As many as three nights a week, Donald J. Trump has been hosting private dinners at Mar-a-Lago, schmoozing with some of the Republican Party’s biggest financiers as he races to address a sizable cash shortfall against President Biden.
There is no request for money from the attendees at these meals, which have included Larry Ellison, the billionaire co-founder of Oracle, and Pepe Fanjul, the sugar magnate, according to people familiar with the sessions. But advisers to Mr. Trump’s campaign and his super PACs hope the charm offensive will eventually pay political and financial dividends.
One of the most pressing issues facing Mr. Trump is the financial disparity he and allied groups now face with Mr. Biden and the Democratic Party. Mr. Biden’s campaign announced on Sunday that it entered March with $155 million cash on hand with the party, after raising $53 million in February. The Trump operation has not released a more recent total, but his campaign account and the Republican National Committee had around $40 million at the end of January.
Mr. Trump enters the general election ahead of Mr. Biden in public polls. But Mr. Biden has taken full advantage of one of the benefits of incumbency, both socking away cash and building out a political operation earlier than his challenger.
Despite years of professing massive wealth and boasting of his desire to “drain the swamp,” the deeply transactional former president is leaning yet again on the cash of others, turning Mar-a-Lago into a staging ground for billionaires and others with their own agendas. One potential leverage point with the biggest G.O.P. financiers is the package of tax cuts Mr. Trump signed into law in 2017. Many of those cuts expire at the end of 2025, and Mr. Biden has vowed not to extend them for the nation’s highest earners.
Money often winds up mattering less in presidential races than in down-ballot races. Voters pay attention to the candidates naturally, especially Mr. Trump, and the key states all wind up awash in advertising by the fall.
Yet recent presidential contests have been so excruciatingly close that everything has mattered, and Mr. Trump is preparing to face an especially large avalanche of Democratic spending this year. Just a single union this week announced plans to spend $200 million, ten times what the main Trump super PAC had on hand. A cash edge can help Democrats tilt or expand the battleground map in their favor.
In a sign of the Trump orbit’s urgent need for cash, at least two donors who made seven-figure pledges to support Mr. Trump this year were nudged to see if they could cut an eight-figure check — meaning $10 million or more — instead, according to a person familiar with the request.
It is an unusually perilous moment for Mr. Trump.
The former president is facing converging financial crunches just as he has become the presumptive Republican nominee. The first is the political cash situation. The others are far more personal.
Mr. Trump recently posted a $91.6 million bond in a civil case in which he was found liable for sexual abuse and defamation of the New York writer E. Jean Carroll. He also must summon the resources to post a roughly $450 million bond, the judgment in a New York civil fraud case against his businesses, in the coming days. And he has mounting legal bills as his first criminal trial nears. Mr. Trump’s Save America PAC, which has been paying his lawyers and those of some witnesses, is set to run dry by summer at the current pace of spending.
Some Trump allies predict they will have enough campaign cash to win, even if it’s less than Mr. Biden.
“Hillary Clinton way out-raised President Trump but he connected with the American people and that was the difference right there,” said Tommy Hicks Jr., a former Republican National Committee co-chair and finance director.
Brian Ballard, a Republican lobbyist, fund-raiser and Mar-a-Lago member, said Mr. Trump was “incredibly engaged” in the political money fight.
“He understands the one advantage the Biden campaign has is financial resources,” Mr. Ballard said, adding “and he understands we need to do all we can to negate that.”
To prepare for the fall, Mr. Trump’s advisers have embarked on an aggressive and speedy takeover of the R.N.C. that included installing his daughter-in-law, Lara Trump, as co-chair, with the intention that she’ll focus in part on shoring up fund-raising. The Trump team imposed mass layoffs in some departments on Monday, and is shipping all of the party’s finance and digital fund-raising staff to the former president’s Florida headquarters by the end of the month.
In a sign of the early Democratic edge, Mr. Biden traveled to Wisconsin this week to promote the 44 party and campaign offices they are opening in the state, at the same time Mr. Trump’s team was laying off or forcing the R.N.C.’s regional political staff to reapply for their jobs.
For now, the Trump operation is ramping up its program for bundlers of midsize donations and planning to conserve cash costs by holding fewer rallies than they did at the end of the primary season.
On Thursday, Mr. Trump formed a new joint fund-raising account with the national party and roughly 40 state parties, calling it the Trump 47 Committee, allowing him to directly raise money in chunks of more than $800,000. A splashy dinner in Palm Beach is being planned in early April to fill the new account’s coffers. One person familiar with the planning said donors have pledged more than $25 million.
Mr. Trump himself is said to be concerned about the fund-raising gap between his orbit and Mr. Biden’s, although he has told advisers that he believes he and his allies will ultimately raise what they need, according to one person with knowledge of the discussions.
But some top donors remain hesitant. Among their privately expressed concerns is a fear that large donations could wind up covering Mr. Trump’s legal fees, even as his advisers have publicly said the R.N.C. won’t do so. Mr. Trump’s main super PAC has, as of January, refunded more than $47 million of the $60 million it had received before the 2024 run began to Mr. Trump’s PAC, which is paying Mr. Trump’s lawyers.
So far, Mr. Trump has reported only a limited well of major contributors during the 2024 race. He has, in the meantime, become increasingly attentive to them.
He recently had a meeting with one of the world’s richest men, Elon Musk, and a brief backstage encounter with Jeff Yass, a billionaire investor in TikTok. Mr. Trump said on CNBC that he and Mr. Yass had not spoken about the company, though he later posted on social media regarding his skepticism about federal legislation that could ban the app, especially if it would benefit the parent company of Facebook.
On Super Tuesday, Mr. Trump’s main super PAC, Make America Great Again Inc., rented out a room at Mar-a-Lago for some of the larger donors to mingle in. Mr. Trump stopped by and thanked some of them, including Trish Duggan, a prominent Florida philanthropist and Scientologist, who has contributed more than $5 million, according to a person who was in the room.
The night he won the New Hampshire primary, Mr. Trump gave shout-outs in his victory speech to the casino magnate Steve Wynn and the hedge fund manager John Paulson, both of whom are billionaires.
“You know what? Put him at Treasury,” Mr. Trump said of Mr. Paulson that night. The April fund-raising dinner, which was first reported by Bloomberg, will be hosted by Mr. Paulson.
On the night of the South Carolina primary, Woody Johnson, the billionaire owner of the New York Jets to whom Mr. Trump gave an ambassadorship during his term, stood behind Mr. Trump.
Another billionaire and regular at Mar-a-Lago, Ike Perlmutter, is supporting a separate super PAC, Right for America, that is being run by Trump ally Sergio Gor. Mr. Trump blessed Mr. Perlmutter’s effort, despite the fact that its existence has caused tension within the broader Trump circle.
The general election cash chasm was apparent in the advertising announced in March.
The main Trump super PAC has purchased about $380,000 in radio advertising targeting Black voters in three states this month. The Biden campaign has announced a $30 million ad campaign over six weeks — a nearly 100 to 1 edge in the first stretch of the race.
That ratio does not include the roughly $500,000 the pro-Trump super PAC spent on an ad that trolled Mr. Biden the day of his State of the Union speech, questioning whether the president would live to 2029, when his second term would end. The provocative commercial exemplifies what underfunded groups typically do: Spend symbolically to generate free media coverage.
Some Republican donors have emphasized that wealthy contributors may write large checks, but they often don’t want to see that fact disclosed, given the controversy that attaches itself to Mr. Trump. A number of donors faced public blowback in 2016 for their support.
An official with the Trump super PAC would not say whether Mr. Yass has given money to the group, but a person close to the campaign said he is expected to make a seven-figure contribution. It’s unclear if that would be to a super PAC or a dark money group that does not have to identify its donors.
After Mr. Musk’s meeting with Mr. Trump was reported, Mr. Musk wrote, “I am not donating money to either candidate for US President.” But should he choose to donate, Mr. Musk, too, could decide to give to an entity in which the money cannot be tracked.
Not everyone is on board just yet.
“Can I just have a moment to be sad over Nikki not being in the race?” the hedge fund executive and G.O.P. financier Ken Griffin said at a conference in Florida this week, referring to Mr. Trump’s last major Republican rival, Nikki Haley. But Mr. Griffin predicted that Mr. Trump would win this fall and left open the possibility of backing him.
The current financial situation is a reversal of the one in 2020.
Back then, it was Mr. Trump who held the White House and had amassed a $187 million advantage by roughly this same point, creating a far larger gap than Mr. Biden has built now. But spending decisions by the Trump team and a deluge of Democratic giving inverted that by the fall.
The Republican National Committee announced that last weekend — the first since Michael Whatley was installed as chairman, and Ms. Trump as co-chair — was its strongest for a fund-raising weekend since 2020. Ms. Trump said on Fox News that she had personally received pledges of $2.7 million.
And a Trump campaign spokeswoman said that February had been its strongest month for small dollar fund-raising of the race. Records show the previous high for online fund-raising was last August, when Mr. Trump raised $22.3 million.
Still, Democratic donors have been pouring money into Mr. Biden’s coffers. The Biden campaign announced it had raised more than $10 million online in the 24 hours after the State of the Union address.
To put that sum in perspective, it more than doubled the biggest day Mr. Trump had in 2023, when his mug shot was released from his Georgia indictment, and he raised $4.2 million online.