On Contempt of Court

Punishing Trump for contempt is easy, if you know how.

The First Amendment forbades the government from making laws abridging freedom of speech. While there are numerous exceptions and limits to this, this essay will focus on one.

It is a generally accepted constitutional principles that freedom of speech does not allow one to threaten or intimidate witnesses, jurors, or those whose jobs are intrinsically connected to the legal system (e.g. prosecutors, counsel, court staff, and the courts themselves). Without that prohibition, we’d have a feudalistic system where disputes were settled through violence and the scales of justice (which are already skewed heavily in favor of those with wealth, power, and privilege) would be abandoned for a cash register.

Donald Trump, who has shown an affinity for mob bosses, prefers a legal system where he is like the Corleones and the Sopranos — legally untouchable.

In real life, unfortunately for Trump and his “fantasy is reality” persona; a slew of organized crime figures have met the jailhouse door not because they lacked the money or power to buy their “innocence”, but due to public objection over the brazeness of saying so openly. John Gotti died in prison over that bit of realism.

Beginning in 2023, a rash of grand jury indictments and unstoppable court dates have rewritten Trump’s legal strategy of dilatory motion practice followed by frivolous appeals of every court order. As a concomitant legal tactic, which fits in well with his political stategy of election denialism, Trump has attacked the courts, prosecutors, and witnesses against him as part of a convoluted plot being orchestrated by Joe Biden.

Of Trump’s four criminal cases, only one seems to be going his way — the Mar-a-Lago classified documents case. The rest seem to be headed towards trial with the only issue being firm dates for trial. And outside of the classified documents case, every judge has imposed limits on what Trump cannot say about the case.

Michael Popok of the Legal AF podcast has opined that with every gag order, either civil or criminal, Donald Trump sits downs with his attorneys and reviews what might get him a contempt charge and what might be merely “toeing the line.”

What’s stopping Donald Trump from actually complely testing those orders?

Three things.

A very real fear of jail. I have no doubt that Trump’s lawyers have told him repeated violations could mean a night in jail. What his lawyers likely have not explained to him is that his “the circus has come to town” antics and attacks on witness, prosecutors, and the courts could mean bail-wise post conviction.

Let’s put a pin in that one.

Donald Trump has likely been told by the Secret Service that they have no power to preclude his being in prison and/or jail. There may be some logistical hurdles, but being protected by the Secret Service is not a “get out of jail free” card. If it were, we’d have seen worse from Trump.

Trump hates losing. A lot. His life has been spent using money and, since being elected in 2016, power as a measuring stick against others. How bad is his aversion to be seen as a loser?

He lost a defamation case against E. Jean Carroll in 2023 (Carroll II), the news of which took a significant back page to potential criminal indictments. So upset about losing and having a $5 million judgment against him that he doubled down in an attempt to counter what he saw as “losing” to someone — a female someone. That second case (Carroll I) cost him $83 million.¹

When you take into against Trump’s rage at being hit with a $464 million judgment for civil business fraud, one can only imagine the psychological meltdown that a criminal conviction will produce. Especially, if it’s a felony conviction.

There is a secret most people don’t know about courthouses in America. Most lawyers don’t know it. In fact, outside of prosecutors, members of the criminal defense bar, and courthouse staff; no one is likely even aware of its existence. Once you read it though, you’ll say “Yeah, I kind of knew that.”

There are jail cells in courthouses; and depending on the Court, there are often either holding pens (just off the court itself) or criminal docks in courtrooms themselves. It’s where prisoners are sat pending a hearing, plea agreement, or sentencing.

Contempt of Court for Donald has been imposed monetarily. It was paid though his lawyer’s Trust Account (for holding client funds). Given the fact that Trump’s supporters are footing his legal bills — not avery effective means of telling The Donald how to behave.

Putting Donald Trump in jail overnight or for the weekend is going to ramp up his circus and clown parade a bit too much to be worth to effectively messge to Trump that 6 plus decades of being a spoiled self-entitled brat is not going to work going forwad with his criminal cases. Plus, I have serious doubts that a trip to Rikers Island isn’t going to aid Trump politically.

The weekly schedule for Trump’s business fraud case before Judge Juan Merchan is going to be Monday, Tuesday, Thursday, and Friday. Yep…a four day, 32 hour, 6-8 week trial with Wednesdays off for golfing, complaining, rallies, and what not.

There is no 24 hour lower limit for being jailed for contempt. Eight hours sitting in the dock like a prisoner unable to tweet, talk, or toe the line might be the prescription needed to end Trump’s attacks.

Less is more as the Philosopher Parr used to say.

1. The E Jean Carroll cases are numbered I and II. Due to a myriad of legal machinations. E Jean Carrroll’s second defamation case went to trial in the Spring of 2023. The first defamation case case went to trial in January 2024.