As Trump’s Criminal Trial Approaches, He May Be His Own Worst Enemy

Donald J. Trump was minutes away from being grilled under oath by the New York attorney general and he was itching to talk. To fend off the state’s fraud investigation, the former president insisted on answering every question, believing he alone knew what to say.

But his lawyer at the time, Ronald P. Fischetti, directed Mr. Trump to keep quiet.

He instructed the former president to invoke his Fifth Amendment right against self-incrimination during the 2022 deposition with the attorney general, Letitia James, according to two people with knowledge of the discussion. Mr. Fischetti warned Mr. Trump that he was risking perjury charges, and that he would come to regret it.

Mr. Trump relented, but his legal problems were only just beginning. Over the past year, he was indicted four times and faced three civil trials. And as the former president’s first criminal trial approaches on March 25, it has become clear — as it was to Mr. Fischetti — that the single person who poses the greatest danger to Donald J. Trump may just be Donald J. Trump.

In two of the recent civil trials, the former president directed his lawyers to object at inopportune moments, ranted about the judges and even stormed out of the courtroom. He lost both trials and was ordered to pay more than half a billion dollars combined.

Now, a new team of lawyers is preparing to defend him in Manhattan, where prosecutors have accused Mr. Trump of covering up a potential sex scandal that could have swayed the outcome of the 2016 election. It is not only Mr. Trump’s first criminal trial, but the first time any former American president has faced prosecution. And how the legal team corrals Mr. Trump — or fails to — could determine whether he is also the first former president to be convicted.

“I would expect Trump to try to act up,” said Ty Cobb, a veteran lawyer who worked in the White House Counsel’s Office during the Trump administration and who has since been critical of the former president. He added: “He needs to be aggressively muzzled by the lawyers if he is to avoid offending the jury.”

This article is based on interviews with 14 people who have either represented Mr. Trump and his family or witnessed up close his outsize influence on his own legal strategy. The people, some of whom requested anonymity to speak freely about Mr. Trump, noted his extensive experience with civil cases, both defending and bringing them.

But there is a difference between civil and criminal trials, and between setting a broad strategy and grasping the nuances of argument and diplomacy that make for a successful defense.

Mr. Trump faces steep odds in his first criminal case, which was brought by the Manhattan district attorney, Alvin L. Bragg. Mr. Trump’s belligerent courtroom antics might not resonate with a jury in Manhattan, where only about 12 percent of voters supported him in the 2020 election. And Mr. Bragg’s evidence is extensive, featuring documents, tape recordings and testimony from Mr. Trump’s onetime confidants.

To avoid conviction, his defense team, led by Todd Blanche and Susan R. Necheles, will have to be stellar. They will most likely argue that the evidence does not directly implicate Mr. Trump, and that the witnesses are liars.

Like Mr. Fischetti, who recently died, Mr. Blanche and Ms. Necheles are experienced criminal lawyers. But they will have to strike a tricky balance: appeasing their powerful and impulsive client without losing the jury or angering the judge, Juan M. Merchan.

For now, Mr. Trump’s behavior at hearings in his criminal cases has differed markedly from the civil trials: There have been no outbursts and less posturing. On Friday, while in a Florida courtroom for one of his federal criminal cases, Mr. Trump appeared almost perky as he smiled and joked with Mr. Blanche, who represents him in three of the four pending criminal trials. When Mr. Trump was president, he appointed the judge overseeing that case.

A spokesman for Mr. Trump’s campaign, Steven Cheung, said that Mr. Trump “and his legal team will continue to fight the Democrat-led witch hunts in the courts and at the ballot box,” an apparent reference to Mr. Bragg and Ms. James being Democrats.

Typically, defendants play a role in preparing their cases, and sometimes an important one. Seldom, though, do they formulate, let alone dictate, trial strategy or make spontaneous tactical decisions from the defense table.

In two of his recent losing civil cases Mr. Trump did exactly that. The major questions in the cases were essentially decided by the time Mr. Trump arrived, but the trials were held to determine what penalties he’d face.

In the first of the trials, Ms. James, the attorney general, accused Mr. Trump of fraudulently inflating his net worth. The former president made regular visits to the courtroom and his influence on the proceedings was apparent as he wrote notes to his lawyers and whispered in their ears.

Early in the trial, to illustrate how Mr. Trump exaggerated his wealth when pursuing potential deals, a lawyer for the attorney general asked a witness about Mr. Trump’s failed effort to buy the Buffalo Bills of the National Football League a decade ago.

When a lawyer for Mr. Trump, Christopher M. Kise, stood up to object, Mr. Trump motioned for him to lean down. After a brief discussion with his client, Mr. Kise declared that Mr. Trump had had enough money to purchase not only one N.F.L. team, but “maybe two or three.”

“Are you testifying as an expert to the N.F.L.?” the judge, Arthur F. Engoron, asked, overruling Mr. Kise’s objections. Mr. Trump later complained to advisers that Mr. Kise had not sufficiently followed his directives.

When Mr. Trump was present, his lawyers seemed more likely to grandstand, as though they were fulfilling his expectations of a performance. During closing arguments, another Trump attorney, Alina Habba, echoed her client’s dire warnings, saying at one point that if Ms. James were to win, “New York is screwed.”

“They are not living in the real world,” Ms. Habba said of the attorney general’s lawyers, waving her hands in the air. “They’re living in this crazy world.”

Justice Engoron, who presided over the case without a jury, cut her off when she attacked Ms. James for supposedly having her shoes off and drinking Starbucks coffee in court.

After the trial, the judge came down hard on Mr. Trump, imposing a $355 million penalty that, after interest, has climbed to more than $450 million. In his ruling, Justice Engoron singled out Mr. Trump’s testimony — Ms. James called him as a witness — writing that when he took the stand, he “rarely responded to the questions asked,” behavior that “severely compromised his credibility.”

Mr. Trump also undercut his lawyers in his other recent civil trial, in which the writer E. Jean Carroll asked a jury to penalize him for defaming her. The former president attended nearly every day of that trial, badgering Ms. Habba, who led his defense.

Mr. Trump audibly exhorted her to “get up” to protest something said by the judge, a witness or Ms. Carroll’s lawyers, at one point banging Ms. Habba’s arm with the back of his hand. Sometimes she took his directives; other times she shook her head lightly, apparently brushing him off.

As the former president prepared to testify, the judge, Lewis A. Kaplan, asked Ms. Habba whether Mr. Trump would heed restrictions the judge had placed on him.

Ms. Habba said that while she did not have a crystal ball, Mr. Trump would “absolutely.” But before she could finish, Mr. Trump interrupted, prompting a scolding from Judge Kaplan.

In pushing his lawyers to be more aggressive, Mr. Trump may be searching for someone to emulate his earliest lawyer and fixer, Roy M. Cohn, an unscrupulous defender against whom Mr. Trump has measured other lawyers for decades. Mr. Cohn, who was known for scorched-earth tactics honed while working for Communist-hunting Senator Joseph McCarthy and Mafia bosses, was eventually indicted and disbarred. He died of AIDS in 1986; Mr. Trump dropped him when he fell ill.

It is no secret that Mr. Trump is not an easy client. Over five decades, he often has failed to pay lawyers — occasionally prompting lawsuits — and has come to believe that he knows better than them all. A key variable in the criminal trial will be whether that self-assurance will lead him to testify.

In the first of the two civil trials that Mr. Trump lost to Ms. Carroll, he did not testify or even attend, and a jury found he had sexually abused her in the 1990s and decades later defamed her when she disclosed it. Mr. Trump was ordered to pay $5 million.

After the verdict, he told The New York Times that he had wanted to testify, but that his lawyer Joseph Tacopina had advised against it. Mr. Tacopina had believed that Mr. Trump’s earlier sworn deposition, in which he denied the abuse, was the best way of addressing the allegations.

After the second defamation trial — in which Mr. Trump did testify and regularly attended — he was ordered to pay $83.3 million.

Lawyers who have represented Mr. Trump view the prospect of him testifying before Justice Merchan as potentially disastrous. The judge is a no-nonsense jurist who presided over the conviction of Mr. Trump’s family business in a tax fraud trial.

If Mr. Trump insists, he could pose a make-or-break challenge for Mr. Blanche and Ms. Necheles.

They recently appeared before Justice Merchan at a pretrial hearing with their client mostly silent beside them, and seemed to test the tightrope he will walk during the trial. Mr. Trump wanted to delay it, but the judge promptly set a March date.

Mr. Blanche lodged objections, none of which swayed Justice Merchan, who quickly bridled. “Tell me something you haven’t already said today,” the judge said.

Shortly thereafter, Justice Merchan asked Mr. Blanche if he was done talking. He was not, but the judge cut him off, instructing Mr. Blanche to “please have a seat.”

“Yes, your honor,” Mr. Blanche replied, sitting down with Mr. Trump.