Trump Organization CFO Allen Weisselberg Indicted for $1.7M Tax Fraud Scheme

The Manhattan District Attorney’s office unsealed criminal charges against the Trump Organization, longtime CFO Allen Weisselberg, and the Trump Payroll Corporation, marking the first criminal case ever brought against former President Donald Trump’s company. Prosecutors charged the defendants with 15 felony counts including scheme to defraud, conspiracy, criminal tax fraud, and falsifying business records in connection with an alleged 15-year scheme to compensate Weisselberg and other executives “off the books” to evade taxes. Manhattan District Attorney Cyrus Vance Jr. called it a “sweeping and audacious” tax fraud scheme in which Weisselberg received more than $1.7 million in untaxed compensation from 2005 to 2021, including luxury apartment rent, Mercedes-Benz leases, private school tuition for his grandchildren, and personal expenses. The indictment represented a significant escalation in criminal investigations of Trump’s business practices, directly implicating the company in systematic fraud that enriched its most senior executive.

The indictment detailed how the Trump Organization structured Weisselberg’s compensation to avoid federal, state, and local taxes through various schemes. The company paid approximately $940,000 in rent for Weisselberg’s luxury Manhattan apartment directly to his landlord rather than as taxable salary. Trump Organization entities leased Mercedes-Benz vehicles for Weisselberg and his wife totaling hundreds of thousands of dollars, recording the payments as business expenses while Weisselberg used the vehicles for personal purposes. The company paid nearly $360,000 in private school tuition for Weisselberg’s grandchildren through personal checks signed by Trump or Donald Trump Jr., disguised as holiday bonuses or other compensation. Weisselberg also received furniture, flat-screen televisions, and cash for personal expenses ranging from utility bills to garage expenses, all unreported as income. Prosecutors alleged Weisselberg underreported his income by approximately $1.76 million, evading $900,000 in federal, state, and city taxes over 15 years.

Corporate Complicity and Systematic Fraud

The indictment’s significance extended beyond Weisselberg personally—it charged the Trump Organization itself with facilitating and benefiting from the scheme. By compensating Weisselberg through untaxed perks rather than salary, the company avoided paying its share of payroll taxes while also enabling Weisselberg’s personal tax evasion. The scheme required extensive corporate involvement: executives signed checks for personal expenses, accounting staff recorded fraudulent business deductions, and multiple Trump Organization entities participated in the conspiracy. The indictment alleged this wasn’t limited to Weisselberg but extended to “other executives,” suggesting a systematic corporate culture of tax fraud. Weisselberg was charged with grand larceny for fraudulently applying for and receiving state tax refunds based on false tax returns, and with offering a false instrument for filing by submitting fraudulent W-2 forms that understated his actual compensation.

Both Weisselberg and the Trump Organization pleaded not guilty to all charges during their July 1, 2021 arraignment. Trump himself was not charged, though prosecutors noted the investigation remained ongoing. The indictment represented the culmination of a three-year investigation by the Manhattan DA’s office and New York Attorney General Letitia James, who announced she would continue investigating Trump Organization practices in a parallel civil case. Defense attorneys argued the case represented selective prosecution and that the charged conduct was standard practice in real estate compensation, though legal experts noted the systematic nature and duration of the scheme went far beyond typical business practices.

Significance

This indictment marked a critical moment in accountability for Trump Organization business practices, transforming what had long been rumored—systematic tax fraud—into formal criminal charges. The case demonstrated prosecutors had obtained detailed financial records and testimony sufficient to charge a major corporation and its top executive with long-running criminal conspiracy. The charges came as Trump was positioning himself for a potential 2024 presidential run, creating political pressure as his company faced criminal prosecution. The indictment’s language—“sweeping and audacious”—and its documentation of fraud signed off by Trump himself and his sons suggested potential future charges against Trump family members. The case showed that even powerful, politically connected organizations could face criminal accountability when evidence of systematic fraud was documented. Weisselberg would eventually plead guilty in August 2022, agreeing to testify against the Trump Organization in exchange for a five-month jail sentence, leading to the company’s conviction on all counts in December 2022. The criminal case established a pattern of corporate fraud that would parallel and support Attorney General James’s civil fraud investigation, which culminated in the $454 million judgment against Trump in February 2024.