• The Trump Organization would be doomed if its ex-CFO pleads guilty this week, a legal analyst said.
  • Allen Weisselberg is expected to take a plea deal with the Manhattan DA's office, NYT reported.
  • The financial consequences for Donald Trump "are huge," said former prosecutor Adam Weissman.

A guilty plea from the Trump Organization's former chief financial officer in the criminal tax case against him would spell financial disaster for former President Donald Trump and his family business, said a former top federal prosecutor on Tuesday.

The New York Times reported that Allen Weisselberg, a longtime top executive for the Trump Organization, is expected to plead guilty in a deal with the Manhattan District Attorney's office as early as Thursday.

He and the Trump Organization face 15 felony counts, which include one count each of scheme to defraud, conspiracy, and grand larceny. Prosecutors said the charges stemmed from a "sweeping and audacious payment scheme" in which Weisselberg avoided paying taxes for up to $1.7 million of his income starting in March 2005.

The Times reported that Weisselberg's deal would see him receive five months in prison, compared to a sentence of at least one year if he was found guilty in court.

"Once Allen Weisselberg pleads guilty, it's over for the Trump Organization," said Andrew Weissmann, a law professor at New York University and former lead prosecutor under Robert Mueller, on MSNBC's "The Last Word" with Lawrence O'Donnell.

He said that crimes committed by Weisselberg would be attributed to the Trump Organization, meaning the company would also be held responsible for the charges.  

The Trump Organization is scheduled to face trial on October 24. If Weisselberg does not take a plea deal and goes to court, he will face trial alongside the business group. Both he and the Trump Organization have pleaded not guilty.

"So the leverage in terms of the financial consequences to Donald Trump doesn't mean he's going to jail, but the consequences for the Trump Organization are huge," Weissman said.

"Remember, for those people who think Donald Trump did this in part for money, that he's venal, this is a big deal," he added.

Weissman said that if he were advising Trump on handling the list of investigations and lawsuits against him, he would prioritize dealing with the consequences of Weisselberg's plea deal.

Trump currently faces six lawsuits, three criminal investigations, and a civil investigation on top of his indictment by the Manhattan District Attorney's office. He has also filed two lawsuits — one against his niece, Mary Trump, and another against his former election rival Hillary Clinton.

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