“Fyre Festival strategy”: Lawyer warns Trump’s stunts in NY fraud trial “just begging for sanctions”

In the weeks leading up to his $250 million civil fraud trial in New York, Donald Trump and his legal team had privately accepted defeat and agreed that fighting the case on appeal was their best bet, sources told Rolling Stone. Those beliefs resulted in their development of a courtroom strategy defined by cacophony and chaos instead of efforts to win the case on the merits, an approach one source close to the former president dubbed “Fyre Festival strategies.”

That method — “let’s just do it and be legends” per the failed festival’s founder — famously led Fyre Fest to be a scandal-laden catastrophe. Trump and his lawyers, however, are hoping that as a legal strategy, the approach will transform the proceedings into a “media circus,” Rolling Stone reports, by boosting the former president’s public relations, shaking the table, angering the judge and gratuitously smearing some of the witnesses.

While the strategy likely aligns with Trump’s typical approach, it also risks undermining his team’s legal work in defending the business empire that elevated him to celebrity status and the Oval Office long term as its future hangs in the balance

New York Supreme Court Justice Arthur Engoron has already fined Trump’s lawyers $7,500 each for repeatedly rehashing legal arguments he’s already dismissed. Trump, however, has privately suggested in recent weeks that his attorneys should “worry” about getting further court sanctions for their planned antics, the sources told Rolling Stone. 

In light of those instructions, the legal team has concocted an aggressive trial game plan that includes what one Trump advisor called “below the belt” attacks on witnesses, prosecutors and the judge, alongside possible threats of retaliatory lawsuits against some of those people. Trump’s trial lawyers — which include Chris Kise, Alina Habba and Jesus Suarez — have also taken to a number of delay tactics meant to upset Engoron during trial, which is scheduled for three months. One such tactic, which they debuted during the trial last week, involves pelting witnesses with lengthy, drawn-out questions and consistently repeating arguments the judge has already thrown out, the sources said.

“A lot of this is just begging for sanctions,” one attorney who’s known Trump for years told the outlet. “It is not how I’d do it, but … maybe that’s a reason I’m not on the [legal] team.”

In the weeks before the trial, Trump specifically discussed with some of his legal and political advisors how much he looked forward to his attorneys making his former fixer, Michael Cohen, “cry” on the stand, a person familiar with the situation told Rolling Stone. The former Trump lawyer is now listed as a witness for New York Attorney General Letitia James’ office and was slated to go toe-to-toe with Trump in a lawsuit the former president had filed against him before Trump dropped it last week.

Trump hopes to relentlessly go after Cohen’s character, intelligence, professional acuity, federal criminal charges and personal life, encouraging his attorneys to “fight rough and fight dirty, if you got to” with his former lawyer and others during the trial, a person close to Trump told Rolling Stone, paraphrasing what he said. The source, who has repeatedly spoken to the former president about this case, added that Trump gets especially worked up when discussing Cohen.

Cohen, however, told Rolling Stone that he is unfazed. 

“I have provided a hundred hours of testimony before members of Congress, law enforcement agencies, and committees whose, on behalf of Donald, primary goal was to denigrate me, discredit me, and harass me. None of it has worked, and it won’t work now when I take the stand in the [New York attorney general’s] case,” Cohen said. “I am certain Judge Engoron will not allow Donald’s legal team to make a mockery of his court and allow these antics to occur.”

But if Trump’s legal team sticks to their plans, Engoron’s interventions won’t stop them from repeatedly trying.

Suarez already provoked the judge last week with a lengthy questioning of former Trump accountant Donald Bender. As the attorney tried to probe Bender with a series of lengthy and repetitive questions pertaining to nearly a dozen years of Trump’s financial filings, Engoron erupted over what he deemed a “ridiculous” line of questioning that he said would “waste time.”

The strategy is textbook Trump, geared toward generating PR buzz as “the Fox News set,” one of the sources briefed on the plans described. It’s also an approach that the judge appears to have caught onto. “Who are you talking to — me, the press, or the audience?” Engoron said to Trump’s lawyers during the second day of the trial.

Even then, among Trump’s slates of attorneys, the method is not without its faults. Trump’s legal teams, including ones litigating the high-stakes civil and criminal cases against him, are fraught with infighting, betrayals, power grabs and resignations. Some Trump legal counselors also believe the strategy could easily blow up in their faces, result in too many costly sanctions and ultimately make an appeal harder to achieve, people with knowledge of the matter told Rolling Stone. There are other Trump attorneys who believe that if the current approach fails, the former president will harshly blame and reprimand his legal team despite it being his preferred methodology to begin with. 

There are few, if any signs of an imminent overhaul on the horizon for Trump’s civil fraud trial legal team, but Trump is leaving his options open. In the past two weeks, he has discussed with some of his longtime associates other possible defense attorneys he could ask to join his New York legal squad, two sources with knowledge of the matter told the outlet. Some of those names were of attorneys who didn’t have a background in the kind of law necessitated by this trial. 

The trial, which entered its second week Monday, represents the beginning of the culmination of James’ yearslong investigation into allegations against the Trump organization. She launched the probe in 2019 and filed a suit against Trump in 2022, accusing Trump, the organization and its other key executives of committing fraud by drastically inflating or deflating the value of its assets by millions of dollars on financial filings. 

Late last month, Engoron ruled that the former president and his sons were liable for defrauding banks and insurers and ordered the dissolution of some of his businesses, a move an appellate court paused last week. 

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That order prompted Trump, who often chooses to skip his legal proceedings, to make a rare public appearance at the start of the trial last week. He took the opportunity to shore up publicity surrounding the case by calling for the judge to be disbarred, pushing baseless claims about the court clerk and earning himself a limited gag order for attacking court staff.

Sources who have spoken to Trump have told Rolling Stone that he has repeatedly underscored that his attendance in court was motivated by a desire to publicly defend his business reputation, his net worth and claims about the value of his assets, all of which the case has brought into question.

The sources added that Trump is especially sensitive to allegations he and his business overvalued his properties and has long placed a lot of emotional value on his status on Forbes’ list of the richest Americans. In a sign of how much the case has affected Trump, a person with direct knowledge of the situation told the outlet that in the past month, the former president has — unprompted — interspersed comments about his wealth in the middle of unrelated conversations, in addition to making complaints that people are “lying” about his personal and corporate network and the value of Mar-a-Lago. 

Trump has also indicated that he wants to testify in the case. “At the appropriate time I will be,” he told reporters last week in New York.

James has also signaled a desire to get Trump, his sons Don Jr. and Eric, and his daughter Ivanka on the stand. She listed all four in a proposed witness list, the Daily Beast first reported.

Though the former president has earned a reputation for saying he’ll take testify during an investigation or court proceeding, his attorneys often later belabor the process with delay tactics, in part, because they fear he’ll lie or possibly incriminate himself under oath.

“Of course that remains an issue, as always,” said a source familiar with the Trump team’s internal discussions on the matter, adding. “But we have a while to go before he would even [possibly] take the stand.” 

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