Inside Trump’s Gambit to Get Rid of a Judge by Suing Him

For nearly a year, Donald Trump has been forcefully trying to replace the state judge overseeing his upcoming bank fraud trial against the New York Attorney General. But by taking the remarkable step of suing the judge and AG together in a higher court this week, the former president has created the illusion of a united front against him—one that could be used as an excuse to yank the judge off the case.

There is now mounting concern—among legal observers and those involved in the case who spoke exclusively to The Daily Beast—that Trump is creating the groundwork for a bogus legal challenge. The idea, they said, would clearly be an attempt to throw yet another wrench in the gears on the eve of a gargantuan trial, which was set to begin Oct. 2.

A source familiar with the inner workings of the investigation said they’re now preparing for something of a one-two punch, with Trump’s lawyers positioning themselves to argue that Justice Arthur F. Engoron can’t possibly be fair and impartial at trial, because he is now a defendant standing opposite the former president in a new ongoing case—never mind that Trump’s the one who decided to sue him.

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“You can’t claim a conflict if you created one. It’s very unlikely that would succeed,” said Cynthia Godsoe, a professor at Brooklyn Law School.

Trump is about to face off with New York Attorney General Letitia James in state court, where she is trying to demolish his real estate empire by draining its profits and revoking its business charters. Her office’s massive investigation discovered what it called a pattern of “persistent and repeated business fraud” by the Trump family, which vastly overstated the value of buildings and properties to score billions of dollars in bank loans and insurance policies.

James, a Democrat, poses a serious threat to Trump’s riches with her $250 million-plus lawsuit. But so does Judge Engoron, whose grip on the gavel has only tightened as the investigation has progressed since 2020.

From the outset, Engoron has been holding the Trumps accountable—and they’ve been trying to get him off the civil case.

In August 2020, the investigation first surfaced in public when the AG’s office asked a judge to step in and force the Trump Organization, some outside contractors, and the real estate tycoon’s son Eric to comply with subpoenas. The first judge quickly and voluntarily recused herself, landing the case before Engoron—a longtime state law clerk who quietly moved up through the ranks in Manhattan’s local courts. Defense lawyers immediately asked for the case to be transferred to a judge at the more business-friendly commercial division, but the civil division’s administrative judge quickly shot that down.

Then came the judicial orders. In September 2020, Engoron instructed the Trump Organization to start turning over documents sought by investigators and ordered Eric Trump, two lawyers, and then-chief financial officer Allen Weisselberg to testify behind closed doors.

At first, he seemed to give the Trump side the benefit of the doubt. When he noted that one lawyer was “hardly punctilious in responding to the subject subpoenas,” he granted extra time to sort through the records.

“Let the punishment fit the crime; to err is human, to forgive is divine,” Engoron wrote.

But as the years went by, Engoron—who is known for keeping his cool—became much less willing to play along with what became obvious delay tactics.

In February 2022, he ordered the former president and the three heirs he made company executives to show up for depositions and turn over records. Then, when Trump failed to do that, Engoron held him in contempt of court and fined him $110,000. Trump eventually relented.

Over the course of several court hearings, Trump’s previous lawyer in the case, Alina Habba, frequently made snippy remarks directed at the court and his law clerk—questioning their ability to make fair decisions and voicing expectations that he’d continually rule against her client.

When the AG filed her lawsuit in September 2022, the case was immediately assigned to Engoron, who was already familiar with its long and arduous history. But Trump lawyers once again tried—and failed—to get the case moved to a judge in the commercial division.

In the months since, Engoron has kept summarily dismissing every legal theory the Trumps have flung at him, firmly rejecting the notion that this was merely a politically driven witch hunt and affirming that the AG did indeed have the authority to pursue this lawsuit.

But the Trumps appear to have scored something of a victory this summer, when the First Department appellate court agreed that some business deals might be too old for the AG to include in this lawsuit and instructed Engoron to draw a cutoff. The judge hasn’t done that yet and was expected to do so in the coming weeks, but the Trump lawyers jumped the gun—asking for a three-week delay in the trial and an immediate cutoff clarification from Engoron. When he rejected that too, lawyers on Thursday made the surprise move of filing what’s called an “Article 78” petition against Engoron himself.

According to legal scholars, that kind of legal action is usually used to stop a state or city agency from breaking the law. It’s also the kind of time-sensitive lawsuit meant to rein in a judge who’s abusing their authority or about to make a hugely detrimental error in a case.

Diane Peress, a former prosecutor who also spent a decade at the New York AG’s office, remembers using it only twice during her career—when trying to stop a judge from releasing grand jury transcripts that she said could have put a witness in danger. But this time, it seems out of bounds.

“Does this Article 78 seem to be premature? Yes. It’s kind of transparent that they’re asking this as they ask for a three-week delay. It’s like, ‘That didn’t work, so let’s throw a wrench in the machinery,’” said Peress, who teaches at John Jay College of Criminal Justice.

According to New York state law, judges who get hit with this kind of lawsuit are typically represented by the AG’s office. But that would naturally create a conflict here, because the judge is overseeing a case involving the AG. So the court system itself is providing his lawyers, and he’s expected to take no stance at all as the case makes its way through a five-person appellate panel in the next two weeks. On paper, however, the case still creates the appearance of an us-versus-them scenario, with Trump on one side and the judge and AG on the other.

Peress said the decision to target Engoron this way is nothing more than a political gambit—and an empty one at that.

She likened it to the way Trump has recently turned his unbridled rage from the prosecutors who keep indicting him to the judges overseeing those criminal cases, like U.S. District Judge Tanya Chutkan in Washington and Justice Juan Merchan in New York. She noted it’s a move Trump has not taken against the MAGA-friendly U.S. District Judge Aileen M. Cannon in Florida, whom he appointed himself and who now oversees his case involving classified documents he hoarded at Mar-a-Lago.

“Is it a Trump tactic, one more of these tactics to get rid of the judge? He’s done it with all the rest of the judges. He finds reasons to try and knock them off the case,” Peress said.

“He’s doing everything he can to provoke some kind of animosity and hostility with the judge,” she added. “Harassing them on social media or bringing an Article 78, these are all different ways of provoking the judge into a position where you can show that the judge can’t be fair and impartial. This is just one more strategy.”

Trump’s legal team did not respond to a request for comment.

The former president, who is drowning in legal trouble as he runs a 2024 presidential campaign, keeps running into brick walls as his characteristic defiance crashes head-on with the American justice system. And this one is no different.

If Trump decides to use this latest lawsuit against Engoron as a pretext to try getting rid of him, he’s likely to get quickly shot down. One reason Article 78 proceedings are rarely used is because they tend to irritate the judge—especially if an appellate court has to correct them—and the case stays with them. The law was designed to do exactly that, according to Brooklyn Law School professor Jayne Ressler.

Judge Won’t Let Banks and Insurers Hide Their Trump Docs

“The idea is that they didn’t want to set up a scheme where you just bring an Article 78 against the judge and get a new judge,” she said. “Otherwise, it would be so easy to say, ‘I don’t like how this case is going. Article 78!’ Then boom, you get a new judge.”

If litigants and people charged with crimes could do that, they’d do it all the time.

“The higher courts are aware of the fact that you want to judge-shop,” Peress said.

Instead, any attempt to boot Engoron off the case must be viewed through a political lens, legal scholars said. If Trump thinks he’s destined to lose the case before the AG, then any long-shot legal gamble or loud protest won’t make things any worse than they already are.

“He’s lost before he started. He’ll say he never got a fair shake and this is the perfect excuse. Any regular individual would do the opposite. But this is Trump. When the coffin is closed, he drills a hole,” Ressler said. “He’s literally cornered, so he might create a political ploy. So now, when he loses, this is his out.”

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