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Over the years, former President Donald Trump's family company has been involved in thousands of business disputes that landed it in civil court, both as plaintiff and as respondent. But The Trump Organization has never been tried in a court of law for crimes, until now.

On Monday in New York State Court in Lower Manhattan, jury selection began in the trial of the Trump Organization, which is accused of evading taxes by compensating employees through off-the-books benefits like luxury cars, apartments, and private school tuition.

The nine counts for which the company will be tried include conspiracy, criminal tax fraud, and falsifying business records. The alleged scheme stretches back to 2005, the year Trump married his third wife, Melania, through his 2016 campaign, his presidency, and the first half-year after his presidency ended.

The Trump Organization has pleaded not guilty

The Trump Organization has pleaded not guilty, and Trump has consistently maintained that he is the victim of politically-motivated prosecutors.

The trial's start comes as Trump faces a mounting array of litigation and investigations. There is a U.S. Department of Justice probe into his handling of classified documents, a Georgia investigation into his efforts to overturn the 2020 election, and a civil fraud case pending against Trump and his company for allegedly lying to financial institutions about the value of his assets.

If the Trump business is convicted on felony charges, this could make it very difficult for the company to continue doing business with banks and insurers.

In charging documents, prosecutors from the Manhattan District Attorney's office called the Trump Organization's alleged conduct "a systematic ongoing course of conduct with intent to defraud."

A co-defendant in the case, former longtime Trump executive and chief financial officer 

Allen Weisselberg, pleaded guilty in August 

and is expected to testify as star witness in the trial. Weisselberg's guilty plea included an agreement to testify truthfully under oath, but he is not a cooperating witness in the way prosecutors had once hoped — sharing evidence with investigators that might implicate Trump himself.

Weisselberg's attorney, Nicholas Gravante, says that his client is being prepped both by the prosecution and the defense in what Gravante calls "a unique plea agreement," while Weisselberg is on paid leave of absence from the Trump Organization.

"It's certainly one of the strangest cases I've ever seen," says Dan Alonso, a former chief assistant district attorney in Manhattan, and now a partner at Buckley LLP. Alonso says questions about who benefits from Weisselberg's arrangement could dog prosecutors.

"The idea that, 'Wait a minute, he's not going as far as maybe people thought he should, he's not gonna implicate Donald Trump himself. Does that mean he is really not telling the truth?' So I'd be a little bit nervous about that," Alonso says.

Weisselberg's guilty plea means there is already a crime that has been proven; prosecutors' task is simply to show that the company was in on it.

"It's a strong case. So in that, I'd be worried about Manhattan juries," Alonso says. "I mean, this is, this is 2022. We are more toxically polarized than ever. Largely thanks to Donald Trump and Manhattan despises Donald Trump, and he's the beneficial owner of this organization. So he may not be the focus of the trial, but he's gonna loom in the back of everyone's mind."

Former President Trump's actions will likely come into focus for the jury

While Trump is not on trial in The People of the State of New York v the Trump Corporation, the actions of the former president will likely come into focus for the jury.

Prosecutors say they can prove that Trump personally signed checks to pay for private school for Weisselberg's family members.

Moreover, while Weisselberg has admitted he benefited from the arrangement, Trump's bottom line allegedly did as well. Charging documents describe a spreadsheet, which recorded off-the-books compensation to Weisselberg. According to the indictment, "The Trump Organization reduced the amount of direct compensation that Weisselberg received in the form of checks or direct deposits to account for the indirect compensation that he received in the form of payments of rent, utility bills, and garage expenses." Those payments were not reported to tax authorities, and taxes were not withheld, they say.

While Trump has not returned to the role of CEO of the Trump Organization since leaving the presidency, he is still the owner of most of the family's assets. The business, which was founded nearly 100 years ago by Trump's grandmother, Elizabeth Trump, has sustained five generations of Trumps, even as it transformed from a small, Queens-based family holding into a sprawling international enterprise, encompassing hotels, golf, clubs, steaks, vodka, mortgages, and ultimately, an American president. 

Crime, Law and Justice

Courts

Politics and Election News

Ilya Marritz

Author

Former President Donald Trump's family company has long been involved in countless business disputes that landed it in civil court. But it has never been tried in a court of law for crimes, until now.

Jury selection begins in the Trump Organization tax evasion trial

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