NY AG Letitia James v. Donald Trump will be a slow-motion, 'eye-glazing' slog, ex-AG insiders say

The NY AG's lawsuit v. Donald Trump has only just begun; here's how three former NY AG prosecutors predict Trump will go 12 rounds to save his empire.

• NY AG Letitia James sued Donald Trump, his three eldest kids, and Trump Organization on Wednesday.
• Her demands — including $250 million in penalties and the hamstringing of his business in NY  — will be fought over for years, experts say. 
• James is now 'just another litigant' in a slow-moving system that Trump knows how to game, they say.

So New York Attorney General Letitia James has sued Donald Trump, his kids, and his company. But don't bother popping any popcorn over this massive fraud lawsuit anytime soon.

Very little will actually happen to Trump, his three eldest children, or the Trump Organization — the former president's Manhattan-based real estate and golf empire — over the next two years and maybe longer, three former prosecutors with the NY AG's office told Insider.

That's because litigating the 222-page lawsuit will be a slow, costly slog, they predict.

"This is going to be an eye-glazing battle" of experts and lawyers, before the lawsuit even goes to trial, one ex-prosecutor, Armen Morian, said of what's to come.

Morian, now in private practice in Manhattan at Morian Law, knows about slow slogs. He prosecuted the New York AG's case against Hank Greenberg, the one-time CEO of insurance giant AIG.

That prosecution took 13 years to reach a 2017 settlement, with Greenberg fighting every step of the way before finally agreeing, at age 93, to pay $9 million to the state of New York.

"You're at the starting line," Morian told Insider. "Now that he's a litigant, Trump is entitled to drag this case out as long as he can. This will play out over years."

First a little judge shopping, perhaps

The first step in that slog? A bit of judge-shopping, Morian and others predict.

The lawsuit's defendants may well want to move the case as far away as possible from the courtroom of NY state Supreme Court Justice Arthur Engoron.

That's the Manhattan judge who repeatedly ruled against Trump in the two-year lead-in to the AG's lawsuit. It was Engoron who held Trump in contempt and ordered he pay $110,000 in fines for not cooperating fully with James' inquiry.

Morian predicts the defendants will try to move the case to a judge in the state court system's commercial division, a paperwork-heavy process that Trump's lawyers have failed at previously.

"The commercial division is set up to handle lawsuits involving only commercial parties, not an attorney general, so that would draw a pretty quick denial," said another former NY assistant AG, Tristan Snell. "But it could buy Trump's side a month or so."

Next: many months of slow-mo motion practice

Next will come many more months of what's called motion practice, with Trump's side kicking the process off.

Lawyers for the defendants — all 17 of them, including Trump Org subsidiaries and former executives — will have 30 days to file response motions, in writing, to the judge, explained author and attorney Kenneth McCallion, a former prosecutor who handled complex litigation in the Department of Justice and the NY AG's office. 

With that, they're off to the races — in excruciating slow motion. A long, litigation timeline is simply built in, given the magnitude of the lawsuit, former AG prosecutors told Insider.

By numbers alone, the lawsuit's scope is staggering.

Millions of pages of evidence

The AG's office reviewed 900,000 Trump business documents totaling 6 million pages. The resulting lawsuit encompasses alleged financial wrongdoing at 23 of the company's properties over the past decade.

The lawsuit is also very complex in what it demands, asking Engoron to throw the book at Trump, litigationally speaking.

Requests, she has a few

It demands the repayment of $250 million that James says Trump illegally pocketed, allegedly by misleading banks about his worth. The banks relied on the iffy math in giving Trump lower interest rates and lending him more money than he would otherwise have been entitled to, she claims.

The lawsuit also demands that Trump and his three eldest children — who have all served as Trump Organization executives — be permanently barred from running a New York corporation.

It demands that Trump personally be barred from buying property in New York and from borrowing from a New York-registered bank for five years and that a court-appointed receiver monitor the company's finances for that period.

And, as perhaps it's most extreme demand, the lawsuit wants the judge to yank the New York papers of incorporation that let Trump Org draw revenue from his New York properties, including the commercial rents at his Manhattan skyscrapers. 

Litigating all those meaty demands and all those shoals of paperwork will take time, particularly pretrial. 

"She will pay for bringing such an aggressive, gargantuan, and unwieldy case," Morian predicted, "assuring that this case will move at a snail's pace, to the defendants' advantage."

Along the way, "it's possible that there will be other lawsuits or other actions by the counter-parties," such as the banks, accountants and appraisers that James' lawsuit also mentions, Morian said.

A battle over the Fifth 

McCallion thinks Trump's decision to plead the Fifth more than 440 times during his court-ordered August deposition before James is the former president's legal "Achilles heel" and will be fought over especially hard.

Should he keep the case, and should it go to trial, Engoron is allowed to hold Trump's refusal to answer questions against him. Much of the pre-trial litigation will involve how much weight the judge can give all that Fifth-pleading.

Finally, as the case lurches closer to trial, it will then enter what Morian calls the "battle of experts" phase, with dueling reports, reply reports, and eventually expert trial testimony. 

The AG and the defendants will likely spend hundreds of thousands of dollars on these experts, who will duke it out on paper and on the witness stand over whether Trump's valuations were reasonable and how common it may be for businesses to offer different appraisals to impress banks, insurance brokers and tax authorities.

James' experts will call fraud on Trump's alleged practice of offering widely varied appraisals for the same properties, depending on the hoped-for outcome, the former prosecutors said. The defendants' experts will call it business as usual.

"A case does not get better with age," McCallion noted of the long, pre-trial haul ahead.

Just another litigant

"The AG is at the height of her powers before she sues," Morian noted, crediting New York's tough executive law, which grants its AGs broad power to subpoena for evidence and testimony and fast-tracks fraud and corruption inquiries.

But after she files the lawsuit, he said, "she's just another litigant," in an often slow-moving legal system Trump knows how to game.

James will push for a tight motions schedule, but, "I'm not sure what basis she'll have for that. Where's the fire?" Morian asked. "Where's the emergency?"

Meanwhile, Trump has every reason to heel-drag.

"He will raise money on it, and he will campaign on it," Morian predicted of the lawsuit. "He doesn't want this resolved before the 2024 election, in case it goes against him."

There's another benefit to dragging out motions practice. The longer the case takes, the more likely the statute of limitations will expire on any potential criminal wrongdoing.

Trump would then be able to testify on his own behalf at any potential civil trial without the threat of incriminating himself.

Any trial testimony would help blunt the fact that Trump pleaded the Fifth some 400 times during last month's deposition at the AG's office in Manhattan.

Could the case drag out 13 years? "Probably not. But who knows," Morian said with a laugh, noting that however long it goes, Trump appears ready for the long haul.

"Whatever you want to say about him," Morian said, "he's a pretty energetic guy."