'Devastating blow': Weisselberg’s agreement to testify could mean 'death penalty' for Trump Org.
President of the United States Donald Trump speaking at the 2018 Conservative Political Action Conference (CPAC) in National Harbor, Maryland. (Gage Skidmore/Flickr)

Former Trump Organization financial chief Allen Weisselberg is expected to admit to a 15-year tax fraud scheme on Thursday and is willing to testify against former President Donald Trump's companies, according to multiple reports.

Weisselberg, the former chief financial officer of the Trump Organization and a longtime Trump confidant going back to his days working for Fred Trump, is expected to admit to 15 felonies, according to The New York Times. Under the deal, he would agree to testify at trial against the Trump Organization if the company does not reach its own settlement, but not against Trump himself or any of his family members.

Under the terms, Weisselberg would receive a five-month prison sentence but only serve about 100 days, according to CNN. He faced up to 15 years at trial. He would also be required to pay about $2 million in restitution, back taxes, penalties and interest, according to the Associated Press.

The deal would be a "devastating blow to the Trump Organization," Daniel Alonso, a former federal and state prosecutor, told The New York Daily News. "It would make it a relatively easy case to prove if you have a high managerial agent on the stand saying, 'I'm guilty.' That's enormously helpful to the prosecution."

Weisselberg was charged with 15 felony counts and the Trump Organization was charged with 10 counts of tax fraud last year. The Manhattan District Attorney's office alleged that the company compensated Weisselberg and other executives "off the books" and that Weisselberg failed to pay taxes on $1.7 million in income, including a free apartment, two Mercedes-Benz cars, and private school tuition for his grandchildren.

Under the deal, Weisselberg would testify against the Trump Corporation and the Trump Payroll Corporation at trial, which is scheduled to begin in October, according to Rolling Stone. Weisselberg is reportedly willing to provide testimony admitting to the same crimes as in his trial but would not cooperate with the investigation into the company.

A source told Rolling Stone that Weisselberg's agreement to testify does not mean that prosecutors will necessarily call him to testify. But his potential testimony would "pose a severe threat to Trump's companies," the outlet reported, potentially securing a conviction against his business and "potentially leading to its demise."

Whether or not Trump was directly involved with the tax scheme, the guilty plea is "serious and significant," Rebecca Roiphe, a New York Law School professor, told Rolling Stone. Though Trump is not currently facing charges, the testimony could have "direct consequences on his business and his work and his business' ability to continue in New York," she said.

"Criminal liability is usually a pretty big deal for a corporation— it's often a death sentence," she explained. "The penalties could be so significant that the organization cannot survive past it. The penalties can be so high the company just doesn't exist, and it could ultimately end in the dissolution of the company."

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Though Manhattan DA Alvin Bragg has not charged Trump, the former president could still face liability in other investigations, including a civil probe led by New York Attorney General Letitia James into his businesses. The Fulton County, Ga., District Attorney's Office is also investigating Trump's efforts to overturn his election in the state. And the Justice Department is investigating Trump under the Espionage Act after he refused to turn over classified documents stored at his Mar-a-Lago home, leading to an unprecedented FBI raid earlier this month. The DOJ has also questioned witnesses before a grand jury about Trump's role in the deadly Jan. 6 Capitol riot.

Trump at a deposition in James' investigation last week invoked his Fifth Amendment rights against self-incrimination more than 400 times.

James is expected to issue a "massive, long-threatened 'enforcement action'" against Trump's family and companies in the probe, Insider reported last week. While the company may face fines and back taxes, "James has signaled she will also seek the dissolution of the business itself under New York's so-called corporate death penalty -- a law that allows the AG to seek to dissolve businesses that operate 'in a persistently fraudulent or illegal manner.'"

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