Donald Trump's Mystery $50M Loan Raises Questions: Ex-Prosecutor

Donald Trump holds up a news story at one of his properties at 40 Wall Street following closing arguments at his civil fraud trial on January 11, 2024 in New York City. The judge in the case appointed Barbara Jones to monitor Trump’s companies.

Donald Trump’s $50 million Chicago loan continues to raise questions about its true nature, the president of Citizens for Responsibility and Ethics in Washington has said.

In an interview released on April 30, Noah Bookbinder, the head of the watchdog organization and a former federal prosecutor, spoke with Jessica Denson, a presenter on the liberal news site MeidasTouch, about the loan, which he called “a little complicated and pretty weird.”

Barbara Jones, the court-appointed independent monitor of the Trump Organization, previously wrote in a report that Trump’s business managers said the loan never existed, even though it was listed on numerous federal election forms that Trump filed.

Trump borrowed the money from one of his companies in Chicago, according to federal election filings. Newsweek has contacted Donald Trump’s attorney for comment via email.

“It does raise the question of why because it’s a pretty weird thing to report a very large loan that isn’t real,” Bookbinder said.

“We have some theories about that. In some ways it doesn’t matter because it’s still a crime to lie. But it is pretty strange,” he continued.

According to Bookbinder, the claim that Trump used the loan to avoid paying taxes is “a little complicated.” But one theory that “seems to make a lot of sense” is that Trump “had a very large loan for real estate in Chicago, and he appears to have refinanced it in a way that resulted in some portion of that being forgiven.”

Rather than paying taxes on the forgiven portion of the loan, which is a gain, Trump may have “created a fake loan obligation to mask the fact that loans were actually forgiven, and he should owe quite a lot of money in taxes on it,” he continued.

Bookbinder added that there was a lot of information “suggesting that this loan that he’s reporting is bogus.” He also said that Trump’s lawyers had agreed that Jones was a suitable person to monitor the Trump Organization’s finances; however, now that she has questioned the reason for the Chicago loan, Trump’s lawyers are calling her “biased and unfair.”

After Jones found that Trump had taken out a $50 million loan that might not have existed, she reported it to Judge Arthur Engoron, who had fined Trump $454 million for falsely inflating the value of his assets.

In February, Engoron found Trump, his sons Donald Jr. and Eric, and the Trump Organization liable for a scheme in which the value of Trump’s net worth and assets were unlawfully inflated to obtain more favorable business deals. Trump has maintained his innocence.

In April, Citizens for Responsibility and Ethics in Washington sent a letter to the FBI and the Department of Justice asking them to investigate whether Trump had falsely reported the $50 million owed to one of his own companies, Chicago Unit Acquisition LLC, as a liability on all nine public financial disclosure reports he filed with the Federal Election Commission and the Office of Government Ethics. Trump filed the disclosure reports between 2015 and 2023, even though the loan “appears to have never existed,” CREW said in the letter.

“It is not clear why Mr. Trump would have reported a non-existent loan as a liability owed to one of his own companies,” the letter continued, “but some reporting suggests that the deal could be part of a tax-avoidance scheme, known as debt parking, that has been used by taxpayers to purchase debt and then leave it in a separately-owned entity rather than incur tax liability on debt which has been forgiven.”

“Others theorize that the loan may be owed to a secret third party,” the letter continued.

CREW wrote in the letter that Engoron had appointed Jones in November 2022 to monitor Trump’s financial statements and financial disclosures after he found that the former president and his co-defendants had a “propensity to engage in persistent fraud by submitting false and misleading Statements of Financial Condition.”

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