As Donald Trump prepares to take the stand in the civil fraud trial that could destroy his business empire, the ex-president and his attorneys have settled on a strategy built on spite and unbridled antagonism. According to two sources familiar with the matter and another person briefed on Team Trump’s legal strategies, the former president and his lawyers are intentionally trying to provoke the judge into a nuclear-level overreaction.

Inviting that kind of response could even lead to the judge ordering Trump to be remanded to a jail cell for the night. The judge in the case had already imposed a gag order on Trump, warning him to refrain from attacks on the judge’s staff. Late last week, the order was expanded to also include Trump’s attorneys. Trump has still shown a brazen willingness to violate it repeatedly. And as bizarre as it may sound, there are attorneys and political advisers to Trump who have told the former president that a so-called “remand order” to put him in custody for repeatedly breaching the judge’s rulings might be a good thing — both legally and politically.

The ex-president’s legal advisers had long ago told Trump that his chances of winning at trial are close to zero — hence, their scorched-earth, “Fyre Festival”-style courtroom performances. According to the three sources, several Trump attorneys and other key allies have advised him that the more the New York judge supposedly “overreacts” — including perhaps remanding Trump — the better their case for an appeal will be. 

“I call it the Chicago 7 disruption strategy,” Alan Dershowitz, the celebrity lawyer who defended then-President Trump during his first impeachment, tells Rolling Stone. 

“When a defendant honestly believes he can’t possibly get a fair trial from the judge, one of the tactics is to antagonize the judge to a point of causing reversible errors,” Dershowitz says. “That is what happened in the Chicago 7 case, and I was one of the lawyers on the appeal in that case. Abbie Hoffman provoked Judge Hoffman to such a degree that the judge made mistake after mistake. And courts of appeal often reverse convictions or verdicts when the judge has made serious errors.”

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In recent weeks, the former president and some of his lawyers in the New York civil fraud trial have discussed the likelihood of Judge Arthur Engoron very aggressively responding to Trump team’s strategy of relentless hostility and defiance. The tactics have included attacks on Engoron’s court clerk, filibustering the prosecution’s witnesses with repetitive questions, and raising legal arguments the judge had already specifically prohibited.  

This has included Trump asking his legal advisers if the judge would, or could, actually go so far as to send him to jail for a short time, the sources tell Rolling Stone. Trump has been told such an order is probably unlikely — though Engoron has publicly put the option on the table. This is one reason why Trump and his counselors have kept up with their brazen strategy of infuriating a judge who has openly threatened the former president with possible jail time. 

The legal team has further assured Trump that even if he were remanded, they would likely be able to deploy a variety of legal tactics to keep him from spending any time behind bars. According to two other sources with knowledge of the situation, some Trump advisers have already reached out to certain outside attorneys to see if those lawyers would be interested in joining that potential fight to keep Trump out of jail. (Some of those lawyers have preemptively turned Team Trump down.)

In addition, there have been recent conversations among some of Trump’s 2024 campaign brass of how much of an immediate fundraising boost they would enjoy, if a New York judge were to try to put Trump in a cell for even a minute. “All the cash in the world,” one Trump political adviser says.

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In the course of the New York civil trial of Trump and his eponymous real-estate organization, Judge Engoron has been visibly enraged by the behavior of the ex-president and his lawyers in court. This has resulted in a limited gag order following Trump’s derogatory remarks about Engoron’s staff, as well as expensive sanctions on both the legal team and Trump. Engoron has made clear that if Trump continues to flagrantly violate his gag order, the judge may take “severe” action, including possibly remanding Trump to jail. Last week, the judge said he and his office have been flooded with “hundreds” of examples of harassment and threats during this trial.

Trump has been surrounded by lawyers who for years have begged him to show restraint or caution. In this case, he is buttressed by attorneys who appear more than willing to join in his preferred public relations, legal, and political tactics of innuendo and mud-slinging. In just the past few weeks, Trump’s attorneys have variously suggested that his former accountant may have “mental health” issues and accused his former attorney Michael Cohen of perjury. 

On Friday, Chris Kise, Trump’s lead attorney in the case, appeared to test the judge’s patience by once again by attacking his court clerk, Allison Greenfield, with claims about her “excessive political donations” from a Wisconsin man who describes himself as “Applying the 69th Amendment to the Internet!” in his Twitter bio.

Kise flagged a Breitbart article which he claimed “raises questions of impartiality” against Trump. The article describes a complaint made by Brock Fredin, who has frequently attacked Engoron and his clerk with crass insults on social media.

Fredin’s attacks had previously helped to land Trump in trouble with Judge Engoron when he posted a screenshot from the man’s Twitter’ account insulting Greenfield on his Truth Social platform. That move earned Trump a gag order and a warning from the judge to steer clear of insulting court staff. 

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But Kise appears undaunted by Engoron’s warnings that he is “very protective” of his staff. On Thursday, he chastised Greenfield for passing notes to the judge, which prompted Engoron to expand Trump’s gag order to include his attorneys. The next day, Kise pressed ahead with gripes about Greenfield in the Breitbart article and claimed that the “defense will have to give serious consideration to seeking a mistrial” because of them.

While Trump’s attorneys stoke the judge’s ire, it’s unclear how far Engoron would likely go with Trump himself should he continue to ignore the gag order against him. Various lawyers, including some retained by Trump, privately concede that if Trump were an ordinary citizen, he likely would have been remanded by now for his behavior. But Trump is not an ordinary citizen. His position as the 2024 GOP presidential frontrunner and leader of the Republican Party would make any decision to impose jail time, even if brief, extremely politically fraught.