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Reagan Judge Scorches ‘Bragging’ Trump for Trampling Constitution

September 30, 2025
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A conservative judge has excoriated Donald Trump over free speech, depicting him as a bully who engages in “hollow bragging” to get his way and seeks to strike fear into people so they don’t speak up.

In a blistering 161-page ruling, federal judge William Young also hit out at ICE agents for using masks to ​​”terrorize Americans into quiescence” and likened wearing them to “cowardly desperados and the despised Ku Klux Klan.”

U.S. District Judge William Young poses for a picture at the court in Boston, Massachusetts, U.S.
U.S. District Judge William Young poses for a picture at the court in Boston, Massachusetts, U.S. U.S. District Court For The District Of Massachusetts/Reuters

And he hit out at the president’s “palpable misunderstanding” that his government simply can’t seek revenge for speech he doesn’t like.

“I fear President Trump believes the American people are so divided that today they will not stand up, fight for, and defend our most precious constitutional values so long as they are lulled into thinking their own personal interests are not affected,” Young added.

“Is he correct?”

Mahmoud Khalil was released from detention on June 30 and reunited with his wife Noor Abdalla (R) and son, as well as U.S. Representative Alexandria Ocasio-Cortez (L), a champion of Khalil's in Congress.
Mahmoud Khalil was released from detention on June 30 and reunited with his wife Noor Abdalla (R) and U.S. Representative Alexandria Ocasio-Cortez (L), a champion of Khalil’s in Congress. Kena Betancur/AFP

The extraordinary ruling was the long-awaited result of a lawsuit brought by university professors, who had accused the administration of attacking free speech by targeting prominent pro-Palestinian campus activists and others who have expressed pro-Palestinian views.

Among those activists was Columbia University’s Mahmoud Khalil, who was detained by ICE earlier this year as the Trump administration moved to deport him.

However, in his ruling, Young said the administration’s effort to deport pro-Palestinian academics was a deliberate attempt to chill free speech “under the cover of an unconstitutionally broad definition of Anti-Semitism.”

Some of the judge’s most extraordinary remarks were devoted to Trump, who he depicted as a showboat who had violated the sacred role of a president to defend the Constitution, which represented a “full-throated assault on the First Amendment.”

In highly unusual remarks for a judge, Young even cited his wife, who had said of the president: “He seems to be winning. He ignores everything and keeps bullying ahead.” The US district court judge from Massachusetts then dissected each part of her sentence.

For instance, when it comes to winning, the Reagan-appointed judge wrote, “Triumphalism is the very essence of the Trump brand.”

U.S. President Donald Trump wears a 'Trump Was Right About Everything!' hat while holding the FIFA World Cup Trophy, as he makes an announcement on the 2026 FIFA World Cup, in the Oval Office at the White House in Washington, D.C., U.S., August 22, 2025. REUTERS/Jonathan Ernst/File Photo
“Triumphalism is the very essence of the Trump brand,” judge William Young wrote. Jonathan Ernst/REUTERS

“Often this is naught but hollow bragging: “my perfect administration,” wearing a red baseball cap in the presidential oval office emblazoned “Trump Was Right About Everything,” or most recently depicting himself as an officer in the First Cavalry Division,” Young said.

“Unfortunately, this tends to obscure the very real and sweeping changes President Trump has wrought in his first year in office.”

On the question of Trump ignoring everything, Young declared: “This is indubitably true. The Constitution, our civil laws, regulations, mores, customs, practices, courtesies — all of it; the President simply ignores it all when he takes it into his head to act.”

And “he keeps bullying on,” Young added.

“His speech dominates today’s American idiom. Indeed, it may be said to define it. It is triumphal, transactional, imperative, bellicose, and coarse. It seeks to persuade—not through marshaling data driven evidence, science, or moral suasion, but through power.”

The ruling was one of the most astounding rebukes a judge has made against the administration to date.

It comes after a lawsuit was filed by the American Association of University Professors and the Middle East Studies Association, which represents hundreds of professors and students across the country.

Police officers stand guard as demonstrators protest in solidarity with Pro-Palestinian organizers on the Columbia University campus, amid the ongoing conflict between Israel and the Palestinian Islamist group Hamas, in New York City
Police officers stand guard as demonstrators protest in solidarity with Pro-Palestinian organizers on the Columbia University campus. REUTERS/Caitlin Ochs

A bench trial was held in July, revealing that the government had looked into more than 5000 people who had been doxxed on a website in a bid to revoke the visas of student protesters.

But according to Young, there was “clear and convincing evidence“ that Secretary of Homeland Security Kristi Noem and the Secretary of State Marco Rubio deliberately sought to “chill the rights to freedom of speech.”

And of ICE agents wearing masks, he said: “In all our history we have never tolerated an armed masked secret police. Carrying on in this fashion, ICE brings indelible obloquy to this administration and everyone who works in it.”

The White House fired back on Tuesday, describing the ruling as “outrageous” and vowing to appeal.

Kristi Noem
Noem’s love for dolling up for the cameras on ICE raids has earned her the nickname “ICE Barbie.” Homeland Security/Handout/Getty Images

“The President is a staunch supporter and defender of First Amendment rights, but violent riots and student harassment are not protected speech,” said spokesperson Liz Huston.

“Studying in the United States is a privilege that the Trump Administration will not allow to foreign nationals who endanger America’s national security or imperil campus safety.

“The administration will immediately appeal this errant decision, and we are confident we will be vindicated on review.”

The post Reagan Judge Scorches ‘Bragging’ Trump for Trampling Constitution appeared first on The Daily Beast.

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