An eight-figure loan involving former President Donald Trump, a financial firm, and his Chicago skyscraper may lead to his next legal challenge after a court-appointed monitor pointed out that the loan may be fake, and legal experts believe it could be a form of tax evasion.

Last week, during Trump’s civil fraud trial, retired judge Barbara Jones submitted a report to the court noting that she found deficiencies in the Trump Organization materials she reviewed. Jones was appointed to oversee the organization’s financial activities and statements after New York Attorney General Letitia James sued the former president and his company for fraud in November 2022.