As Trump’s criminal trial approaches, he could be his own worst enemy

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

But his then-lawyer, Ronald P. Fischetti, ordered Trump to keep his mouth shut.

He instructed the former president to invoke his Fifth Amendment right against self-incrimination during the 2022 deposition to Attorney General Letitia James, according to two people with knowledge of the discussion. Mr. Fischetti warned Mr. Trump that he risked being charged with perjury, and that he would regret it.

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

In two of the recent civil trials, the former president instructed his lawyers to object at inopportune moments, railed against the judges and even stormed out of the courtroom. He lost both lawsuits 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 affected the outcome of the 2016 election. It is not only the first criminal trial against Trump, but also the first time that a former American president has been prosecuted. And how the legal team holds Mr. Trump together — or fails — could determine whether he is also the first former president to be convicted.

“I would expect that Trump would try to take action,” said Ty Cobb, a veteran lawyer who worked in the White House Counsel’s Office during the Trump administration and 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 represented Mr. Trump and his family or witnessed first-hand his outsized influence over his own legal strategy. The people, some of whom requested anonymity to speak freely about Mr. Trump, noted that he has extensive experience in civil cases, both defending and bringing them.

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

Trump faces long odds in his first criminal case, brought by Manhattan District Attorney Alvin L. Bragg. Trump’s combative courtroom antics may 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, including documents, tape recordings and testimony from former confidantes of Mr. Trump.

To avoid conviction, his defense team, led by Todd Blanche and Susan R. Necheles, will have to be excellent. 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 passed away, Mr. Blanche and Ms. Necheles are experienced criminal defense attorneys. But they will have to strike a tricky balance: appease their powerful and impulsive client without losing the jury or angering the judge, Juan M. Merchan.

For now, Trump’s behavior during hearings in his criminal cases has differed markedly from that in 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 seemed almost perky as he smiled and joked with Mr. Blanche, who is representing him in three of the four pending criminal cases. When Mr. Trump was president, he appointed the judge who oversaw that case.

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

Suspects usually play a role in the preparation of their case, and sometimes an important one. But rarely do they formulate, let alone dictate, test a strategy or make spontaneous tactical decisions from the defense table.

In two of his recent losing civil cases, Trump did just that. The key questions in the cases had essentially been decided by the time Trump arrived, but the trials were held to determine what punishments he faced.

In the first trial, 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 evident as he wrote notes to his lawyers and whispered in their ears.

To illustrate how Mr. Trump exaggerated his wealth in pursuing potential deals, a lawyer for the attorney general asked a witness early in the trial about Mr. Trump’s failed attempt to buy the National Football League’s Buffalo Bills ten years ago.

When a lawyer for Mr. Trump, Christopher M. Kise, stood up to object, Mr. Trump motioned for him to lean forward. After a brief conversation with his client, Mr. Kise stated that Mr. Trump had had enough money to buy not just one NFL team, but “maybe two or three.”

“Are you testifying as an expert for the NFL?” asked the judge, Arthur F. Engoron, as he overruled Mr. Kise’s objections. Mr. Trump later complained to advisers that Mr. Kise had not adequately followed his directives.

When Mr. Trump was present, his lawyers seemed more inclined to stand on the stand, as if fulfilling his expectations of an appearance. During closing arguments, another Trump lawyer, Alina Habba, echoed her client’s dire warnings, saying at one point that if Ms. James won, “New York is screwed.”

“They don’t live in practice,” Ms. Habba said of the attorney general’s lawyers, waving her hands in the air. “They live in this crazy world.”

Judge Engoron, presiding over the case without a jury, interrupted her as she attacked Ms James for allegedly taking off her shoes and drinking Starbucks coffee in court.

After the trial, the judge came down hard on Mr. Trump, imposing a $355 million fine, which, after interest, has risen to more than $450 million. In his ruling, Judge Engoron highlighted Mr. Trump’s testimony — Ms. James called him as a witness — and wrote that when he took the stand, he “rarely responded to the questions asked,” behavior that “seriously compromised his credibility.” .

Mr. Trump also undermined his lawyers in his other recent civil lawsuit, in which the writer E. Jean Carroll asked a jury to punish him for defaming her. The former president attended that trial almost every day and harassed Ms. Habba, who led his defense.

Mr. Trump audibly urged her to “stand up” to protest something said by the judge, a witness or Ms. Carroll’s lawyers, at one point pressing the back of his hand on the woman’s arm Mrs. Habba hit. Sometimes she followed his directives; other times she shook her head slightly and apparently waved him away.

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

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

In pushing his lawyers to be more aggressive, Mr. Trump may be looking for someone to match his first lawyer and fixer, Roy M. Cohn, an unscrupulous defense attorney against whom Mr. Trump has been counting other lawyers for decades. Mr. Cohn, who was known for scorched-earth tactics he honed while working for communist-hunting Senator Joseph McCarthy and mob bosses, was eventually indicted and disbarred. He died of AIDS in 1986; Mr Trump dropped it when he became ill.

It’s no secret that Mr. Trump is not an easy client. Over the past fifty years, he has often failed to pay lawyers – occasionally leading to lawsuits – and has come to believe he knows better than them all. A key variable in the criminal trial will be whether that self-confidence 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 that he had sexually assaulted her in the 1990s and defamed her decades later when she did so made public. 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 believed that Mr. Trump’s earlier affidavit, in which he denied the abuse, was the best way to address the allegations.

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

Lawyers who have represented Mr. Trump view the prospect of him testifying before Judge Merchan as potentially disastrous. The judge is a no-nonsense lawyer who led 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 Judge Merchan at a pretrial hearing, with their client standing near them in near silence, appearing to test the tightrope he will walk during the trial. Trump wanted to postpone it, but the judge promptly set a date in March.

Mr. Blanche filed objections, but none moved Judge Merchan, who quickly reined in. “Tell me something you haven’t said today,” the judge said.

Shortly afterwards, Judge Merchan asked Mr Blanche if he had finished talking. That was not the case, but the judge interrupted him and instructed Mr Blanche: ‘Please sit down.’

“Yes, Your Honor,” Mr. Blanche replied, sitting down with Mr. Trump.