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. He spent nearly 50 years with the company, starting in 1973.

Weisselberg became central to multiple criminal investigations and civil lawsuits connected to former President Donald Trump and his business empire. He's been convicted twice on felony charges. First came tax fraud in 2022, then perjury in 2024. Both resulted in jail time at Rikers Island, with the sentences just 15 months apart.

Background and Career

In 1973, Weisselberg joined the Trump Organization. He started working for Fred Trump, Donald Trump's father. Eventually he became Donald Trump's personal financial gatekeeper and rose to Chief Financial Officer. For decades he ran the company's financial operations and was one of Trump's most trusted advisors, with deep knowledge of how the business actually worked.

Tax Fraud Investigation and Prosecution

The Scheme

In August 2022, Weisselberg pleaded guilty. He'd orchestrated a 15-year tax fraud scheme where he and other Trump Organization executives got much of their pay "off the books" to skip taxes. From roughly 2005 to 2021, the Trump Organization handed Weisselberg and other employees unreported benefits while not withholding the proper taxes.

Court documents show Weisselberg ducked taxes on $1.76 million in unreported income from the Trump Organization. The benefits included:

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

There's more. The scheme involved improper bonuses to Weisselberg and other executives. They were categorized as non-employee compensation on IRS 1099 forms instead of salary subject to withholding.

Guilty Plea and Cooperation

Weisselberg pleaded guilty to all 15 charges. These included 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, he admitted engaging in the scheme with the Trump Corporation and Trump Payroll Corp. He directly implicated the Trump Organization in criminal conduct. His plea agreement required him to testify at the criminal trial of two Trump Organization entities. He also had to pay back $1,994,321 in taxes, penalties, and interest.

Trump Organization Trial

December 2022 brought Weisselberg to the witness stand. He testified as the prosecution's star witness in the criminal trial of two Trump Organization subsidiaries. His testimony laid out the various schemes in detail. He'd received bonus checks for hundreds of thousands of dollars, signed by Trump. They were logged as if he were an independent contractor. Those funds went into Keogh retirement plans, which are tax-deferred pension accounts for self-employed people.

The jury convicted two Trump Organization entities on 17 felony counts. They were fined $1.6 million. Trump himself wasn't charged in that case.

First Sentencing (2023)

Judge Juan Merchan sentenced Weisselberg on January 10, 2023. Five months at Rikers Island, plus five years probation. During sentencing, the judge said he was "most offended" by one particular scheme. A $6,000 check made out to Weisselberg's wife so she could qualify 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."

They handcuffed him right there and took him to Rikers Island. He was released in April 2023 after roughly 100 days, getting credit for good behavior.

Civil Fraud Trial and Perjury

New York Attorney General Lawsuit

New York Attorney General Letitia James sued, naming Weisselberg as a defendant. She wanted $250 million. The lawsuit accused Trump, his three eldest children, Weisselberg, and others of defrauding lenders, insurers, and tax authorities by inflating property values.

Weisselberg testified in October 2023 about his knowledge of the Trump Organization's financial statements. Judge Arthur Engoron, who ran the civil case, later said his testimony was "highly unreliable" and "intentionally evasive, with large gaps of 'I don't remember.'"

Triplex Apartment Controversy

The perjury case centered on Trump's triplex at Trump Tower. It was less than 11,000 square feet. Yet Trump's financial statements listed it as 30,000 square feet. Nearly three times the actual size. Weisselberg testified it was "almost de minimis relative to his net worth" and he "never even thought about the apartment."

Forbes magazine had evidence contradicting this. Weisselberg had worked hard to convince Forbes that the apartment was exactly as big as Trump's statements said. Prosecutors showed him emails from Forbes reporters and a letter he'd signed certifying the inflated square footage to the Trump Organization's accounting firm.

Perjury Charges

Weisselberg committed perjury just 32 days after release from his first sentence. During a May 2023 deposition, he lied to investigators. The Manhattan District Attorney's Office charged him with multiple counts of perjury.

In March 2024, he pleaded guilty to two felony counts of perjury. He admitted giving false testimony about how much he knew regarding the triplex size. He knowingly misled investigators to help get favorable loans, insurance rates, and "other economic benefits" for the Trump Organization.

Second Sentencing (2024)

Judge Laurie Peterson sentenced him on April 10, 2024. Five months back at Rikers Island. His second stint in just over a year. The hearing lasted about two minutes. When asked if he had anything to say, he replied simply, "No, your honor."

Part of his perjury plea deal: prosecutors agreed not to call him as a witness in Trump's separate criminal trial over hush money payments to Stormy Daniels.

Civil Fraud Judgment

Judge Engoron ruled in February 2024 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. That amount represented what he'd already received from his $2 million severance agreement with the Trump Organization, as "ill-gotten gains."

Release and Separation from Trump Organization

Weisselberg got out on July 19, 2024, after 100 days of his second sentence. Again receiving credit for good behavior. By his first sentencing, he wasn't an employee anymore, though the separation reportedly went smoothly. He received a $2 million severance package. The Trump Organization also paid for his legal representation and hired a prison consultant (Craig Rothfeld) to help him prepare for incarceration.

Terminology

• Rikers Island: New York City's main jail complex. Known for tough conditions. Weisselberg was held in an infirmary unit rather than general population during his time there.

• Faithless Servant: A legal doctrine that could require an employee to give up compensation earned during a period of disloyalty. It came up in discussions about Weisselberg's severance agreement.

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

• Statement of Financial Condition: A document showing an individual's or company's assets and liabilities. Used to obtain loans and insurance. It was central to the civil fraud allegations against Trump and Weisselberg.

Frequently Asked Questions

Q: Why did Allen Weisselberg go to prison?

Weisselberg worked as Chief Financial Officer of the Trump Organization for decades. He's been convicted twice. In 2022, he pleaded guilty to tax fraud for receiving off-the-books compensation worth roughly $1.7 million. This included 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 brought a jail sentence.

Q: How long was Allen Weisselberg in jail?

For his 2022 tax fraud conviction, he was sentenced to five months at Rikers Island. He served about 100 days before being released. For his 2024 perjury conviction, he was sentenced to five months again at Rikers Island. The second sentence meant Weisselberg, who was 76 by that time, went back to jail in spring 2024.

Q: Did Allen Weisselberg testify against Trump?

His cooperation was limited. Under 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. But he notably refused to implicate Donald Trump personally and didn't cooperate in the broader investigation into Trump's business practices. His subsequent perjury conviction came 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 for decades. He joined the company in 1973 working for Donald Trump's father, Fred Trump. He became one of the longest-serving and most trusted executives, with deep knowledge of its finances and operations. Prosecutors had hoped he'd become a cooperating witness in their investigation of Donald Trump, given how integral he was to the company.

Q: Where is Allen Weisselberg incarcerated?

Both sentences were served at Rikers Island, New York City's main jail complex. His cases were state matters rather than federal, so he went to a city jail instead of a federal prison. Rikers Island is known for harsh conditions and has faced significant criticism and reform efforts.