Allen Weisselberg

Allen Howard Weisselberg
Born:	August 1948 New York
Charges:	Grand Larceny, Tax Fraud, Scheme to Defraud, Falsifying Business Records (15 counts, 2022); Perjury (2 counts, 2024)
Sentence:	5 months jail (2023, tax fraud); 5 months jail (2024, perjury)
Facility:	Rikers Island (New York City)
Status:	Released (July 2024)

Allen Howard Weisselberg (born August 1948) is an American businessman and former Chief Financial Officer of the Trump Organization, where he worked for nearly 50 years beginning in 1973.

Weisselberg became a central figure in multiple criminal investigations and civil lawsuits involving former President Donald Trump and his business empire. He holds the distinction of being convicted twice on felony charges—first for tax fraud in 2022 and again for perjury in 2024—resulting in two separate jail sentences at Rikers Island within 15 months of each other.

Background and Career

Weisselberg joined the Trump Organization in 1973, initially working for Fred Trump, Donald Trump's father, before becoming the personal financial gatekeeper for Donald Trump himself. He rose through the ranks to become Chief Financial Officer, serving in that role for decades and overseeing the company's financial operations. During his tenure, Weisselberg became one of Trump's most trusted advisors and had extensive knowledge of the company's financial dealings.

Tax Fraud Investigation and Prosecution

The Scheme

In August 2022, Weisselberg pleaded guilty to orchestrating a 15-year tax fraud scheme in which he and other Trump Organization executives received substantial portions of their compensation "off the books" to avoid paying taxes. The scheme, which operated from approximately 2005 to 2021, involved the Trump Organization providing unreported benefits to Weisselberg and other employees while failing to withhold appropriate taxes.

According to court documents, Weisselberg evaded taxes on $1.76 million in unreported income that the Trump Organization paid him in the form of benefits, including:

• A rent-free apartment on Riverside Boulevard in Manhattan
• Utilities and garage privileges related to the apartment
• Multiple Mercedes-Benz automobiles
• Private school tuition for his grandchildren
• Unreported cash payments
• Furnishings for his apartment and home in Florida

The scheme also involved improper payment of substantial bonuses to Weisselberg and other executives, categorized as non-employee compensation reported on IRS 1099 forms rather than as salary subject to withholding.

Guilty Plea and Cooperation

Weisselberg pleaded guilty to all 15 charges in the indictment, including one count of Grand Larceny in the Second Degree, three counts of Criminal Tax Fraud in the Third Degree, one count of Scheme to Defraud in the First Degree, one count of Conspiracy in the Fourth Degree, one count of Criminal Tax Fraud in the Fourth Degree, four counts of Offering a False Instrument for Filing in the First Degree, and four counts of Falsifying Business Records in the First Degree.

In his plea allocution, Weisselberg admitted that he engaged in the scheme together with the Trump Corporation and Trump Payroll Corp., specifically implicating the Trump Organization in criminal conduct. As part of his plea agreement, Weisselberg was required to testify at the criminal trial of two Trump Organization entities and to make full repayment of taxes, penalties, and interest totaling $1,994,321.

Trump Organization Trial

In December 2022, Weisselberg testified as the prosecution's key witness in the criminal trial of two Trump Organization subsidiaries. During his testimony, he provided detailed explanations of the various schemes, including receiving bonus checks for hundreds of thousands of dollars, signed by Trump, that were logged as if Weisselberg were an independent contractor. He testified that these funds were used to set up Keogh retirement plans, tax-deferred pension accounts designed for self-employed individuals.

The jury found two Trump Organization entities guilty of 17 felony counts, and the companies were fined $1.6 million. Trump himself was not personally charged in that case.

First Sentencing (2023)

On January 10, 2023, Judge Juan Merchan sentenced Weisselberg to five months in jail at Rikers Island, plus five years of probation. In imposing the sentence, Judge Merchan noted that of all the fraudulent conduct, he was "most offended" by a $6,000 check made out to Weisselberg's wife so she could become eligible for Social Security benefits. "It was driven purely by greed," Merchan said. "Your client was already making seven figures, they did not need Social Security benefits."

Weisselberg was immediately handcuffed and transported to Rikers Island to begin serving his sentence. He was released in April 2023 after approximately 100 days, receiving credit for good behavior.

Civil Fraud Trial and Perjury

New York Attorney General Lawsuit

Weisselberg was also named as a defendant in a $250 million civil lawsuit brought by New York Attorney General Letitia James, which alleged that Trump, his three eldest children, Weisselberg, and others defrauded lenders, insurers, and tax authorities by inflating the value of Trump Organization properties.

During the civil trial, Weisselberg testified in October 2023 about his knowledge of financial statements used by the Trump Organization. Judge Arthur Engoron, who presided over the civil case, later found Weisselberg's testimony "highly unreliable" and "intentionally evasive, with large gaps of 'I don't remember.'"

Triplex Apartment Controversy

A central issue in Weisselberg's perjury case involved his testimony about Trump's triplex apartment at Trump Tower. The apartment, which was less than 11,000 square feet, had been listed on Trump's statements of financial condition as 30,000 square feet—nearly three times its actual size. When questioned about this discrepancy, Weisselberg testified that it was "almost de minimis relative to his net worth" and that he "never even thought about the apartment."

However, Forbes magazine published evidence that Weisselberg had played a key role in trying to convince the publication that the apartment was as large as Trump's financial statements represented. Prosecutors confronted Weisselberg with emails from Forbes reporters and a letter he had signed certifying the excessive square footage to the Trump Organization's accounting firm.

Perjury Charges

Just 32 days after his release from his first jail sentence, Weisselberg committed perjury during a May 2023 deposition, according to the Manhattan District Attorney's Office. The DA subsequently charged him with multiple counts of perjury related to his false testimony.

In March 2024, Weisselberg pleaded guilty to two felony counts of perjury, admitting he gave false testimony regarding his knowledge of the size of Trump's triplex apartment. He acknowledged knowingly misleading investigators in order to help obtain favorable loans, insurance rates, and "other economic benefits" for the Trump Organization.

Second Sentencing (2024)

On April 10, 2024, Judge Laurie Peterson sentenced Weisselberg to five months in jail, his second stint at Rikers Island in just over a year. The hearing lasted approximately two minutes. When asked if he had anything to say, Weisselberg replied simply, "No, your honor."

As part of his plea agreement in the perjury case, prosecutors agreed not to call Weisselberg as a witness in Trump's separate criminal trial involving hush money payments to Stormy Daniels.

Civil Fraud Judgment

In February 2024, Judge Engoron ruled that Trump and his executives, including Weisselberg, had engaged in years of fraud. Trump was ordered to pay more than $450 million including interest. Weisselberg was found liable for fraud and ordered to pay $1 million—representing the amount he had already received from his $2 million severance agreement with the Trump Organization—as "ill-gotten gains."

Release and Separation from Trump Organization

Weisselberg was released from his second jail sentence on July 19, 2024, after 100 days, again receiving credit for good behavior. By the time of his first sentencing, he was no longer an employee of the Trump Organization, though reports indicated the separation was amicable and included a $2 million severance package. The Trump Organization also reportedly paid for Weisselberg's legal representation and a prison consultant (Craig Rothfeld) to help prepare him for incarceration.

Terminology

• Rikers Island: New York City's main jail complex, known for its challenging conditions. Weisselberg was placed in an infirmary unit rather than general population during his incarceration.

• Faithless Servant: A legal doctrine that could require an employee to forfeit compensation earned during a period of disloyalty; referenced in discussions of Weisselberg's severance agreement.

• Keogh Plan: A tax-deferred retirement plan for self-employed individuals; Weisselberg admitted to improperly using one funded by bonus payments categorized as non-employee compensation.

• Statement of Financial Condition: A document summarizing an individual's or company's assets and liabilities, used to obtain loans and insurance; central to the civil fraud allegations against Trump and Weisselberg.

Frequently Asked Questions

Q: Why did Allen Weisselberg go to prison?

Weisselberg, the longtime Chief Financial Officer of the Trump Organization, has been convicted twice. In 2022, he pleaded guilty to tax fraud charges for receiving off-the-books compensation worth approximately $1.7 million, including rent-free apartments, luxury cars, and private school tuition for his grandchildren. In 2024, he pleaded guilty to perjury for lying under oath during depositions in the civil fraud case against Trump and the Trump Organization. Each conviction resulted in a jail sentence.

Q: How long was Allen Weisselberg in jail?

For his 2022 tax fraud conviction, Weisselberg was sentenced to five months in jail at Rikers Island, of which he served approximately 100 days before being released. For his 2024 perjury conviction, he was sentenced to five months in jail, again at Rikers Island. The second sentence meant Weisselberg, who was 76 years old at the time, returned to jail in spring 2024.

Q: Did Allen Weisselberg testify against Trump?

Weisselberg's cooperation was limited. In his 2022 plea deal, he agreed to testify truthfully at the Trump Organization's criminal trial, which resulted in the company being convicted of tax fraud. However, he notably refused to implicate Donald Trump personally in any wrongdoing and did not cooperate in the broader investigation into Trump's business practices. His subsequent perjury conviction stemmed from false testimony he gave while trying to protect Trump in civil proceedings.

Q: What was Allen Weisselberg's role at the Trump Organization?

Weisselberg served as Chief Financial Officer of the Trump Organization for decades, beginning his career with the company in 1973 working for Donald Trump's father, Fred Trump. He was one of the longest-serving and most trusted executives in the organization, with deep knowledge of its finances and operations. He was considered so integral to the company that prosecutors had hoped he would become a cooperating witness in their investigation of Donald Trump.

Q: Where is Allen Weisselberg incarcerated?

Weisselberg served both of his sentences at Rikers Island, New York City's main jail complex. His cases were state rather than federal, which is why he was held at a city jail rather than a federal prison. Rikers Island is known for harsh conditions and has been the subject of significant criticism and reform efforts.