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Looks Like Trump Accountant Allen Weisselberg Is Headed Back to Jail

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Trump’s longtime accountant, Allen Weisselberg, has pleaded guilty to even more crimes—this time, perjuring himself and frustrating the bank fraud case against his former boss.

Trump Organization's former Chief Financial Officer Allen Weisselberg walks handcuffed at Manhattan Criminal Court.
Brendan McDermid/Reuters

After spending nearly three months at New York City’s dreaded Rikers Island jail, longtime Donald Trump finance guru Allen Weisselberg looks like he has booked a return trip back there on Monday when he admitted to lying about his former employer’s bank fraud schemes.

He now faces another five months in jail, this time for frustrating law enforcement efforts to get at his former boss.

Weisselberg, the Trump Organization’s ex-chief financial officer, turned himself into the Manhattan District Attorney’s Office to plead guilty to perjury. Local prosecutors are swooping in to hold him accountable for frustrating a parallel investigation at the New York Attorney General’s Office. The disgraced accountant, who keeps trying to protect Trump, admitted that he lied to the AG’s investigators in depositions and at her recent bank fraud trial.

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It’s the latest in an ongoing legal headache that has dogged the 76-year-old for half a decade.

Weisselberg was at the center of the Manhattan DA’s tax fraud trial against Trump companies that resulted in a $1.6 million guilty verdict and the New York AG’s bank fraud trial against the Trumps that hit them with a $464 million judgment. But Weisselberg always played the role of a reluctant witness, refusing to point the finger at Trump as the mastermind behind the persistently dishonest behavior at the real estate company.

The conspicuously timed plea deal comes just three weeks before Trump himself faces trial against the DA for criminally interfering with the 2016 election by covering up his sexual affair with a porn star—yet another scandal that involved Weisselberg. And it raises the question as to whether Weisselberg will finally be willing to testify openly against his former boss.

According to the plea agreement he signed, Weisselberg acknowledged he wouldn’t be truthful when discussing his involvement in the way Trump repeatedly faked the size of his palatial triplex apartment at Trump Tower. The accountant helped Trump vastly inflate the value of his personal assets by some $200 million when they claimed the three-floor, 10,996 square foot apartment was actually closer to 30,000 square feet.

As part of the plea deal, Weisselberg admitted he lied to the AG during a July 2020 deposition, when he told state investigators that he remained clueless about the real size of the triplex until a journalist called him out on the fabrication.

“We didn’t find out about the error until the Forbes article came out,” he told the AG’s team, according to a transcript cited in court documents.

In reality, DA prosecutors say, emails show that Weisselberg was fielding questions from Forbes reporters and involved with internal discussions about the matter for months.

However, Weisselberg apparently kept up that lie even after he came under the Manhattan DA’s microscope for dodging taxes at the Trump Organization. In 2022, Weisselberg struck a plea deal with the DA and later testified at the criminal trial. But new details first revealed on Monday show that he kept up the act even after his 99-day stint in jail.

In the plea deal, Weisselberg admitted that he lied to the AG during a May 2023 deposition in the run-up to her bank fraud trial, claiming he wasn’t involved in determining the property values that made up Trump’s personal financial statements. Then he lied a third time at the three-month bank fraud trial last fall, when he testified in court on Oct. 10, 2023, that he “never focused on the triplex” and “never thought about that apartment.”

Weisselberg and his defense lawyer, Thomas Rotko, signed a plea deal on Monday that levies two felony counts of perjury against the accountant. They agreed to “a definite sentence of 5 months in jail.”

According to New York state court records, Weisselberg will be sentenced on April 10—which would put it two weeks into Trump’s first ever criminal trial in the very same building.

Weisselberg is also on the hook for $1.1 million, the hefty penalty issued by New York Supreme Court Justice Arthur F. Engoron for his role in Trump’s bank fraud. And it’s a sum that’ll keep increasing by $246 in prejudgment interest every day he doesn’t pay it off.

Rotko did not immediately respond to a request for comment.

DA communications director Danielle Filson issued an office statement noting it is a crime to lie in depositions and at trial—“plain and simple.”

“Allen Weisselberg took an oath to be truthful, and then committed perjury both at depositions during the New York State Attorney General’s Investigation and Proceeding, as well as at their recent trial. Today, Allen Weisselberg is pleading guilty to this felony and being held responsible for his conduct,” Filson said.