The Trump Organization is set to face criminal tax evasion charges on Monday in New York in a lawsuit that could begin to unravel the many allegations against the company and by extension its patriarch, Donald J Trump.

It comes as the former US president faces a maze of legal hassles and mounting costs – by some estimates at nearly $4 million a month to his Leadership Pac — on his attempts to overturn his 2020 election defeat, the removal of government documents from the White House when he left office and a defamation case related to an allegation of rape.

Monday’s case centers on accusations that his Manhattan-based real estate company defrauded New York tax authorities by awarding 15-year “off the book” compensation to company executives, including payouts of rent for cars, apartment rent and school fees for parents instead of a certain salary, allowing the company to escape paying social charges.

If found guilty, the company, which is run by Donald Trump Jr. and Eric Trump, could face fines of $1.6 million and have his ability to operate hotels, golf courses and other assets hampered.

But the lawsuit will likely be most interesting for its subplots and how it intersects with a separate civil investigation led by New York State Attorney General Letitia James, who garnered a 200-page indictment last month accusing the Trump Organization, Trump and three of his adult children of overestimating Trump’s property values ​​and net worth to obtain favorable bank loans and insurance coverage.

Manhattan’s investigation into Trump’s business followed its own rocky path to a jury trial. It started under District Attorney Cyrus Vance Jr and is now in the hands of his successor, Alvin Bragg. Two prosecutors who led the investigation resigned in February, with one saying felony charges should be brought against the former president.

Lawyers for the Trump Organization claimed the case was a “selective prosecution” motivated by opposition to Trump’s political views – a claim that the judge handling the case, Juan Merchan, dismissed. They also said prosecutors were seeking to punish Trump’s company because “a handful of its executives allegedly failed to report employee benefits on their personal tax returns.”

But the stakes for both parties – prosecutor and defendant – are high. Unlike Trump’s failed efforts to challenge the 2020 election results, the Trump Organization brought in an A-team of attorneys to counter claims by an equal array of prosecutors to meet a high burden of proof in criminal trials.

Eyes and ears will be on the testimony of then-Trump Organization chief financial officer Allen Weisselberg, 75, who was charged in the prosecutor’s 2021 indictment but has since pleaded under 15 charges ranging from grand theft to tax evasion to falsifying business documents in exchange for his testimony.

Weisselberg was subpoenaed to testify but he is not a cooperating witness. Yet his five-month sentence agreed with prosecutors hinges on truthful testimony. Crucially, the Manhattan prosecutor made sure that Weisselberg’s sentencing would be deferred until after the case.

To prove that the company is guilty, the government is entitled to place the responsibility not only on Weisselberg, but also on other executives of the company, including potentially donald trump himself, of whom they can try to show that they were aware of the alleged tax scheme.

“It’s strategically a really tough case for both Weisselberg and Trump because they could end up winning the battle and losing the war,” said Andrew Weissmann, a former federal prosecutor who now teaches law at the University of New York. York.

“If they do a typical Weisselberg defense cross-examination and they catch him lying, then his deal is over and the pressure on him to return [on Trump] will be that much bigger.

Under these circumstances, Trump Organization lawyers cannot simply try to eviscerate Weisselberg’s credibility, Weissmann points out, without potentially rewarding investigators with evidence that their career biggest, Trump himself, was aware of the provisions to reward managers with untaxed compensation.

“The idea that Trump didn’t know is going to be the critical thing Weisselberg is asked about. If he denies that Donald Trump knew, you can see the judge say, ‘I don’t believe it and I’m going to stand by it. account when I condemn you”.

Under these circumstances, Merchan could kick out Weisselberg’s sentence of up to 15 years in prison, not five months on Rikers Island – an onerous sentence for a 75-year-old.

Additionally, Letitia James’ civil complaint alleges that Weisselberg committed fraud by making false statements to Zurich’s North American Insurance Company. In theory, Weisselberg could still be indicted by Bragg if his testimony is found to be false.

“Obviously they still want Weisselberg to cooperate,” says Weissmann.

But as the trial begins next week, there is a feeling Bragg’s case could be easier to prove than James’ complaint, which focuses on building valuations but requires a lower burden of proof.

“Bragg’s allegations are much more concrete because they purport to make payments that were clearly part of the person’s salary, keeping track of them, but only reporting what was listed as salary,” Weissmann said.

“The problem for the defense is that if they say it’s a gray area and not a crime, they have to say Weisselberg is lying. If the judge agrees, Weisselberg is in a difficult position.