Allen Weisselberg is the former chief financial officer of the Trump Organization who pleaded guilty to felony tax fraud in 2022 and to perjury in 2024, served two five-month sentences at Rikers Island, and was permanently barred from any financial-control role at a New York company through the state attorney general’s civil fraud judgment. He spent roughly five decades working for the Trump family and remained loyal to Donald Trump through both prosecutions, never implicating him personally in criminal conduct.
Five Decades With the Trumps
Weisselberg began working as an accountant for developer Fred Trump Sr. in 1973 and stayed on when Donald Trump took over the family business in the mid-1980s, eventually rising to chief financial officer. He was one of the few employees who worked for both father and son.1ABC7 New York. Allen Weisselberg Trump Organization Investigation: Who Is He
When Donald Trump was inaugurated as president in January 2017, Weisselberg was appointed as a trustee of the Trump Organization alongside Donald Trump Jr. and Eric Trump. After his 2021 arrest his title was changed from CFO to senior adviser, and he was later placed on leave. His employment formally ended on December 30, 2022.2WJCL. Trump Org CFO Allen Weisselberg Sentenced3New York Attorney General. Allen Weisselberg Severance Agreement Two of his sons also had ties to the Trump business world: Barry managed ice skating rinks and a carousel in Central Park for the Trump Organization, and Jack worked at the commercial lending firm Ladder Capital.4CBS News. Weisselberg Family Trump Organization Trial New York
The 2022 Tax Fraud Guilty Plea
On July 1, 2021, a Manhattan grand jury indicted Weisselberg along with the Trump Corporation and Trump Payroll Corp. after an investigation led by then-Manhattan District Attorney Cyrus Vance Jr. and New York Attorney General Letitia James.5WTTW News. Trump Organization CFO Surrenders Ahead of Expected Charges Prosecutors alleged that over roughly 15 years, Weisselberg collected more than $1.7 million in untaxed compensation, including a rent-free luxury apartment on Manhattan’s Riverside Boulevard, lease payments on two Mercedes-Benz vehicles, private school tuition for his grandchildren, cash holiday tips, and home furnishings for a Florida residence. He was also accused of falsely claiming he was not a New York City resident to avoid city income taxes.6CBS News. Trump Organization Indicted Allen Weisselberg Tax Fraud Scheme Donald Trump himself was not charged.
On August 18, 2022, Weisselberg pleaded guilty to all 15 counts, which included grand larceny in the second degree, scheme to defraud in the first degree, conspiracy in the fourth degree, criminal tax fraud, and multiple counts of offering a false instrument for filing and falsifying business records. The plea deal called for five months at Rikers Island, five years of probation, and more than $2 million in back taxes, penalties, and interest paid to New York State and New York City. The agreement also required him to testify truthfully at the upcoming corporate criminal trial. If he refused, prosecutors could seek up to 15 years in state prison.7Manhattan District Attorney’s Office. D.A. Bragg: Trump Organization CFO Allen Weisselberg to Serve 5 Months in Jail, Testify in Upcoming Criminal Trial Against Trump Organization
Judge Juan Manuel Merchan imposed the agreed sentence on January 10, 2023. Weisselberg declined to make any statement at the hearing.8Courthouse News Service. Loyal Trump CFO Weisselberg Sentenced to Prison With time off for good behavior, he was released after 100 days, on April 19, 2023.9CBS News. Allen Weisselberg Released From Jail
What He Said On the Stand
Weisselberg testified over three days at the Trump Organization’s criminal trial. He admitted evading taxes through off-the-books compensation and confirmed that the arrangement also benefited the company by reducing its payroll tax burden, telling jurors that “my own personal greed” drove him.10ABC News. Former Trump Organization CFO Allen Weisselberg Sentenced He described certain off-the-books practices as dating back to the 1980s and said they were stopped after Trump’s 2016 election as part of a “cleanup process.”8Courthouse News Service. Loyal Trump CFO Weisselberg Sentenced to Prison
He did not implicate Donald Trump personally. He testified that he hid the scheme from the company’s outside accountant and said Trump and his family were unaware the arrangements were designed to evade taxes, though he acknowledged Trump had authorized specific perks such as the apartment lease and company cars. Defense lawyers used that gap to argue Weisselberg had “gone rogue.”11PBS NewsHour. Trump’s Longtime Finance Chief Testifies at Company’s Fraud Trial He testified while still on the Trump Organization payroll at a $640,000 annual salary, with a potential $500,000 bonus.12Courthouse News Service. Still on Trump Payroll, Former CFO Testifies at Tax Fraud Trial
On December 6, 2022, a jury convicted both Trump corporate entities of a combined 17 felony counts. Judge Merchan later imposed the maximum fines permitted under New York law: $810,000 for the Trump Corporation and $800,000 for Trump Payroll Corp., totaling $1.61 million.13Manhattan District Attorney’s Office. D.A. Bragg: Trump Corporation, Trump Payroll Corp. Sentenced to Pay Maximum Fines Under Law Following Felony Trial Conviction
The New York Civil Fraud Case
Weisselberg was also a defendant in the civil fraud lawsuit that Attorney General Letitia James filed in September 2022 against Donald Trump, the Trump Organization, Donald Trump Jr., Eric Trump, Weisselberg, and Trump Organization controller Jeffrey McConney. The suit alleged a decade-long scheme to inflate the value of Trump’s assets on annual financial statements submitted to banks, insurers, and lenders.14New York Attorney General. Attorney General James Wins Landmark Victory in Case Against Donald Trump
Weisselberg sat at the center of how those statements were produced. He was the Trump Organization’s primary contact for its outside accounting firm, Mazars USA. Accountants later testified that they would not have issued the statements without Weisselberg’s representation that the underlying data conformed to generally accepted accounting principles.15New York Attorney General. People v. Trump Decision The Attorney General’s office said Weisselberg “engineered Trump’s financial statements to meet his demands that they show increases in his net worth” and “signed off on lofty valuations for assets despite appraisals to the contrary.”16WHYY. Donald Trump New York Civil Business Fraud Lawsuit Trial Weisselberg Witness Stand
After a trial in late 2023, Judge Arthur Engoron issued a judgment in February 2024 that imposed specific penalties on Weisselberg: a $1 million disgorgement, a permanent ban on serving in any financial control role at a New York corporation, and a three-year ban on serving as an officer or director of any New York company. Engoron called Weisselberg’s trial testimony “intentionally evasive” and “highly unreliable.”17CFO Dive. Ex-Trump CFO Faces Legal, Financial Troubles After Civil Fraud Ruling18PBS NewsHour. Former Trump Executive Allen Weisselberg Sentenced to 5 Months in Jail for Lying in Civil Fraud Case
On August 21, 2025, the Appellate Division, First Department, vacated the disgorgement awards, finding the financial penalty was an excessive fine barred by the Eighth Amendment. The panel upheld the injunctive relief, including the bans on Weisselberg from serving as an officer or director of a New York entity, and deferred to Engoron’s finding that his testimony was not credible. Attorney General James announced she would appeal the disgorgement ruling to the New York Court of Appeals.19CBS News. Trump Civil Fraud Case New York Appeals20Justia. People v. Trump, Appellate Division First Department
The 2024 Perjury Plea
Weisselberg’s civil-trial testimony triggered a second criminal prosecution. Manhattan District Attorney Alvin Bragg charged him with five counts of perjury for lying under oath about his knowledge of the valuation of Donald Trump’s Manhattan triplex penthouse. The apartment had been listed on Trump’s financial statements at roughly 30,000 square feet, nearly three times its actual size of about 11,000 square feet, inflating its stated value to as much as $327 million. Weisselberg had testified that he had “little knowledge” of how the property was valued and did not “walk around knowing the size” of the apartment. Prosecutors said he knew the true dimensions well before a 2017 Forbes article exposed the discrepancy and continued to list the inflated figure afterward.21Courthouse News Service. Allen Weisselberg Sentenced to Five Months in Jail for Perjury in Trump’s Civil Fraud Case
The false statements spanned three occasions: a July 2020 deposition in the Attorney General’s investigation, a May 2023 deposition, and live testimony at the civil fraud trial in October 2023.18PBS NewsHour. Former Trump Executive Allen Weisselberg Sentenced to 5 Months in Jail for Lying in Civil Fraud Case22BBC News. Allen Weisselberg Pleads Guilty to Perjury23CNN. Allen Weisselberg Trump Org CFO Plea Perjury
Judge Laurie Peterson sentenced him to five months in jail on April 10, 2024.21Courthouse News Service. Allen Weisselberg Sentenced to Five Months in Jail for Perjury in Trump’s Civil Fraud Case He served roughly 100 days at Rikers Island and was released on July 19, 2024.24ABC News. Former Trump Organization CFO Allen Weisselberg Released From Jail
The $2 Million Severance
The day before his January 2023 tax-fraud sentencing, Weisselberg signed a six-page severance agreement with the Trump Corporation. Signed on behalf of the company by Eric Trump, it provided for $2 million in payments structured as eight quarterly installments of $250,000 each.25PBS NewsHour. Trump Civil Fraud Trial Resumes With Ex-CFO Weisselberg Testifying The agreement included a non-disparagement clause and barred him from cooperating with investigators or parties bringing claims against the company “except for acts or testimony directly compelled by subpoena or other lawful process.”26Courthouse News Service. Eric Trump Takes Full Responsibility for Allen Weisselberg’s Shady Severance Package The $2 million figure was close to what he owed in back taxes, penalties, and interest under his plea deal. Judge Engoron’s February 2024 judgment ordered him to disgorge $1 million of the severance, though the appellate court vacated that portion in August 2025.19CBS News. Trump Civil Fraud Case New York Appeals
Why He Never Turned on Trump
A through-line across both prosecutions was Weisselberg’s refusal to cooperate against Donald Trump personally. His plea deals required testimony against the corporate entities, not against Trump or his family, and at the corporate trial he explicitly shielded them, attributing the tax scheme to his own greed.11PBS NewsHour. Trump’s Longtime Finance Chief Testifies at Company’s Fraud Trial
Manhattan prosecutors pushed for more. After his first incarceration, the DA’s office reportedly threatened additional charges related to insurance fraud to pressure him into providing information about Trump’s personal involvement.27ABC News. Manhattan DA Threatens Former Trump Organization CFO Allen Weisselberg Prosecutors also used the possibility of charging his son Barry as leverage, a tactic his defense attorneys challenged as a due-process violation.28CBS News. Prosecutors Trump Organization CFO Allen Weisselberg Son Barry He absorbed two jail sentences rather than testify against the man he had worked for since 1973.