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Trump financial officer Allen Weisselberg sentenced to five months in jail

Steeply reduced sentence comes in exchange for testifying against Trump Organization last year

Former Trump Organization executive Allen Weisselberg arrives for a sentencing hearing at Manhattan Criminal Court in New York City on Tuesday. (Michael M. Santiago/Getty Images)
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NEW YORK — Longtime Trump Organization finance chief Allen Weisselberg, who pleaded guilty in August to 15 counts, including tax fraud, conspiracy and grand larceny, was sentenced on Tuesday to serve five months in jail and five years on probation.

Before his sentencing, he paid the state $2.3 million in back taxes, penalties and interest.

The judge overseeing his case promised Weisselberg, 75, a steeply reduced sentence in exchange for testifying against the Trump Organization in a criminal tax fraud case. He had faced up to 15 years in prison.

On Tuesday, New York Supreme Court Justice Juan Merchan rejected an attempt by Weisselberg’s lawyer to get him a further break on his jail sentence. Defense lawyer Nicholas Gravante Jr. asked Merchan to either reduce the number of months his client would be incarcerated by issuing him a shorter sentence or allow Weisselberg to serve half the time under house arrest.

Merchan, citing Weisselberg’s sworn testimony at the trial to more than a decade of tax evasion, said that had he not already promised a five-month sentence, “I would be imposing a sentence much greater than that.”

He noted in particular Weisselberg’s admission at the company’s trial to issuing his wife, who was unemployed, a $6,000 check from the company to get her access to Social Security benefits she was not entitled to. Weisselberg’s wife had never worked for the Trump Organization.

Merchan called it “offensive” that Weisselberg helped his wife cheat the Social Security system “when so many Americans work so hard in the hope that they may one day be able to benefit from Social Security.”

Of the criminal acts Weisselberg admitted to, “perhaps nothing spoke as loudly as that $6,000 payment,” Merchan said.

After the sentencing, Gravante said Weisselberg finalized his official departure from the Trump Organization on Tuesday and noted Weisselberg was pleased with a severance package he accepted. The attorney said he was not involved in the severance talks and could not disclose the terms of Weisselberg’s departure. Weisselberg was on the Trump Organization payroll through the trial.

When given the chance to speak at the proceeding, Weisselberg deferred to comments made in court by his attorney saying that Gravante “expressed my thoughts and feelings adequately.”

Minutes later, he was handcuffed by court officers and escorted to a holding cell. He came dressed-down in a green pullover and causal pants in preparation for his transfer to New York City Department of Correction custody.

Outside the courthouse, Gravante spoke as a handful of Trump critics held up signs and heckled him. The lawyer said Weisselberg was apologetic to the Trump Organization and the Trump family.

Weisselberg, testifying as a witness for the prosecution during a Trump Organization criminal trial in New York Supreme Court in November, said on cross-examination that he was embarrassed by his conduct and that his actions betrayed the Trump family, for whom he had worked for a half-century. Weisselberg testified that he was acting only for his own benefit.

The company was convicted of tax crimes in December. It had been charged with scheme to defraud, conspiracy, criminal tax fraud and falsifying business records. Former president Donald Trump was not charged with wrongdoing.

The testimony by Weisselberg revealed some of the inner workings of the Trump Organization’s structure and finances.

He admitted to avoiding taxes on $1.7 million in company benefits from 2005 to 2017 by receiving perks that should have been taxed as income but weren’t. He benefited from a number of unreported high-priced items that should have been counted as compensation, including a Manhattan apartment, Mercedes-Benzes and tuition payments at a pricey private school for his grandchildren.

Some of the expenses amounted to gifts from the company or from Trump and others Weisselberg refunded, allowing him to pay for personal expenses in what were in essence pretax dollars, instead of using his taxed income.

Weisselberg is expected to go to the Rikers Island city jail complex to serve about 100 days of his sentence on the expectation he will be credited for good behavior and released in April, according to Gravante. His age or health conditions could also mean he will be placed in the medical ward, or he could be segregated from the general population of inmates because of his notoriety.

At the Trump Organization criminal trial, Weisselberg told the jury that he acted only with another executive, comptroller Jeffrey McConney, to cheat on taxes in various ways relating to executive compensation. Weisselberg blamed himself for the crimes, saying it was his “own personal greed that led to this” and maintaining that the Trump family was not involved in the scheme.

Weisselberg also orchestrated a way to give annual bonuses to himself and other executives by issuing them from Trump Organization subsidiaries and categorizing them as non-employee contractor payments. That saved the company about $25,000 in payroll taxes, Weisselberg said.

He also said he saved the company money by taking compensation in non-monetary forms — that the Trump Organization would have had to raise his salary if he hadn’t.

The Trump Organization faces fines and penalties of up to $1.6 million. The company will be sentenced Friday for scheme to defraud, conspiracy, criminal tax fraud and falsifying business records.

The former president has not been charged with wrongdoing, and Manhattan District Attorney Alvin Bragg is still considering whether to charge Trump — who has announced his candidacy for the 2024 election — with other potential crimes stemming from a probe that started under his predecessor Cyrus R. Vance Jr. in 2019.