In the weeks leading up to the start of his $250 million civil fraud trial in New York, Donald Trump and his attorneys privately discussed how they believed defeat in this trial was preordained. Their best chance — and it wasn’t much, according to two sources familiar with the matter and another two people briefed on internal deliberations — would be to fight the case on appeal.
This belief led to the development of an approach to the case that centers around chaos and cacophony, rather than any attempt to win it on the merits. One person close to Trump describes it as the “Fyre Festival strategies.”
That approach — “let’s just do it and be legends,” in the words of the festival’s founder — famously turned Fyre Fest into a scandal-riddled disaster. But Trump and his lawyers are hoping that their legal strategy in their ongoing courtroom “suicide mission” will score some political and public-relations points for Trump, kick up as much dirt as possible, enrage the judge, gratuitously trash some of the witnesses, and turn the process into a media circus.
The aggressive approach is likely to appeal to the former president’s notable taste for the jugular. But the client-pleasing strategy also risks undermining the longer term legal work of defending the Trump business empire that propelled him to fame and the presidency as its future hangs in doubt.
Judge Arthur Engoron has already fined Trump’s attorneys $7,500 each for repeatedly bringing up legal arguments he had already barred. But in recent weeks, Trump has privately suggested that his lawyers should not “worry” for now about getting further sanctions by the court for their planned procedural antics, the sources tell Rolling Stone.
Instructed to ignore such concerns, his attorneys have crafted a courtroom game plan that leans on heavy-handed tactics such as deeply personal, at times (in the phrasing of a Trump adviser) “below the belt” attacks on witnesses, prosecutors, and the judge, and also planned threats of retaliatory lawsuits against some of those same people.
Trump and his lawyers — who include Chris Kise, Alina Habba, and Jesus Suarez for this trial — have also long settled on a roster of delay tactics that are almost guaranteed to antagonize Judge Engoron. This includes going into trial, which could last months, with the intention of grilling witnesses with lengthy, meandering questions and repeating again and again arguments that the judge has already deemed frivolous, the sources say.
“A lot of this is just begging for sanctions,” says one attorney who’s known Trump for years. “It is not how I’d do it, but…maybe that’s a reason I’m not on the [legal] team.”
In the weeks prior to the start of the trial, Trump had specifically discussed with some of his legal and political advisers how much he was looking forward to his attorneys making Michael Cohen “cry” on the stand, a person familiar with the situation says. Trump’s former lawyer and fixer is now a listed witness for New York attorney general Letitia James’ office, and the ex-president constantly has revenge on his mind.
Trump hopes that this will be achieved by relentlessly attacking his ex-fixer’s character, intelligence, professional acumen, federal criminal charges, and even personal life. The former president has encouraged his legal team to “fight rough and fight dirty, if you got to” with Cohen and others during the trial, a person close to Trump says, paraphrasing the ex-president. This source has spoken repeatedly to Trump about this case, and adds the former president gets especially animated or agitated when Cohen comes up.
Cohen, however, insists he’s not worried.
“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,” the former Trump attorney tells Rolling Stone. “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.”
If the team sticks to their, and their client’s, plans, Engoron’s interventions won’t stop them from trying — many times.
Suarez, in particular, has already earned Engoron’s ire with a lengthy questioning of Trump’s former accountant, Donald Bender.
As the Trump attorney tried to walk Bender through a lengthy series of repetitive questions concerning nearly a dozen years worth of Trump financial filings, Engoron blew up at what he called a “ridiculous” line of inquiry that would “waste time.” At one point Suarez even asked Bender if he had “any mental health reasons [he] can’t testify today,” prompting an objection from the attorney general’s office.
It is a bombastic, quintessentially Trumpian legal strategy that’s less geared towards impressing a judge who Trump openly despises, and more a PR blitz aimed at “the Fox News set,” one of the sources briefed on the plans characterizes.
And it’s a strategy that Engoron appears to be aware of. “Who are you talking to — me, the press or the audience?” he barked at Trump’s lawyers on Tuesday.
Still, among Trump’s many attorneys and different legal teams, this approach is not without its detractors. Trump’s legal teams, including ones now tasked with handling the high-stakes civil and criminal cases against him, are routinely fraught with infighting, backstabbing, power grabs, and turnover. There are some Trump legal counselors who believe this strategy could easily backfire, result in too many expensive sanctions, and ultimately make an appeal harder, not easier, people with knowledge of the matter say. There are also some Trump attorneys who are convinced that if the current strategy fails to deliver for the ex-president, he will harshly blame and scream at his legal team, even though the mud-slinging was his own preferred strategy in the first place.
There are scant signs of imminent shakeup for this particular Trump legal crew. But that doesn’t mean the former president isn’t keen on keeping his options open. In the past two weeks, Trump has discussed with some of his longtime associates the names of other defense attorneys who he has considered asking to join the New York legal team, two sources with knowledge of the matter say. Some of the names that Trump recently floated were lawyers who didn’t even have a background in the kind of laws at the center of this trial.
The civil trial currently playing out in a New York courtroom represents the culmination of a years-long investigation by New York state attorney general Letitia James into allegations of fraud against the Trump Organization, the heart of the 45th U.S. president’s business empire. James initiated the investigation in 2019 and brought a suit against the former president’s company in 2022, claiming that the organization had engaged in fraud by dramatically overvaluing its assets to the tune of many millions of dollars.
In late September, Engoron ruled that Trump and his sons were liable for fraud alleged in the suit, revoking their business licenses and putting the financial stability of Trump’s family business at risk.
That helped prompt Trump, who has often preferred to skip legal proceedings, to make a rare — and voluntary — public appearance in court last week. He has used the occasion to bask in the publicity surrounding the case, call for the presiding judge, Engoron, to be disbarred, floated baseless conspiracy theories about the court clerk on social media, and earned himself a gag order for the attack on court staff.
Sources who have spoken to the former president say that Trump has repeatedly stressed that his visits to the courthouse were motivated by a desire to publicly defend his long-curated reputation as a talented businessman, his net worth, and claims about the value of his assets — all of which have come into question as a result of the case.
The sources say that the former president is uniquely sensitive to allegations that he and his business inflated their value and has long attached a strong emotional weight to his status on the Forbes magazine list of richest Americans.
In an apparent sign of how much the case has rattled Trump, a person with direct knowledge of the matter tells Rolling Stone that in the last month the former president has repeatedly interjected comments, entirely unprompted, about his wealth in the middle of unrelated conversations. In these sudden outbursts, Trump complains that people are “lying” about his personal and corporate net worth and the value of his Florida club, Mar-a-Lago, the source adds.
Furthermore, Trump has signaled he wants to testify in the case. “At the appropriate time I will be,” he told reporters on Tuesday in New York. James, too, has indicated a desire to put the former president, his sons, Don Jr and Eric, and his daughter, Ivanka, on the stand. As The Daily Beast first reported, the New York attorney general listed all four Trumps in a proposed witness list.
The former president is famous for delivering public bluster about how much he’d relish testifying for an investigation or during an official proceeding, only to later have his attorneys deploy delay tactic after delay tactic. This is in part due to his legal teams’ recurring fears over the many years about just how much he would uncontrollably lie or possibly incriminate himself under oath.
“Of course that remains an issue, as always,” says a source familiar with the Trump team’s internal discussions on this.
“But,” this person predicts, “we have a while to go before he would even [possibly] take the stand.”