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Donald J. Trump took his seat at the dining table in his triplex penthouse apartment atop Trump Tower on the last Sunday in September, alongside some of the most sought-after and wealthiest figures in the Republican Party.
There was Paul Singer, the billionaire hedge fund manager who finances Republican campaigns and pro-Israel causes, and Warren Stephens, the billionaire investment banker. Joining them were Betsy DeVos, the billionaire former education secretary under Mr. Trump, and her husband, Dick, as well as the billionaire Joe Ricketts and his son Todd.
Some politicians might have taken the moment to be charming and ingratiating with the donors.
Not Mr. Trump. Over steak and baked potatoes, the former president tore through a bitter list of grievances.
He made it clear that people, including donors, needed to do more, appreciate him more and help him more.
He disparaged Vice President Kamala Harris as “retarded.” He complained about the number of Jews still backing Ms. Harris, saying they needed their heads examined for not supporting him despite everything he had done for the state of Israel.
At one point, Mr. Trump seemed to suggest that these donors had plenty to be grateful to him for. He boasted about how great he had been for their taxes, something that some privately noted wasn’t true for everyone in the room.
The rant, described by seven people with knowledge of the meal who spoke on the condition of anonymity to discuss private conversations, underscored a reality three weeks before Election Day: Mr. Trump’s often cantankerous mood in the final stretch. And one of the reasons for his frustration is money. He’s trailing his Democratic rival in the race for cash and has had to hustle to keep raising it.
Not only does Ms. Harris have far more money to buy ads and pay for staff after raising $1 billion in less than three months as a candidate — a sum greater than the total Mr. Trump raised all year — but she has also been freed from having to plead directly to donors anymore. She raised more than twice as much as Mr. Trump in July, August and September.
At almost the exact time Mr. Trump was sitting down to dinner at Trump Tower, Ms. Harris was taking the stage at a JW Marriott ballroom 3,000 miles away in Los Angeles, at an event that raised $28 million.
It was the last fund-raiser she is scheduled to attend before the election, her advisers said.
Mr. Trump remains in a tight race, and a memo his campaign released this week asserted that he was leading in all of the battleground states, although his leads in those surveys were all within the margin of error. His campaign has been more clearly yoking Ms. Harris to President Biden and making the case that she failed to get her agenda through in three and a half years as vice president. And he is more comfortable calling donors for support this election cycle than he has been in the past.
Still, Mr. Trump has groused about the amount of time he is having to spend raising money, angry that he is not on the trail doing what he draws energy from — his rallies.
That tension has become more acute since Mr. Trump’s campaign has had to adjust some events because of heightened security threats against him. Because of those threats, he’s given up playing golf, his favorite method of relaxation, for the remainder of the campaign.
Karoline Leavitt, a spokeswoman for Mr. Trump, did not comment on the dinner but said that the former president had won before while being outspent and again predicted victory.
“If money guaranteed electoral success, Hillary Clinton would have been president,” she said. “Kamala Harris has spent hundreds of millions of dollars and is still performing worse than any Democrat who has ever ran against President Trump. Meanwhile, President Trump is in a better financial position than ever before, and he’s leading in the polls.”
Mr. Trump did not make a direct financial request at the Trump Tower dinner, which included members of the American Opportunity Alliance, a network of G.O.P. financiers. Some of the dinner attendees left shaking their heads at the former president’s behavior, but there’s no indication that the interaction will have any effect on their giving.
“President Trump was in good form,” Todd Ricketts, whose family owns the Chicago Cubs, said in a statement. “It was a great dinner and we left more emphatic than ever to help get him back into the White House.”
One person familiar with Mr. Trump’s thinking said his comments reflected a mind-set that he was speaking to a group of donors whose network had mostly backed his primary rivals.
And even Mr. Trump’s most caustic remarks did not appear to leave a real mark. One dinner attendee who is Jewish said to the former president that if he was frustrated by Jewish voters, he should imagine how his right-leaning Jewish supporters feel, according to a person with knowledge of what was said.
Ms. DeVos’s attendance was notable in part because she had resigned from Mr. Trump’s cabinet the day after the Jan. 6, 2021, riot at the Capitol, criticizing his rhetoric in the lead-up to the violence.
This month, Mr. Trump has been forced to hold hat-in-hand events in noncompetitive states. Three days after that Trump Tower dinner, he traveled to Texas for fund-raisers in Houston and Midland. Ms. Harris traveled the same day to the battleground state of Georgia to speak about the recovery efforts after Hurricane Helene.
Next Wednesday, Mr. Trump is set to hold a “candlelight dinner” at his Mar-a-Lago club for donors who give or raise $924,600. Those who contribute $250,000 can join a private round table. He is slated to hold a bigger reception for smaller contributors — those who fork over at least $5,000. Ms. Harris will be campaigning the same day in the crucial battleground of Pennsylvania, according to a person briefed on her plans.
Mr. Trump had been anxious about how much money Democrats would have even before Ms. Harris replaced President Biden atop the ticket and unleashed a flood of donations.
In July, Mr. Trump sent a nasty series of text messages to Miriam Adelson, the widow of the casino magnate Sheldon Adelson and a donor who’s already giving tens of millions of dollars to support him. They have since repaired the relationship, but earlier this year, Mr. Trump told associates he expected $250 million from her, an eye-popping amount from any single donor, according to one person with knowledge of the figure he used.
Such absurdly large demands have become standard practice for Mr. Trump. In a meeting in April at Mar-a-Lago with representatives from major oil and gas companies, Mr. Trump told the executives his policies were so good for them that they should raise him $1 billion.
Mr. Trump, whose assets make him a billionaire, has not funded his own campaign since 2016, nor has he reported giving any money to a political action committee affiliated with him, Save America, which has paid legal fees related to his indictments and one criminal trial that resulted in felony convictions.
Ms. Harris has more than doubled Mr. Trump’s financial haul in the last three months, an advantage that has played out online, on television and at voters’ doors in the key swing states. In the last 90 days, for instance, Ms. Harris has poured more than $77 million into advertising on Meta’s platforms, including Facebook and Instagram. Mr. Trump has spent only a fraction of that, $9 million, company records show.
Ms. Harris spent more than double what Mr. Trump did on television in September, according to AdImpact, the ad-tracking service: $101.6 million to $48.3 million. He is, however, on pace to nearly match her spending in October and November, according to current reservations.
Mr. Trump’s team appears to have found other ways to conserve cash in the closing stretch. For instance, he is attending an Oct. 23 rally in Georgia as a “special guest” of an allied group, Turning Point PAC, that can foot the bill for the event.
It is the same approach a cash-strapped Gov. Ron DeSantis used during the Republican primary. Another group, Building America’s Future, is hosting a “Hispanic round table” in Nevada this weekend that Mr. Trump is attending as a guest.
And while Mr. Trump has been lifted by some donations from billionaires, such as Timothy Mellon, the reclusive banking heir who has given $125 million to supportive super PACs, Democratic super PACs are flush with cash, too. All told, pro-Harris groups are set to outspend pro-Trump forces in October and November by 30 percent on television, according to AdImpact.
Still, the dinner with the billionaires last month pointed to Mr. Trump’s durability in reshaping a party whose donors are now mostly accepting of the former president’s outbursts as they view defeating Ms. Harris as a crucial imperative.
After the Sept. 29 meal, Mr. Singer, who has already given $5 million to a Trump super PAC, left the event and took a clear message back to his network of donors, according to a person with knowledge of the conversations. He implored them to donate extensively to Republicans — and to Mr. Trump.
Theodore Schleifer contributed reporting.
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