Trump v. The First Amendment: A Mismatch for the Ages

by C. Moore
September 20, 2025

Trump’s $15 Billion Tantrum: When a Lawsuit Becomes Performance Art

President Donald J. Trump’s $15 billion lawsuit against The New York Times has been tossed like yesterday’s fast-food wrapper, for now.

Calling the president’s 85-page magnum opus of grievance “decidedly improper and impermissible,” U.S. District Judge Steven D. Merryday effectively told Trump to either learn how to write like a lawyer or go back to yelling at clouds. The judge, apparently unamused by the creative writing project, noted that the suit only contained two actual claims of defamation — Count I appearing on page 80, Count II on page 83 — buried beneath 79 pages of ego stroking, political invective, and what could best be described as a rejected campaign speech.

Judge Merryday reminded the former president that a legal complaint is supposed to be a “short and plain statement” of facts, not a “megaphone for public relations” or a “passionate oration at a political rally.” Translation: save the ranting for Truth Social. Oh, and trim it down to 40 pages or less — think of it as Twitter with footnotes.

This latest courtroom spectacle follows Trump’s ongoing legal vendetta tour against the media — having already aimed lawsuits at ABC, CBS, and The Wall Street Journal. His beef with The Times? That it acted as a “mouthpiece” for Democrats and gave Kamala Harris a campaign contribution in the form of journalism he didn’t like. In other words, reporting = rigging.


Free Speech, Unless You’re Pro-Palestinian

Meanwhile, in Trumpworld, free speech is sacred — unless you say something he doesn’t like. Multiple lawsuits have been filed against the administration’s alleged policy of targeting pro-Palestinian non-citizens for deportation, simply for expressing political views. Critics call it a direct violation of the First Amendment, creating a climate of fear on university campuses.

Take the case of Mahmoud Khalil, a Columbia University alum and legal U.S. resident. On September 17, 2025, an immigration judge in Louisiana ordered him deported — either to Algeria or Syria — over alleged misrepresentations on his green card application. Federal courts, however, are still blocking his deportation while his case proceeds. The irony, of course, is that Trump insists on defending the “freedom” of Confederate statues while trying to silence actual human beings.


The Pentagon Redefines “Free Press”

Not to be outdone, Defense Secretary Pete Hegseth unveiled new rules limiting Pentagon press access. Reporters now risk being banned for “unprofessional conduct” or even attempting to obtain information — whether classified, unclassified, or simply embarrassing to the administration.

In short: report at your own risk. The rules are so broad, you could probably lose access for asking where the bathroom is without “appropriate authorizing official” approval.


Trump’s Top Hits: Freedom Edition

As academics around the world scratch their heads, one burning question remains: which Trump-era attack on free speech is the most idiotic?

  1. Renaming the Gulf of Mexico the “Gulf of America” — because nothing says freedom like renaming water.

  2. Renaming the Department of Defense the “Department of War” — because why bother hiding it?

Perhaps, in the end, Trump’s lawsuits and renamings are all just a form of performance art — a legal and political avant-garde movement where coherence, constitutionality, and common sense are strictly optional.

Trumpenomics: The Decline of America

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