People around the former and would-be president see a candidate knocked off his bearings, disoriented by his new contest with Kamala Harris and unsure of how to take her on.
The August 2 dinner at the home of Howard Lutnick, the Cantor Fitzgerald CEO, was a high-powered affair. Among the roughly 130 people who attended were some of Donald Trump’s wealthiest supporters, including billionaire hedge fund financier Bill Ackman 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.
Answering a question that voiced concerns about the upcoming election during a roundtable discussion, 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.
According to two people present, Trump also brought up his remark, made two days earlier, in which he had questioned Vice President Kamala Harris’ racial identity.
It had been a display of flagrant race-baiting, 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 donors that Friday night.
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.
Trump has found the change disorienting, those who interact with him say. He had grown comfortable campaigning against an 81-year-old incumbent. Suddenly, he finds himself in a race against a Black woman nearly 20 years younger who is drawing large and excited crowds.
The people around Trump see a candidate knocked off his bearings, nothing like the man who watched last month 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.
A spokesperson for Trump, Brian Hughes, said that the former president “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.
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 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 he privately asked his advisers whether they had known about Vance’s comments about childless women before Trump chose him.
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, Governor Tim Walz of Minnesota, on the campaign trail.
Despite his public insistence that he would rather face Harris than Biden, those close to Trump 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 galvanising new rival, a potential Iranian assassination threat against him and new layers of security that have brought a bunker-like 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. 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.
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 favoured “Crazy Kamala.”
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 on 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.
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.
This article originally appeared in The New York Times.
Written by: Maggie Haberman and Jonathan Swan
Photographs by: Doug Mills, Louise Johns, Kenny Holston and Nicole Craine
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