Author: Jaleel Jialiu, BlockBeats
Original title: On the 154th day after taking office, Trump paid off more than $100 million in debt
The U.S. president only serves two terms, so people often say that the main theme of the president’s second term is often not “governing” but “making money.”
June 23 was the 154th day of Trump's second term. He used $114 million in cash to pay off the most difficult debt in his business empire 13 days before the loan was due.
This $114 million is equivalent to the salary of the US president for 400 years. According to the most popular calculation method, "a suitcase can hold at most $1 million in 100-dollar bills," at least 114 suitcases are needed to pack and load this amount of money.
This loan came from the famous Manhattan skyscraper he owns - 40 Wall Street, also known as The Trump Building.
40 Wall Street, also known as Trump Tower
Shadow banks, Trump's creditors
"When Trump needs a loan, he usually calls Ladder Capital," an insider once revealed.
In 2015, as a $5 million loan from Capital One was about to expire, Trump decided to refinance 40 Wall Street. This time, instead of looking for an established bank, he turned to Ladder Capital, a small and unknown shadow bank.
After the appraisal, Ladder quickly agreed to take action and issued a $160 million commercial mortgage loan for the building with an interest rate as low as 3.67%. Within a few weeks, the debt was quickly packaged, divided into four notes, and sold to investors along with dozens of other properties, flowing into the secondary financial market.
Ladder Capital and Trump Tower Debt Notes
This is a loan that comes at a critical juncture for Trump.
In fact, since the financial crisis in the early 1990s, large banks such as Citigroup and JPMorgan Chase have been almost unwilling to deal with Trump. At that time, Trump was on the verge of bankruptcy due to a series of failed investments. Assets such as the Plaza Hotel and Trump Airlines were taken over by banks, and several major banks suffered heavy losses in stop-loss. Deutsche Bank was the last financial giant willing to support him, but in 2008, the two sides went to court due to a dispute over the delayed repayment of the Chicago project. Since then, even though Deutsche Bank once again issued a loan for his Washington project in 2014, the relationship is far from restored.
Ladder Capital not only agreed to lend him money, but also gave him a very low interest rate. Generally speaking, the interest rates for commercial real estate loans in the United States hover between 5.5% and 10%, and office assets are higher. For a long time, Ladder Capital and Deutsche Bank were the largest creditors of the US President. The interest rate Deutsche Bank gave to the Trump Group was between 5% and 7%. It can be seen that the 3.67% interest rate given by Ladder Capital is extremely low in comparison.
When something is abnormal, there must be something wrong.
According to reports, the relationship between Ladder Capital and Trump is far more than just a "creditor and borrower" relationship. Jack Weisselberg, a senior executive of the company's founding team, is the son of Allen Weisselberg, the chief financial officer of the Trump Organization. This network of connections allowed Trump to obtain hundreds of millions of dollars in funds at extremely low interest rates even when mainstream Wall Street banks collectively avoided him.
As a real estate investment trust (REIT), the core of Ladder's business is to provide financing for high-risk projects that traditional banks dare not touch. They do not rely on depositors' deposits, but instead quickly package and sell loans through asset securitization in exchange for liquidity and income. In Trump's 2017 financial disclosure, Ladder Capital held debt claims on at least four of his properties, including Trump Tower on Fifth Avenue, with a total debt of more than $280 million.
As he drifted away from the mainstream financial system, Trump gradually became dependent on shadow banking systems like Ladder. This relationship also reveals the prosperity of the shadow banking industry in New York.
Shadow banking refers to a type of financial institution that is not subject to regular banking supervision, including hedge funds, private equity, money market funds and REITs. They issue loans and conduct financing, but do not need to bear the same regulatory requirements as commercial banks. The asset size of shadow banking in the United States has reached 14 trillion US dollars, which is not small compared with the traditional US commercial banking system of 16 trillion US dollars.
But shadow banking is a weak link in the U.S. financial system. Commercial banks operate on the basis of government-guaranteed deposits, while shadow banking relies on short-term financing, which means that once market liquidity is tight, their funding chain may break instantly, just as Lehman Brothers and Bear Stearns experienced in 2008.
But this is just a small part of Trump's aggressive business style.
Gwenda Blair, author of The Trump Family: Three Generations Building an Empire, pointed out that the reason why Trump was able to successfully enter the Wall Street banking system in his early years was because his father, Fred Trump, was one of the most respected developers in the New York real estate circle. The bank believed in Fred and was willing to give his son a chance.
But after Donald's reckless behavior, patience soon ran out. Bankers began to worry that if they continued to lend to him, they would not only fail to get their money back, but also face difficulties explaining themselves to the board of directors and shareholders. As a result, several major banks tacitly expelled this "high-risk client" from the mainstream credit circle.
40 Wall Street, a skyscraper that cannot be rented out
The Trump Building at 40 Wall Street has always been Trump's most talked-about "legendary investment."
He repeatedly mentioned this deal in public speeches and writings: "I bought the building for only $1 million in 1995." In his autobiography, Never Give Up, he wrote: "Sometimes people ask me what my most proud investment is, and I always think of 40 Wall Street - this building has some special magic that makes me stand out forever."
Indeed, this skyscraper, which was built in 1930, briefly became the world's tallest building before the completion of the Chrysler Building. With 70 floors and 282.5 meters in height, it is located in the financial heart of Manhattan and was named a New York City landmark in 1998. It has witnessed the rise and fall of Wall Street as a whole, and also witnessed Trump's promotion from developer to president.
Many people don't know that Trump does not own the land under the building. He only has a long-term lease, which can last up to 200 years. The actual owner of the land is a group of low-key German tycoons and industrial giants. In 1995, Trump took over the lease and restructured it, and had to pay a fixed rent to these Germans every year.
It was in this context that Trump decided to refinance the building in 2015. He obtained a $160 million loan from Ladder Capital to replace the $5 million debt that was about to mature that he had previously borrowed from Capital One.
Trump Tower, source: The New York Times
At the time, Ladder Capital was confident in the building's cash flow. Data showed that the building's occupancy rate in 2015 was as high as 94.5%, 1 percentage point higher than similar office buildings. According to their forecast, the building could generate $43.1 million in revenue each year, with total operating costs not exceeding $20.6 million, and net income should reach more than $11 million.
However, the operation of the building was not as smooth as expected in 2015, so some financial institutions were worried that Trump would not be able to repay the loan as before.
Since 2019, with the outbreak of the epidemic and the sharp drop in office demand, the building's occupancy rate has been declining, from 89.1% to 74.2% in 2023. Rental income has also dropped from US$41.7 million in 2019 to US$30.9 million in 2022. Although it rebounded slightly to US$33 million in 2023, it has never been close to the original forecast.
At the same time, operating costs remain high. From $20.9 million in 2017 to $23.2 million in 2023, the cost of repairs and maintenance is almost twice the original valuation. In the end, the building's net operating income in 2023 was only $12.8 million. In August 2023, rating agency Fitch directly downgraded the credit rating of the Trump Group's loan from investment-grade BBB- to junk-grade BB.
This is not the worst.
Trump's annual rent to the Germans was $1.6 million in 2015, and has now risen to $2.3 million. What's more tricky is that after 2033, according to the lease reset clause, the rent will soar to $16 million, which will almost eat up all the profits.
After paying the annual loan interest of $9.8 million and deducting renovation and rental expenses, Trump actually made only $1.2 million from the building.
The major tenant Duane Reade has already terminated its contract and evacuated four and a half years in advance, and other tenants have either postponed their move-in or delayed their lease extension. By the first quarter of 2025, the building "barely achieved balance." Against the backdrop of rising interest rates and high operating costs, this "balance" looks more like a fragile illusion.
From casinos to tower blocks, Trump's six bankruptcies
How to repay the money has become one of the key indicators for observing Trump's financial situation and political bargaining chips. What is even more tense is that just last year, the New York Attorney General made it clear that if Trump cannot pay the compensation for the civil fraud case, the building will face the risk of being confiscated according to law.
Using one's own funds to repay part of the principal and then borrowing new debt to pay the rest is still a possible solution. But many financial institutions have already expressed concerns - will Trump be unable to repay again as he did in the past? He may also simply declare 40 Wall Street bankrupt.
If so, it would be his seventh bankruptcy filing. Amyatosh Purnandam, a finance professor at the University of Michigan, said that unless Ladder Capital still holds a share of the loan, the company may not be able to do anything about it. "The ones who really suffer are the investors who bought these bonds," he said. "They could be banks, insurance companies, or hedge funds."
Since the 1990s, Trump has been known for his radical style of "high leverage, heavy bets, and betting on the future." He has declared bankruptcy for his companies six times.
Trump's first bankruptcy was in 1991. The Atlantic City casino, which he once hailed as the "eighth wonder of the world," cost $1.1 billion to build, but was mainly financed through junk bonds with an annual interest rate of 14%. The recession hit in 1990, and the casino's cash flow was cut off. The casino's business declined rapidly and was on the verge of bankruptcy. Trump applied for Chapter 11 bankruptcy protection, divested some assets and turned creditors into shareholders, only then did he retain the right to operate.
The second to fourth bankruptcies were in 1992, when Trump Castle, Trump Plaza and Plaza Hotel, three major real estate businesses, were in crisis and almost simultaneously fell into debt. Plaza Hotel once had a debt of more than $550 million and its cash flow dried up. Trump once again filed for bankruptcy reorganization, and through stock reductions and debt-to-equity swaps, he resumed operations while retaining management rights, allowing the "Trump" brand to continue to survive.
During this period, in 1999, Trump's father Fred passed away, and the real estate empire was passed on, and the "Trump era" officially began. But soon, Trump immediately faced his fifth bankruptcy. In 2004, Trump Hotels & Casino Resorts declared bankruptcy. The company was burdened with $1.8 billion in debt and lost nearly $50 million in the first quarter. Another round of Chapter 11. Trump avoided imprisonment by injecting capital and reducing his own holdings, while continuing to collect management fees.
That year, Trump began to appear frequently on television screens: cameos in movies and the reality show "The Apprentice" were popular, bringing him back to the public eye. Media exposure soared, but unfortunately, the global financial crisis came. In 2008, the collapse of Lehman Brothers triggered a rapid contraction in the real estate market, and all of Trump's real estate projects were dragged down.
In 2009, Trump Entertainment Resorts filed for bankruptcy protection again due to failure to repay $53.1 million in debt. In 2014, with the continued deterioration of asset management, he filed for bankruptcy again. In the end, he chose to withdraw from management and sold the casino to billionaire Carl Icahn and other hedge funds.
It is worth noting that all six bankruptcies occurred at the corporate level, and Trump himself has never filed for personal bankruptcy. With the help of legal isolation, he successfully protected his private assets. More importantly, in each reorganization, he tried his best to retain management rights or brand licensing rights to ensure that the name "Trump" can continue to generate cash flow for him.
Judging from past practices, Trump is undoubtedly good at three things: using bankruptcy protection to resolve crises, using public relations and media to repair his image, and using brand licensing to continue to monetize. But this time, Trump used $114 million in cash to pay off all the loans at once.
But it is precisely this practice of "repaying all the debts in cash" that has raised new questions: How much money does Trump have left? Where did the money come from?
Where does Trump get the money to pay back his debts in cash?
Just after the news of Trump paying off his loan broke, some netizens keenly discovered that on June 22, a sum of USDT worth 112 million was destroyed from the TRON chain, and this amount of money was likely the source of his repayment.
(BlockBeats Note: USDT being “destroyed” or transferred to an exchange usually means it is redeemed for U.S. dollars — that is, it is removed from on-chain circulation and returned to a real-world bank account.)
Not only that, BlockBeats also found that ARKHAM data showed that at 10:00 UTC on June 22, a USDT of $100 million was transferred from the TRON network to a Binance deposit address starting with TQdkj. The path and time of the funds were almost in contrast to the speculation of some netizens.
Data source: ARKHAM
What has attracted more market attention is another layer of speculation: Are Trump’s recent repeated statements on the Israel-Iran issue not just a diplomatic strategy, but an intentional attempt to influence market sentiment and thereby profit?
Image source: Twitter
On June 20, Trump hinted at a "pause" action against Iran, and U.S. stocks fell immediately, and oil prices fell 2%. During the same period, Bitcoin jumped about 2%, rising back to $106,000. This wave of market closely matched the rhythm of Trump's statements on the Israel-Iran conflict, and market sentiment loosened instantly, and risky assets rebounded immediately.
On the 23rd, he further declared that "Israel and Iran agreed to a ceasefire", and Bitcoin soared 5% during the session, breaking through the $105,000 mark. With Cryptostocks such as Coinbase soaring 12% and MicroStrategy also rising by more than 1%, the entire crypto sector strengthened simultaneously. This rhythm of "speech-market reaction-cash out" is extremely subtle.
Looking back at his past market behavior, this is not the first time that suspicions of manipulation have been raised:
On the eve of the suspension of tariffs on April 9, Trump posted on Truth Social, "Now is a good time to buy, DJT!" A few hours later, he suddenly announced the suspension of tariffs on most countries. As a result, US stocks rose 9.5% and the Dow Jones Industrial Average rose 8%. Trump usually does not add his initials to the end of his posts. These letters happen to be the same as the stock code of Trump Media Technology Group, which controls Truth Social, and Truth Social's stock price soared 22% that day. This quickly attracted public doubts about "insider trading" and "market manipulation" and congressional attention.
During the crypto peak in March this year, analysts such as Peter Schiff called Trump's operation to push up crypto assets a "pump-and-dump" and called on Congress to investigate whether he manipulated the virtual currency market through policy statements. In addition, as early as 2019, JPMorgan Chase created the "Volfefe Index" based on Trump's tweets to measure the immediate influence of his tweets on the U.S. Treasury market.
At the same time, discussions surrounding the source of Trump's wealth and market motives have reached a new climax.
Last Friday, Trump's team submitted a more than 230-page financial disclosure report, the first time he has officially released his balance sheet since his second term. The data in this document ends in early 2025 and covers the flow of funds and new assets throughout the 2024 campaign.
The most notable of these was the $57 million he made from selling cryptocurrency tokens through WLFI, a cryptocurrency company controlled by his family that lists Trump's three sons as co-founders on the company's website.
In addition to the direct income from the WLFI token sale, Trump also holds 15.75 billion governance tokens held through his ETH wallet. The financial documents calculate its value as around $1,000-15,000, and the income is recorded as less than $201. But it is worth noting that the unit price of WLFI in the first round of sales was $0.015, and the second round of sales was $0.05. If calculated at the current over-the-counter price of $0.1, the tokens held by Trump are worth $1.57 billion.
In addition to WLFI, the Trump family also controls another more secretive cash-out channel - Meme coin.
Although his personal meme coin "$TRUMP" is not included in the financial report because it was issued in January 2025, we can get a glimpse of it from the "$MELANIA" coin under the name of his wife Melania: According to Lookonchain monitoring, in the past 4 months, Melania's team has sold a total of 821,800 MELANIAs through 44 wallets, accounting for 8.22% of the total supply, and cashed out a total of approximately US$35.76 million.
The market value and liquidity of $TRUMP are much higher than $MELANIA. Based on this estimate, the cumulative cash out amount of the Trumps through these two currencies from the second half of 2024 to date may have exceeded $100 million.
In addition, he also holds $1 million to $5 million worth of Ethereum, further consolidating his image as the "most crypto-friendly president." He even publicly stated during the campaign that he would take a "more relaxed and non-interventionist" regulatory stance than previous administrations.
If crypto assets are Trump's hidden wealth, then brand licensing income is his cash cow.
He has licensed dozens of products bearing his name and likeness, from a "God Bless America" edition Bible, limited edition Trump sneakers and perfume, to a Swiss-made "Trump watch" and a signed guitar engraved with the number "45."
These products will bring him a total of millions of dollars in royalty income in 2024, and the three golf courses in Florida and the Mar-a-Lago Club alone will contribute $21.77 million in annual cash flow.
In addition, he is the largest shareholder of Trump Media & Technology Group (DJT.US), holding more than 53%. The company is listed on the Nasdaq, and Trump's shares are valued at billions of dollars and are held in a revocable trust controlled by his eldest son.
According to the latest estimates, Trump's current net worth is about $4.8 billion, of which cash and liquid assets account for about $400 million. But he also has more than $600 million in debt, much of which is directly related to outstanding lawsuits.
For example: he had to pay $454 million in civil fraud compensation to the New York Attorney General; in the civil defamation case with writer E. Jean Carroll, he was ordered to pay $5 million and $83 million respectively; these judgments are under appeal and have not yet been finalized.
After six bankruptcies, countless lawsuits and trials, and even the first time in American history that he was “convicted” in the presidential election, Trump has not only paid off his 10-year loan, but has also built a new wealth empire spanning reality and virtuality with the help of cryptocurrency, personal branding, and media platforms.
Perhaps after dodging that bullet, Trump really believed that he was destined to be a winner.
