Donald Trump and his legal team are using a high-stakes strategy in his ongoing civil fraud trial in New York. As Trump faces the possibility of his business empire crumbling, his lawyers are reportedly provoking the presiding judge, Arthur Engoron, to the extent of risking jail time for the ex-president.
Celebrity lawyer, and Martha’s Vineyard outcast, Alan Dershowitz explains that this tactic, reminiscent of the Chicago 7 disruption strategy, is used when a defendant believes they cannot receive a fair trial. By antagonizing the judge, the defendant aims to induce reversible errors, potentially strengthening their case for an appeal.
This trial is not just about the legal intricacies of property valuation. It’s a litmus test for the rule of law and the accountability of those in power. The former president’s decision to assail the judge and the attorney general from the stand is indicative of a broader trend of undermining judicial and legal authority. He is pushing the boundaries and his MAGA chuds are eating up like sweet sugar.

Trump’s behavior in court has been defiant, with rants about his “haters” and dodging questions, leading Judge Engoron to repeatedly scold him and warn his attorneys to control their client. Engoron has even threatened to draw negative inferences if Trump’s conduct continues.
A negative inference in a civil trial refers to a conclusion a judge or jury can draw from a party’s failure to present evidence or testimony that could have been material to the case and that was within their control to provide. This usually occurs when it is expected that the evidence or testimony would have been adverse to the party’s case if it were presented. Basically refusing to answer because the answer is bad for your defense.
Despite the risks, some of Trump’s advisors see a potential remand order as beneficial both legally and politically. They believe that an “overreaction” from the judge could aid their appeal and even boost Trump’s 2024 campaign fundraising efforts.
This strategy seems to be consistent with how Jason Miller has as advised Trump previously. Miller has been a longtime Trump aide, and recently joining the 2024 presidential campaign as a senior advisor. He has previously served as a top advisor and also as Communications Director for Trump’s 2016 and 2020 campaigns. Miller is a slash and burn, take no prisoners type of strategist. This fits perfectly in Trumps wheelhouse.
In the last weeks, the trial has been marked by contentious moments, including attacks on Engoron’s court clerk and suggestions of mental health issues with Trump’s former accountant. A few days ago, attorney Chris Kise, tested the judge’s patience, particularly with claims about the court clerk’s political donations. When challenged on his sources, Kise remarked ‘Breitbart’ which set the courtroom onto a wave of muted laughter.

Yesterday, however, Trump was in rare form giving testimony. This was an obvious attempt to delegitimize the indictment specifically, and the court system generally:
“I think this case is a disgrace. Many people are leaving New York because of exactly this kind of thing. It’s election interference because you want to keep me in the courthouse.” — Donald Trump
Kevin Wallace, the NY AG attorney, asked Trump if the $550M valuation for 40 Wall Street is accurate, Trump responded nonsensically with a crack about the statute of limitations, which then sent Judge Engoron into beast mode.
“Five year statute of limitation. You’re still on 2014,” Trump said. Engoron responded, “Mr. Kise that was a simple yes or no question. We got another speech. I beseech you to control him if you can. If you can’t, I will. I will excuse him and draw every negative inference that I can.”
While Trump’s legal team continues to stoke the judge’s ire, it remains unclear how far Engoron will go before acting. Trump’s status as the former president and current presidential candidate complicates the potential for jail time, despite behavior that might have led to remand for an ordinary citizen. Engoron could remand Trump for a day or a weekend, but this is most likely counterproductive. I think Engoron is going to take most of it without acting; using all the crap Trump dishes in his written opinion.
Tomorrow, the NY AG is expected to rest its case after Ivanka Trump testifies. She will likely be the last witness for the state before Trump’s defense team will begin presenting its case next Monday. This could include Trump himself taking the stand again, as well as testimony from other witnesses and experts.
My prediction for the next phase of the trial is utter chaos. Kise elected not to cross-examine the witness so far, it seems like he’s waiting for his chance at direct examination to blow up the tenor of the courtroom. He will probably ask long, leading questions, to give ample opportunity for the witnesses to make speeches. Let’s see if Engoron goes along.
I took a look at the witness list Trump submitted (PDF), and it omits the witness’s affiliation. It is just names with a few descriptors. What I don’t believe will happen is a long parade of bankers and insurance executives testifying that ‘they don’t look at financial statements’ and that ‘we didn’t need those higher interest rates’ that the NY AG showed were worth at least $168M in lost income due to Trump’s manipulation of his financials when seeking financing or insurance coverage.
Because he’s already lost on the first, most impactful indictment count, the defense phase of the trial is entirely performative surrounding the additional counts where the NY AG has to prove there were material negative consequences for Trump’s counterparties (and that this negative impact violated NY financial law).
Stephen Sondheim brings it home:
Don’t you love the farce
My fault, I fear
I thought that you’d want what I want
Sorry my dear
But where are the clowns
Send in the clowns
Don’t bother they’re here