Being Held in Contempt Might Not Be Trump’s Biggest Problem

Donald Trump’s extraordinary inability to keep his mouth shut has been costly this year — and it could get a lot worse.

The defamation verdict in the E. Jean Carroll lawsuit already took him for nearly $100 million, and on Monday, he was again held in contempt for violating a gag order that prohibits attacks on witnesses and jurors in his Manhattan hush money trial. It marked the 10th time Trump’s comments had officially crossed the line, and Justice Juan Merchan has been fining him $1,000 per violation. Of perhaps more consequence to Trump, Merchan also warned the former and potential future president that he could be sent to jail if he continues to defy the gag order.

It’s hard to imagine Trump will stop railing against the case on social media and at his campaign rallies, but it’s possible that he can manage just enough impulse control to stay on the right side of the court’s orders going forward.

Unfortunately for Trump and his lawyers, he has already materially damaged his own legal defense in at least two distinct ways. First, he may have created more evidence that prosecutors might be able to use against him in the case.

Second, and much more importantly, Trump is increasing the odds that he will have to spend some time in prison if he is convicted and loses his reelection bid.

The recent statements at issue that Trump has made on social media and in interviews fall into two categories — attacks on witnesses and attacks on the jurors.

In particular, Trump recently took to Truth Social to attack Stormy Daniels, the adult film star with whom he allegedly had an extramarital sexual relationship. Trump has also posted on multiple occasions attacking Michael Cohen, the credibility-challenged former Trump lawyer who turned against him and is now a key witness in the case.

Perhaps most notably, Trump has repeatedly disparaged the jurors on the case. He has echoed Fox News host Jesse Watters’ claim that there were “undercover Liberal Activists lying to the Judge” in order to get on the jury and by claiming that he cannot get a fair trial because the jury was drawn from “a purely democrat area.” The comments that got Trump held in contempt again on Monday came from an interview in which he said that the “jury was picked so fast — 95 percent Democrats.”

Jurors have been instructed to avoid news coverage of the trial, but I consulted several lawyers and law professors with deep experience considering thorny evidentiary issues in New York courts, and the rough consensus was that at least some of these comments could very well be admissible in the case against Trump.

Indeed, Merchan already agreed to allow prosecutors to introduce certain statements made by Trump prior to his indictment that prosecutors characterized as “threats” and “harassing comments on social media and in other public statements” directed at Cohen and Daniels. Merchan concluded that Trump’s lawyers had opened the door to this evidence by attacking the witnesses in their opening statement and said that he would allow the government to introduce Trump’s comments in order “to explain what I will describe as a lot of back and forth amongst the witnesses” and to “explain that they have not made as much money as the defense would have people think” by turning against Trump.

The same logic would apply to Trump’s most recent attacks on Cohen and Daniels, which largely fueled the contempt rulings.

It’s slightly more likely that Trump’s attacks on the jurors themselves might be withheld. Those are so inflammatory that prosecutors — or the judge — might reasonably conclude that they should be kept from the jurors so that they can remain focused on the core issues at hand during their deliberations.

Regardless, prosecutors appear to see the value of using Trump’s own outbursts against him. At the start of the case in mid-April, prosecutors told Merchan that they might introduce some of the statements Trump made that they already believed were in violation of the gag order.

If they were to do that with Trump’s broadsides since the trial began, the effect could be potent: The jurors would get to see just how inappropriately Trump has been acting outside the courtroom while he has been on trial — and while the jurors, whose lives have been upended and permanently changed by their participation in the case, have been trying to carry out their civic responsibility.

In a bizarre twist of fate, however, Trump may have been saved by none other than Harvey Weinstein — or, more to the point, the recent decision from New York’s highest court that threw out Weinstein’s 2020 conviction on sex crimes. The court concluded that prosecutors in the Manhattan D.A.’s office had improperly introduced irrelevant and unduly prejudicial testimony about alleged sexual assaults by Weinstein that were distinct from those directly charged in the case.

The jury has so far been shielded from Trump’s contempt proceedings. Particularly given the Weinstein ruling, prosecutors are now likely to be wary of a higher court later concluding that the judge inadvertently let the government back-door the contempt finding in this way when it otherwise would not have been admissible.

The much bigger problem for Trump, however, is that he is materially increasing the odds that he will be sent to prison if he is convicted at the end of the trial.

Since the start of this case, many observers — myself very much included — have questioned whether Trump would serve any sort of prison sentence if he is convicted at the close of the case. After all, the case is novel; this is the first-ever criminal prosecution against a former president; and New York courts tend to go easy on first-time white-collar offenders.

Trump’s running public commentary, however, is clearly angering both prosecutors and the judge.

At the hearing last week about whether Trump should be held in contempt of court for a second time, one of the prosecutors expressed the office’s frustration sharply — telling Merchan that Trump’s statements have been “corrosive to this proceeding and to the fair administration of justice” and that Trump has been trying to “make this about politics, and it’s not — it’s about his criminal conduct.”

And here was Merchan on Monday, again slapping Trump with criminal contempt: “Your continued willful violations of this court’s orders threaten to interfere with the … administration of justice and constitute a direct attack on the rule of law.” Trump’s attacks on the jury and its selection, he added in his written ruling, “again raised the specter of fear for the safety of the jurors and of their loved ones.”

If Trump is convicted, it will be up to this same team of prosecutors to decide whether to seek a prison sentence for Trump, and it will be up to the same judge to determine the sentence.

Judges are generally granted very wide latitude in crafting sentences, and they are free to consider a broad array of factors that are specific to the offense and to the offender — including the need to deter the defendant from further misconduct and to send a message to the community about the sort of conduct that is prohibited by the law. Indeed, under federal law, judges are explicitly required to craft sentences that consider (among other things) the need to “promote respect for the law,” which Trump clearly lacks.

The odds that Trump might face some time in prison after a conviction were already quietly creeping up thanks to the fact that Allen Weisselberg, his company’s former CFO, has been sentenced to two different five-month stints on Riker’s Island after pleading guilty to conduct that benefited Trump. Weisselberg first pleaded guilty to a tax-fraud scheme that benefited the Trump Organization and resulted in a conviction of the company itself. In March, he pleaded guilty to lying under oath during the New York Attorney General’s civil business-fraud trial against Trump.

Prosecutors and judges are supposed to ensure that the sentencing process is fair in a variety of respects, including by ensuring that different defendants are treated equally and fairly. If Trump is convicted and prosecutors decide to seek a prison sentence, he will need a very good argument to explain why he should get probation after his employee served two prison sentences following guilty pleas that stemmed from conduct to benefit Trump himself.

Trump’s behavior outside the courtroom will make matters even worse for him if the day arrives when Merchan has to hand down a sentence for him.

The problem will not just be the statements that Trump has made that run afoul of the gag order — statements that appear designed to influence the proceeding by intimidating witnesses and to delegitimize a potential guilty verdict by smearing the judge and the jury with baseless allegations that they are corrupt or biased against him.

Trump told supporters in Wisconsin and Michigan last week that his trial is “fake” and “bullshit” and that he is in a “kangaroo court.” Over the weekend, Trump sent messages complaining that he was the victim of “fascist prosecutors” and that he “can’t listen to that DISGUSTING judge for another second.” According to the New York Times, he also railed against his criminal cases at a donor retreat in which he accused the Biden administration of orchestrating the prosecutions and claimed that they were “running a Gestapo administration.” These comments technically do not run afoul of the gag order because they do not target witnesses or jurors, but they are similar efforts to undermine the legitimacy of the proceeding and New York’s criminal justice system.

Prosecutors and the judge are well within their rights to be angry about Trump’s behavior and to factor it into their assessment of the appropriate punishment if he is eventually convicted.

Trump is in a perilous situation as he manages his multi-pronged criminal defense alongside his bid for the White House. He either can’t help himself or he thinks it is necessary to denounce his criminal cases in order to maintain the support of his base — but if he doesn’t win his reelection bid, he is certainly exposed to potential prison time in his two federal criminal cases.

I had previously assumed that Trump would have a good shot at getting off with probation if he’s only convicted in the Manhattan case. He seems to want to test that proposition.