Does the Supreme Court Favor Trump on Speech?

Two years ago, free speech champion Greg Lukianoff came on the show to express his concerns about conservative students getting cancelled on college campuses. Today, he’s terrified of the President of the United States. The CEO of the Foundation for Individual Rights and Expression (FIRE) has spent decades defending free speech against overzealous university administrators. But in Trump’s second term, Lukianoff finds himself fighting a much scarier adversary: a government hostile to free speech. Law firms have capitulated under threats of losing security clearances. Students have been deported for saying the wrong thing. And Trump keeps admitting he’s targeting people for their viewpoints—virtually guaranteeing he’ll lose in court while expanding executive overreach anyway.

1. The Complete Reversal: Trump Adopted the Left’s Censorship Playbook The administration that campaigned against campus “cancel culture” now deploys the exact tactics it once condemned—misinformation claims, hate speech codes, viewpoint-based punishments. “They rediscovered hate speech” after Charlie Kirk’s assassination, Lukianoff notes, using it as justification to silence critics despite previously arguing hate speech should be protected.

2. Law Firms Chose Cowardice Over Principle Major law firms immediately capitulated to Trump administration threats of losing security clearances and federal building access—effectively ending their ability to practice. Only Covington & Burling fought from the start, and those who resisted have largely won in court. “It’s cowardice and self-interest, to be honest,” Lukianoff says. “They try to make it sound like this is an existential battle... And it’s like, yeah, that’s why you fight then.”

3. Trump’s Own Admissions Guarantee He’ll Lose in Court Trump can’t help himself: he publicly admits he’s targeting people for their viewpoints, which is “the sine qua non of what you’re not allowed to do under the First Amendment.” His ego and need for credit constantly undermine his administration’s legal strategy. “Trump wants credit for all of this stuff,” creating a paper trail of constitutional violations.

4. Students Are Being Deported for Protected Speech FIRE is challenging Marco Rubio’s use of obscure 1950s-era powers that allow the Secretary of State to deport non-citizens based solely on his opinion that they’re “adverse to foreign policy.” The only previous court challenge ruled these provisions unconstitutionally broad—by Trump’s own sister, a federal judge who died in 2023.

5. The Real Red Line: When Trump Ignores the Courts “Our big red line is if he just stops following the courts entirely,” Lukianoff warns. The nightmare scenario isn’t losing cases—it’s Trump pulling an Andrew Jackson moment, saying “the court made the ruling, let it enforce it,” and simply continuing anyway. Nine months into the term, Lukianoff won’t say it’s likely, but he won’t rule it out either: “Would I be totally shocked? Unfortunately, no.”

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