Allen Weisselberg Pleads Guilty to 15 Felonies, Agrees to Testify Against Trump Organization

Allen Weisselberg, the longtime Chief Financial Officer of the Trump Organization who served the company for nearly five decades, pleaded guilty in New York state court to 15 felony counts related to a 15-year tax fraud scheme, admitting he failed to pay taxes on $1.7 million in income including luxury perks such as Manhattan apartment rent, Mercedes-Benz leases, and private school tuition for his grandchildren. As part of the plea agreement, Weisselberg agreed to serve five months on Rikers Island and testify truthfully at the upcoming criminal trial of the Trump Organization, scheduled for October 2022. Manhattan District Attorney Alvin Bragg stated the plea agreement “directly implicates the Trump Organization in a wide range of criminal activity and requires Weisselberg to provide invaluable testimony in the upcoming trial against the corporation.” The guilty plea represented a significant victory for prosecutors and a major threat to the Trump Organization, as Weisselberg’s testimony would provide insider knowledge of decades of fraudulent business practices.

Under the plea agreement, Weisselberg admitted to scheming to defraud, conspiracy, grand larceny, and multiple counts of criminal tax fraud and falsifying business records. He acknowledged receiving approximately $1.76 million in unreported compensation from the Trump Organization between 2005 and 2021, evading approximately $900,000 in federal, state, and local taxes. The scheme involved systematic corporate participation: the company paid $940,000 directly to his landlord for a luxury Manhattan apartment; leased Mercedes-Benz vehicles for Weisselberg and his wife worth hundreds of thousands of dollars; and paid nearly $360,000 in private school tuition through checks signed by Donald Trump or Donald Trump Jr. Weisselberg admitted these benefits were structured specifically to avoid taxes, with the Trump Organization recording them as business expenses while he enjoyed them for personal use without reporting them as taxable income.

Testimony Agreement and Corporate Implications

The plea agreement’s requirement that Weisselberg testify against the Trump Organization created enormous legal jeopardy for the company. As CFO for decades, Weisselberg possessed intimate knowledge of Trump Organization financial practices, accounting schemes, and executive decision-making. His testimony would provide prosecutors with an insider’s account of how the company systematically structured compensation to evade taxes, how executives approved fraudulent arrangements, and how the corporate culture enabled and encouraged such practices. The agreement specified that Weisselberg would receive his five-month sentence only if he testified “truthfully”—meaning prosecutors retained leverage to ensure his cooperation was complete and accurate. With good behavior credits, Weisselberg’s actual time served would be approximately 100 days, a relatively light sentence for 15 felonies that emphasized prosecutorial focus on securing testimony against the corporation rather than maximum punishment for the individual.

Significantly, the plea agreement did not require Weisselberg to cooperate against Donald Trump personally or other Trump family members—he agreed only to testify about Trump Organization practices. This limitation suggested either prosecutorial strategy to secure conviction of the corporate entities first, or insufficient evidence to charge Trump individually at that time. Defense attorneys noted Weisselberg’s advanced age (75) and argued the lenient sentence reflected the weakness of the case, but prosecutors emphasized they had secured admissions of guilt that directly implicated Trump Organization business practices and would enable conviction of the company itself.

Significance

Weisselberg’s guilty plea to 15 felonies transformed him from Trump’s loyal CFO of nearly 50 years into a cooperating witness against the organization he helped build. The admission that he participated in systematic tax fraud “with the knowledge and consent” of Trump Organization executives established corporate complicity in criminal activity, making it substantially easier for prosecutors to prove the company’s guilt at trial. The plea came 13 months after Weisselberg’s initial indictment in July 2021, suggesting prosecutors built overwhelming evidence that made fighting the charges untenable despite Weisselberg’s decades of loyalty to Trump. The five-month Rikers Island sentence—though light for the scale of fraud—carried symbolic weight: Trump’s longtime financial gatekeeper would be imprisoned for crimes committed while serving the organization. Weisselberg would ultimately testify at the Trump Organization’s trial in November-December 2022, providing crucial testimony that led to the company’s conviction on all 17 criminal counts on December 6, 2022. His subsequent guilty plea to perjury charges in March 2024 for lying about the Trump Tower triplex size during depositions demonstrated the systematic dishonesty that characterized Trump Organization operations and Weisselberg’s willingness to commit crimes to protect Trump’s interests.