Cashing in on his comeback, Trump rescues frail finances

Japan Times

a day ago

Last spring, even as Donald Trump's march back toward the White House dominated public attention, his finances, largely out of view, faced serious threats.
His office building in lower Manhattan generated too little cash to cover its mortgage, with the balance coming due. Many of his golf courses regularly lacked enough players to cover costs. The flow of millions of dollars a year from his stint as a television celebrity had mostly dried up.
And a sudden wave of legal judgments threatened to devour all his cash.
Then, with his clinching of the Republican nomination, everything began to change.
In the following months, Trump, along with his two eldest sons, Eric and Donald Jr., refocused the family business, forming a series of partnerships, especially in cryptocurrency, with investors who were willing to bank on his victory.
Once Trump won the presidency in November, that approach kicked into overdrive.
His family business announced numerous new deals that would financially benefit Trump directly, even as he made policy decisions that affected those industries or that involved countries in which the United States had political interests. Most glaringly, Trump is now both a partner in several crypto ventures and, as president, crypto's chief policy regulator, and he has signaled that he wants his administration to have a hands-off approach to digital currencies.
Today, those moves are seen by Trump's detractors as a money grab of historic proportions. But an analysis by The New York Times of thousands of pages of internal Trump Organization documents filed in one of the legal actions against him suggests a more urgent motivation for Trump's behavior: a need, rather than simply a desire, for easy money to keep his empire intact.
In late 2023, Trump boasted of having between $300 million and $400 million in cash when he testified as part of that legal action, a lawsuit brought by the New York attorney general that accused the Trumps of defrauding their lenders. His cash stockpile, Trump said, showed "how good a company I built,' and, he added in earlier testimony, "especially for a developer.'
Contrary to those assertions, records filed in the fraud case suggest that Trump's cash was not the product of a steady and strong empire. His balance had fluctuated wildly, hitting a low of $52 million in 2018, a small figure for the size of his operation. The subsequent increase came largely from the sale of properties and a payout of more than $150 million from a passive investment.
Moreover, the version of Trump's business that he projects - a real estate development company that executes large, complex tasks - hasn't existed for a nearly a decade, since the Trumps' last two major construction projects failed to make money.
Instead, Trump's wealth is now built on monetizing the family name in new ways and, intentionally or not, the office of the presidency. It is an enterprise in pursuit of multimillion-dollar checks - from actual real estate developers, from cryptocurrency and social media enterprises run by others. It is also a business that hawks Trump-branded trinkets such as watches and gold-toned mobile phones to the president's passionate supporters.
Many of the deals open multiple channels for anyone to funnel cash to a sitting president, often in ways that are untraceable under current disclosure requirements. And because some of what is being sold is use of the president's name, there are no clear metrics to gauge whether he has received market rate, a premium because of his office or, in effect, a hopeful bribe.
The White House press secretary, Karoline Leavitt, has said that Trump abides by all conflict-of-interest laws and acts with only the interests of the American public in mind.
In response to questions from the Times, Eric Trump, who runs his father's businesses, issued a written statement saying the company is stronger than ever and largely debt free thanks to "the most iconic' properties and "cryptocurrency ventures on Earth.'
"I have never been more proud of our company,' the statement said. "Our portfolio is operating flawlessly, and 2025 will mark the strongest year in the remarkable history of the Trump Organization.'
Perfectly assessing Donald Trump's privately held businesses at any point in time is nearly impossible. But within months of his testimony in the New York civil fraud trial, all of his cash and liquid investments looked to be at risk.
His businesses had often required cash infusions before a judge in the trial entered a judgment against the Trumps of $355 million. Trump faced a second judgment of $88.3 million in the sexual abuse and defamation lawsuits brought by writer E. Jean Carroll.
Trump has not yet had to pay the judgments, which now total more than $600 million with interest. But he did have to put up cash totaling $175 million in the fraud case, and cash and bonds totaling $97 million in Carroll's cases, to pursue appeals.
He also faced a potential hit of $100 million from a long-standing tax audit, though it now appears unlikely that his political appointees at the Internal Revenue Service would sign off on such an assessment - another benefit of having returned to the Oval Office.
To be sure, Trump was not facing a calamity. He could have sold more properties, at the expense of his family's future wealth, to cover any shortfall.
The Trumps found a different path.
"His approach to almost everything at this point now seems to be that he's going to get away with whatever he can get away with, and sort of dare people to try to find legal or political ways to stop him,' said Noah Bookbinder, president of the watchdog group Citizens for Responsibility and Ethics in Washington, a liberal-leaning nonprofit group.
Escalator to nowhere
When Trump completed construction on Trump Tower four decades ago, its five-floor atrium was filled with luxury retailers from around the globe - Asprey of London, Buccellati, Cartier - creating a destination for high-end shoppers and tourists alike.
Those spaces, and the office rentals above, provided Trump with one of his most reliable sources of profits for decades, a 2020 analysis of his tax returns by the Times found.
The famed shimmering escalators leading up to the top retail floors are now roped off, the stores there having departed over the years. Two smaller spaces on the ground floor and below offer Trump-branded merchandise, such as license-plate frames and sweatshirts.
The atrium's signature design feature — a multistory marble water wall — has been turned off and covered by a large U.S. flag. Only one major retailer remains: Gucci, in the one space with visibility from the sidewalk.
At 40 Wall St., Trump's office tower in lower Manhattan, 25% of the building has been vacant since last year. In March, Fitch Ratings reported that, after covering basic expenses, the building generated $2 million per year less than Trump needed for his mortgage payments, and in a few years he will face a multimillion-dollar jump in the rent he pays for the ground under the building.
Vacancies have also haunted Trump's most recent large-scale construction site, a 92-story tower in Chicago. With most of the apartments and hotel rooms sold off years ago, Trump's ownership stake is comprised mostly of some 70,000 square feet of retail space that he had hoped would produce millions of dollars a year in rental income. Designed below street level with little visibility to passersby, those floors remain empty 16 years after the building was finished.
Things did not go measurably better with Trump's redevelopment of the Old Post Office in Washington, which opened as a hotel in 2016. He never recorded a profitable year there - despite its becoming a destination for acolytes of Trump during his first administration.
He sold his interests in 2022 to a private equity firm for $375 million, a price that elicited excitement from the Trumps. "To say the result is a financial success would be an understatement,' Eric Trump wrote in an email to company employees.
But company documents filed in the fraud case show that the sale did not cover Trump's costs on the project.
The hotel's buyer could not cover closing costs and borrowed $28 million from the Trumps before defaulting on the loan. Without that repayment, Trump was going to be left with $79 million from the sale after paying taxes, according to a spreadsheet created by his accountant and filed in the fraud lawsuit. Another company record filed in the case shows that he had invested about $100 million in the project.
It has now been nearly a decade since the Trumps completed the hotel. The years since have been marked by contraction.
In addition to the Washington hotel, in recent years Trump has sold control of a golf course in the Bronx, a mansion in Los Angeles, land on a Caribbean island, numerous luxury condominiums that he had held as rentals in buildings he constructed and the developable land around his golf course near Los Angeles.
Each sale brought a wave of cash, but also a diminished opportunity for future earnings.
Not looking to build
Trump rarely escapes to anywhere on weekends and vacations other than his own golf courses, where he goes to exercise, relax and be seen.
He has said that those 14 courses do not represent a "major business' for him, rather investments that reflect his love of the game. He spent hundreds of millions of dollars remaking them to his tastes, often with ornate clubhouses and elaborate artificial waterfalls.
Those investments have not always paid off.
A golf course appraisal expert for the New York attorney general's office examined the financial records of all but one of Trump's golf courses for 2011 through 2021 and found that at least half of them reported negative cash flow for multiple years.
One email showed Allen Weisselberg, the company's longtime head of finance, notifying Trump's two elder sons that the Trump Organization produced only $2.2 million in 2017, before taxes or disbursements to the family. A primary culprit was the golf courses, where the Trumps had spent almost $13 million more than planned on maintenance and improvements, while the courses brought in $15 million less in operating profits than expected.
Trump has also described his courses as real estate development projects in waiting. But the Trumps have not created a record of success toward that goal. Their efforts to add homes to his two courses in Scotland, for example, stalled.
The Trumps did win approval in January for a major development in the parking lot at Trump National Doral, a golf resort near Miami. The project would include nearly 1,500 condominium apartments and more than 140,000 square feet of commercial space.
But that plan does not appear to be the one that will restart the Trumps' real estate development business anytime soon.
During his deposition in the fraud case, Trump said that he might build there in a decade, leave it for his children to develop or "sell it to another developer for a lot of money and let them do it.' He said he often sought zoning approval to develop, just in case.
Regardless, Trump added, "we're not actively looking to build.'
In 2021, Deutsche Bank, which held Trump's mortgage, hired the firm Newmark to appraise Doral, Trump's highest-revenue resort, with four courses and 643 hotel rooms. The resulting analysis concluded that Trump had spent $379 million buying and renovating the resort, and that it was worth only $297 million.
The appraisal included an even more jarring finding. While Doral, like several of Trump's properties, was known to benefit from people looking to buy proximity to a president during Trump's first term, his managers believed even more potential customers stayed away because of him.
Trump's divisive public comments over time had pushed down bookings and room rates for six years running, his managers told the appraisers. The managers believed that "the Trump brand has negatively impacted' revenues at Doral.
Newmark's experts agreed, writing that "we believe that with a different brand, the subject might perform better.'
Spigot turned back on
The Doral appraisal highlights perhaps the starkest turn in the Trump family's finances.
The value of the Trump name as a brand on real estate projects and mass-market consumer goods made by others, both here and abroad, was central to sustaining his businesses during his peak years on "The Apprentice.'
The annual reports that the Trumps sent to their lenders showed television and licensing profits totaled $259 million from 2011 to 2017. But even with that deluge of cash, Donald Trump still reported an overall negative cash flow of $46.8 million from his empire.
Donald Trump Jr. testified glowingly during the fraud trial about those licensing deals. Compared with real estate development, they required no investment and little labor.
"I don't want to say it was free revenue,' he said, but "it was a pretty spectacular system that we were able to create.'
But the cash gusher from entertainment had slowed to a trickle by the time the elder Trump entered politics, and after he entered the White House in 2017, the company fell into a dry spell for new licensing deals. Some of that was because the Trump Organization pledged not to sign new foreign deals in an attempt to avoid conflicts of interest.
After Trump left office in January 2021, the Trump Organization did not announce a major new branding agreement until late 2022 — for a golf resort in Oman.
The spigot of foreign branding deals did not fully turn back on until after Trump clinched the Republican nomination and a second term seemed within reach.
After that, nine deals were announced in rapid succession: one each for developments in Vietnam and Serbia, two in India and five on the Arabian Peninsula, including a golf resort in Qatar, a residential tower in Jeddah, another tower in Dubai and two more in Riyadh.
All but one of the new licensing contracts came from relationships that predated Trump's first presidency. And some of those paying for the Trump name have made clear that his official stature was part of the attraction.
Kalpesh Mehta, a real estate developer in India, signed his first licensing deal with the Trumps 12 years ago. Mehta has said he met Donald Trump Jr. while they were both studying at the Wharton School of the University of Pennsylvania. Donald Trump Jr. has joked that they are "like an old married couple.'
During inaugural events in January of this year, Mehta met with Eric Trump at Mar-a-Lago and the president-elect at the Trump golf course in Virginia. Weeks later, the Trumps and Mehta signed a new licensing deal for a commercial office tower in Pune, India. They announced yet another deal - their sixth - in April.
Mehta did not respond to requests for comment but has said that Trump-branded properties draw heightened interest in India.
Donald Trump's deals on the Arabian Peninsula all share a connection to one man: Ziad El Chaar, a Lebanese-born construction executive who first brought Trump into a branding agreement in 2013, for a golf course in Dubai, through a construction company based there called DAMAC.
El Chaar has since become CEO of DarGlobal, a subsidiary of Dar Al Arkan Real Estate, a large Saudi Arabia-based construction company with ties to the Saudi government. He has signed five more deals with the Trumps since last summer.
During a DarGlobal event introducing the Oman project, El Chaar said the Trump name "immediately put the project on the global map.'
Through a spokesperson, El Chaar declined to discuss DarGlobal's contracts with the Trumps.
Financial support from Saudi Arabia has also helped Trump's golf courses.
Since 2022, the Saudi-backed LIV Golf league has paid him to host annual tournaments at his resorts in Doral, Florida, and Bedminster, New Jersey. Neither the league nor Trump has revealed the amount of money involved. Trump has used his presidential bully pulpit to advocate for a merger between the U.S.-based PGA Tour and LIV Golf, which could reunite the world's top golfers on courses Trump owns.
On his federal financial disclosure forms, Trump has not been required to divulge the full amount promised to him in any of his licensing deals, only what he receives during a given year, which sometimes includes a management fee.
What information he has released suggests that the Trumps have raised the price for use of their name.
Trump's tax returns during his television celebrity years showed payments in round numbers when he signed a licensing contract, typically $750,000 or $1 million. Financial disclosure forms he recently filed showed payments of exactly $5 million each for the deal in Vietnam and one with El Chaar's company.
But in terms of the potential for anyone, from anywhere, to transmit hundreds of millions of dollars to a U.S. president, the recent wave of licensing agreements was only a warmup.
A massive stockpile
Last December, just months after Trump and his two eldest sons made their first public comments in support of digital currencies, Eric Trump was invited to appear as the keynote speaker at a bitcoin conference in Abu Dhabi.
He addressed the question he presumed to be on everyone's mind: Why are you here?
"I know all of you are thinking: 'Eric, you're from real estate family. You've spent your entire life in real estate, concrete, drywall,'' he said. "I built Trump Chicago,' he added twice, referring to a four-year project completed when he was 24.
Sixteen years after completion of the Chicago tower, the Trumps still invoke its memory to establish business gravitas and their chosen identity as real estate developers.
But their recent moves into crypto and other enterprises bear more in common with Donald Trump's licensing deals: little or no investment, risk or operational responsibility. Trump, and to a lesser extent his sons, generally serve as a means to draw attention and convert the president's political supporters into investors and paying customers.
Trump has invested nothing in Trump Media, the parent company of the social media site Truth Social, and has no official duties. But he received more than half of the company's stock, a stake that has fallen in value but is still worth $2 billion.
In crypto, the Trumps have entered into a series of partnerships. Their partners were the ones who have invested most or all of the capital, or raised money through token sales, and run the businesses. The crypto coins issued to the Trump family through its first foray into the sector, World Liberty Financial, have recently been worth at least $236 million.
The Trumps' sale of meme coins, otherwise worthless collectible digital trinkets, has been particularly lucrative. The fees collected by Trump and his associates on those sales have so far totaled $320 million, according to Chainalysis, a crypto analytics firm. The meme coins have proved to be a multimillion-dollar leap from the Trump-branded Bibles, guitars and watches that the Trumps sold during last year's campaign.
The long-term viability of the new businesses remains unclear, as does the liquidity of some of Trump's holdings in them. He cannot yet sell most of his crypto coins. And he would most likely crush Trump Media if he unloaded his stock, even as the company continues to lose money and struggles to produce $1 million per quarter in revenue, roughly the average of a single McDonald's restaurant.
But the new cash has already helped solve old problems.
Last month, the Trumps paid off the $115 million mortgage coming due on 40 Wall St. Analysts had said that the building's low rental income would make banks squeamish about refinancing.
Going forward, the new enterprises represent a massive stockpile with the potential to cover legal judgments, mortgage payments and holes in balance sheets for years to come.
This article originally appeared in The New York Times © 2025 The New York Times Company