Trump Org’s Monday criminal trial expected to be ‘quite the chess game’: analysis

Manhattan District Attorney Alvin Bragg's prosecution of the Trump Organization for fraud is set to go to trial on Monday.

Longtime Trump Org Chief Financial Officer Allen Weisselberg pleaded guilty to fifteen counts in August and is required to testify. His sentencing has been delayed until after the completion of the trial as the extent of his punishment is contingent on his cooperation.

"Prosecutors say the case focuses on what they describe as a 15-year tax cheating scheme involving untaxed benefits like luxury cars and expensive apartments for company executives including Weisselberg, who has been painted as the linchpin to the tax avoidance operation," The Washington Postreported. "Weisselberg began his employment at the Trump Organization in 1973."

The Trump Organization is unlikely to plead guilty as Weisselberg did, a source "familiar with the inner workings of the Trump Organization" told Time magazine.

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“If convicted, Trump would rather it be by a jury, in a trial that he could blame as biased and flawed, as opposed to authorizing a representative of the company to walk into court and admit guilt," the source said.

Former senior DOJ official and Mueller prosecutor Andrew Weissmann said, "all eyes will be on evidence of Trump’s knowledge and role in the scheme."

"Normal defense strategy is to attack [government] witnesses as liars," he explained. "But if former CFO is treated that way successfully, he may flip finally against Trump. The court has said if [Weisselberg] lies he will throw the book at him at sentencing."

"We will be watching quite the chess game," Weissmann predicted.

Trump is also facing a $250 million civil suit brought by New York Attorney General Letitia James.

The trial will begin with jury selection in the New York State Supreme Court in Manhattan.

If the Trump Organization is convicted it could face the same New York "corporate death penalty" law that was used to shut Trump University and the Donald J. Trump Foundation.