The U.S. President's term is limited to two administrations, so people often say that during the President's second term, the main focus is not on "governing" but on "making money."

On June 23, it was the 154th day of Trump's second term. He used $114 million in cash to fully repay one of the most troublesome debts in his business empire just 13 days before the loan's maturity.

This $114 million is equivalent to 400 years' worth of salary for a U.S. President. According to the most widely circulated calculation — "a suitcase can hold a maximum of $1 million in $100 bills," it would take at least 114 suitcases to pack and transport this money.

And this loan was precisely from his famous Manhattan skyscraper — 40 Wall Street, also known as The Trump Building.

40 Wall Street, also known as The Trump Building

Shadow Banking, Trump's Lender

"When Trump needs a loan, he usually calls Ladder Capital," revealed an insider.

In 2015, due to an upcoming $5 million loan from Capital One, Trump decided to refinance 40 Wall Street. This time, instead of going to traditional banks, he turned to Ladder Capital — a relatively small and lesser-known shadow bank.

After evaluation, Ladder quickly agreed to provide a $160 million commercial mortgage loan for the building, with an interest rate as low as 3.67%. In a matter of weeks, this debt was promptly packaged, split into four notes, and sold to investors along with dozens of other properties, flowing into the secondary financial market.

Ladder Capital and the debt notes of The Trump Building

For Trump, this was a timely loan that came to his rescue.

In fact, since the early 1990s financial crisis, large banks such as Citigroup and JPMorgan Chase have been reluctant to do business with Trump. Back then, Trump faced multiple investment failures and was on the brink of bankruptcy, with assets such as the Plaza Hotel and Trump Shuttle being taken over by banks, causing heavy losses to several major banks. Deutsche Bank was the last major financial institution willing to back him, but in 2008, they ended up in a legal dispute over a delayed repayment regarding a Chicago project. Even though Deutsche Bank extended a loan for his Washington project in 2014, the relationship was far from fully restored.

However, Ladder Capital not only agreed to lend to him but also offered him an extremely low loan rate. In general, commercial real estate loan rates in the US usually range from 5.5% to 10%, with office assets having slightly higher rates. For a long time, Ladder Capital and Deutsche Bank were the largest creditors of the Trump Organization, with Deutsche Bank offering rates between 5% and 7%, making Ladder Capital's 3.67% rate exceptionally low by comparison.

When things deviate from the norm, there must be something unusual going on.

According to reports, the relationship between Ladder Capital and Trump goes far beyond the surface level of "lender and borrower." The executive of the founding team of this company, Jack Weisselberg, is actually the son of Allen Weisselberg, the Chief Financial Officer of the Trump Organization. This personal connection allowed Trump to secure hundreds of millions of dollars in funding from Ladder Capital, even while facing avoidance from mainstream Wall Street banks, and at an extremely low interest rate.

As a Real Estate Investment Trust (REIT), Ladder's core business is to provide financing for high-risk projects that traditional banks are reluctant to touch. They do not rely on deposits from customers but instead rapidly package and sell loans through securitization of assets to gain liquidity and returns. In Trump's 2017 financial disclosure, Ladder Capital held debt on at least four properties owned by him, including the Trump Tower on Fifth Avenue, with total debt exceeding $280 million.

As Trump distanced himself from the mainstream financial system, he increasingly relied on shadow banking systems like Ladder. This relationship also sheds light on the rise of New York's shadow banking industry.

Shadow banking refers to a type of financial institution that operates outside conventional banking regulations, including hedge funds, private equity, money market funds, and REITs. They issue loans and provide financing but are not subject to the same regulatory requirements as commercial banks. The shadow banking assets in the US amount to $14 trillion, which is not insignificant compared to the traditional $16 trillion commercial banking system in the US.

However, shadow banking is a weak link in the U.S. financial system. While commercial banks operate based on government-guaranteed deposits, shadow banks rely on short-term financing—meaning that once market liquidity tightens, their funding chain could instantly break. Just like what Lehman Brothers and Bear Stearns experienced in 2008.

But this is only a small part of Trump's reckless business style.

In her book The Trumps: Three Generations That Built an Empire, author Gwenda Blair points out that Trump was able to smoothly enter the Wall Street banking system in his early years because his father, Fred Trump, was one of the most respected developers in the New York real estate circle. Banks trusted Fred and were willing to give his son a chance.

However, after the "Trump-style" recklessness, patience quickly ran out. Bankers began to worry that if they continued to lend to him, not only would they not get their money back, but they might also find it difficult to explain to their boards and shareholders. So, several major banks tacitly kicked this "high-risk customer" out of the mainstream credit circle.

40 Wall Street, the Skyscraper That Couldn't Be Rented Out

This Trump building at 40 Wall Street has always been Trump's most talked-about "legendary investment."

He has repeatedly mentioned this deal in public speeches and writings: "In 1995, I acquired this building for only $1 million." In his memoir, Never Give Up, he wrote, "Sometimes people ask me what is my most proud investment, and I always think of 40 Wall Street—this building has a certain special charm that makes me forever unique."

Indeed, this skyscraper built in 1930 briefly became the tallest building in the world before the completion of the Chrysler Building. With 70 floors, 282.5 meters tall, located in the heart of Manhattan's financial district, it was designated a New York City landmark in 1998. It witnessed the rise and fall of the entire Wall Street, as well as Trump's rise from a developer to the president.

Many people do not know that Trump does not own the land under this building. He only has a long-term lease, which can last up to 200 years. The actual owners of the land are a group of low-profile German tycoons and industrial giants. In 1995, Trump took over the lease and restructured it, needing to pay fixed ground rent to these Germans each year.

It was in this context that Trump decided to refinance this building in 2015. He obtained a $160 million loan from Ladder Capital to replace the expiring $5 million debt he had borrowed from Capital One.

Trump Building, Image Source: New York Times

At the time, Ladder Capital was confident in the building's cash flow. Data showed that in 2015, the building had an occupancy rate as high as 94.5%, which was 1 percentage point higher than similar office buildings. According to their projections, the building could generate $43.1 million in revenue annually, with total operating costs not exceeding $20.6 million, resulting in a net income of over $11 million.

However, the building's operational performance was not as smooth as expected in 2015. Therefore, at one point, some financial institutions were concerned that Trump would default on the loan just like before.

Starting in 2019, as the pandemic hit and office demand plummeted, the building's occupancy rate continuously declined from 89.1% in 2019 to 74.2% in 2023. Rental income also dropped from $41.7 million in 2019 to $30.9 million in 2022. Although there was a slight rebound to $33 million in 2023, it still fell short of the initial forecasts.

Meanwhile, operating costs remained high. It surged from $20.9 million in 2017 to $23.2 million in 2023, with maintenance and repair costs nearly doubling the original estimate. Ultimately, the building's net operating income in 2023 was only $12.8 million. Rating agency Fitch also directly downgraded the credit rating of this loan from Trump Organization from investment-grade BBB- to junk-grade BB in August 2023.

And that's not the worst of it.

The ground lease payments Trump has to make to the Germans were $1.6 million in 2015 and have now risen to $2.3 million. Even more challenging, after 2033, according to the lease reset clause, this ground lease will skyrocket to $16 million, which will almost devour all profits.

After repaying $9.8 million in annual loan interest, deducting renovation and leasing expenses, Trump truly only pockets $1.2 million from this building.

Major tenant Duane Reade has already terminated its lease four and a half years early, while other tenants either postponed moving in or delayed renewals. By the first quarter of 2025, the building only "barely achieved breakeven." In the context of rising interest rates and soaring operating costs, this "balance" appears more like a fragile illusion.

From Casinos to Skyscrapers: Trump's Six Bankruptcies

How to repay this money has become a key indicator for observing Trump's financial situation and political leverage. Even more nerve-wracking, just last year, the New York Attorney General made it clear that if Trump fails to pay the settlement for a civil fraud case, this skyscraper would face the risk of being seized through legal means.

Using personal funds to repay part of the principal amount and then borrowing new debt to pay the remaining portion remains a possible solution. However, several financial institutions have long expressed concerns — will Trump once again be unable to repay? He may instead simply declare bankruptcy for 40 Wall Street.

If this were to happen, it would be his seventh bankruptcy filing. Amitosh Purdanam, a finance professor at the University of Michigan, pointed out that unless Ladder Capital still holds a portion of this loan, the company would also be helpless. "The real losers are those who bought these bonds," he said. "They may be banks, insurance companies, or hedge funds."

Since the 1990s, Trump has been known for his aggressive style of "high leverage, heavy betting, and gambling on the future." He has declared bankruptcy for his enterprises six times.

Trump's first bankruptcy was in 1991 when his Atlantic City casino, once hailed by him as the "Eighth Wonder of the World," with a cost of $1.1 billion, was mainly financed through junk bonds with a 14% annual interest rate. The 1990 economic recession hit, causing a cash flow crisis in the gambling city. The casino's operations rapidly declined, nearing bankruptcy. Trump filed for Chapter 11 bankruptcy protection, divested some assets, and allowed creditors to become shareholders to retain control.

The second to fourth bankruptcies were in 1992 when Trump Castle, Trump Plaza, and Plaza Hotel's three major real estate businesses collectively faced distress, almost simultaneously under heavy debt pressure. Plaza Hotel's debt once exceeded $550 million, and cash flow dried up. Trump again filed for bankruptcy reorganization, salvaging operations through share reduction, debt-to-equity swaps, and other methods while retaining management rights, keeping the "Trump" brand alive.

During this period, in 1999, Trump's father Fred passed away, and the real estate empire passed into his hands, marking the official start of the "Trump era." However, Trump soon faced his fifth bankruptcy. In 2004, Trump Hotels & Casino Resorts declared bankruptcy. The company carried $1.8 billion in debt and nearly $50 million in losses for the first quarter. Another round of Chapter 11. Trump avoided imprisonment by injecting capital, reducing his stake, and continued to collect management fees.

That year, Trump began to appear frequently on TV screens: guest-starring in movies, and the reality show "The Apprentice" was a hit, bringing him back into the public eye. His media exposure skyrocketed, but unfortunately, the global financial crisis hit. In 2008, the collapse of Lehman Brothers triggered a rapid contraction in the real estate market, affecting all of Trump's real estate projects.

In 2009, due to the failure to repay a $53.1 million debt, Trump Entertainment Resorts once again filed for bankruptcy protection. In 2014, amid continued deterioration of asset management, he filed for bankruptcy again, eventually choosing to relinquish control and sell 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. Using legal isolation, he successfully protected his personal assets. More importantly, in each restructuring, he tried to retain management or brand licensing rights, ensuring that the name "Trump" could continue to generate cash flow.

From his past practices, Trump is undoubtedly skilled at three things: using bankruptcy protection to resolve crises, using public relations and media to restore his image, and using brand licensing to continue monetizing. However, this time, Trump used $114 million in cash to fully repay all loans.

But it was precisely this "full cash repayment" approach that raised new questions: How much money does Trump really have? Where did this money come from?

In a domineering manner, Trump repays in cash, where does the money come from?

Soon after the news of Trump's loan repayment emerged, some netizens keenly observed that on June 22, a whopping $112 million worth of USDT was burned on the TRON blockchain, and this fund is likely to be the source of his repayment.

(BlockBeats note: USDT being "burned" or sent to an exchange usually means it has been redeemed for dollars—removed from circulation on the blockchain and returned to a real-world bank account.)

Moreover, BlockBeats also found that ARKHAM data shows that at 10 a.m. UTC on June 22, there was indeed a $100 million USDT transferred from the TRON network to a Binance deposit address starting with TQdkj. The fund's path and timing align closely with some netizens' speculations.

Data Source: ARKHAM

What has drawn even more market attention is another layer of speculation: Was Trump's recent back-and-forth on the Israel-Iran issue not just a matter of foreign policy, but a deliberate attempt to influence market sentiment for gain?

Image Source: Twitter

On June 20, Trump hinted at taking "pause" action against Iran, causing a subsequent drop in the U.S. stock market and a 2% plunge in oil prices. Meanwhile, Bitcoin surged by about 2%, rising to $106,000. This market movement closely followed Trump's statements on the Israel-Iran conflict, causing an instant shift in market sentiment and a rebound in risk assets.

On the 23rd, he further claimed that "Israel and Iran have agreed to a ceasefire," leading to a 5% intraday surge in Bitcoin, breaking the $105,000 mark. As Cryptostocks like Coinbase soared by 12% and MicroStrategy also rose by over 1%, the entire crypto sector rallied in sync. This "speech-market reaction-cash out" rhythm is extremely delicate.

Reflecting on his past market behaviors, this is not the first time he has raised manipulation suspicions:

On April 9, on the eve of tariff suspension, Trump posted on Truth Social saying, "Now is a good time to buy, DJT!" A few hours later, he suddenly announced the suspension of tariffs for most countries, resulting in a 9.5% rise in the U.S. stock market and an 8% increase in the Dow. Trump usually does not include his initials at the end of his posts. These letters happen to be the same as the stock code of the Trump Media & Technology Group, which controls Truth Social. On that day, Truth Social's stock price quickly surged by 22%. This promptly triggered speculation about "insider trading" and "market manipulation," drawing attention from Congress.

During the peak of the crypto market in March of this year, analysts like Peter Schiff referred to Trump's actions to boost crypto assets as a "pump-and-dump" scheme and called on Congress to investigate whether he manipulated the cryptocurrency market through policy declarations. Moreover, back in 2019, J.P. Morgan created the "Volfefe Index" based on Trump's tweets to measure their immediate impact on the U.S. bond market.

Meanwhile, the discussion surrounding Trump's sources of wealth and market motivations has reached a new peak.

Last Friday, the Trump team submitted a financial disclosure report spanning over 230 pages, marking the first formal disclosure of his balance sheet since his second term began. This document, with data up to early 2025, covers the fund flows and new assets throughout the entire 2024 campaign period.

One of the most notable items is the $57 million income he received from selling cryptocurrency tokens through WLFI. WLF is a cryptocurrency company held by his family, and Trump's three sons are listed 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 through an ETH wallet. The financial document values them at around $1,000-$15,000, with the income recorded as less than $201. However, it is worth noting that the WLFI token's first-round sale price was $0.015, the second-round sale price was $0.05, and at the current OTC price of $0.1, Trump's token holdings are valued at $1.57 billion.

In addition to WLFI, the Trump family also controls another more clandestine cash-out channel—Meme coins.

His personal Meme coin "$TRUMP," while not included in the financial report due to its issuance in January 2025, can be glimpsed through his wife Melania's "$MELANIA" coin: according to Lookonchain monitoring, over the past 4 months, the Melania team has sold a total of 821,800 MELANIA tokens through 44 wallets, accounting for 8.22% of the total supply, totaling approximately $35.76 million.

Meanwhile, $TRUMP's market value and liquidity far exceed that of $MELANIA. By this estimate, the cumulative cash-out amount by the Trump couple through these two coins from the second half of 2024 to date may have exceeded $100 million.

Furthermore, he also holds Ethereum worth $1 million to $5 million, further solidifying his image as the "most crypto-friendly president." He even publicly stated during the campaign that compared to previous administrations, he would adopt a "more relaxed and non-interfering" regulatory stance.

If cryptocurrency assets represent Trump's hidden wealth, then brand licensing income is his cash cow.

He has licensed dozens of products bearing his name and likeness: from the "God Bless America" edition Bible, limited edition Trump sneakers, perfume, to Swiss-made "Trump Watch," and a signature guitar engraved with "45."

These products brought him a total of millions of dollars in royalty income in 2024 alone, with just three golf courses in Florida and the Mar-a-Lago Club contributing $21.77 million in annual cash flow.

Additionally, he is the largest shareholder of the Trump Media & Technology Group (DJT.US), holding over 53% of the shares. The company has been listed on the Nasdaq, valuing Trump's shares in the billions of dollars, held in a revocable trust controlled by his eldest son.

According to the latest estimates, Trump's current net worth is approximately $4.8 billion, with cash and liquid assets accounting for around $400 million. However, he also carries over $600 million in debt, a significant portion of which is directly related to outstanding litigation judgments.

For example, he is required to pay a $454 million civil fraud settlement to the New York Attorney General; in a civil defamation case with writer E. Jean Carroll, he has been ordered to pay $5 million and $83 million respectively; these judgments are all under appeal and have not been finalized.

Having weathered six bankruptcy filings, numerous lawsuits and trials, and even became the first person in U.S. history to step onto the presidential campaign stage as a "convicted" individual. But now, Trump has not only paid off a ten-year loan, but has also built a new empire spanning reality and the virtual world through cryptocurrency, personal branding, and media platforms.

Perhaps, after dodging that bullet, Trump truly believes that he is destined for greatness.

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