Donald Trump’s wealthiest supporters, including billionaire hedge fund financier Bill Ackman, who sat next to the former president, and Omeed Malik, the president of another fund, 1789 Capital.
Some guests hoped Trump would signal that he was recalibrating after a series of damaging mistakes. He did not.
Before the dinner, answering a question that voiced concerns about the upcoming election during a small roundtable discussion inside Lutnick’s house, Trump said, “We’ve got to stop the steal,” reviving yet again his false claims about the 2020 election — claims that his advisers have urged him to drop because they don’t help him with swing voters.
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According to two people present, Trump also brought up his remark, made two days earlier at a gathering of the National Association of Black Journalists, in which he had questioned Vice President Kamala Harris’ racial identity.
It had been a display of flagrant race-baiting that was egregious even by Trump’s standards, and it instantly reprogrammed America’s TV news chyrons: He falsely claimed that Harris had only recently decided to identify as Black for political purposes.
But Trump showed no regret. “I think I was right,” he told the rattled donors that Friday night.
Later, at dinner under the tent, Harrison LeFrak, the scion of a New York real estate family, whose father is an old friend of Trump’s, asked how Trump planned to take the narrative back from Democrats, and what his positive vision for the country would be. It appeared to be a request for reassurance.
Trump provided none. Instead, he criticized Harris on a range of fronts, before adding: “I am who I am.”
The fundraiser came amid a stretch of flailing and self-harm that began after President Joe Biden’s July 21 withdrawal from the race and endorsement of Harris to succeed him. Close Trump allies have described this as the rockiest period of Trump’s campaign — and easily the worst since a late 2022 spree in which he mused about terminating parts of the Constitution and dined at Mar-a-Lago with a white supremacist and an outspoken antisemite.
Since then, Trump has picked fights with allies publicly and privately, including a broadside against Gov. Brian Kemp of Georgia at an Atlanta rally — the kind of mean-spirited public attack on a popular Republican that his own allies believe helped sink two Senate races in Georgia in January 2021 and could harm Trump in the state, a vital battleground in November.
This story is based on interviews with more than a dozen people close to Trump, nearly all of whom insisted on anonymity to describe private discussions and events.
As Harris — long ridiculed and underestimated — has transformed the contest, campaigning energetically and drawing roughly even with Trump in many polls, Trump has responded with one unforced error after another while struggling to land on an effective and consistent argument against her.
He has found the change disorienting, those who interact with him say. Trump had grown comfortable campaigning against an 81-year-old incumbent who struggled to navigate stairs, thoughts and sentences. Suddenly, he finds himself in a race against a Black woman nearly 20 years younger, one who has made history and who is drawing large and excited crowds.
The people around Trump see a candidate knocked off his bearings, nothing like the man who reclined serenely July 15 as he watched as thousands of delegates cheered him on the first night of the Republican National Convention. Then, Trump, his ear bandaged, was a living martyr after the assassination attempt two days before. Inside the Milwaukee arena, the Democrats had been defeated; the only thing left to wonder about was the margin of Trump’s victory.
In a statement in response to the reporting for this story, a spokesperson, Brian Hughes, said that Trump “continues to run a winning campaign and has built a movement focused on making our nation great again.” Another spokesperson, Steven Cheung, insisted Trump had put forward a “positive” vision for the country that contrasted with “the dangerously liberal policies” of Biden and Harris.
But to Trump’s close allies, that first night in Milwaukee now seems a foggy memory, as if it never happened.
A Foul Mood
At the Aug. 2 dinner, Trump told donors that the news media had been incorrectly suggesting that he had mellowed since the assassination attempt. “I’m not nicer,” he said, according to one person in attendance.
Another said Trump described himself as “angry,” because “they” — unspecified adversaries that the attendee took to mean Democrats — had first tried to bankrupt him and then to kill him.
Indeed, Trump has often been in a foul mood the past few weeks. He has ranted about Harris. He has called her “nasty,” on “Fox & Friends,” and a “bitch,” repeatedly, in private, according to two people who heard the remark on different occasions. (“That is not language President Trump has used to describe Kamala, and it’s not how the campaign would characterize her,” Cheung said.)
His quickness to anger has left him susceptible to manipulation, even among close allies.
A week before the Hamptons fundraiser, on July 25, Trump stunned one of his wealthiest patrons, Miriam Adelson, the widow of casino magnate Sheldon Adelson, by having an aide, Natalie Harp, fire off a series of angry text messages to Adelson in Trump’s name, according to three people with knowledge of what took place.
The texts were particularly jarring because Adelson and Trump had a friendly meeting just a week earlier at the Republican National Convention, according to a person briefed on the matter.
The texts complained about the people running Adelson’s super political action committee, Preserve America, into which she is pouring millions of dollars to support Trump.
At the time, Preserve America was spending nearly $18 million on a week’s worth of ads aiding Trump in three battleground states. The texts said that the officials running Preserve America were “RINOs” — Republicans in name only — and that Adelson’s late husband would never have tolerated that, the people said.
According to two of the people, aides to Adelson later discovered that the outburst against her had been encouraged by another major Trump donor, Ike Perlmutter, the former chair of Marvel Entertainment, who had hoped in vain that Adelson would contribute to a rival super PAC that he backs. (A lawyer for Perlmutter did not respond to an email seeking comment, and an adviser to Adelson, Andy Abboud, declined to comment.)
The text messages prompted concerns — as yet unrealized — that Adelson might scale back her support of Trump.
Over the past two weeks, Trump has fielded complaints from donors about his running mate, JD Vance, as news coverage exploring Vance’s past statements unearthed — and then exhaustively critiqued — remarks including a lament that America was run by “childless cat ladies.”
Trump dismissed out of hand donors’ suggestions that he replace Vance on the ticket. But Trump privately asked his advisers whether they had known about Vance’s comments about childless women before Trump chose him.
And, at the Aug. 2 fundraiser, according to two people with knowledge of what took place, when a donor at the roundtable discussion asked about Democrats trying to paint the Republican ticket as “weird,” Trump replied: “Not about me. They’re saying that about JD.”
Trump didn’t reveal any loss of confidence in Vance. Rather, he offered him simple advice: Attack, attack, attack. And Trump has been impressed over the past week as Vance attacked Harris and her new running mate, Gov. Tim Walz of Minnesota, on the campaign trail — praising him and taking credit for scouting him, according to two people who have spoken to Trump. They said Trump had described Vance as a great political “athlete.”
Whipsawed by Events
Trump deals more in projection than subtext, and his recent posts on Truth Social reveal how blindsided he feels about the upturned election.
Despite his public insistence that he would rather face Harris than Biden, those close to him say that is untrue. He had been on a glide path to an all-but-certain victory. Now, he needs to work for it.
But Trump has also been whipsawed by a seven-week roller-coaster-ride of events: an attempt on his life, the selection of a running mate, a nominating convention, his opponent’s withdrawal from the race, the entry of a galvanizing new rival, a potential Iranian assassination threat against him and new layers of security that have brought a bunkerlike feel to his properties, more than at any time since he was in the White House.
Also unsettling to him: For the first time in Trump’s political life, his opponent has received more sustained news coverage than he has, beating him at the game of “earned media,” the kind that costs campaigns nothing to produce.
Moreover, the coverage of Harris has overwhelmingly been positive.
Harris “has gotten the equivalent of the largest in-kind contribution of free media I think I have ever seen in all the years I’ve been doing presidential campaigns,” said Tony Fabrizio, the Trump campaign’s chief pollster.
Trump has seemed to want to wish his new situation away. He claimed on Truth Social, without evidence, that Biden regretted his decision to drop out and wanted to undo it. He has talked repeatedly about how badly he thinks Democrats mistreated Biden. He has complained about how unfair it is that he’s had to start the race over again. He has vented about wasting time, energy and millions of dollars on Biden, only to find himself facing a new opponent for the final 100-day sprint.
And Trump told one aide that Democrats were trying to “steal” the election again from him — comparing the reshuffling of the Democratic ticket to when state legislatures changed voting rules midway through the 2020 election cycle because of the COVID pandemic.
He has also peppered his advisers with questions about whether Harris can sustain her momentum, constantly asking what new polling shows.
Soon after Harris replaced Biden atop the Democratic ticket, Fabrizio, the Trump pollster, stressed to the campaign staff that the polls would get worse before they got better. Fabrizio has insisted, though, that the race has not fundamentally changed, that once voters are educated about Harris’ liberal record on crime and her role in Biden’s unpopular policies — especially on immigration — they will sour on her.
Fabrizio has predicted to campaign colleagues that Harris will have two to three more good weeks, through the Democratic National Convention, and then her poll numbers will turn in the other direction.
Others are more concerned about what they are seeing in private polling. Two private polls conducted in Ohio recently by Republican pollsters — which Trump carried in 2020 with 53% of the vote — showed him receiving less than 50% of the vote against Harris in the state, according to a person with direct knowledge of the data.
Struggling to Frame the Attack
Nearly three weeks since Harris became his Democratic opponent, Trump and his campaign are still struggling to settle on how to define her, what message with which to attack her, and even what nickname with which to belittle her.
He initially called her “Laffin’ Kamala,” mocking her laugh, before cycling through other epithets, including “Crooked,” an insult he had used against both Hillary Clinton and Biden. Lately, he has favored “Crazy Kamala.”
His advisers have gone to great lengths testing policy-based attacks to see which work best with voters in the battleground states. They have privately described having so much material against Harris — from interviews to policy statements to her record as a prosecutor — that condensing it all into a specific frame can feel like a challenge.
Yet most of Trump’s top advisers have urged the campaign and the candidate to focus on the economy, immigration and crime — issues on which Trump’s message resonates powerfully with the so-called persuadable voters they are targeting.
Sometimes, Trump has done so. Other times, he has not.
His advisers have urged Trump to portray Harris as someone who frequently changes her positions, some of them recalling how successfully President George W. Bush used that strategy against John Kerry in the 2004 presidential race.
Trump has called her “fake” — but in self-defeating ways, like questioning whether Harris, who is Black, is Black.
Outside advisers and allies have also called Trump to impress on him the political peril of continuing with those kinds of attacks. Kellyanne Conway, who managed his 2016 campaign, recently told Trump to stick to policy contrasts, rather than personal attacks, and to treat Harris as a formidable adversary, as he had Clinton.
That advice has gone unheeded. At his news conference Thursday in Palm Beach, Florida, Trump again attacked Harris as “nasty,” denigrated her intellect and said she was “very disrespectful” to both her Black and Indian heritages.
Trump’s mood improved a little in recent days, people who have spoken with him said, after Harris named Walz her running mate. He had become convinced that she would choose Gov. Josh Shapiro of Pennsylvania, and that Shapiro could help her carry a must-win state. On “Fox and Friends,” Trump called Walz “a shocking pick,” adding, “I could not be more thrilled.”
Griping About Circumstances, but Not Staff
Summertime has been a challenging season for Trump in election years: In June and again in August 2016, he replaced his campaign leadership. In July 2020, he fired his campaign manager.
However, changes to his team do not now appear likely; Trump has privately expressed faith in his top advisers, even as he gripes about his current circumstances.
On Aug. 2, before the Hamptons fundraiser, Trump met at his club in Bedminster, New Jersey, with his daughter-in-law, Lara Trump, whom he had installed as a co-chair of the Republican National Committee, and with Conway, according to three people with knowledge of the meeting. Lara Trump, reached by phone, said there was no discussion of replacing any senior aides. Conway declined to detail her conversation with Donald Trump, but also said she had not discussed any personnel by name, saying she was there instead to discuss policy, strategy and how to beat his new, female rival.
In an angry phone call to a New York Times reporter Friday afternoon, Trump denied that he was making any changes to his team, saying he was “thrilled” with his top advisers, Susie Wiles and Chris LaCivita, and asking why he would even want to make such a change.
(In the same call, Trump threatened to sue the Times over a story about his description in Thursday’s news conference of a near-death experience on a helicopter ride with Willie Brown, a former California politician. Brown denied ever having flown on a helicopter with Trump.)
Trump’s own behavior remains one of the most unpredictable factors in his campaign.
And after years of holding only a few rallies a month and still managing to play plenty of golf, while Biden held very few campaign events, Trump now has an opponent who is outworking him politically.
Perhaps the clearest indication that Trump’s knack for forcing the public discussion to take place on his terms was failing him came a week ago, when he abruptly declared in a midnight social media post that a debate on ABC News, to which he had agreed when Biden was running, was now “terminated” and that he would only debate Harris on the more hospitable terrain of Fox News.
Trump was widely mocked as fearing a confrontation with Harris.
On Thursday, he reversed himself, declaring in his news conference that he would, indeed, show up for the ABC debate — and proposing two others.
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