Donald Trump Is Any Defense Attorney’s Nightmare
“A regular defendant would have been locked up a long time ago.”
They say that a man who represents himself has a fool for a client. So, perhaps, does a person who represents Donald Trump.
To most people, attacking someone with influence over one’s freedom and fortunes is self-evidently unwise, but that is precisely what Trump has been up to. This week, the former president attended a civil trial in Manhattan to determine what damages he might have to pay in a case about his company committing a massive, yearslong fraud. Justice Arthur Engoron, the judge in the case, has already ruled that fraud did occur, and Trump is furious about it.
“This is a judge that should be disbarred,” he said outside of the court on Monday. “This is a judge that should be out of office. This is a judge that some people say could be charged criminally for what he’s doing. He’s interfering with an election.”
The next day, Trump’s campaign issued a lengthy statement portraying Engoron as a Democratic operative, and Trump attacked Engoron’s law clerk on his social-media site, Truth Social. Engoron then placed a gag order on the former president, barring him from attacking the clerk. (Trump’s message was later deleted.) These incidents follow earlier broadsides against Tanya Chutkan, the federal judge overseeing the case against him in Washington, D.C., for trying to steal the 2020 election. Trump called her “a fraud dressed up as a judge,” “a radical Obama hack,” and a “biased, Trump-hating judge.” (He has also insulted prosecutors in bracingly personal terms, but then again they are already literally out to get him.)
“It’s like being a football player and every time you go back to your position, you kick the ref in the shins,” Ty Cobb, an attorney who served as special counsel in the White House during the Robert Mueller probe, told me. “You gradually sacrifice the benefit of the doubt, or you put a lot of strain on someone who’s supposed to be evenhanded.” Ken White, a criminal-defense attorney and writer, was even blunter, telling me, “He is who he is. It’s crazy, and I’m sure his lawyers are horrified.”
And yet things could be going much worse. With the exception of this week’s narrow gag order, Trump has not been punished directly by judges, who could instruct him not to comment on cases and even imprison him if he doesn’t comply. Department of Justice Special Counsel Jack Smith asked Chutkan for a partial gag order, which Trump promptly misrepresented publicly; she has scheduled a hearing on the question for October 16. Courts seem slow to sanction Trump because they are wary of being seen as infringing on a major political figure’s speech, and because setting a rule would require enforcing it—and Trump is possibly too big to jail.
“He knows the judges are less likely to do something to him, because they’re kind of backed into a corner. He’ll say, They’re taking it so personally; they’re being biased. They hate me because I exercise my free speech,” Titus Nichols, a defense attorney and former prosecutor who represented the whistleblower Reality Winner, told me. “A regular defendant would have been locked up a long time ago.”
That doesn’t mean that the outbursts have no downside. The fraud trial is being heard by Engoron with no jury. (He says that Trump’s lawyers declined to request a jury.) Although Engoron is ultimately bound by the law, a trial includes many opportunities for a judge to make dozens of minor, discretionary choices.
“When it comes down to individual rulings, you really want the judge to be as open-minded as possible. But if you’ve spent all this time saying, The judge is stupid, the judge is a disgrace, what do you think’s going to happen when you get to those rulings?” Nichols told me. “And that’s why it’s a bad strategy to insult the judge, because while the judge might not directly reprimand you, there’s so much judicial discretion.”
Attorneys I spoke with told me they advise defendants to keep a low profile ahead of a trial and to stay off social media. In addition to the danger of alienating a judge, anything they say could be brought up during proceedings. “You tell stories about how publicity can harm you, how it doesn’t land the way you think it’s landing, how your friends and cronies will love it, but the judge and probably jury will hate it,” White told me. A lawyer might even choose a prominent example from the news to illustrate the danger: “If you’re anyone but Donald Trump, you point at Donald Trump.”
It’s possible to construct a theory under which Trump’s outbursts at judges aren’t all that disastrous. Trump often seems to prioritize his political fortunes—fervor among his base, fundraising, press coverage—over his apparent best interest. But if you presume that losses in both the fraud and election-subversion cases are already foregone conclusions, then his strategy makes some sense. Engoron has already ruled that Trump committed fraud, and the facts in the election case are damning. (Cobb told me he expects a conviction in the federal election case: “If you’re a juror in a case like that, you come back pretty fast.”) Any conviction (or damages, in the civil cases against him) will likely be appealed, but at the trial level, Trump may have already accepted he is likely to lose, and thus may stand to gain the most by wrapping himself in a lost cause.
But even if the self-inflicted wounds in any individual case are incidental, his tendency to create unnecessary nightmares for defense teams (along with his history of stiffing contractors) means that he is less able to attract high-quality representation. Top-tier lawyers have repeatedly declined to work for him, and among those who have taken the job, many don’t stay for long. Over time, that could deepen his risk in all of the cases against him.
“If you go to 30,000 feet, what his defense lacks is a general—someone who has stature, experience, and knowledge to manage all these trial teams,” Cobb told me. “It’s a leaderless defense, which de facto makes Trump the leader of the defense.”
In other words, Trump is acting as his own chief attorney—and we know what people say about a man who represents himself.