The Trump machine: the former president’s dash for campaign cash

Just hours after he was ordered by a New York judge to pay $454mn for fraudulently inflating the value of his properties, Donald Trump held a fundraising event at his ritzy Mar-a-Lago resort in Palm Beach.

The biggest donors received signed Make America Great Again caps. They also drank a 2020 vintage of Trump Meritage wine and sat on Opera chairs for a speech where Trump railed against the ruling, according to a person present. 

The colour of the chairs, the “Maga” on the caps, and the “Trump” lettering on the wine bottle were all the same — gold. 

Part of the proceeds for the event went to a group that pays for his lawyers. On the same evening, Trump fans saw new Facebook ads leading to a donation page claiming, “They’re not after me. They’re after you.”

“He’s a fighter,” says Bryan Eure, an insurance broker and Trump donor at the February 16 event. “There’s no coincidence that all of these court cases are happening all at once. It’s just ridiculous.”

The 2024 Trump campaign is unlike any other. Money comes in to send him to the White House. But just as quickly, some goes straight out to protect him from jail.

Trump has used each of his four indictments as fundraising tools, selling T-shirts with his mugshot, which helped pro-Trump groups to raise roughly $190mn in 2023. But the same groups also spent more than $50mn on his legal fees.

Although he is ahead in most of the polls for November’s election, Trump’s campaign is at a huge financial disadvantage to Joe Biden.

Pro-Biden groups entered 2024 with about $118mn on hand, compared with about $66mn for Trump. The difference — $52mn — was equal to the legal expenditures pro-Trump groups spent.

By the end of February, Biden’s campaign and the Democratic National Committee had more than twice as much on hand as Trump and the Republican National Committee. In March, the Biden campaign opened up dozens of offices in swing states, while the RNC fired dozens of staffers, as Trump’s campaign took it over.

Future Forward, a pro-Biden super Pac has already booked more than $130mn in ads this year, according to AdImpact data. Maga Inc, a pro-Trump super Pac, has booked just $6.5mn.

As he puts together $175mn to post bond and appeal his New York civil court case, Trump has licensed out his likeness to sell tennis shoes and relics of his suit. Over Easter, he even offered supporters Trump-themed Bibles — at $59.99 a time.

Money matters in US elections; the congressional or presidential candidate with the most typically wins. In 2020, Joe Biden vastly outraised Trump and became the first presidential candidate in US history to raise more than $1bn from donors. The 2024 rematch could prove even costlier.

“Once you get behind in the money race, it acts like a dark cloud that follows your campaign around in a negative way,” says veteran GOP strategist Scott Reed, who worked on a pro-Mike Pence super Pac.

The shortfall is also important because it could have an impact on the way he approaches the election. Trump is now trying to woo two very different types of donors, each with opposing views about what sort of campaign they want him to conduct — and about what sort of administration he would run.

Trump has his own group of loyalists, donors who embrace the Maga rhetoric and enjoy the message of “retribution” that allowed him to easily overcome his opponents in the Republican primary. This includes hundreds of thousands of small-dollar donors, who thrill at his attacks against a “woke” elite and his defence of those involved in the January 6 insurrection.

Trump has mounted “the biggest political comeback in history”, says Omeed Malik, a Mar-a-Lago member and Tucker Carlson media investor, who has promised this year to raise millions for the former president.

“The Democrats decided to make him a martyr,” adds Malik. “If you make someone a martyr, people are going to flock to them.”

However, the Trump campaign is also seeking support from among the more traditional Republican mega donors, who are concentrated in the New York financial world.

Many of them are wary of handing over money that will end up paying the candidate’s legal bills and are unlikely to support his radical plan for a 10 per cent tariff on all imports.

Billionaires Ken Griffin, Stanley Druckenmiller, Paul Singer, and Warren Stephens spent combined more than $13mn helping Trump’s rival Nikki Haley in the primaries; Jeff Yass spent roughly $5mn for Vivek Ramaswamy and Stephen Schwarzman spent $2mn on a pro-Chris Christie super Pac.

Most of them are now pondering their options — whether to turn to Trump, flip to Biden, support a third-party group, or stay on the sidelines. The movements of elite Republican donors will indicate whether they think Trump will win.

Hedge fund investor John Paulson is one of the traditional GOP donors Trump can rely on — he will host a Palm Beach, Florida fundraiser for the former president on April 6 that is expected to bring in $33mn.

But Paulson’s policy preferences chime with the sorts of issues that many old school GOP donors will be pressing on the Trump campaign — a very different tone and set of interests than his more loyalist backers. Paulson says his second term wish list includes: “lowering our trade deficit and restoring our global manufacturing competitiveness,” “supporting a strong domestic energy industry” and “securing our borders”.

During the primaries, Trump threatened that donors to Haley, the former South Carolina governor, would be blackballed. Now, he wants their support, even though he has done little to appeal to her voters.

Art Pope, chair of a North Carolina-based retail chain and a Haley donor, says he will never vote for Biden, but is undecided on Trump. “It depends on . . . whether he welcomes traditional conservatives and listens to them on issues where there are differences,” he says, and “whether he runs a positive campaign rather than a grievance campaign.”

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The Republican party is very much in need of new sources of funding.

The RNC had only $11mn on hand at the end of February — compared with more than $26mn for the DNC. Trump’s small-donor army also appears to have diminished since the last cycle: he entered the 2024 election year with roughly 200,000 fewer donors than in 2019.

But Trump fans say the money will come. He has a windfall potentially worth several billion dollars through his social media company Truth Social, although there is a lock-up period before he can sell his shares. It is also not clear if Trump would put any of the money from that company into his campaign, but he could use the proceeds to pay his legal fees.

Supporters point out that Trump only became the presumptive nominee in March, allowing him to raise more money per person for himself and the RNC. Even his lawyers are pitching in; Chris Kise, who represented Trump in the New York case, co-hosted a fundraiser with two of his firm’s partners for him in Miami.

Trump has brought in his own large donors. Four days after the New York verdict, Trump headed to casino developer Wallace Cheves’ South Carolina home for a $7mn fundraiser.

Three of the event’s top donors — Cheves, investor Scott Bessent and Florida injury attorney Dan Newlin — gave a variety of policy and personal reasons why they supported Trump.

Cheves, a fan of Trump’s old NBC show The Apprentice, wants Trump to stop the flow of fentanyl. But he also wanted to express his gratitude for the Trump administration’s decision to approve an application allowing him to develop a North Carolina casino with a Native American tribe.

“I thought that having a businessman that understood gaming was right up my alley,” says Cheves. “He’s a real doer. For us to hold a thank you event for him in my home was an absolute pleasure.”

Bessent, who joins Paulson on the list of potential Trump picks for Treasury secretary, says the “co-ordinated lawfare attacks” against Trump backfired and increased his popularity.

Founder of investment firm Key Square Group, Bessent says Trump will do a better job than Biden in tackling the US debt — he blames the pandemic for the $7.8tn added during Trump’s White House — and believes that 2024 will probably be “the last opportunity to grow out of the problem without substantially increasing taxes and slowing growth”. 

Newlin, whose billboards are well known in central Florida, gave relatively small amounts to Democrats in the past, including Hillary Clinton in 2016. But in 2021, he met Trump when he hosted a concert for the public to honour the military featuring country singer Toby Keith. Trump called into the show and gave him a shout out for organising the event.

“When you have somebody do that, you say, you know what — that guy is an everyday person. He truly believes in what’s right for America,” says Newlin. “Let’s face it . . . Had President Trump pulled out and decided not to run for office, none of all these trials and civil lawsuits in New York — none of this would have happened.”

At the February fundraiser, Newlin wore a red “Make America Great Again” cap, and took a photo with Trump. Newlin asked how the former president would end the war between Russia and Ukraine; Trump responded that because of Russia’s “massive military might,” it will not be billions in US aid that provides peace, but a diplomatic deal.

“He’s the right person to end this,” says Newlin. “We will see some sort of a deal cut between Ukraine and Russia.”

Among established Republican donors, Trump expects to depend upon Oklahoma oil tycoon Harold Hamm and casino magnate Miriam Adelson, who stayed neutral in the primary.

But he has attracted new billionaires: Tim Mellon, a scion of the Mellon banking family who wants to “build the wall”, Texas oil titans Kelcy Warren and Tim Dunn, Trish Duggan, a Florida scientologist divorced from venture capitalist Bob Duggan, World Wrestling Entertainment co-founder Linda McMahon, Wisconsin roofing distributor Diane Hendricks and his old Sin City friend Phil Ruffin, who owns the Treasure Island Hotel & Casino and part of the Trump International Las Vegas hotel.

Hamm says Biden’s advantage in fundraising will not help much. “We’ve seen all the money in the world not do some candidates any good,” adds Hamm. “People don’t believe in him.”

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One of the big questions now facing the Trump team is whether they can also poach the donors of his rivals from the primaries.

Dick and Liz Uihlein, the shipping and packaging billionaires, gave more than $3mn to Ron DeSantis but have flipped back to Trump. 

Liz Uihlein says she wants to see DeSantis run again. “I think it’s the most demanding job going and we got two old guys,” she says. But she adds that Trump’s court cases “enormously” helped him with voters in the party’s primary. “The American people see through things,” she says. “It’s so trumped up.”

Although she supports Trump’s policies, she says she would never talk like he does to her nearly 10,000 employees.

“There’s a lot of things to like about him,” says Liz Uihlein. “But nobody can control the bad part of him, where he just says terrible things about people.”

Tom Klingenstein, chair of the right-wing Claremont Institute, says he has always been “a super big Trump fan” and wants Trump to fire “woke generals” and name Vivek Ramaswamy, who he supported in the Republican primaries, as his “anti-administrative state tsar” next year.

Robert Bigelow, a Las Vegas property developer who has also funded research into UFOs, was DeSantis’s top donor but went to Trump after Hamas invaded Israel — he says he wants an “ass kicker” as commander-in-chief. 

Personal connections also mattered. Bigelow told the FT last year that he found DeSantis to be “a user of people” after he did not get an expected call to discuss abortion policy. In January, Bigelow told Reuters that he enjoyed a two-hour dinner with Trump at Mar-a-Lago — and committed $1mn to the ex-president’s legal fees and $20mn to the 2024 bid.

Bigelow will co-chair Paulson’s fundraiser for Trump on Saturday along with Cantor Fitzgerald CEO Howard Lutnick, former commerce secretary Wilbur Ross, conservative mega donors Robert and Rebekah Mercer, and Trump’s former US ambassadors to the UK, Spain and France — Woody Johnson, Duke Buchan, and Jamie McCourt.

After they dropped out of the race, DeSantis, Tim Scott, Doug Burgum and Ramaswamy endorsed Trump, but Mike Pence, his vice-president, and Christie said they would not. Haley has yet to say if she will support Trump.

One of the biggest fundraising challenges for Trump’s campaign is winning back Haley’s deep-pocketed donors.

In the final days of her campaign, Haley warned that Trump would use the party’s finances as a “legal slush fund.” New RNC co-chair Lara Trump, the ex-president’s daughter-in-law, told NBC that Republican donors could “opt out” of contributing to Trump’s lawyers.

Americans for Prosperity Action, a super Pac backed by billionaire Charles Koch’s network, supported Haley and warned that Trump would drag down the rest of the party in 2024. Republicans are trying to retain the US House and flip the Senate.

“The last three election cycles have painted a very clear picture of what we can expect from voters who consistently rejected Donald Trump and his impact on the Republican party brand,” wrote AFP senior adviser Emily Seidel in a memo in February. “And we should expect this to increase further as the criminal trials progress.”

The group will now stay on the sidelines of the presidential campaign. Haley’s wealthy donors are also wondering whether they should do the same.

Francis Rooney, a former Congressman and ambassador to the Vatican under George W Bush, opposes Trump’s “isolationism” and tariffs, and has deep concerns about his authoritarian tendencies, from when he “incited” a mob on January 6 to today, as he continues to promote “ridiculous,” false claims that he won the 2020 election.

“I may have to vote for Jeb [Bush] again,” says Rooney.

Chris Redlich, a $1mn-plus Haley donor and retired shipping executive, is also aghast at the choice this November. “This is possibly, nay the, worst presidential election in the history of the country,” says Redlich.

He derided Biden’s energy policies and the chaos in Gaza, and criticised Trump for “inciting extreme views,” a “very naive approach” towards Ukraine and “bad behaviour” on January 6.

Asked if he would support Trump or Biden, Redlich retorted, “I’ll be in the Bahamas.”

Additional reporting by Jamie Smyth in New York

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